I need to tell you something that sounds like it ends my career.

I’m the person you hire to find the ceiling—or shatter it. Fifteen years, thousands of engagements, over a billion dollars in lifted outcomes. If anyone on earth should believe the highest number wins, it’s me.

Right?

And the smartest executives I’ve ever represented—the ones who play this game across decades, who compound instead of climb—routinely don’t take the highest offer.

Not because they couldn’t get it. We got it. The ceiling was located, priced, and put on the table.

They looked at it. And they picked something else. They don’t have the illusion of choice. Rather, they exercise their choice regularly. An enviable position to many others.

The first few times I watched this happen, I thought I’d failed. The number was right there.

It took me years to understand what they were actually doing.

It’s likely because I’ve always had a tenuous relationship with working for somebody else’s company—and thus always pushed for the highest compensation possible.

But they weren’t doing offer math.

They were planning moves way ahead of what any market expert could predict.

They were doing decade math.

Offer Math vs. Decade Math

Offer math is the arithmetic everyone knows. Base, bonus, equity, sign-on. Stack the columns, compare the totals, circle the biggest one. It answers a single question: what am I worth today?

Decade math asks a different question: what does this deal build?

And the moment you ask that question, the columns change. The biggest package and the best deal stop being the same thing—sometimes they’re not even close.

Decade-thinkers read the term sheets everyone else skims

Equity quality, not equity quantity. Two offers, same equity value on paper. One is common stock behind three preference stacks at a company that hasn’t refreshed a grant in four years. The other is a cleaner instrument, a real refresh culture, and a credible path to liquidity.

The paper says they’re equal.

The decade says one of them is a lottery ticket and the other is a real stake. Offer math can’t see the difference. It’s not in the columns.

Board access. The room you sit in determines the next three offers you’ll ever receive. A slightly smaller package that puts you in front of the board eight times a year is worth more than a bigger one that buries you two layers down—because the people in that room run other companies, sit on other boards, and make other calls.

You’re not being paid in dollars alone. You’re being paid in proximity.

Proximity compounds. Dollars depreciate.

Future deal flow. Every seat is a node, not a destination. The decade-thinkers ask what this role generates: which relationships, which stories, which proof.

“I took a business from 40 to 200” is an asset that pays out for fifteen years. The seat that produces that sentence is worth more than the seat that pays 20% better and produces nothing you can carry out the door.

Scaffolding. The support around the role—the quality of the team, the clarity of the mandate, the sponsor who wanted you there.

A top-of-market package for a role you’re set up to fail in isn’t a win. It’s a down payment on a scar. The decade-thinkers walk the scaffolding before they price the seat, because comp for eighteen doomed months is the most expensive money you’ll ever earn.

Especially if you snatched an inflated title that the market doesn’t respect while you try to figure yourself out for the next several years.

None of this shows up in the offer letter’s bold total. All of it shows up in the decade.

Why They Love the Deal Everyone Else Fears

They are not afraid of performance-based compensation. They prefer it.

Milestone triggers. Outcome tranches. Comp that only breaks the band when the business breaks its plan. The structures most candidates flinch at—what if I miss?—are the structures decade-thinkers ask for by name.

The reason is simple, and it’s a little confronting.

Performance comp is only frightening if you’re not sure you’re the person you’ve been claiming to be.

It’s a signal of confidence, competence, and certainty—for both you and the employer.

The decade-thinkers know.

They’d rather own their upside than rent their certainty. Guaranteed money prices them at the market’s confidence level; outcome money prices them at their own. And in every scenario where the bet pays, the company won bigger too—which means the check gets written with a smile instead of a grudge.

That’s not risk tolerance. That’s self-knowledge with a term sheet attached.

I’ve written the full playbook for structuring these deals—the sequencing, the scripts, the supplemental-agreement path. The mechanics matter. But the mechanics were never the barrier. The barrier is that betting on yourself requires knowing what you’re betting.

The decade-thinkers know. That’s the tier.

The Turn Nobody Sees Coming

Now the part I’ve never written before. The part that decade math produces which offer math cannot compute.

Sometimes the answer is less.

Not less because you couldn’t get more. Less because you looked at what more costs, and declined to pay it.

I need to say this carefully, because everything I publish teaches you to find the ceiling.

Find the ceiling. Always.

Curiosity over certainty, range over fog, clean asks over hedges.

But finding the ceiling and living at the ceiling are two different decisions—and the second one deserves as much rigor as the first.

Because the ceiling has a price tag that never appears in the offer letter.

The tall poppy is real. The highest-paid executive in the building is the first name the CFO’s sort function surfaces when the quarter goes sideways.

The premium you captured is remembered by everyone who approved it—and quietly resented by a few. Maximum comp buys maximum scrutiny, and scrutiny is a tax you pay in cortisol.

And that’s the cheap part.

The expensive part is the ledger nobody audits.

Every yes is a no you didn’t say out loud.

The 80-hour weeks are a yes—to the package, the mandate, the scoreboard.

The no’s they contain don’t get itemized:

• Your best thinking, which doesn’t happen at hour eleven of a day.

• Your healthiest remaining years, which are not evenly distributed across your life and are not for sale back to you later.

• The attention your kids are still young enough to want.

• The parents who are aging on a schedule that doesn’t care about your vesting cliff.

Money doesn’t solve a single item on that list.

Past a threshold—and executives at your altitude passed it a while ago—each additional dollar buys measurably less life. The returns diminish.

The costs don’t.

A year and a half ago I wrote a line in passing: you can always get more money, but you can’t get more time.

I no longer think I said it strongly enough.

What Would Your Life Look Like With Less?

Try asking the question. Actually asking it—not as a thought experiment you dismiss on the way to the counter.

What would your life look like with less?

It’s a deeply un-American question. Everything in the water we swim in says maximize: the bigger title, the bigger package, the bigger exit. More is the default setting, and defaults, as you know by now, are scripts somebody else wrote.

Up and to the right—so to speak.

That’s the part that took me the longest to see.

The reflex to maximize is itself predetermined. Nobody sat you down and asked whether the top of the range was where you wanted to live. The culture decided, the scoreboard decided, the LinkedIn feed decided—and you executed a decision you never made.

The decade-thinkers make it on purpose.

Some of them max the deal, clear-eyed about the costs, because the mission is worth it and the season is right. Some of them take the 70% package with the four-day reality, the board seat, the equity that might actually matter—and buy back Tuesday afternoons with their daughter while she still wants them.

Both are winning. Because both are choosing.

I know this one from the inside. I could have scaled my practice into a firm years ago—partners, associates, leverage, a number with more commas.

I chose a solo practice in a small Montana town instead, and built the structure so the work got bigger while my hours got smaller. I deleted a LinkedIn following most people in my field would trade a limb for, because the scoreboard it kept was measuring a game I’d stopped playing.

By offer math, I’ve left a fortune on the table.

By decade math, I’ve never done a better deal.

Negotiation Isn’t For Sharks

Now you know the real reason.

People assume that someone who does what I do must be an extraction machine—teeth, leverage, pound of flesh. The assumption isn’t just wrong about me.

It’s wrong about the game.

The shark thesis assumes the maximum is the point.

But I’ve sat close enough to the maximum, for long enough, to see what it costs the people who capture it without choosing it.

The biggest checks I’ve ever lifted are not the deals I’m proudest of. The deals I’m proudest of are the ones where the structure fit the decade—where the executive walked in aligned, stayed aligned, and five years later the deal still looked smart from every seat at the table, including the dinner table.

Alignment and fulfillment beat everything in the end.

Not as a greeting-card sentiment. As an observed, repeated, fifteen-year pattern in the outcomes of the most successful people I know.

So before you sign the next one, run the decade questions:

• What does this deal make possible in year five—not year one?

• What am I saying no to? Name the no’s. Out loud. All of them.

• And what does enough look like—written down before the offer arrives, so the number doesn’t get to define it for you?

Find the ceiling. That part never changes—you can’t choose what you never discovered, and walking away from money you could have had is only a choice if you could have had it.

But then make the second decision. The one nobody’s watching. The one the scoreboard can’t see.

The highest offer is a fact about the market.

The right offer is a decision about your life.

Enough, chosen on purpose, is the most predetermined-proof number there is.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

Last month I sat in on a mock negotiation with a client. President-level role. Eight-figure package over four years if the equity performs.

For forty minutes he was flawless. Commanded the business case. Handled the hard questions. Sounded like the peer of everyone who’d be in the real room.

Then we got to the number, and he said this:

“I was thinking maybe somewhere in the mid-eights, if that works on your end.”

Read that slowly.

There are four separate retreats hiding inside that statement.

I was thinking—past tense.

He’s already distancing himself from the ask, like it belongs to an earlier version of him he’s prepared to disown.

Maybe—the number isn’t a position. It’s a suggestion.

Somewhere in the mid—not even a number. A fog bank where a number should be.

If that works on your end—permission requested. The other side now owns the verdict on his worth.

Forty minutes of executive presence, dismantled by one sentence.

In the real room, the person across the table hears all four retreats before you finish the sentence.

Because they’re trained to. It leaves them with a feeling that you’re not convinced of your own worth. So why should they be?

The Same Sentence, Every Altitude

Last week I showed you the company’s script—the four rituals they run to keep the negotiation from ever happening.

This week is harder. This week is your script.

Track a career from the floor to the top and listen for one sentence.

• The analyst, three years in: “I was thinking maybe I could sit in on the client meeting?”

• The director, year ten: “I was thinking maybe I could take on the platform team as well?”

• The executive, year twenty, staring at the biggest package of her life: “I was thinking maybe somewhere in the mid-eights?”

The rooms changed. The stakes grew a thousandfold.

The sentence never changed.

That’s the part few recognize. We assume the habits of the floor get shed on the climb—that somewhere between manager and C-suite, the deferential language falls away with the cubicle.

It doesn’t.

The hedge rides along, invisible to the person carrying it, glowing like a flare to everyone else.

Two Hedges. Only One Has a Price Tag.

You know what a hedge is on Wall Street. A calculated instrument. You pay a known premium to cap your downside. Nobody buys a hedge without asking what it costs—the cost is the entire point of the conversation.

Now look at the other hedge. The one in your mouth.

Just. Maybe. I feel like. Sort of. I was thinking. Sorry to ask, but. This might be a dumb idea, but. If that works for you.

Same instrument, inverted.

The financial hedge caps your downside at a price you chose.
The linguistic hedge caps your upside at a price you never see.

And you deploy it a dozen times a day for free.

Except it isn’t free.

It’s the most expensive hedge you own—you just get the bill later, bundled invisibly into an offer that came in lower than it had to, a counter that stayed thinner than it should have, a “yes” that arrived suspiciously fast.

Why Your Mouth Buys Insurance You Didn’t Order

Now I’m supposed to tell you to stop using weak words, as if this were a vocabulary problem.

It’s not a vocabulary problem.

The hedge is a safety behavior.

It’s your body trying to shrink the ask so the rejection will have less surface area. If the request is small—just a quick question, maybe something in the mid-eights, only what I was thinking—then the no, when it comes, lands on something small.

The hedge is pre-paid pain relief for a wound you haven’t received yet.

For a lot of us, that reflex is old. Some of us learned early that playing small was how you stayed safe. The words aren’t a style choice. They’re armor from a life you left behind decades ago.

Which is exactly why “just be more confident” is useless advice.

You can’t out-vocabulary a threat response. But you can do something better: you can recognize that the threat is miscalibrated. The rejection you’re insuring against costs you nothing—a no is a data point.

The insurance costs you everything—because of who’s listening.

The Trained Listener

The person across the table has heard ten thousand asks. Comp conversations are your once-every-three-years event and their Tuesday.

That volume turns them into something you need to understand: a leverage-reading machine.

They are not parsing your sentence for meaning. They’re parsing it for softness. And the hedge answers every question they have before they ask it.

• I was thinking maybe tells them the number is negotiable before the number arrives.

• Somewhere in the mid-eights tells them the bottom of the fog is your real floor—so they can land beneath the middle of it.

• If that works on your end tells them a thin counter will close you, because you’ve already assigned them the authority to rule on your worth.

None of this requires malice. That’s what makes it dangerous.

The system prices what you signal.

Hand them a hedged anchor and you’ll get the oldest move in the book—the split. They’ll meet you “in the middle” between their number and your soft one, and the middle of a hedge is always closer to their end than yours.

It feels like compromise. It’s a discount you wrote yourself. And again, you never find the ceiling.

And when a recruiter asks that famous question—“What would it take to get you to a yes?”—understand what’s being harvested.

They’re not exploring. They’re inviting you to hedge a ceiling into existence so they never have to reveal theirs.

Go Fish is a much easier game when your toddler can’t keep their cards from tipping toward your gaze.

Delete the On-Ramp

So what’s the practice?

Not aggression. Not bravado.

You don’t need harder words—the executives who overcorrect into chest-thumping lose just as much, differently.

You need fewer words.

Every hedge is an on-ramp: a stretch of runway you build in front of the ask so you can approach it gradually. The fix is almost embarrassingly simple.

Delete the on-ramp. Start at the ask.

Script A—the hedge:
“I was thinking maybe somewhere in the mid-eights, if that works on your end?”

—

Script B—the ask:
“I’m at 1.05 to 1.7.”

Then nothing.

The silence after your number is not a gap to fill. It’s the second half of the sentence—and it belongs to you.

Now look closely at Script B, because it breaks a rule you might have expected me to hand you.

It’s a range.

Isn’t a range the fog bank I just spent a thousand words demolishing? No—and the difference is worth millions.

“Somewhere in the mid-eights” is a range built around your hope. It’s hedged at both ends, it drifts downward, and the trained listener lands beneath the middle of it every time.

The clean range is built above your number. In my practice, the bottom of the range sits roughly 20% above the figure my client would happily sign. The top runs toward double it. My client wanted mid-eights. The range opened at 1.05.

The fog anchors down. The range anchors up.

The research backs this architecture twice over.

Galinsky’s work at Columbia found the first number on the table explains as much as 85% of where a deal finally lands.

And Ames and Mason—Columbia again—found that ranges anchored upward from your target outperform single numbers: the other side feels pulled to respond inside the range rather than beneath it, and reads you as more cooperative while you’re anchoring higher.

Let that sink in.

The bolder structure makes you look easier to work with.

And the deals still don’t get rescinded.

Run the same demolition across the rest of your vocabulary:

• “Just following up on my last note” becomes “Following up.”

• “I feel like the scope justifies more” becomes “The scope justifies more.”

• “Sorry to push on this, but” becomes—nothing.

Delete it entirely.

You are not pushing. You are working together, and standard business requests don’t require an apology, because no transgression occurred.

“Does that work for you?” becomes silence.

If it doesn’t work for them, they’ll tell you. That’s their half of the negotiation. Stop doing it for them.

Notice what none of these revisions do: none of them add force.

“I’m at 1.05 to 1.7” is not aggressive. It’s not even firm, exactly. It’s just complete—an ask with nothing stapled to it.

The warmth you’re afraid of losing doesn’t live in the qualifiers. It lives in your tone, your pacing, the genuine curiosity you brought to the whole conversation before this moment.

If you need proof, researchers tested exactly this fear in 2019.

Firm first offers drew better counteroffers than warm, friendly ones—and here’s the part that should release you: the other side liked their counterpart no less.

The firm sentence wins, and nobody resents you for saying it.

Keep the warmth where it works—and please negotiate in person, on a walk-and-talk, or on a casual phone call or Zoom. Email is where pleasant tone and context go to die.

Precision and warmth were never opposites. Warm delivery of an exact sentence is the most disarming combination in any room I’ve ever worked.

And when they ask what would make you say yes? Don’t hand them a ceiling. Hand the question back:

“Let’s flip it—what does the business need this role to produce in the first eighteen months? If we get that right, the yes takes care of itself.”

The Distance Is Linguistic

The gap between the floor of your career and the top of it is not, at this point, a competence gap. You closed that years ago. Everyone at your altitude is competent.

The remaining distance is linguistic.

It’s the difference between seventeen words and five. Between an ask wrapped in insurance and an ask that stands there, unarmored, and survives.

The hedge protects you from a rejection that costs nothing.

And guarantees a discount that costs everything.

You already know your number. You’ve known it for weeks. The only question left is whether you’ll say it like a suggestion—or say it like a fact, start the range above it, and let the silence do its work.

Drop the maybe.

Keep the warmth.

Say the number.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

The offer arrived at 4:52 PM on a Friday.

Warm subject line. Exclamation point. “We’re thrilled to extend...”

Then, three paragraphs down, almost apologetic: we’ll need your decision by Monday morning.

My client forwarded it to me with one line: “They seem really excited. I don’t want to blow this by pushing.”

That sentence is the product.

Not the offer. The sentence.

The company spent three months and eleven interviews engineering the moment where a senior executive—someone who negotiates eight-figure vendor contracts without blinking—looks at his own compensation and thinks I don’t want to blow this by pushing.

Companies don’t want to beat you at negotiation.

They want the negotiation to never happen.

The Discipline Nobody Tells You About

The recruiting industry has a name for this. They call it candidate control.

It’s not a conspiracy theory. It’s a training curriculum. Recruiters are taught the trial close, the close, and the re-close. They’re taught to test your motivations with hypotheticals weeks before an offer exists—if we came in around this range, is there anything that would stop you from signing?

They’re taught to inoculate you against counteroffers from your current employer before you’ve received one. One industry training puts the doctrine in a single sentence: the deal is made long before a candidate formally signs.

Read that again.

The deal is made long before you sign.

Which means the deal is made before you think the negotiation has started. Which means by the time you sit down to “negotiate,” you’re not negotiating.

You’re confirming.

None of the people running this playbook are villains. Most recruiters are decent, most hiring managers are sincere, and most of them believe the rituals are just how hiring works. That’s what makes a ritual a ritual—the people performing it don’t experience it as a choice.

But you should.

Because every one of these rituals has the same objective. Make the calibrated number feel like weather. Something that happens to you. Something nobody decided.

Somebody decided.

Here are the four rituals I see most, what each one is actually doing, and the move that breaks it.

Ritual One: The Weather Report

The line: “This is just what the role pays.”

Sometimes it arrives as “the band for this level is X.” Sometimes it’s “we have to maintain internal equity.” Always delivered in the tone of a meteorologist. Nobody’s fault. Nothing to be done.

Bring an umbrella.

What it’s doing: Converting a decision into a fact of nature. Bands are not weather. Bands are policies—written by people, revised by people, and exceeded by people, constantly.

Every company that tells you the band is fixed has approved an above-band offer in recent memory. I know because I’ve been on the other side of the paper when they did.

The Weather Report works because arguing with weather feels insane. You can push back on a person. You can’t push back on the sky. So the company removes the person from the sentence and lets the sky say no.

The break: Never argue with the band. Change the question.

“I understand the band—and I’m not asking you to break it for no reason. It sounds like this is a unique scenario. Help me understand the exception process. Who approves above-band offers here, and what do they typically need to see?”

Every band has an exception path. Your job isn’t to win a debate about the band’s existence. It’s to find out who owns the exceptions and what evidence moves them—then supply it.

This is another reason why having internal advocates that you’ve worked with prior plays such an important role in compensation dynamics—and why influence is the gateway to breakout compensation structure.

And one more question, because the band conversation hides a bigger one: the fastest way to change what the role pays is to change what the role is. If the number is capped, the scope is the negotiation.

“What would this role need to own for it to sit a level higher?”

Ritual Two: The Ally Without Authority

The line: “Share your number with me so I can fight for you.”

Later in the process, the same person returns with: “I pushed hard, but the comp committee’s hands are tied.”

What it’s doing: This isn’t about whether recruiters are good people. Most are. It’s about what the role is designed to do—and the role is designed so that “no” never has an author.

Notice the architecture.

The person you talk to can’t say yes. The people who can say yes never talk to you. Your number travels up stripped of your reasoning, and the ceiling travels down stripped of its owner. When the answer disappoints you, there’s no one in the room to be disappointed at.

The committee is always absent. The hands are always tied. The tying is the point.

Sounds eerily family to the sales manager at your local car dealership running a circled payment figure by finance only to shatter your counter numbers.

And the opening move—share your number so I can fight for you—is the oldest extraction in the book. Since salary-history questions started getting banned, “expectations” became the new anchor.

Your ally isn’t collecting ammunition to fight for you. They’re collecting your ceiling to file it.

The break: Warmth toward the person. Questions about the system.

“I appreciate you advocating for me—genuinely. Since you’ll be carrying this forward, I’d rather arm you with the case than a number. Here’s the specific problem I solve and what it’s worth to the business. And so I understand the process: who actually approves the final structure?”

You give the messenger a story to carry, not a ceiling to cap. And you map the room where the decision actually lives—because that’s the room your narrative has to reach, with or without you in it.

Ritual Three: The Gift Wrap

The line: “We put together something special for you.” Or its cousins: “Leadership personally approved this.” “We really stretched here.”

What it’s doing: Turning an offer into a gift. And you know what you don’t do with a gift.

You don’t negotiate it. You say thank you.

This is the most elegant ritual of the four because it weaponizes your best quality—your decency—against your own family’s balance sheet.

The moment the offer becomes personal, a counter becomes ingratitude.

They handed you something wrapped, and now asking about the contents feels like tearing the paper in front of the person who wrapped it.

Here’s what fifteen years inside these deals lets me tell you—the bespoke offer is almost never bespoke. The number came off the same calibration as everyone else’s.

What was tailored for you was the presentation. “We stretched” is not a fact about the budget.

It’s a preemptive strike against your counter—if they already stretched, there’s nothing left to ask for, is there?

There’s usually plenty left.

The break: Accept the relationship. Decline the frame.

“I’m genuinely grateful for the care that went into this—and it’s exactly why I want to get the structure right. This is a multi-year commitment for both of us. Let’s make sure the package maps to the mandate.”

Gratitude and negotiation are not opposites.

Separating them is the skill. The people are the people; the paper is the paper. You can love the first and mark up the second—and the executives who can’t hold both at once are the ones the Gift Wrap was built for.

Ritual Four: The Friday Countdown

The line: “We’ll need your decision by Monday.”

Delivered, with uncanny consistency, late Friday afternoon.

What it’s doing: The company took three months to decide on you. Fifteen interviews. Panels, take-homes, backchannel calls you never knew about. Then it hands you the largest financial decision of your decade and gives you a weekend.

That asymmetry is not sloppy scheduling.

The clock is designed to think for you.

A hard deadline reads to your body as a closing door, and a closing door narrows everything—suddenly you’re not evaluating a decade of equity structure, you’re staring at a countdown. The offer stops being an opportunity to assess and becomes a possession about to be taken away.

That’s when smart people sign bad paper. And remember, no deal is better than a bad deal. We need to do better than that.

Now the part that should make you angry, or laugh, or both.

Researchers at INSEAD ran the exploding offer through behavioral experiments and found it doesn’t even work. Candidates accepted pressured offers at roughly the same rate as patient ones—and the ones who accepted under the gun punished the employer afterward with less commitment and less effort. The researchers called it the reciprocation curse.

So the deadline doesn’t capture more candidates. It just captures them worse. And companies keep doing it anyway—because the ritual was never about the match.

It’s about making sure the calibrated number gets signed before you can test the market, compare paper, or think. Haste once again equals risk.

The break: Test the clock. Calmly.

“Thank you—I’m excited about this, and a decision of this scale deserves a real evaluation. I’ll have my answer by Thursday.”

No apology. No permission sought. A statement, delivered warmly, followed by silence.

Here’s what happens next, in almost every case: nothing.

The deadline was theater, and theater evaporates when one actor declines the scene. In fifteen years I have watched countless deadlines dissolve under a single calm sentence—because by the time a company extends an offer, walking away from you costs them a restarted search, an embarrassed hiring manager, and a story they have to tell the board.

Your extra four days cost them nothing—though it could make a backup candidate waiting in the wings sweat a bit longer—and challenge how they keep them engaged while they really focus on you.

If the offer detonates (which I have never seen FWIW) because a serious executive took until Thursday?

You just received the cheapest possible preview of how that company treats people under pressure. Some tuition is worth paying before you enroll.

The Part That’s Up to You

Look back at the four breaks.

A question about the exception process. A story handed to a messenger. A thank-you that keeps its wallet closed. A calm sentence and four days.

Not one of them is aggressive. Not one requires you to become the shark you’re afraid these conversations will turn you into. That’s the misunderstanding that keeps executives compliant—the belief that the alternative to accepting the ritual is combat.

It isn’t. You don’t beat a ritual by fighting it.

You beat it by declining to perform your part.

The company wrote a script in which the band is weather, the recruiter is your ally, the offer is a gift, and Monday is a law of physics. You were cast in that script without auditioning. Every ritual depends on you reading your lines.

Put the script down.

The number was calibrated before you walked in. Whether it stays that way is the only part of this that was never predetermined.

That part is you.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

Last week I ended on a trap.

How do you know what you’re worth?

A few of you wrote in with variations on the same question: fine, but seriously—how do I know?

Here’s the harder answer.

You don’t.

And that is the point.

I Didn’t Know Mine Either

For most of my career, I could have answered that question in half a second.

I had a number. I had a rate. I knew what my time was worth because I’d done the math everyone does—what I made last year, divided by the hours, adjusted for ambition.

My earnings averaged around $300K a year. Solid. Respectable. Predictable.

Then I stopped pricing my time and started pricing what my work was worth to the person across from me.

My income more than tripled—past $1M a year—while I spent 50 to 70% less time with each client.

Read that again. Less time. More money. Higher expectations, more thrill, and more respect.

I didn’t get three times smarter that year. My résumé didn’t change. My track record didn’t change.

What changed was the question.

I stopped asking what am I worth and started asking what is this outcome worth—to this person, in this moment, with this much on the line.

Those are not the same question. The first one is self centered and the second one is market centered—a different answer in every room.

And once I saw that in my own business, I couldn’t unsee it in yours.

The Most Dangerous Career Advice Ever Given

Know your worth.

It’s on LinkedIn banners. Career coaches homepages. And on your well-meaning mentor’s lips.

And it has quietly cost executives more money than every lowball offer combined.

Because you did what the advice told you to do. You researched. You pulled the comp reports. You opened the Levels.fyi tab and cross-referenced the recruiter whispers. You triangulated a number that felt defensible.

And you walked into the room wearing that number like armor.

It wasn’t armor.

It was a ceiling. And you installed it yourself.

The moment you become certain of your worth, you’ve done the other side’s job for them. You’ve replaced their ceiling with your own—and yours is almost always lower, because yours was built from averages.

Averages of what?

Of everyone who negotiated poorly before you. The benchmark isn’t the market. The benchmark is the graveyard of accepted offers.

There’s a reason certainty feels so good in that moment, and it isn’t strategy. An open question about your own value is one of the most uncomfortable states a high performer can sit in. Your brain wants the question closed. A number—any number—ends the discomfort.

Certainty is anesthesia.

It doesn’t make you more valuable. It just makes not knowing stop hurting.

Worth Is Not a Fact. It’s an Event.

A price tag lives on a commodity. A gallon of milk. A barrel of oil. A rideshare across town.

Commodities have price tags because they’re interchangeable. One is as good as another, so the market clears at one number.

You are not interchangeable. Which means you don’t have a price.

You have a range. And the range is a function of the room, not the résumé.

Consider the same hour of the same person’s time. One buyer pays $100 for it. Another pays $50,000.

Neither of them is wrong.

They’re not disagreeing about the person’s worth. They’re each answering a completely different question: what is this worth to me, given my problem, my stakes, and my alternatives?

The $100 buyer has a small problem. The $50,000 buyer has a $50 million problem—and a genuine belief that this hour moves it.

This is what executives miss when they anchor to “market rate.”

Nobody pays you what you’re worth. They pay you a share of the value they believe you’ll create—discounted by their doubt that you’ll create it.

Which means your compensation is a function of three things, and only one of them is you:

• The size of their problem.

• The depth of their belief that you’re the one who solves it.

• And the moment—what it costs them, right now, to keep living without you.

Your job title doesn’t make the list.

The Room Gets Smaller as You Climb

I recognize that this is uncomfortable. That’s how you know you’re on the right track.

Discomfort is where growth happens. You either seek it or become complacent.

The higher you rise, the fewer rooms exist where your full value can be recognized.

There are ten thousand companies that can value a director. A few hundred that can value you at the level you’ve actually reached.

Maybe a dozen where your specific pattern of experience is worth the top of your range—where their problem and your history collide so precisely that the number stops obeying gravity.

Most executives never find those rooms. Not because the rooms don’t exist.

Because they stopped looking the moment they became certain of their number. Certainty ends the search. Why keep discovering the market when you already “know your worth”?

This is why your narrative has to sharpen as you climb, not soften.

At the top of the market, you’re no longer competing on competence—everyone in the room is competent. You’re competing on precision. The buyer who values you highest needs to recognize their exact problem in your exact story, fast.

Vague seniority gets benchmark offers.

Precise relevance breaks the band.

What Certainty Costs

A prospective client came to me earlier this year already certain—and boasting about their negotiation acumen from a top investment banking program.

He’d done everything right. Pulled the data. Talked to peers. Landed on his number—call it $1.3M—and defended it beautifully through the process. The offer came in at $1.3M almost to the dollar.

He felt like he’d won. We didn’t end up working together.

But the problem was that the approved range went meaningfully higher.

The board had already blessed a number over double what he asked for. I knew this because the company hired two other executives meaningfully higher just a few weeks earlier.

One was a client of mine with 10 years less experience in a peer-adjacent title. His deal landed 90% higher per year and nearly 8 figures more over a standard 4-year period. The other was reporting into the same team, not a client FWIW, but a stronger negotiator.

She brought in 30% more.

The budget existed. The willingness existed.

The only thing standing between him and that money was his own certainty.

And he didn’t even ask.

Nobody lowballed him. Nobody played games.

He named a number, they met it, everyone shook hands—and a fortune stayed in a spreadsheet he never knew existed.

This is the quiet violence of “know your worth.” The companies don’t even have to negotiate you down.

You arrive pre-negotiated even when they already had the upper hand.

Compare that to the clients who come in curious instead of certain. Who treat the process as discovery. Who ask more than they declare. Those are the engagements where we’re not fighting for 10% over the band—we’re finding out the band was never the real ceiling in the first place.

The certain executive defends a number.

The curious executive discovers a market.

I want to be clear that you don’t always need to pull every last ounce out of a deal. If you’ve named a number that works for you and everyone aligns on it, I’m not suggesting that you’ve made some terminal error or should be reprimanded.

I’m simply suggesting that the ceiling is likely higher than you think.

Trade Declaration for Discovery

So what can you tactically change about you don’t know what you’re worth?

You stop trying to answer the question and start running the discovery.

Watch the difference.

Script A—the certain executive:

“Based on my research, market rate for this role is $580–620K in total compensation. That’s my expectation.”

Sounds strong. Feels strong. And it just handed them your ceiling, wrapped in a bow, before you learned a single thing about what this role is worth to them.

Script B—the curious executive:

“Before we get to numbers—help me understand what this role needs to accomplish. What does the business look like eighteen months from now if this hire goes exactly right? And what does it cost us if it goes wrong?”

Script B isn’t a deflection. It’s the actual work.

Because their answers tell you what room you’re standing in. If the honest answer is “this role protects $200M in revenue,” you are not in a $600K conversation anymore—no matter what the benchmark says. And now they’ve said it, out loud, in their own words. You didn’t argue your value.

They discovered it.

That’s the whole mechanic. When you declare your worth, you’re selling. When they articulate what solving their problem is worth, the number that follows belongs to a different universe than the one in the comp report.

A few rules for the practice:

• Never name the number that ends the search. Every figure you state with certainty becomes the top of your range. Silence and questions keep the range open.
  

• Anchor to their outcome, not your history. Your last comp is what someone else’s problem was worth. It says nothing about this one.
  

• Treat every process as market research. Even the deals you walk away from are data. Each conversation updates your model of what’s possible—which is the only way the model ever moves up.

And the rule underneath all of them, the one I left you with last week:

• Never be so sure of your worth that you wouldn’t accept more.

You’re Not Supposed to Know

Here’s where this lands.

You don’t know what you’re worth sounds like bad news. It isn’t. It’s the best news in your career.

Because if worth were a fact—fixed, knowable, printed on a tag—then the benchmark would be the truth and the band would be the law and the best you could ever do is arrive at your number.

But worth isn’t a fact. It’s an event.

It happens in a room, between a specific problem and a specific person, at a specific moment. Which means it can happen bigger. In a better room. With a buyer whose problem is the exact shape of your story.

The executives who capture the top of the market are not the ones most certain of their value.

They’re the ones most curious about it.

Stop trying to know your worth.

Start discovering it.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

I noticed a YouTube comment on my appearance on Lenny’s podcast.

“You would think Jacob was this pushy shark to be a comp negotiator. But he’s so measured and balanced—a modern-life Dale Carnegie.”

I read it twice. Then a third time, and the structure of the sentence kept catching my eye.

You would think.

The “but” was doing all the work, as it often does.

The word “negotiator” had locked in the mindset before I could.

I have spent my entire career being the exact opposite of a shark—someone on my team once said, “Jacob, you have to realize, you swim with sharks everyday, but you know you’re a dolphin—right?”

It sort of felt like a put-down, but maybe that’s part of the problem.

We buy into the myth of the apex predator, forgetting a basic rule of the ocean: grown dolphins don’t get eaten by sharks. They out-maneuver them.

My work has always run on influence, not aggression—on the kind of presence that makes the other side want to keep talking to you long after the deal closes.

Some of that is my temperament.

Some of it is older than that—a childhood where playing small was how you stayed safe, and reading a room was how you found any sense of control at all.

But the word negotiation arrives first. And negotiation always arrives heavy.

That YouTube comment was the kindest version of a problem I have watched eat my business from the inside for years.

People almost always call me after the offer lands.

We do great work.

But it’s a fraction of what’s possible.

I am the strategist you bring into the rooms that bend a career—for the narrative, for the influence, for the moments that decide what the next decade looks like.

The real work—the narrative, the influence, the architecture—starts weeks before anyone mentions compensation.

The problem is the word “negotiation.”

But the word isn’t only doing that to me. It’s doing the same thing to you.

The moment you decide you need to negotiate, you have quietly agreed to walk in as an adversary. A problem to be managed. Someone on the other side of a table to deal with.

You didn’t ask for that framing. You didn’t choose it.

It arrived with the word, and everything the word has come to mean.

And you have been paying for it your entire career.

It Isn’t You. It’s the Word.

You feel this too.

You felt it the last time someone said, “Let’s talk about negotiating your comp,” and a small door closed in your chest.

You felt it when a recruiter said, “We’re entering the negotiation phase,” and something in your body went still.

You felt it when you sat down to prepare for the conversation, opened a fresh document, typed Salary Negotiation Prep at the top, and immediately wanted to be somewhere else.

That wasn’t weakness.

That was your nervous system reading the word.

The same body that runs a $400M P&L. The same body that chairs a board meeting on three hours of sleep.

That body hits the word negotiation and goes quiet.

You’ve blamed yourself for this for years. You’ve read the books. Practiced the scripts. Wondered why this conversation always feels different.

The problem isn’t you.

It’s the word.

The word doesn’t arrive empty. It arrives carrying every awkward money conversation you’ve ever had. Every parent who flinched when bills came. Every performance review that felt smaller than your contribution.

You can put any qualifier you want in front of it.

Principled negotiation.

Collaborative negotiation.

Win-win negotiation.

The qualifier sits in the conscious mind.

The word sits in the body.

By the time your mind reads collaborative, your body has already decided what kind of conversation this is.

Half a Century of Fixing a Word From Inside the Word

I owe an enormous debt to the people who built this category.

Herb Cohen taught us to care—but not too much. Roger Fisher and William Ury showed us that positions create conflict while interests create value. Chris Voss taught tactical empathy. William Ury kept pushing the conversation toward possibility instead of confrontation.

Each fundamentally improved how negotiation is practiced.

Each kept the word.

And that’s the part I can’t stop thinking about.

What I’m beginning to notice is that the obstacle may arrive before any philosophy has a chance to help. Before tactical empathy. Before principled negotiation. Before collaborative negotiation.

The word itself may already have told your nervous system what kind of conversation this is.

There is one exception worth naming.

Robert Cialdini didn’t write Persuasive Negotiation. He didn’t write Collaborative Negotiation. He wrote Influence.

That choice matters.

If Cohen taught me how to hold a room, Cialdini taught me why the room moves. Reciprocity. Commitment. Social proof. Authority. Liking. Scarcity. The mechanics underneath human decision-making.

And notice what he called the discipline.

Influence.

Not negotiation.

Just influence.

The most influential scientist in this field quietly sidestepped the word altogether.

I don’t lean heaviest on Cialdini, though.

I lean on Aristotle.

More than 2,300 years ago, he described persuasion with remarkable clarity: ethos, pathos, and logos. Credibility. Emotion. Logic.

Executives are trained relentlessly on ethos. Build credibility. Earn the title. Accumulate the track record.

They’re trained just as hard on logos. Build the model. Make the business case. Show the numbers.

But almost no one teaches pathos.

And pathos is where the room actually moves.

Influence is how you reach it.

Negotiation is simply how you know you got there.

The number. The terms. The outcome.

That’s the receipt.

Most executives try to negotiate before they’ve influenced. They try to influence without understanding emotion. Then they wonder why the conversation feels narrow. Feels extractive even.

The problem with negotiation was never the framing.

It may have been the word itself.

What Changes the Moment You Stop

I am working this out in real time.

From the last few months of client work, and the book I’m building underneath it, and the way I’ve watched the frame keep sharpening as I stop reaching for the word that got me here.

Here is where my head is right now.

The book I am writing is called Predetermined. And what it is really about—the thesis underneath every page—is this:

Who decides what you’re worth. And how to make sure it’s you.

Notice what is not in that sentence.

Negotiation.

Because the moment you remove the word negotiation, what creates the outcome comes into focus.

Not the tactics at the table.

Everything that happens before the table exists.

It comes from your mindset—the internal position from which you enter every conversation about your worth.

It comes from your pregame—the narrative you build in your network, the language you use about your own trajectory, the words you refuse to let other people put on you.

It comes from your influence—the curiosity to discover what is possible before assuming what is offered. The willingness to understand the other side’s motivations well enough that the deal design gets obvious.

It comes from the discipline of caring, but not too much—the willingness to walk from the wrong deal so you’re free to recognize the right one.

It comes from ongoing improvement—the habit of getting a little clearer, a little more precise, a little more yourself, across an entire career. Not one negotiation at a time. Every conversation.

And then—only at the end—it comes from the tactics. The scripts, the counters, the phrasing that cements the deal.

Most executives try to start at the last step.

They open the deck at tactics. They chat with AI about “how to counter a lowball offer” the morning the offer lands. They call someone like me at the eleventh hour because they think the tactics are the game.

The tactics are the receipt. The game is everything before the receipt.

The Word You Use Is the World You Walk Into

The next time the thought forms—

• I need to negotiate my raise.

• I need to negotiate my offer.

• I need to negotiate my exit.

Try a different sentence.

I am going to advocate for my worth.

Then notice what your body does.

Notice how your shoulders move. Notice how your jaw moves. Notice whether you feel the door close in your chest, or whether something opens.

That’s the difference.

If you call it advocating for your worth, you walk in as the person you already are.

You don’t need scripts. You need clarity.

You don’t need tactics. You need to know what you are worth, be willing to say it without flinching, and let the silence after it belong to you.

The reframe is the practice.

You are not negotiating. You never were.

You are advocating for your worth.

But that distinction raises a different question.

How do you know what you’re worth?

Here’s the trap.

The moment you’re certain, you’ve anchored yourself. You’ve replaced their ceiling with your own.

Never be so sure of your worth that you wouldn’t accept more.

Advocacy isn’t a declaration.

It’s the discipline of staying curious about what is possible.

More on that next week.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

I was staring at an encrypted Signal thread a few days ago, facilitating a counter-scenario between an elite AI researcher and a leadership team I’m not at liberty to name.

The numbers already on the screen were deep into the eight figures—the kind of package that reshapes generational wealth. We had doubled it in two hours of consultation.

My hand hovered over the keyboard.

The muscle memory—fifteen years, more than a billion dollars in lifted career negotiations—told me to run a delay. A pause.

Let the other side sit with their own offer and feel its weight.

In the last few weeks alone, simple holds have moved millions across my client base. It’s one of the most reliable tools I own. Low risk. High yield. Works almost everywhere.

Almost.

At the highest altitudes, there’s no time for games.

The people on the other end of that thread aren’t waiting—if talent hesitates, for any reason, they move to the next. Artificial scarcity doesn’t always read as leverage.

Sometimes it reads as doubt.

So instead of stretching the timeline, we sent a direct, high anchor. The number made my client visibly uncomfortable.

That discomfort was how I knew we’d gotten it right.

We won another eight figures in just a few hours.

I gotta be honest, I’ve learned more in the last three months than in the previous several years combined.

Since my appearance on Lenny’s podcast, I’ve been dropped into the cockpit of a hyperdrive talent market—helping clients secure more than $50M in annualized compensation increases across quant machine learning, product leadership, and specialized AI roles at OpenAI, Anthropic, Google, Meta, Cerebras, Vercel, and the companies racing to pull people away from them.

It’s been exhilarating. It’s also been humbling.

The playbooks I spent a decade perfecting weren’t fully built for this exact moment, and I’ve had to tear parts of my own methodology—and contracts—down and rebuild them in real time.

A good problem to have, so I hear.

It used to be that a typical C-suite or Fortune 500 package was a chess match—four to twelve weeks of careful, sequenced planning. And many still are.

However, now I’ve negotiated opposite over a dozen billionaires with the frequency of these deals picking up more momentum.

I know what power looks like across a table.

But the race for specialized talent right now is something else entirely.

Frothier. Faster. Far more delicate. Subtle mistakes evaporate millions, and sometimes tens of millions.

More and more often, I’m noticing that when timing and opportunity collide, the window to move millions doesn’t span weeks.

It spans a few concentrated hours.

One recent pregame call lifted a client’s pay by $1.8M a year. For another, a two-session sprint unlocked an eight-figure sign-on bonus. I find myself challenged with updating my own pricing models in real time.

The fundamentals of leverage and human psychology haven’t changed.

But the margin of execution has gone razor-thin—and at this level, there’s less patience for games.

Here’s why this matters to you even if you’ll never see eight figures on a screen.

The person negotiating ten thousand more, the one chasing a hundred, the one staring down a million-dollar package, and the researcher fielding a generational offer are not playing the same game.

They’re playing several nuanced games that happen to share a name.

The lever that wins at one altitude is the exact move that loses at the next.

I’ve watched how a tactic that adds $40K at one level would evaporate $4M at another.

Most advice flattens all of this into “negotiation.” And it’s all about getting to yes.

That’s the mistake.

The fundamentals hold the whole way up—but what you actually do with them changes shape at every level.

Today’s article maps that climb—what changes as the number rises into the stratosphere, and the few truths that stay anchored to the floor no matter how high you go.

Winning Tens of Thousands: The Win Is in the Ask

At this altitude, you’re usually working with a recruiter and a range.

There’s a band the role was approved for.

The recruiter knows the top of what they can say yes to. The hiring manager knows more—but won’t reach for it unless you’re truly special or have prior relationships.

Either way, you don’t know what’s possible. And that’s our advantage.

The number they open with isn’t an assessment of your worth—it’s an anchor calibrated to what you, or others like you, are used to accepting. Usually nudged up just enough to feel like a win, while sitting well under what’s actually available.

Your old comp follows you like a ghost—especially if you name it, or let them pressure you into sharing your expectations.

I call it the Zombie Number.

It doesn’t matter that the role is bigger, the market is hotter, the title is heavier. The first offer is reverse-engineered from your history, not your value.

If you let it.

Believe it or not, at this level, the single highest-leverage move is simply asking for more.

Out loud.

It can be soft — “What’s the chance there’s more room here?”

Or it can be a specific number anchored higher.

Either can work.

But whichever you choose, the move that follows is identical, and it’s the one part most people skip.

You say it. Then you stop talking.

Not a tactic. Not a sequence. The ask, and the silence after it.

Because the constraint here isn’t strategic—it’s permission.

The recruiter has room. The band has a top. The real negotiation is happening inside your own head, not across the table—and most people lose it before the recruiter says a word.

They talk themselves down to a number they’ve decided is reasonable, then negotiate from there. They fold to manufactured urgency and borrowed authority.

This mindset trap exists at every altitude. But it’s most punishing here—because this is where you learn whether you can do it at all.

If you can’t make the small ask, you never earn the chance to make the big one.

You lose thousands before the conversation starts. And it compounds—every future offer anchors off this one, so a small surrender early becomes millions left on the table over a career.

State the bigger number. Then stop talking.

It can really be that simple.

It’s uncomfortable. Do it anyway.

That last part—the stopping—is the constant. The thing that never changes no matter how high the number climbs. The silence after you name your number belongs to you.

Don’t fill it.

At ten thousand or ten million, the person who speaks first to break the quiet is the person who gives ground.

But notice what does change.

At this altitude, the ask is almost the whole game.

One rung up, it’s barely the entry fee—it’s expected. Walk into a million-dollar negotiation with nothing but a confident number and you’ll get a polite, well-rehearsed no. Because at that level, asking isn’t leverage.

Having somewhere else to go is.

Which is where the game changes shape entirely.

Hundreds of Thousands to Millions: The Craft of Leverage

This is the altitude everyone pictures when they hear the word negotiation.

The competing offers. The strategic silence. The bidding war.

This is where the movies live—and for once, the movies are mostly right.

At this level, the ask is table stakes. Everyone asks.

What separates outcomes is often whether you have somewhere else to go, and whether you can hold your nerve while the leverage does its work.

This is also the one altitude I’ve already taken apart in full.

A few weeks ago I wrote You Don’t Win a Bidding War. You Engineer One. The entire mechanics of manufacturing optionality, owning the timeline, and reshaping the role itself. If you’re negotiating in this band right now, read that one next.

It’s the field manual.

So I won’t repeat it. I’ll name the one thing that matters most at this altitude, because it’s the hinge the whole band turns on:

Leverage here is almost never the offer in front of you. It’s the offer beside it or the perceived other options.

A single number, however confident, is a wish. Two numbers become a market.

The entire craft at this level is the patient, ethical engineering of a second, third, even fourth option.

And sometimes the most powerful option is none at all.

The willingness to walk—the understanding that no deal beats a bad deal—is its own form of leverage. Especially when you’re playing a long career, not a single hand. The person who can stand up from the table is the person who never has to.

So when you finally speak, you’re not asking.

You’re choosing.

And everyone in the room can feel the difference.

What almost nobody understands about that field of options is that it isn’t built in the room.

It’s built over months and years.

The people who win at this altitude learned something at the floor—that the game starts long before the offer does. They engineer their optionality with precision, far in advance, through the most underrated lever in all of compensation: narrative.

• How you talk about your work to your network.

• The language of optionality you use without ever sounding like you’re selling.

• Which pursuits you decline—and how you let people know you declined them. “I’ve been weighing a couple of CEO conversations, but I’m leaning toward operator roles like X right now, because…”

That one sentence, said to the right person, does more than any counter-offer.

It tells the market you’re scarce, you’re chosen, and you’re not waiting.

Turning down the wrong recruiter, communicated correctly, creates more leverage than accepting ten of them.

By the time you’re at the table, the bidding war isn’t something you start.

It’s something you’ve already built.

The silence still matters—it’s the constant, all the way up. But here it does different work. At tens of thousands, silence is courage: you name your number and resist the urge to talk yourself back down. Here, silence is leverage: you let a live competing offer sit on the table and say nothing, because the quiet is doing the math for them.

Just two weeks ago, silence paired with a patient value reframe turned a “best and final” of $1.1M a year into $2.5M.

It took thirteen days of holding. At this altitude, you have them.

To be fair, this strategy made my client very uncomfortable. Perhaps needless to say, I have their full trust now.

Same tool. Heavier load.

And then the climb takes one more turn—the one almost nobody sees coming.

Because everything up to a few million runs on the same logic: more leverage, more options, more pressure, better outcome.

Asking. Engineering. Holding.

At the very top, that logic inverts. Here’s how.

Tens of Millions: Where the Best Negotiators Stop Negotiating

At the very top, all of what I’ve shared still holds. The fundamentals don’t just survive the altitude—they get louder. Influence, persuasion, rhetoric, information, timing, power: every one of them matters more, not less.

And yet the logic inverts.

Because now you’re not negotiating with a recruiter working a band, or a hiring manager protecting a number. You’re negotiating with masters of the craft—billionaires, and the teams they hand-picked to carry their vision.

People who have seen every move you know, run most of them themselves, and read maneuvering the way a chess master reads a beginner’s opening.

Information asymmetry in its peak form.

I’ve sat fingerprintless across from Musk, Altman, Amodei, Nadella, and others.

I know what that kind of power feels like in a room.

And here’s what it taught me:

At this altitude, a tactic isn’t leverage.

It’s a tell.

The delay, the engineered competing offer, the strategic pause—the moves that print money one rung down—rarely read as sophistication up here.

They read as doubt.

I say rarely, not never, on purpose.

A delay can still be the right move at this altitude—but only when you know precisely who’s across from you, what pressure they’re actually under, and how much rope the moment will bear.

That read takes years to develop, and the cost of getting it wrong is a generational outcome. So the discipline isn’t “never pause.” It’s knowing, in your bones, the handful of moments that can absorb one—and treating every other moment as one that can’t.

The moment you start maneuvering, you’ve told the most perceptive people in the world that you’re not actually one of the few who can do this thing.

You’re someone performing scarcity instead of possessing it.

Because the real lever at the top—the only one that matters—is this: are you really one of the few people on earth who can do this?

If the answer is yes, you don’t need to manufacture anything.

The value is the leverage. The urgency is the leverage. Their fear of you walking to a competitor—that’s the leverage.

Your job isn’t to play games. It’s to make the value undeniable and then get out of its way.

Which is why, at this altitude, you often must anchor high. Very high.

One rung down, an anchor that aggressive would be reckless—you’d anchor high and then engineer your way toward the number through options and timing. Up here, the engineering is the doubt. Conviction is the signal.

A high, clean number says: I know exactly what I’m worth, and I’m not nervous about saying it.

A hedge says the opposite, and they hear it instantly.

In a recent deal, we simply mentioned the numbers would need to be near nine figures to even be interesting—to even be worth the trouble.

Yes, you read that right. Nine.

Then we stopped talking. Because at this altitude, silence isn’t a tactic either.

It’s just what certainty sounds like.

It produced the largest single-year and multi-year lift of my career.

Now—a fair confession about that ceiling. I’ve orchestrated more than a dozen $10M+ deals in the last few months, and the average lift has been over 100% of the starting offer. More than double the typical lift at lower tiers.

It makes me question where the real cap even is.

But I’ll tell you what I tell my clients: when you’re already winning, you don’t need to win more just because you can.

So we’ll theorize about the highest-leverage play, then deliver a winning strategy one notch below it. I’m not interested in gambling a client’s reputation to find the true ceiling.

The discipline to stop is its own form of mastery. Or at least that’s what I tell myself.

And then there’s the thing nobody talks about—because by definition, you mostly can’t.

These negotiations don’t happen over email and a shared offer letter.

They happen on Signal. Encrypted. No recordings.

Usually verbal, often deliberately undocumented until the structure is locked. The people at this level are intensely private, highly structured, and legally careful—every word weighed, counsel never far from the conversation, confidentiality a default—not a request.

For years I read that caution as friction. And at lesser levels, it is. But here, I was wrong.

The discretion is the altitude.

When a negotiation runs through encrypted channels, with lawyers on standby and nothing committed to paper until both sides are certain—that environment punishes games even harder. There’s no room for a clever email or a manufactured deadline.

Everything is deliberate. Everything is serious.

And against that level of seriousness, a tactic doesn’t just fail to land.

It marks you as someone who doesn’t belong in the room.

So the work changes completely.

The hours are concentrated and absolute. When the window opens, you move—on their timeline, in their channel, at their level of precision. You’re not running a four-week chess match. You’re delivering one calibrated, high-conviction position into a thread that could close in an afternoon.

Strategized and often executed in under three hours.

And here’s the part that keeps me up at night, in the best way.

Because these deals live on encrypted threads, under NDA, in rooms with no recordings—almost no one ever sees them.

The candidate sees their own deal. The company sees their side of their own deals. But the pattern across all of them—the live, real-time data on what these packages actually look like, what moves them, where the ceilings are bending this month—sits with the small handful of people sitting in seat after seat after seat.

Right now, I’m not sure anyone has a clearer view of that data than I do.

That’s not a boast. It’s a quirk of the vantage point.

I happen to be in more of these rooms, more often, than almost anyone—and the lessons compound with every thread. The playbook for this moment doesn’t exist in a book. It’s being written in real time, deal by deal, on threads that disappear.

I’m just one of the few people watching it happen.

What Never Changes

So let me bring this all the way back to you, wherever you’re standing on the climb.

The truth that holds at ten thousand and ten million and every rung between:

Every stage is negotiable.

The number in front of you—whatever altitude it’s at—is not fixed. It was never fixed.

It feels predetermined, handed down, final. It isn’t.

The recruiter has room. The band has a top—or you’ll keep your level and get comped in the band above, which happens all the time.

The “best and final” has thirteen more days in it. The nine-figure ceiling bends. At every level I’ve ever worked, the first number was a starting point dressed up as a conclusion.

That part never changes.

What changes is the margin for error.

At tens of thousands, you can fumble the words, hesitate, ask clumsily—and still win, because the act of asking at all puts you ahead of nearly everyone. The floor is forgiving. That’s why it’s the place to learn.

Get reps. Build the muscle. Fail small.

By the time you’re playing for a million, the margin’s thinner.

A misread on timing, a competing offer you couldn’t back up, silence held a beat too long or not long enough—those cost real money now.

One thing scales the other direction, though.

The higher you climb, the more deceit costs you. A bluff that gets shrugged off at the floor becomes a permanent mark at the top—these rooms are small, the players talk, and a reputation for games follows you into every deal that comes after.

I’ve built a fifteen-year practice on the opposite: get the lawsuit number without any mess of lawsuit.

Power through influence—not through threat of aggression.

Push to the edge of what’s real, and never one inch past it. Leverage is what you’re actually worth, made undeniable—not a lie you can hold your face straight through.

This isn’t extraction. The best deals aren’t won by manipulation; they’re built through value, collaboration, and influence that leaves everyone better than it found them.

At the top, an extractive mindset doesn’t just cost you the deal—it blacklists you from the room forever.

And at the top, the margin for error vanishes.

One hedge, one tactical misstep, one game run against people who invented the game—and a generational outcome evaporates in an afternoon. The moves that felt safe at the floor become the moves that kill the deal.

This is the part almost no one understands, and the part I’ve spent fifteen years learning in real time: the higher you climb, the more is possible—and the less room you have to get it wrong.

That’s not a reason to stay on the floor. It’s a reason to respect the altitude you’re at, and to know — with precision — which moves belong to it.

It’s why I do this work. Not because the numbers are big, though they are. Because the cost of a small mistake gets catastrophic at the top, and the discipline to know exactly how hard to push — and exactly when to stop — is the whole game. It’s the difference between leaving a fortune on the table and reshaping a life.

Most people will spend a career assuming their number was decided before they walked in.

It wasn’t.

It never was.

Now go find out what’s actually possible.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

I named this newsletter over five years ago on a Sunday night.

It was a riff on Sex and the City—not that everyone catches it.

For reasons I need not explain, I’ve seen the HBO series 4 or 5 times over. Maybe more. As a man, I’m not embarrassed by that, I just caught myself thinking.

And when I decided that I was no longer interested in being perceived as employable in corporate America, I decided to start bitching about what I’d seen.

Sorta like Carrie Bradshaw.

Simply calling the plays like I saw them unfold, because it sometimes seems like people are unwilling or afraid to talk about the bs we encounter publicly during our careers. Probably for fear of retribution.

We’re long past that now.

Execs and the City was born.

Clever enough, and it made people smile when they said it out loud.

I’ve kept it for years because it seems to work, and because the name of the thing rarely feels urgent when the thing itself is already making an impact.

You don’t stop to repaint the door when people are finally walking through it and sharing it.

But as the writing and strategies evolved, so has the vision.

Welcome to Predetermined.

The Gap I Felt

For over a year, every article in this newsletter has circled a single question.

You’ve felt it even when I didn’t say it outright.

• Was your last offer calibrated before you ever saw it?

• Was the salary band a law of physics—or just a story someone repeated until everyone believed it? A habit, not a steadfast rule.

• Was the ceiling you were told about real, or inherited?

The question underneath my mission has always been the same.

What is predetermined in your life?

Or do we too often cap our own lives by thinking we’re limited by a predetermined outcome?

At its most fundamental level—isn't that what every negotiation actually is? A refusal to accept the predetermined?

And all the while, the masthead at the top of the newsletter said something about an early 2000’s TV show.

Meh.

Side note, comment on whether you think I’m Carrie, Charlotte, Miranda, or Samantha. And for the sake of ego, I’ll take Aidan or Mr. Big — but if you say Berger or Trey, you’re disowned.

Our work has been pointing in one direction. But the newsletter’s name has been pointing to another.

You can run that way for a long time, perhaps into perpetuity, but you shouldn’t run that way forever if you plan to continue to impact more people with your biggest life lessons.

It’s time I bite the bullet. Thank you for understanding.

The Rename Isn’t Branding. It’s Alignment.

So as of today, execsandthecity.com is predetermined.com.

Still me—and vetted guest publishers occasionally.

What changes is that the address bar now asks the question instead of describing the crowd. And that provides clarity on our direction.

Type it in.

Every time you do, you’re asking exactly what the work has been asking you to ask. That’s the whole point. The name and the thesis finally live at the same address.

And it organizes the vision for the next several years.

I’ve said before that the practice stays small with ThinkWarwick Global, and the ideas go wide with Predetermined. The representation work serves a few dozen high profile deals a year where the stakes are measured in millions—and tens of millions more recently.

The ideas—the writing, the frameworks, the question—belong to everyone, at every altitude.

Predetermined is the name for our movement.

Just because it’s always been done a certain way doesn’t make it true.

Be the one who proves it isn’t.

A Quick, Boring, Important Note

Nothing you rely on disappears.

Every old link still works—bookmarks, the pieces you’ve shared, the URLs buried in your sent folder. They forward automatically. Your subscription, free or paid, carries over untouched. The full archive is intact. You don’t have to do anything.

If you catch a bug, please let me know so I can ask AI how to fix it.

If you’ve recommended this newsletter to someone using the old name, it’ll still find them. And you get bragging rights—you knew it back when. The Execs and the City days.

So trendy. So hip. You first mover you.

Now—the part I’m most excited about.

What’s Next

Here’s what Predetermined clears the runway for.

More analog. More in person.

There’s something the inbox can’t do. So I’m hosting more workshops on the road, more live sessions, more cities—small rooms where we work the actual conversations you’re walking into—your board presentation, your comp negotiation, your exit—in real time, out loud, with other people who operate at your level.

The first of these is already on the calendar in July.

More dates are coming, and subscribers here will always hear about them first.

The monthly AMA becomes a fixture.

I run a live open session for paid subscribers—office hours, no agenda, no slides—bring whatever’s on your mind.

I send an email just to you the first week of every month with a new Zoom link.

Whether you’re sitting on an offer at 11pm or just trying to think through your next move, that’s what it’s for. I’ll keep the format simple and I’ll keep showing up.

Consistency is the entire value—so I’m treating it that way.

More of the work, shown openly.

A lot of you are here because you’re building something too—a practice, a career, a business—and you’ve told me that watching how I build mine is part of why you stay.

I’m leaning into that, not away from it.

That means more of the real mechanics. The deals I’m learning from at this new altitude. The pricing calls and why I made them. The services I walked away from. The misses, not just the wins. The tension between wanting to serve more people and knowing the work gets better when I serve fewer.

It also means the bigger swings are still coming.

Guest appearances on other people’s stages.

A podcast tour.

Then our own podcast.

Then the book.

And a portion of everything this body of work produces goes to the Cody Dieruf Foundation and the Cystic Fibrosis Foundation and Big Brothers Big Sisters.

That’s the version of predetermined I care about most, and we’re baking it directly into our founding documents and structure.

What You’ve Taught Me

I don’t say this enough.

You’re the reason any of this exists—but it’s more than that. You’ve taught me what’s worth writing about.

Every reply that told me I’d named something you’d felt for years but couldn’t say. Every note from someone who walked into a negotiation different than they walked out of the last one. Every story you’ve trusted me with—the offer you turned down, the title you stopped defending, the room you finally stood up in.

All the times I heard, “Jacob, your voice has been in my head this whole time and it’s changed the way I value myself and others.”

That’s where the ideas come from.

Not from me, alone at a keyboard. Though, I’ll admit, it used to be like that.

Rather, my best ideas all come from you, telling me what actually matters when the stakes are real.

You’ve made the work sharper than I could have on my own. You’ve kept me honest. And every time you forwarded a piece to someone who needed it, or quietly became a paid subscriber because you wanted to bet on the work, you didn’t just support me—you widened the room.

Thank you. For reading. For sharing. For teaching me what’s important.

The newsletter grew up. It needed a name that told the truth about what it’s been trying to say all along.

It’s not Execs and the City anymore.

It’s Predetermined.

And the only thing that question has ever asked of you is that you refuse to assume the answer.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

Two weeks ago I led a negotiation and influence workshop for a room full of senior leaders at the PTTOW Summit, held at the Conrad in Orlando.

My co-host Dan Robbins kicked off the session with one simple question—a question I’d invite you to answer for yourself right now.

Who has an important outcome you need support on in the next thirty days?

Every hand went up.

Keep it up if you have a repeatable way to influence that outcome in your favor—every time.

Almost every hand dropped.

That gap—between the outcomes every senior leader is responsible for closing and a repeatable way to close them consistently—is where influence stops being optional and becomes the dominant trait for success at the top.

Nobody gets in this room by accident.

And if you’re reading this publication, you’re likely running brands, building companies, and sitting at the top of your function.

You know how to do the work. The functional work.

But what gets you in the room and what keeps you there are two different challenges. This publication exists to make sure you have the skills and systems for the part that happens before your work ever gets evaluated.

The game changed and nobody told you

The corporate climb rewards being good at your job. Competence. Logic. A track record you can point to.

That’s what gets you in the room.

Aristotle would call this mastering Ethos and Logos.

Then—somewhere around VP—the game quietly changes.

The outcomes stop depending on whether you’re right and start depending on whether the right people were already on your side before the conversation began.

Network. Presence. Emotion.

Now the third leg of rhetorical control is the one that matters—Pathos. And the Carnegies and Cialdinis of the world have piled on decades of research showing exactly how it gets built: shared identity, likeability, reciprocity, trust, etc.

Nobody hands you that memo. It’s just expected.

So most leaders keep playing the only game they were ever rewarded for—be excellent, be prepared, let the work speak.

And the work does speak. It just doesn’t decide anything.

The people who stall out a level below where they should be are rarely the least capable in the building. They’re the ones still trying to win on merit in a game that stopped being scored that way years ago.

This has always bothered me.

And it probably bothers you too—though if you’re like the senior leaders in that room at PTTOW, you’re nodding along right now.

You negotiate for yourself five, maybe ten times in your entire career.

The organization across the table does it thousands of times a day.

You are an amateur walking into a room of professionals—and nobody warned you about that either.

So you show up the day of the conversation, ready to make your case, and you discover the case was mostly decided before you opened your mouth. Most leaders feel that and conclude it’s just how these things go.

Predetermined.

It isn’t. They just arrived three years too late.

Because influence doesn’t start when you sit down at the table.

It started three years ago.

I once represented a VP of Communications who moved from a major tech company to a Fortune 50 in the middle of total chaos. Our outcome?

Moving from $600K to $1.4M annually—with an additional $800K signing bonus to boot.

She didn’t negotiate harder than anyone else. She’d spent years building shared identity and quiet advocates long before the conversation existed—and we nurtured those relationships for fourteen months to make this number happen while protecting her career.

By the time the offer hit the table, the deal was already closed. The conversation about moving the numbers across the board wasn’t a headache. It was a formality.

And for someone initially fearful of negotiation and being perceived as difficult, the outcome wasn’t just a number. It was proof she should have believed in herself all along.

It’s not manipulation. It’s a bigger pie.

A lot of sharp people hear the word “negotiation” and recoil. It sounds gross—combative, something you do to someone instead of with someone.

That feeling is the frame. And the frame is wrong.

Most people think negotiation is about dividing a fixed pie. Zero-sum. My slice against yours.

It isn’t.

The job is to bake a pie so big that everyone in the room wants you doing it again. You only get there with genuine curiosity about what motivates the people across from you—and real enthusiasm for making everyone around you more successful.

I once worked with a CMO whose comp was capped—not by appetite, but by structure. The entire executive team was leveled to the same band, and there was no room to move her cash or equity without breaking the model for everyone above and beside her.

The CEO was proud of this equality across the board. Understandable.

So we stopped pushing on the number.

Instead, we negotiated severance protection for the whole C-suite—not just for her. The CEO got to play the hero who looked after his team, a reputation he’d already told us he wanted to build.

She became the person who made it happen. And what started as one capped offer turned into a groundswell of momentum for the entire executive team.

She didn’t take a bigger slice. She baked a bigger pie—and everyone in that room wanted her doing it again. She was welcomed onto the team with genuine gratitude—not eyed as one more leader to jostle with.

Because the way you negotiate is the relationship. It’s due diligence. It’s how you find out whether you’ll actually enjoy working with these people. It’s how you build an enjoyable career—and yes, more compensation.

It’s worth mastering right now.

Information is the only currency that compounds

You don’t increase your power by pushing harder. You increase it by knowing more—and earlier.

Herb Cohen built his whole career on this in You Can Negotiate Anything—power, timing, and information are the three variables in every deal, and information is the one that quietly governs the other two.

Information sits upstream of everything. Particularly information about what motivates the people around you.

Your power and your timing are downstream of it.

Most people assume the outcome is fixed because they never spent a single minute understanding the motivations of the person across the table.

Curiosity begets empathy. Empathy makes you likable. And likability makes people want to tell you things. It’s the through line from Aristotle, Cialdini, and Carnegie to Cohen, Voss, and the work I do every day.

A client was told $8M was the absolute max by the recruiter handling their negotiation.

We asked one curious question instead of arguing.

The number moved up 50% in a single text.

Then we proposed a higher anchor—and inside twenty-four hours, we’d landed at nearly double the initial maximum.

The ceiling was never real.

They’d told us exactly where it was—and we’d simply decided not to verify it.

That’s the whole game, right there. The ceiling is almost always a story somebody told you. It is almost never a load-bearing wall.

There’s a structure for it

The part of the workshop people felt in their chest was the structure—the thing you can run in any room, every time.

I call it CLOSE.

• Clarify the real mandate—the decision nobody said out loud.

• Label the tension everyone feels and no one has named.

• Overview their landscape, and show them something they hadn’t seen for themselves.

• Shape the vision—the first ninety days with the decision already made, until they’re the ones running the simulation.

• Execute—never end passively; you set the pace.

Run that sequence and you don’t need to win the argument. It is won upstream by how you control and influence every conversation.

I broke the full framework down a couple weeks ago—including the stage I cut, and why explaining yourself is the fastest way to lose a room.

The question we left them with

We closed the room the same way I’ll close this.

Whether you believe your story is predetermined or not—you’re right.

The salary band is a compliance filter, not a law of physics. The recruiter repeating the budget is fixed is reading a script written before they were hired. The ceiling is a story, and most of the people telling it to you don’t even know they’re telling it.

So the only question that matters:

What’s the chance your story is not predetermined?

Where this goes next

The PTTOW Summit was the first time we ran Signed, Sealed, Delivered live.

The energy in that room told me it shouldn’t be the last.

Tell me what cities you’d want us to come visit next.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

I owe you an update.

Some of you have been reading this newsletter since the early days—back when I was writing from a home office in Tahoe with a handful of clients and a thesis that nobody was representing senior leaders the way they deserved to be represented.

A lot has changed.

And the people who’ve been along for the ride deserve to hear what’s happening inside the business, not as a press release, but as a real conversation.

So here’s what’s going on.

The Lenny Effect

A few months ago I appeared on Lenny Rachitsky’s podcast.

What happened next was unlike anything I’ve experienced in fifteen years of doing this work.

Demand increased 6x immediately.

In two weeks, the practice closed $450K in new engagements—with active conversations pushing that north of $1M.

I wasn’t expecting it.

Not because the work wasn’t ready—but because I had spent the months leading up to that moment doing the opposite of what every growth playbook tells you to do.

I deleted my LinkedIn profile.

I narrowed my channels. I stopped trying to be everywhere and started investing in fewer surfaces with more depth.

The conventional wisdom says that’s how you shrink.

Instead, demand exploded.

I’m sharing those numbers not to impress you—I’m sharing them because they created a decision I wasn’t expecting to make.

At least not now.

And I know that many of you follow my newsletter and attend my monthly AMA sessions for ideas on how to run your consulting or solopreneur business.

I’ll keep sharing the mistakes and the wins—because the way you build matters as much as what you build.

Most practitioners—most business owners, frankly—would look at that kind of demand and do the obvious thing.

Hire. Scale. Build a team. Productize. Franchise the model. And many talented people have advised me to do just that.

Yet, I’m doing the opposite.

And I want to explain why, because I think the reason matters—especially if you’re building something of your own.

What Fifteen Years Taught Me About the Room

After thousands of negotiations and over a billion dollars in lift outcomes for clients, I’ve found the following to be true.

The most important work of a senior executive’s career happens in maybe four or five rooms across a lifetime.

The package that sets the decade. The exit that funds the next phase. The severance that protects the family. The equity conversation that changes generational math.

You set a precedent that compounds for the rest of your life.

Those rooms don’t need more consultants. They need the right one.

If I were to scale this practice—as many have advised I do—I would hire associates and train them on my frameworks and send them into rooms where the stakes are measured in millions.

But then every client gets a slightly diluted version of the person they actually hired.

The services model dilemma.

I’ve watched it happen across all consulting, wealth management, executive coaching, and now compensation representation. The incentive to scale always degrades the craft, because the craft is unique to the practitioner.

You don’t scale craft. You pay for it, or you don’t get it.

That sentence sounds like confidence—perhaps arrogance.

It’s really a lesson I learned the hard way—by watching other practices expand past the point where the founding partner could be in the room, and then watching the outcomes drop.

I experienced it every day while leading a team of 25 as the CEO of Discover Podium too.

You’ve seen it all around you.

And many of those firms are fighting for their lives in the wave of AI.

They drop in quality enough that the client who needed extraordinary got ordinary with better branding.

I don’t want to build that.

I love working both on and in the business—and the combination of flexibility and agility that my model affords.

What’s Changing

With these lessons nagging at me top-of-mind, I know that ThinkWarwick Global must continue to tighten.

Fewer clients. Higher stakes.

The Calendly offering has been consolidated to a single session type, priced to reflect the altitude of the work. The engagement floor is going up. Every session still credits toward full representation when appropriate—that hasn’t changed.

Since I made that change four weeks ago, I’ve negotiated four $10M–$15M, two $15M–$20M, and two $20M+ compensation packages.

And I’ll be honest—I’ve learned more in the last two months at this altitude than I did in the two years before it. The complexity scales faster than the numbers do.

Board dynamics, multi-entity equity structures, international tax implications, performance-vesting schedules that require their own legal teams, eight-figure buyout provisions on restrictive covenants—this is a different craft than the one I was practicing eighteen months ago.

And it requires the kind of focus that a scaled team model would make impossible.

The scarcity isn’t manufactured—though I know the discerning reader says, “Right, the guy who espouses Cialdini like gospel pulling the oldest trick in the book—you sly dog you.”

No.

Rather it’s been a relatively painful decision to make. As painful as dropping resume and LinkedIn writing from my service offerings years ago—services that were generating over $1M a year at Discover Podium.

Looking back, I’m glad I did.

I’m also dropping job search consulting from the practice entirely.

In its place: annual senior leadership representation—ongoing advisory for the clients I already represent, not one-off search engagements.

This one was hard. I love supporting job search work.

Helping executives think through positioning, target companies, build a search strategy from scratch—it’s deeply satisfying and I’m good at it. But the math doesn’t lie.

Job search consulting, no matter how well I do it, keeps my effective rate in the low hundreds.

The interview and negotiation work—where the stakes compress into a handful of critical conversations—regularly yields multi-five-figure effective hourly rates on the value created.

It’s why I built a free course around the job search process—so the methodology is still available to anyone who needs it.

The clients I have in active job search right now will be my last.

Once they land, the practice narrows to what it does best—the critical conversations.

Board presentations. Interviews. Keynotes. Negotiations.

The moments where executive presence, rhetoric, and influence determine the outcome. That's the work.

Again, this is uncomfortable for me.

But I want to keep growing and challenging myself at the highest levels of this work—you can’t do that by continuing to do more of the same. It’s passion and obsession in equal measure. If it wasn’t fun, I’m not sure my ADHD mind would let me stick with it this long.

I’ve just done the math—and the combination of value based pricing and the strength of outcome doesn’t lie. It’s the math of what quality representation at this level requires.

I can only serve a finite number of clients at the level I insist on, and demand now exceeds that number.

I had a moment a few months ago—an engagement where my effective hourly rate on the value we created together crossed $50,000. Not because I charged that. Because the outcome we produced in a few hours moved the needle multiple millions per year.

That’s the kind of room I want to be in. And I can’t be in that room meaningfully if I manage a team of twelve.

The pricing hasn't been the friction I expected.

I've structured my contracts around a 10:1 ROI on outcomes. When the math is that clear, the conversation isn't about cost. It's about value. For those running your own business—keep that lesson close.

What This Means for You

If you’re reading this and wondering whether you’re being priced out—the honest answer depends on what you’re navigating.

If you’re in a seven-figure comp conversation, a board-level equity negotiation, or a critical conversation where the next twelve months determine the next decade—the math works in your favor.

The practice is built for those moments—and the ROI reflects it.

If you’re not at that altitude yet—the content isn’t going anywhere.

The newsletter is free. The frameworks are public. More podcast appearances and workshops are coming. The book is coming. And the media work I’m doing over the next year is specifically designed to put the ideas into the world at scale, even as the practice stays tight.

That’s the distinction I want to be clear about.

The practice stays small with ThinkWarwick Global. The ideas go wide with Predetermined.

The principles that change a $15M negotiation are the same ones that change a $30K one—and the same ones that change how you show up at home.

The altitude is different. The architecture is the same. I’m driven to bring that to everyone.

The book, the podcast appearances, the frameworks I publish here—that’s how the work scales. Not by putting more people in rooms, but by putting the thinking into more hands.

Why I’m Telling You This

Many of you follow this newsletter because you’re building something too—a practice, a career, a business—and you’ve told me that watching how I build mine is part of why you’re here.

So I’m going to keep showing the work.

The pricing change. The reasoning behind it. The deals I’m learning from. The moments where I got it wrong. The tension between wanting to serve more people and knowing that the work is better when I serve fewer.

I don’t have all of this figured out. I’m fifteen years in and still recalibrating in real time.

But I know one thing for sure—the practitioners who last in this business aren’t the ones who figured out how to be everywhere.

They’re the ones who figure out where they belong and stay there.

I belong in the room. And I’m staying.

Thank you for following along.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

There’s a moment I see over and over again in my practice.

A senior leader—brilliant operator, proven track record, the kind of person many other leaders respect—walks into what may be the biggest conversation of their career—and does exactly what they were trained to do.

They answer questions.

Thoroughly. Thoughtfully. With precision.

They tell great stories. They demonstrate self-awareness. They do the thing every career coach, every talent consulting firm, every well-meaning mentor told them to do.

They show up prepared to be assessed. Highly credentialed and packed to the gills with logical arguments.

And then—somewhere around the thirty-minute mark—the room probes on something uncomfortable. A gap in the logic. A new idea. A function they haven’t immediately prepared for beforehand.

The executive does the responsible thing.

• They explain.

• They give context.

• They show what they learned.

• They preempt the concern before it becomes an objection.

And the room tilts.

Not dramatically. Not visibly.

Just—a half-degree shift in dynamic that you feel in your chest before you can name it.

The room goes from leaning in to sitting back. The energy goes from peer to panel.

By the time the leader debriefs—sometimes days later, sometimes weeks—the outcome reflects the tilt. The budget got trimmed. The initiative got scoped down. The terms came back conservative. The room gave them something—but not what they walked in to get.

The dynamic was set before the real conversation ever started.

I diagnose this pattern constantly.

The reality is, the moment you stop leading and start explaining—you lose the room. The transition to the back

foot quickly becomes the most expensive five minutes of your career.

And it all happens invisibly.

The Posture That Costs Millions

The senior leaders who win—who build the coalition, secure the resources, close the room on the outcome they came for—are not the ones who prepare the best answers or have the strongest pedigree.

They’re the ones who never answer questions at all.

Not literally. They’re not politicians.

Rather, they respond. They engage. They’re generous with their thinking.

But they don’t answer—in the way a student answers an exam, or a defendant answers a cross-examination. They don’t sit inside someone else’s frame and try to perform well within it.

They acknowledge—and then set the frame that best suits their strengths.

They walk into the room already operating at the altitude the conversation requires.

They treat every critical meeting the way the best enterprise sellers treat a first conversation with a strategic buyer—as the opening of a working relationship between peers, not as a pitch for permission.

The result is that by the time the formal decision is made, the decision has already been made.

The meeting was the audition for influence. Not the assessment of competence.

Competence gets you in the room—influence keeps you there.

Your brain knows the difference between these two postures—even if you’ve never had language for it.

Think about the last time you sat across from someone who was clearly performing for your approval.

You could feel it.

The slight over-eagerness. The answers that were a beat too polished—and with too many damn buzzwords.

The way they tracked your reaction after every sentence, adjusting in real time.

Now think about the last time you sat across from someone who was simply there—present, direct, already thinking about the work.

Not performing. Contributing.

Your nervous system registered the difference before your conscious mind caught up. The second person felt like a peer. The first one felt like a pitch.

That distinction—pitch versus peer—determines the outcome of every high-stakes conversation you walk into.

Bigger than experience. Bigger than credentials. Bigger than how well you prepared your talking points.

You’re not on the outside hoping to be let in—you’re already part of the tribe. Speaking the language, naming the real problem, adding value before a single decision has been made.

What I Use to Fix It

I’ve spent the last several years codifying what separates the senior leaders who close the room from the ones who leave it hoping.

Not as a theory. As an architecture that you can adapt for every critical conversation where the outcome depends on influence—not authority.

A five-stage discovery sequence that converts on your terms.

I call it CLOSE.

Five letters. Five stages. Each one builds on the last. Skip a stage and the ones that follow lose their foundation.

Clarify — why you’re in the room. Not the agenda. The hidden mandate. The decision criteria nobody said out loud. The person who actually owns the outcome—especially when they’re not sitting in front of you.

Label — the problems the room hasn’t quite found language for. The unspoken tension. The strategic contradiction that everyone feels but nobody has named. You name it with precision, and the conversation stops being a presentation and starts being a diagnostic session between people who already see the same problem.

Overview — the landscape. A structured read of what’s working, what’s missing, and where the leverage lives. Delivered as analysis, not critique. The moment you show someone something about their own situation they hadn’t quite seen for themselves, the dynamic shifts from evaluation to working session. And it doesn’t shift back.

Shape — the vision. Not your credentials. Not your résumé. The next 90 days with the decision made. Concrete. Specific. Anchored in the pain you just surfaced. You’re not asking them to believe in your track record. You’re helping them picture a future—and once they’re running that simulation in their head, the decision has already been made.

Execute — the next step. You propose it. You name it. You take control of the process before someone else sets the pace. And you follow up within 24 hours with something the room didn’t expect—something your internal champion can paste into the decision conversation verbatim when you’re not there to advocate for yourself.

That’s the architecture.

The previous version I was using had six stages (CLOSER). One of them was dedicated to preemptively explaining your weaknesses before they surfaced.

I killed it.

Not because anticipating concerns is wrong—it isn’t.

But the moment you start explaining yourself, the dynamic the rest of the framework exists to build is over. You don’t explain. You execute. The next move belongs to you.

Why This Works — Even When It Feels Uncomfortable

I know what you’re thinking.

This sounds aggressive. This sounds like I’m supposed to walk in and take over the conversation. These people have authority over the outcome.

Fair.

But here’s the thing nobody tells you about high-stakes rooms.

The people across the table are not looking for someone to evaluate. They’re looking for someone to stop worrying about. They have a problem they can’t solve with the people they already have—and they’re sitting in a room hoping the person in front of them makes the problem go away.

Everyone wants you to be successful. When you are—and you take the lead—you reduce cognitive friction all around you.

When you show up prepared to be assessed, you’re asking them to do more work. To probe. To test. To figure out whether you’re the one.

When you show up already operating—clarifying the real mandate, labeling the tension, overviewing the landscape, painting the first 90 days—you’re answering the question they came to the meeting with.

Can this person do it?

Not in theory. In the room. Right now. In front of me.

The discomfort you feel about “taking control” of the conversation is the exact discomfort that separates the leaders who close rooms from the ones who leave them hoping.

Your nervous system doesn’t want to do this. It wants safety. It wants to let the other side lead, because letting someone else lead feels like cooperation—and cooperation feels safe.

But the part of your brain that’s wired for survival is not the part that should be running your career strategy. The prefrontal cortex—the part that does long-term planning and strategic thinking—goes quiet under social pressure.

The amygdala takes over. And the amygdala’s playbook is simple: don’t get rejected.

It is a catastrophic playbook for a career-defining conversation.

What This Looks Like in Practice

A client of mine—CRO candidate, mid-cap SaaS—walked into the final round last quarter running the full CLOSE sequence.

She opened by clarifying the real problem. Not “tell me about the role.”

Instead—“From what I’ve gathered, the board is pushing for 40% ARR growth but the current GTM structure was built for the company you were two years ago. What do you think about that gap?”

The CEO paused. Then leaned in.

She labeled the tension—“It sounds like the sales org has been optimized for retention, not expansion. Which means the person in this seat isn’t just being hired to grow revenue—they’re being hired to rebuild the engine while it’s running.”

She overviewed the landscape—where the current team was strong, where the competitive pressure was forming fastest, and why the company’s TAM was bigger than their current ICP suggested.

Then she shaped the vision—the first three hires she’d make, the first dashboard she’d build, the first conversation she’d have with the VP of Product about pipeline attribution—and helped the CEO visualize the other side of her transformation.

The CEO was running the simulation before she finished the sentence.

She executed the next step herself—a working session with the head of product before the offer conversation, because the integration between sales and product was the real unlock and she wanted to validate her thesis before either side committed.

The offer came in above the previously disclosed range—what I call the invisible lift. We engineer bigger initial offers by differentiating so completely that the company adjusts the number before we ever negotiate it.

She got that deal because she was the only candidate who showed up as a partner. The only person the CEO could picture working alongside—and the one they’d regret losing if they didn’t move aggressively.

That’s the interview version.

But CLOSE works the same way in every room where the outcome depends on influence.

• The VP who needs board approval for a reorganization that nobody asked for.

• The founder pitching a strategic partner who has twelve other calls that week.

• The CMO trying to align product and sales around a GTM motion that neither team believes is their responsibility.

The architecture is the same.

1. Clarify why you’re in the room.

2. Label the tension.

3. Overview the landscape.

4. Shape the vision.

5. Execute the next step.

The executives who do this deliberately don’t need to win the argument.

The argument was won upstream.

What This Changes About Every Outcome Downstream

When the room closes right, every conversation that follows is different.

You’re not justifying the ask. You’re not hoping someone carries your case into a room you weren’t invited to.

You’re resolving a problem the room has already agreed is worth solving—and the terms reflect that.

That reframe—from pay for a person to pay for an outcome—is the value leverage that shapes every subsequent number on the page.

Every resource allocation. Every headcount decision. Every term in the deal.

The leader who ran CLOSE doesn’t show up to the decision conversation hoping the other side is generous.

They show up knowing that the room has already pictured them in the seat, has already run the simulation, and has already started adjusting their model to include this person.

That’s the Phantom Close I’ve discussed in prior articles—the moment the other side has emotionally committed before the formal commitment is named. And every subsequent step in the process is a confirmation of a decision that has already been made.

The conversation is the negotiation.

Most leaders don’t realize it until the decision is already made and the outcome is already anchored to a frame they didn’t set.

Whatever room is on your calendar next—the difference isn’t a better answer. It’s a better question, asked from the right posture, at the right moment.

Next time, use CLOSE and lead with curiosity.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

The call came on a Wednesday.

My client—SVP of Product, enterprise SaaS—had just finished her final round with what she thought was the company. The one she wanted. The role she’d been circling for two years.

She was ready to take the offer.

I asked her one question.

“What else are you considering?”

Nothing.

She’d been running a single process. All her energy, all her preparation, all her emotional bandwidth—poured into one opportunity with one company.

She had done everything right inside that process. Crushed the interviews. Built genuine rapport with the CEO. Left the room with the kind of energy that makes hiring managers send the “we loved her” text to their recruiter before the candidate reaches the parking lot.

And none of it mattered—because the company knew she had nowhere else to go.

The offer came in near the bottom of “the band.” Equity was weak. Signing bonus was absent. Severance wasn’t mentioned.

Not because they didn’t want her. Because they didn’t have to compete for her.

She had given away the single most valuable asset in any negotiation before the negotiation ever started.

Optionality.

I see this all the time.

Across levels. Across industries. Across executives who are, by every measure, the strongest candidate in every room they enter—even the ones who already won the process and are just waiting on the offer.

They run one process at a time.

They fall in love with one company. They put their career trajectory in the hands of a single decision-maker—and then wonder why the offer doesn’t reflect what they’re worth.

The most financially successful senior leaders I work with don’t hope for a good offer. They engineer the conditions that make a bad offer impossible.

Let me tell you how.

Bidding War Realities (That Nobody Taught You)

A bidding war is not an accident.

It is not luck. It is not something reserved only for people who are fortunate enough to be in the highest demand.

It is a microeconomic event that we create on purpose.

The formula is simple.

One candidate. Multiple buyers. A compressed timeline (that we control). And the specific, credible implication that the window is closing.

That’s it.

Supply and demand plus a sprinkle of scarcity and urgency—applied to your career with the same discipline you’d apply to any other market.

When there is one of you and three companies competing for your attention on overlapping timelines, the math changes in your favor in ways that no amount of interview preparation or negotiation scripting can replicate.

The company that was planning to offer you a $400K base starts hearing from their recruiter that you’re in final rounds elsewhere. The internal conversation shifts from “what’s the minimum we can offer?” to “what’s it going to take to win?”

That shift—from pricing you as a cost to pricing you as a competitive asset—is worth more than any single tactic I could teach you.

And most executives never create the conditions for it to happen.

Why Most Executives Don’t Do This

Perhaps because it may be perceived as dishonest. Or exhausting. Or impossible.

I hear it all the time.

“Jacob, I don’t want to lead companies on. I know where I want to go.”

“I don’t have time to run four processes at once.”

“The timelines never align. Some take three weeks. Others take three months. Some six.”

Let me take these one at a time.

Running multiple processes is not dishonest. It is the responsible management of the most consequential financial decision you’ll make in a decade.

You wouldn’t buy a house without looking at comparable properties. You wouldn’t accept the first term sheet if you were selling a company. Your career deserves the same diligence.

You do have time.

You’re just spending all of it on one process that may or may not materialize—and if it doesn’t, you’re starting from zero with nothing to show for months of effort.

And the timelines don’t align by accident. They align because you align them. That’s the skill.

We work to control time. To use the authority trigger of other companies you’re speaking with and the scarcity trigger that you may just get away.

Owning the Timeline

This is where most executives lose the game before they realize they’re playing it.

They enter a hiring process and let the company dictate the pace. Interview when the company says. Wait when the company says. Follow up when the company says.

They are being led through someone else’s process—and it is quietly the most expensive passivity of their career.

The executives who engineer bidding wars do the opposite.

They set the cadence.

It sounds like this:

“I’m grateful for the opportunity to discuss this role—it’s the team I’ve been most excited about. I want to be transparent that I’m approximately two to four weeks out from a decision on another opportunity. I want to respect your process, but I also want to make sure the timing works for both of us. How are you thinking about your timeline?”

That is not aggressive. That is not dishonest. That is an executive managing their own career with the same competence they’d bring to managing a P&L.

You are communicating three things simultaneously.

Interest. Scarcity. Urgency.

All of them should be true. All of them delivered with the kind of directness that senior leaders respect because it’s exactly how they’d handle the same situation.

And you repeat a version of that conversation across every process you’re running—calibrating the timing so that decisions converge within a ten-day window.

Not because the stars aligned by chance.

Because you aligned them.

Building the Field

The discipline of a bidding war is not a sprint. It’s a sustained campaign of opportunity creation that most executives dramatically underinvest in.

You cannot spark a bidding war if you have one live process.

You need three to five concurrent opportunities at various stages—some early, some mid-process, some approaching decision—so that by the time your top choice reaches the offer stage, you have real alternatives applying real pressure.

That means the prospecting never stops. Even when you’re deep in a final round with the company you love. Especially then.

The moment you stop building the pipeline is the moment you’ve decided to negotiate from a position of weakness.

You just don’t know it yet.

I had a client last year—C-suite, tech—who came to me with a single offer in hand.

Strong company. Good role. Mediocre package.

We didn’t negotiate. Not yet.

Instead, we spent two weeks reactivating conversations he’d let go cold. Reached out to three companies that had expressed interest months earlier. Re-engaged a recruiter who had been circling him for a role he’d initially passed on.

Within ten days, he had two additional processes in late stages and a third scheduling final rounds.

Then we went back to the original offer.

The company didn’t just improve the package. They restructured it.

Base went up. Equity was re-tiered around performance milestones. A signing bonus appeared that hadn’t been on the table two weeks earlier. Severance provisions were added without us asking—because the company’s internal calculus had shifted from “what’s fair” to “what does it take to not lose this person.”

The total lift across the negotiation was north of $500K in year-one value.

Nothing about his qualifications had changed. Nothing about the role had changed. Nothing about the company’s budget had changed.

What changed was the competitive environment. The company went from being the only buyer to being one of several—and the economics did the rest.

Reshaping the Role

A bidding war doesn’t just change the money. It changes the job.

When you have competing offers, you have something more powerful than negotiating leverage. You have a mirror. You can show a company what another organization is willing to build for you—and let them decide whether they want to match it.

It sounds like this:

“I want to be honest with you. I’m leaning toward your team—the culture, the mission, the CEO’s vision. But I’m weighing another role that is scoped as SVP of Revenue with ownership across the full commercial stack. The title and scope here are narrower. If we can align the role to include the revenue operations function and adjust the title to reflect that, I’ll sign this week—and I suspect we’ll both be more impactful because of it.”

You’re not bluffing. You’re not threatening to leave. You’re giving them a problem they want to solve—because solving it means they win you.

And the company that was offering a VP of Marketing role is suddenly building an SVP of Revenue seat—because losing you to a competitor who sees more in you than they did is the outcome nobody on their side wants to explain to their board.

The bidding war didn’t just improve the comp. It improved the career.

Often we can leverage the sunk cost fallacy in your favor—it’s cheaper to give you what you want than to restart the search.

A Note on Respect

There’s a principle underneath all of this that I need to name directly.

Every company in your process needs to believe there is a real path to getting you. Not a guaranteed path. But a credible one.

If a company has zero chance of winning you and you’re keeping them in the process purely as leverage decoration—you are wasting their time. I don’t teach that. I don’t condone it.

What I do teach is keeping your aperture wider than your instincts want it to be.

Deals that look like they’re miles apart are often closer than either side thinks. The role that seems too narrow gets rescoped. The package that looks 30% light gets restructured when the competitive pressure changes the math. The company you almost wrote off becomes the one that builds something better than the job you originally wanted.

I’ve seen it happen thousands of times.

The executive who was ready to cut a process loose at the 11th hour ended up signing there—because the company, when faced with losing them, found budget and flexibility that didn’t exist the week before.

So I don’t want you writing opportunities off too early. I want you running every credible process with genuine engagement and honest curiosity about what it could become.

The standard is simple: if the right offer materialized, would you take it?

And if the answer is yes—show them that.

Every company in your process should feel your genuine enthusiasm for what you’d build together. If they don’t believe they can win you, they won’t try. And a company that stops trying is a company that stops competing—which defeats the entire purpose.

If the answer is no under any circumstances, let them go.

They deserve the same respect you’d want if the roles were reversed.

Integrity Questions

I want to be direct about something because I know what the cynical reader is thinking.

“Jacob, couldn’t I just fabricate competing offers and bluff my way to more money?”

You could.

And some people do.

But a fabricated bidding war is a house of cards that collapses the moment someone asks for specifics you can’t provide—or calls the reference you didn’t expect them to call—or compares notes with a recruiter who knows you’re not actually in process where you said you were.

The executive world is smaller than you think. Reputations are longer than any single deal.

Every strategy I teach is built on real market validation. Real conversations. Real interest from real companies with real timelines.

The leverage is honest because the demand is honest. The skill is in how you amplify real demand through rhetoric, influence, and persuasion grounded in behavioral psychology.

Honest leverage is the only kind that compounds—because the company that hires you knowing you had real alternatives treats you differently from day one than the company that suspects you were bluffing.

The way you negotiate is the relationship.

What This Actually Requires

I’ll be direct about the cost.

Engineering a bidding war requires sustained effort over weeks—sometimes months.

It requires running multiple processes simultaneously while performing at the highest level in each one. And if you’re doing all of this while still in your current seat—leading a team, hitting your numbers, showing no signs of leaving—the bandwidth demand is real.

It requires emotional discipline—the ability to stay genuinely engaged with a company you might not choose while keeping your top choice from knowing they’re your top choice.

It requires you to resist the most seductive lie in executive job search—that you’ve found the one and you can stop looking.

You haven’t. And you can’t. Not until the ink is dry.

The executives who do this work—who maintain the discipline of concurrent opportunity creation while running CLOSE in every room they enter—don’t negotiate from behind.

More on exactly how to run CLOSE in a few weeks for paid subscribers.

They don’t hope for generosity. They don’t wait for the company to decide what they’re worth.

They walk into the offer conversation with the most powerful sentence in negotiation:

“I have options.”

Not as a threat. As a fact.

Delivered with the same calm that comes from knowing you’ve done the work—and that the person across the table knows it too.

That is the bidding war. Not a trick. Not a bluff. Not a lucky break.

A discipline. Engineered upstream. Executed with integrity. And worth more than any single framework I could hand you.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

The pavement in California holds heat differently on a summer night.

Thinking back, I can still smell the oil of the asphalted urban jungle.

I’m 24—barely a decade ago—sleeping at the Maidu skate park in Roseville.

I had figured out that if you lay flat on the asphalt around 11 PM, you could feel the day still radiating up through your back.

Oddly relaxing; nostalgic.

I had a BMW parked a block away that I couldn’t afford and couldn’t sell without going further upside down on the loan. I was trading Magic cards to 12-year-olds for L&L BBQ and Little Caesars $5 pizza on Sunrise boulevard.

And I remember looking up at the stars thinking—how nice is this? How lucky am I?

That sentence has stayed with me. Not because it was profound. But because it was true.

I had absolutely nothing and absolutely everything at the same time. I had perspective.

If this is the worst it gets, why am I so afraid to live?

I had decided the answer was that I shouldn’t live, just a few days earlier.

I even had a plan.

I was standing on the railing of the Foresthill Bridge, 30 minutes north.

I had been there a while. I don’t remember most of what I was thinking—I remember the kind of quiet that arrives when you’ve stopped negotiating with yourself.

Someone drove by and shouted “Jump, pussy.”

Gee. Thanks.

And it snapped me out of the trance.

I gasped for a breath—and my heart pumped ice through my veins.

I climbed down. I drove back to Roseville shaken to the core.

A few nights later I was in the skate park, looking at stars, feeling the heat come up through my back, asking the wrong question of myself for the first time in years.

Not “Why should I keep going.”

“Why am I so afraid to live?”

What I Was Supposed to Be

I am the child of rape.

My mother was 20, in Narcotics Anonymous trying to get clean from heroin, when she was assaulted.

She kept me.

I didn’t know any of this until I was almost 30. Perhaps ignorance really is bliss.

The man who raised me, who I will forever call my father, came into my mother’s life when she was seven months pregnant and chose this.

He was 20.

When I was 20, I could barely do my own laundry.

By many measures, I was not supposed to be here at all.

There are entire forums on the internet dedicated to arguing that pregnancies like the one that produced me should be ended early.

I am the poster child for that argument.

It is a strange thing to reconcile with the life I have today.

That was just the beginning.

I grew up inside substance abuse and domestic violence.

The house I came home to was not safe.

I learned early to read tone, footsteps, the angle of a jaw, the ounces remaining in a fifth of hard liquor or how many spilled rings of Bacardi hung around the base of a shot glass.

You know—all the small signals that tell a kid how the next hour is going to be.

I made myself small.

I quieted my footsteps in the hallways of my own house.

I still do.

Grown ass man, six-three, walking through my own home in Montana with nothing to fear—but I catch myself stepping softly through my house to avoid alerting the demons.

Some things you don’t unlearn. You just notice about yourself.

By other measures, I was not supposed to make it past the bridge.

And I am not even the worst case in my own house.

My wife Mary’s predetermined outcome was worse than mine.

She was the youngest of five girls raised in a single trailer in the woods, born to meth-addicted parents—five girls to multiple fathers, the kind of household that has a script for how it ends.

Her mother found out she was pregnant with Mary during a car accident, four and a half months along, high on meth.

Mary refused to read the script. It’s one of the countless things I adore about her.

When I met her, she had more clarity about what her life was going to be than I have ever had about anything.

She learned from the mistakes of others. She refused to be a victim—coming from a world where success looked like not getting pregnant at 12.

She is the one who taught me what self-agency looked like, because she had it before I knew it was an option.

In ‘23 our first son Noah was born with cystic fibrosis.

Less than a decade ago, his life expectancy was under 7 years.

The medical literature said don’t bother.

By the time he was born, gene modulators like Trikafta had changed the math so completely that he will likely never experience symptoms and has a full life expectancy.

The Cystic Fibrosis Foundation funded the research that made that true. The Cody Dieruf Foundation, here in Montana, makes sure families in the Northern Rockies—hours from any specialized care—can actually access it.

I will spend the rest of my life paying both of them back.

Our second son Nathan was born premature and spent weeks in the NICU, his lungs fighting to do what lungs are supposed to do. It didn’t look good.

Let’s just say, his lungs are working damn good now as testament to his 4am escapades.

The question I have been carrying since the skate park, and the question this newsletter has been circling for over a year—and the question my forthcoming book is named after:

What is predetermined in your life?

What I Got Wrong About It

For most of my life, I thought the answer was most things.

I thought the way you were born determined how the world treated you. I thought the situations you got placed in defined the ceiling. I thought job descriptions were laws of physics. I thought salary bands were real.

I thought authority—the kind that came from titles and credentials and gray hair and pedigree and money—was something other people had access to and I didn’t.

I was wrong about almost all of it. I learned that it could be manufactured.

Cialdini would approve.

The disadvantages are real. I am not pretending otherwise.

Mary and I spend a lot of time talking about how to engineer adversity into our kids’ lives precisely because we know what its absence does. Jeesh, what an incredibly privileged thing to say.

Unfairness is real. The systems built to write your future before you walk into the room are real.

What I got wrong was assuming the story was finished.

I started applying for jobs that required credentials I didn’t have. I got some of them. I started naming my own number instead of accepting what was offered.

The offers changed. They got bigger.

I started telling people what to think about me before they could fill in the blanks themselves.

They thought what I told them to think.

To be honest, most of what I did—didn’t work.

For every job I got that I had no business getting, there were hundreds of rejections I deserved and a few I probably didn’t. I applied to a thousand jobs in a day—when easy apply was truly easy.

I must have got nine hundred and ninety something nos. The other few became something I could learn from.

My rejection ratio never really improved.

The thing I had going for me wasn’t talent. It wasn’t credentials. It wasn’t even the chip on my shoulder, though that helped.

It was that none of the rejections compared to the house I’d come from. None of them compared to the bridge.

So when someone told me no, I laughed.

What were they going to do—make me feel small? M’kay.

Make me feel scared? Try harder.

I never cared much for the people telling me no. So I didn’t care much about what they had to say.

Rather, I focused on finding the few who did.

None of this was magic. None of it was easy.

Most of it took breakthroughs I cannot fully explain, lucky breaks I did not deserve, and the kind of grinding unglamorous work that is invisible to everyone except the person doing it.

Mary’s belief in me did most of the heavy lifting—all granted through God’s grace.

So did the strangers who, for reasons I still don’t understand, decided to give a young kid with a chip on his shoulder and no degree a chance at jobs that should have gone to someone with three.

Ignoring “the rules” started working for me.

But if I could have you as the reader understand one thing from every article I’ve ever published in this newsletter it’s that:

The predetermined story is the story you accept. Not the story that’s true.

The Cost of Refusing

From 2016 to 2021, I had built a company called Discover Podium to a few million in ARR.

Twenty-five employees. A thousand clients a year.

The kind of momentum that gets you on lists.

We helped executives find work at companies like Google, Apple, Cisco, and the hundreds of mid-market tech companies that were hiring like crazy in the late 2010s.

I had no business running a company at all, let alone one that was working.

Then COVID hit.

By April of 2020, I had spent a month on the phone with my employees and their spouses, telling them I would do everything in my power to keep their family employed through whatever this was about to become.

• Some of them had just had babies.

• Some were caring for elderly parents.

• All of them had trusted me when I made that call.

I spent countless hours on the phone negotiating with former satisfied clients that had disputed their charges on services rendered over 12 months prior in economic panic.

Losing the funds for your payroll while accounts are in dispute for 90 days is maddening, I tell ya.

We weathered the storm and bounced back stronger.

Later in the year, I got an offer to sell the business for several million dollars.

The condition was that I had to fire my team.

I said no.

Then I went into personal debt and unwound the company over the course of a year.

I took the PPP loans the government issued and gave every dollar of them to my staff—paid them probably too generously, structured it like severance, pointed half my sales team’s bandwidth at finding placements for the other half.

By the end, the business was worth nothing.

The thing that could have made me wealthy was gone.

I moved my family to a 1,200-square-foot house in Montana with the last $10,000 I had to my name. Gained 100 pounds in sadness over the next year—and sat with whether any of it had been worth it.

I tell that story not because it was virtuous.

I tell it because predetermined-refusal isn’t a feel-good slogan.

It is a discipline that costs you things. It’s real life.

The predetermined good outcome was right there. Sell the company. Take the money. Move on. Everyone would have understood. My advisors actively wanted me to.

My soul did not.

The people I was trying to protect would have been laid off three months later anyway when the buyer restructured—that’s how those deals always end.

Refusing it cost me a number I still don’t entirely want to think about.

Most of the people I protected don’t remember me. A few of them probably still think I was the toxic CEO who couldn’t keep the company alive. The math doesn’t reconcile. It still doesn’t.

That was the trade. I would make it again.

The point isn’t that I made the right call.

Reasonable people would have made the other one and slept fine. The point is that the call existed at all—and that the predetermined script for that moment was so loud, so obvious, so endorsed by everyone around me, that I almost couldn’t hear myself thinking otherwise.

That’s the cost of treating other people’s voices as your predetermined decision.

It doesn’t tell you the wrong answer.

It removes the question. It destroys your curiosity—no matter how naive it seems in challenging it.

Where the Thesis Lives Now

Everything I just told you about my own life applies to your career.

Not as metaphor. As mechanism.

If you are reading this as an executive, here is what predetermined means for you:

Your last comp number is not your next one. The ceiling you were told exists doesn’t.

• The salary band is a compliance filter, not a law of physics.

• The recruiter who told you the budget is fixed is repeating a script that was written before they were hired.

• The room you are in right now is not the only room.

• The people deciding your future are not deciding it with information you don’t also have access to.

• The story you have been told about what kind of trajectory is realistic for someone like you was written by people who needed you to believe it.

Most of them don’t even know they were writing it.

The script is institutional. Nobody is twirling a mustache.

The HR business partner who told you the comp band caps at $X genuinely believes the comp band caps at $X. The recruiter who said we don’t have flexibility on equity genuinely believes there is no flexibility on equity.

They are not lying to you. They are repeating what was repeated to them.

That is what makes it dangerous.

The script doesn’t need a villain to keep working. It just needs everyone in the room to stop questioning it.

Your job is to question it.

If you are reading this as a CHRO, a board comp committee member, or someone who designs the systems on the other side of the table, here is what predetermined means for you:

The compensation architecture you inherited is telling your best people their futures are predetermined.

The bands. The merit cycles. The succession plans.

The we don’t make exceptions for individual contributors at that level.

All of it is a story your organization is telling about what people are worth—and your sharpest leaders are starting to notice the gap between the story and the math.

You are losing the people you cannot afford to lose because they figured out the script before you did. The fix is not better retention bonuses. The fix is honest architecture.

It’s about value-expansion through alignment not slice-carving through adversarial positions.

The most expensive talent decision your company makes this year will not be the one you flag as a comp decision. It will be the one your most valuable VP makes quietly at her kitchen table on a Tuesday night when she finally lets herself ask the question her boss has spent two years training her not to ask:

What if none of this was actually predetermined?

That question, asked one time, is worth more than any retention package you will ever write.

What’s Coming

I have been quiet about most of this until now. The readers who have been showing up here every Thursday for several years deserve to know what they have been part of building.

The book is real.

Predetermined: Rewrite The Rules To Command Your Life is in active development with a Q3 2027 launch.

Publisher conversations are underway. The manuscript is being shaped from the same material that has been showing up in these articles—the frameworks, the client stories, the thesis that became the title.

A preorder waitlist is opening soon.

It serves from survival all the way through self-actualization.

A portion of every book sold will go to the Cody Dieruf Foundation. If this thesis means anything, it means making sure other families don’t have to figure out how to fight a rare disease alone in the Northern Rockies.

That is the version of not predetermined I care about most.

The podcast is coming.

I am building a show about leaders who have overcome predetermined circumstances—the people whose statistical outcomes said one thing and whose actual lives said another. Different stories than mine. Bigger stories than mine. The conversations I wish I had been able to find when I needed them most.

More on the format and the first guests soon. The show will live alongside this newsletter, not replace it.

This newsletter has made all of it possible.

Every share. Every comment. Every reply. Every person who forwarded an article to a friend who needed it. Every reader who became a paid subscriber not because they needed the perks but because they wanted to bet on the work.

You are the reason any of this gets to exist.

The “Why I Finally Called It Quits With LinkedIn” piece reached more people than I knew how to reach on my own.

You did that. Not me. Not the algorithm I had just deleted.

You.

I do not take that lightly.

One thing I would love your help on.

If you want on the preorder waitlist when it opens, drop the word PREDETERMINED in the comments below.

I will make sure you are first in line when the doors open, and first to know about the podcast launch, the early chapter reads, and anything else that comes from this body of work in the months ahead.

This is the part of the work I cannot do alone.

The Conversation

Nils Vinje asked me on his podcast what I think is actually predetermined for us in life.

We talked for 90 minutes. It is the most I have ever said out loud about any of this—the skate park, the biological father, the company shutdown, and the question I have been carrying for the last decade plus.

If the article was the thesis, the podcast is the evidence.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

The compliment I hear most often from clients isn’t about the money.

It’s this:

“Man, I wish I’d known about you twenty years ago.”

I nod. I smile. I say something gracious.

And I think to myself—what if you had?

What if I had?

What if someone had sat 16-year-old me down and said here’s the one thing you need to know before you walk into any room for the rest of your life.

Not a framework. Not a tactic. Not a seven-step playbook.

One idea. Small enough to fit in a kid’s head. Big enough to change a life.

I’ve spent fifteen years negotiating executive contracts against some of the most sophisticated compensation teams in the world. Over a billion dollars in outcomes. Thousands of engagements.

And when I strip all of it back—every tactic, every framework, every piece of IP I’ve built—it all sits on top of a single idea I didn’t learn until I was almost 30.

Here it is.

Most of what you think are rules are just habits other people got tired of questioning.

That’s it.

• The salary band is a habit.

• The job description is a habit.

• The “we don’t make exceptions” is a habit.

• The seven rounds of interviews.

• The merit cycle.

• The comp band.

• The hierarchy.

• The way meetings work.

• The way promotions work.

• The way somebody decides what you’re worth.

All of it was written by people who are no longer in the room.

Most of the people enforcing those rules today can’t tell you who wrote them, when, or why. They’re repeating what was repeated to them.

Nobody is lying. Nobody is being malicious.

The system just keeps running because nobody thought to press pause and ask whether the rules still make sense.

That’s not a conspiracy. That’s just how institutions work.

And once you see it, you can’t unsee it.

What This Looks Like in Real Life

I had a client last year—brilliant operator, first-generation career professional, terrified of asking for more than what the recruiter offered.

Her mother raised her to be grateful. Her father raised her to work hard.

Both of them raised her on rules they learned from their parents—rules built for a labor market that no longer exists.

She walked into the negotiation believing the offer was the offer.

We added $340,000 in year-one comp and a severance provision her recruiter told her wasn’t possible.

The company agreed to all of it in under 72 hours.

Nothing had changed on their end.

They hadn’t suddenly gotten more budget. The “no flexibility” wasn’t a fact—it was a habit. A script the recruiter had been trained to recite because most candidates stop asking the moment they hear it.

My client didn’t stop asking.

That’s the whole difference.

The Version I’d Give a Kid

Here’s how I’d say it to my 16-year-old self. Or to yours. Or to Noah and Nathan when they’re old enough to hear it.

Most of the rules you’re going to run into in your life were written by somebody else for somebody else a long time ago.

Some of them are real. Gravity is real. Kindness is real. The consequences of lying are real.

Many of them aren’t.

Question everything.

Many of them are just the path of least resistance—the version of reality that’s easiest for everyone to agree on because questioning it would take work.

Spoiler alert: You’re allowed to question it—and in some cases, you’ll be rewarded for it in an outsized manner.

And finding success doing so—especially over and over again—is highly addictive.

You’re allowed to ask why does it work this way? out loud. You’re allowed to ask who decided that? and when? and what happens if I don’t?

You’re allowed to look at the rule. Look at the person enforcing it. Look at the cost of breaking it. And make your own decision.

That is the whole skill.

Not confidence. Not charisma. Not some special gift.

Just the willingness to ask one more question after everyone else has stopped.

Why Nobody Teaches This

Because it’s dangerous.

Not to you—to the system.

If every kid grew up knowing that most rules were negotiable, institutions would have to work a lot harder to enforce them.

• Schools would have to explain why the bell rings every 47 minutes.

• Companies would have to explain why the raise is capped at 4%.

• Governments would have to explain a lot of things they’d rather not.

So the skill gets buried. Not maliciously. Just by default.

The kids who learn it usually learn it by accident—from a weird uncle, a rebellious friend, a book nobody assigned them, or a hard-enough life that following the rules stopped feeling like an option.

I learned it the hard way. Most of my clients learned it the hard way. Almost nobody learns it on purpose.

That’s what I’m trying to fix.

My Ask

If you have kids, tell them.

But maybe tell them to questions others and not simply defy your parental authority. Spoken from my experience raising a one year old and three-nager.

Not when they’re 25 and already mid-career and wondering why their salary hasn’t moved in four years. Tell them now. Tell them at 10. Tell them at 14. Tell them at 22 before the first offer letter shows up.

Most of what you think are rules are just habits.

You’re allowed to ask why.

You’re allowed to ask what if.

You’re allowed to walk in and build a life that looks nothing like the one the script had in mind for you.

That single sentence, delivered at the right age, is worth more than any MBA, any network, any inheritance.

It’s the thing this entire body of work is built on.

And next week, I’m going to tell you where it came from — and what it cost me to learn.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

I need to tell you something that might be uncomfortable.

I represent the executives you’re trying to hire.

SVP through C-suite.

F500. Tech. Healthcare. Financial services. PE portfolio companies.

For fifteen years, I’ve sat across the table from your recruiters, your comp committees, your investor talent scouts, your CHROs, and your boards—advocating for the candidates you spent months courting.

All the while being fingerprintless.

I know what they say about your offers. Not what they tell your recruiters or hiring managers.

What they tell me. What they’re too kind to tell you.

And what I’m hearing—across thousands of engagements—is that the money is often wrong. Anchored to a midpoint. Calibrated to last year’s market. Read by the executive as a lowball before they finish the first page.

However, I’m sure you expected that. Everyone wants more.

What I find more interesting is that the compensation structure and alignment is what’s often most wrong.

Your offers look like you don’t believe in the person you’re hiring.

They look exactly like what everyone else is putting in front of them.

You demand transformational results—yet you don’t offer transformational compensation.

I get it. I’ve been a CEO.

One thing before we start. I'm not the boogeyman.

I know I'm often treated like one—the guy on the other side who's coming to take a pound of flesh out of your offer.

That's not what I do.

I don’t do deals where the company loses. The companies always win.

The companies that work with executives I represent end up with better-aligned leaders, clearer expectations, and structures that pay for themselves in the first year. Because we put in the work.

We’re not here to shrink your pie. We’re here to show you where the pie is bigger than you thought—and how to capture it for both sides.

Everyone thinks they’re top talent. Most aren’t. Some are lying to you.

Most are lying to themselves.

You don’t want to absorb the risk of someone who can talk the talk but can’t walk the walk.

But the problem is what your compensation structure tells high-performance leaders about how you see them.

A flat benchmark offer—base, target bonus, four-year vest—tells an A-player you’re buying a seat-filler.

That your comp design was built to manage cost, not attract conviction. That your system is optimized for the average hire, not the transformational one.

The best executives notice when a company has put thought into the deal. They notice when it has simply copied the band. Pay data is everywhere now—they’ve already guessed at your range before they walked in.

And they know when they’re being lowballed.

They go from excited to deflated. Yes, that same person you spent months convincing to take the call.

They read your offer as evidence of organizational maturity—and they self-select toward the companies that signal confidence and away from the ones that signal caution.

These leaders are watching big deals land all around them—they have networks that talk too. Expectations have moved. If your offer hasn’t, you’re not competitive—you’re nostalgic.

But this isn't about the people on the other side of your table.

It's about the architecture of the table itself—and how the companies that redesign it are the ones winning the leaders everyone else is losing.

This is the first piece I’ve ever written for companies and those managing compensation committees.

Sixty-two articles in this publication have been for the executive.

How to negotiate. How to see the system. How to build a career that compounds.

But I keep running into the same wall from the other side.

CHROs know the wall is there.

They need language they can take to their CEO, their board, and their comp committee—language that makes the case before the next key hire walks away. Before they're the one standing in a conference room explaining how much it just cost, and why they didn't bump the range.

The companies that lose top talent aren’t just losing on dollars.

They’re losing on architecture. And no amount of recruiter outreach or employer branding fixes a structural problem—it's the most expensive problem most CHROs never get to name out loud.

So here’s the intelligence I’d normally only share with the person sitting across from you—turned around and pointed at your own process.

Take this as a starting point.

The work begins when both sides stop negotiating against each other and start building toward the same outcome.

Six mistakes. Over and over. And the framework I’ve built—from thousands of negotiations—for how to fix them.

Mistake 1: You’re Paying for the Seat, Not the Outcome

Last fall I advised a senior leader through two competing offers.

The first was an SVP role at one of the largest companies in the world.

Base. Target bonus. Annual equity. New hire grants. A $1 million signing bonus on top.

Total package across the accelerated vesting period we negotiated landed at roughly $4.5 million.

Competitive by every benchmark. Pave-approved. Board-sanctioned.

They turned it down.

They took a VP role at a high-growth public company instead. Smaller title.

Smaller logo on the resume.

We lifted the package to roughly $5.2 million guaranteed across the vesting period—plus $1.5 million in performance accelerators tied to three dated milestones the board was already tracking weekly.

Read that again.

They walked away from an SVP title at a household name. For a VP role at a smaller company that paid more, vested cleaner, and tied every dollar of upside to outcomes the board already cared about.

This is the trade many CHROs don’t think A-players will make.

They assume title and brand carry more weight than they do. They assume the safer, bigger-logo offer wins by default.

It doesn’t. Not with the leaders you actually want. Not with the leaders who actually mean it when they say title isn't everything.

Both companies lowballed from their ceiling.

But the second company wasn’t paying for the role. They were paying for what this leader would do in it. Their upside was much larger—but only in the scenario where the company’s upside was much larger too.

The first company priced the seat. The second company priced the outcome.

This is the fundamental error in how most companies design executive compensation.

HR pulls market data. They build a band. The comp committee approves a range. The recruiter delivers the number. And the number has nothing to do with what the executive will deliver.

Here’s what that structure actually does.

It sets a ceiling on what the executive can earn, no matter how much value they create. And a ceiling isn’t just a cap on compensation—it’s a cap on motivation.

Why would an A-player deliver 2x what you projected? Why would they deliver 5x?

There’s no mechanism that pays them for it.

Their best-case outcome is the same as their base-case outcome. The market rate is the floor, the ceiling, and the whole room.

So they deliver what the structure asks for. Exactly what the structure asks for. And then they start looking for the next seat—the one that lets them bet on themselves.

For your average hire, this works fine.

For the hire who will reshape your trajectory—the one you spent six months recruiting and three rounds of board interviews evaluating—the benchmark is a ceiling on your own upside.

Design compensation around what the executive will deliver, not what the role “should” pay.

Define milestones. Define triggers. Define acceleration tied to the business outcomes that justify the hire in the first place.

When you structure the outcome instead of the seat, you only pay more if they help you win more. Breaking the so-called comp band is funded entirely by the value your leaders create.

Your CFO should love this. Your board should love this.

And the executive you’re trying to land will see a company that thinks the way they think.

Mistake 2: Your Stakeholders Aren’t Aligned on What Success Looks Like

I’ve seen executives whose performance bonuses are tied to metrics their own CEO doesn’t track.

Think about that.

The comp committee approved triggers. The executive signed the contract. And the metrics that determine whether they earn the performance component have no relationship to the outcomes the board is actually measuring the business against.

This happens because comp design is often a conversation between HR and the candidate—with the board hearing about it after the fact.

Sometimes the hiring manager wants to stay out of it. Let HR and the recruiter handle it. Sign whatever lands on the desk.

That’s how you end up with a leader who isn’t aligned to the role before they walk in the door—no matter what the offer letter says.

Because here’s what you don’t see from your side of the table: the executive can’t get to you. The recruiter is gatekeeping. HR is gatekeeping.

Every clarifying question about what success actually looks like has to route through someone who doesn’t know the answer—and the executive knows that going around them costs political capital they haven’t even started to spend yet.

So they stop asking.

They sign a deal with at-discretion bonuses, vague performance language, and triggers that sound like they mean something. And they show up on day one already guessing at what you actually want.

You created an alignment vacuum the moment you decided to be hands-off.

The hiring manager’s goals aren’t reflected in the triggers. The investors’ return thesis isn’t wired into the milestones. The CEO’s priorities live in a board deck that nobody cross-referenced with the offer letter.

The result: a structure where the executive can hit every trigger and the board still considers the hire a disappointment. Or worse—the executive delivers exactly what the company needs and doesn’t earn the performance component because nobody aligned the metrics.

Most corporate comp designers miss something important. The models that work—the ones that align every stakeholder around the same outcomes and reward overperformance instead of just presence—already exist.

They just don’t exist inside corporate America.

They exist in Hollywood. In professional sports. In music. In every industry where the talent is the product and everyone has figured out that the only way to get the best version of the talent is to tie the money to the work.

• A-list actors don’t get base-plus-bonus. They get backend.

• Athletes don’t get cliff vesting. They get escalators for hitting specific, measurable outcomes.

• Producers and showrunners don’t get at-discretion bonuses. They get profit participation tied to “getting credit” for the thing they’re being asked to create.

I’ve spent the last three years advising agents at CAA on deal architecture for actors, directors, writers, and the people they represent.

What strikes me every time I’m in those conversations is how much more sophisticated talent deal structures are than corporate executive comp.

The people building deals for A-list talent have been thinking about alignment, milestone triggers, and compounding upside since the studio contract era ended.

Corporate executive comp is still catching up.

The cleanest example I’ve ever seen of how this should work is public record.

When Tom Brady signed with Tampa Bay, every trigger in his contract aligned every stakeholder.

Win games. Make the playoffs. Win the conference. Win the Super Bowl. Win MVP.

Each trigger was visible, measurable, and created compounding value for every party at the table. Nobody had to interpret “exceeds expectations.”

There was no review meeting where someone had to argue whether he’d earned it. The scoreboard was the review meeting.

The structure eliminated the argument.

Executive comp should work the same way.

The executive, the board, the investors, and the operating team should all win when the same things happen.

If your CMO’s bonus is tied to pipeline acceleration but your board is measuring brand equity and market position, you’ve built a structure that rewards behavior the company doesn’t actually value.

Worse, you’ve forced your CMO to starve the work that makes the pipeline possible in the first place. Brand building. Narrative. Category positioning. The communications infrastructure that turns a cold prospect into a warm one before sales ever picks up the phone.

The CMO cuts the brand budget to hit the pipeline number. Sales closes the warm leads that brand created. Sales takes the credit. The CMO gets measured on the next quarter’s pipeline number—with a weaker brand than the one they started with.

You didn’t hire a marketing leader. You hired a demand gen manager with a bigger title and a budget you’re slowly strangling.

The executive will optimize for what you incentivized—and you’ll be frustrated they optimized for the wrong thing.

That’s not a talent problem. That’s an architecture problem.

Mistake 3: Nobody Can Explain the Deal in Plain English

If your General Counsel can explain the performance triggers but your CHRO can’t—you have a problem.

If the executive you just hired can’t articulate what they need to deliver to earn the performance component—you have a bigger problem.

I’ve seen deals where the executive left money on the table because the trigger was buried in legal language they didn’t fully understand.

I’ve seen comp plans where nobody at the company understood what they’d actually signed—like junior account executives pulling $700,000 a year at $4M ARR companies, because the plan had no ceiling and nobody read it carefully enough to notice.

The AE wasn’t the problem. The plan was—and walking it back later was a much bigger problem.

I’ve seen “exceeds expectations” used as a performance trigger with no dollar value attached—a phrase so subjective it guarantees a fight at review time—or worse, a quiet acceptance the executive will resent until they find a new company to bolt to.

Opacity in comp design doesn’t protect the company. It erodes trust.

When an executive signs an offer they don’t fully understand, they don’t feel grateful.

They feel cautious.

They’re spending their first ninety days figuring out what they signed instead of figuring out how to deliver. Many have buyer’s remorse—and sometimes after relocating across the country.

And the first time a trigger doesn’t pay out the way they expected, you don’t have a comp dispute.

You have a trust collapse and a flight risk.

Transparent governance signals institutional confidence.

It tells the executive: we know what we’re buying, we know what success looks like, and we’re not afraid to put it in plain language.

Make every trigger visible and comprehensible to everyone in the room—the executive, the comp committee, the board. If you can’t explain the deal to a smart person in two minutes, the deal is too complicated.

Mistake 4: You’re Negotiating to Win Instead of Designing to Attract

Procurement mindset applied to talent acquisition.

That’s what most executive comp negotiations are. Minimize cost. Hold the line. Let the candidate know there isn’t much room.

Grind out an extra $250,000 at the offer stage—money the executive earned in the room and you knew you could pay—and lose a five-million-dollar executive eighteen months later because the deal felt extractive on day one.

That $250K, by the way, is roughly what you’ll pay the search firm to replace them.

I have seen this pattern so many times I can predict it from the first email.

The companies that grind every dollar at the offer stage are the same companies whose executives have updated their LinkedIn within a year. Not because the comp wasn’t enough—but because the conversation itself signaled something the executive could not unsee.

It signaled that the company saw them as a cost to be controlled, not a partner to be aligned with.

Here's what CHROs must remember.

This is a shared risk, not a one-sided one.

Your hiring manager stuck their neck out to sponsor the search. Your recruiter put their reputation behind the slate. Your board approved the package. But the executive is also uprooting their life to take it.

They’re leaving a stable seat. Uprooting a spouse’s career. Pulling kids out of schools. Walking away from unvested equity worth more than the signing bonus you’re offering. And in many cases, doing all of that because you poached them.

And then you tell them you can’t do severance. You can’t do a guarantee on year one. You can’t do the relocation grossed up.

You can’t, you can’t, you can’t.

That isn’t fiscal discipline. It’s a failure of basic human decency dressed up as governance.

The negotiation dynamic is a preview of the working relationship.

Executives know this intuitively.

When the comp conversation feels like a fight, they start calculating how every future conversation will go.

Promotion discussions. Resource allocation. Board interactions.

If you’re squeezing me now—when you want me most—what happens when the leverage shifts?

The companies that win top talent don’t negotiate to win.

They design to attract.

They treat the offer as a deal they’re co-designing with the executive, not a number they’re defending from them. And they understand that the negotiation itself is the first piece of evidence the executive has that the company will actually be what it said it was in the recruiting pitch.

Get that part right and the executive walks in already committed. Get it wrong and you’ve spent six months recruiting someone who’s quietly counting the days until they can leave without it looking strategic.

This isn’t soft. It’s strategic.

The $250K you grind for in an adversarial negotiation isn’t a savings—it’s a signal. And it costs you multiples in replacement search fees, delayed execution, and the reputation you’ve now built with every other candidate in the market who talks to the one you just alienated.

Mistake 5: Your Offer Is Invisible to the Market

Many companies treat the offer as an administrative step. HR sends a number. The candidate accepts or counters. Legal cleans it up.

Done.

But the offer is not an administrative step. It is a signal.

A flat, benchmark-matching offer tells the executive you’re replaceable. We’d pay this to anyone in this seat.

A performance-loaded offer tells them we believe you’ll deliver, and we’re willing to invest in that belief.

The difference isn’t dollars. It’s identity.

Last year I restructured the comp architecture for a Fortune 500 leadership team—multiple senior leaders, all in critical seats, all being aggressively poached after the CEO made bullish public statements on a quarterly earnings call.

The competition came hunting within days.

The old structure was failing everyone. Standard base. Standard bonus. Standard four-year vest. The kind of package that reads as “we’d pay this to anyone in this chair.”

Which is exactly what every competing recruiter was telling these leaders on the calls they were taking after hours.

We rebuilt the comp around milestones tied to outcomes the board was already measuring the business against. Combined lift north of $10 million annually across the team.

Life-changing money for the executives.

And for the company, it saved somewhere between $300 million and $500 million in value that would have walked out the door if even one of those leaders had left during the critical execution window—and pulled their teams out with them.

Read those numbers again.

A $10 million annual lift in executive comp protected $300–500 million in enterprise value. That’s a 30-to-50x return on the comp redesign in a single year. (I wrote about this restructuring in more depth in The Deal That Proves Where Executive Comp Is Heading.)

Your CFO will not find a better use of $10 million this year.

Nowhere on the P&L is there a line item where you can spend that and protect that.

This is what compensation architecture actually does when you treat the offer as a signal instead of a cost line.

The best executives self-select toward companies that let them bet on themselves. They want to be somewhere that says—if you’re the real thing, we have a structure that rewards you for proving it.

Your offer design is a talent filter. Not a cost line.

The companies that attract through compensation architecture don’t just get better candidates. They get candidates who show up on day one already committed to outcomes—because their economics are tied to them.

You get the talent you incentivize.

If your structure rewards presence over performance, you’ll attract people who are very good at being present.

And the market is already moving here, with or without you.

The Hollywood-style talent deals migrating into AI research—$100M to $250M packages structured as layered architectures of guarantees, milestone payments, and performance triggers—are not an aberration.

They’re a preview.

The companies competing for the leaders who move markets are already designing this way.

Compensation architecture is becoming a recruiting moat. The companies that figure this out first will not have to outbid their competitors for talent.

They will out-design them.

Mistake 6: Your Retention Strategy Is a Trap, Not a Reward

Cliff vesting. Deferred comp. Repayment clawbacks. Non-competes that read like prison sentences.

This is what most companies call a retention strategy. The executive stays because it’s expensive to go—not because it’s rewarding to stay.

An executive trapped by golden handcuffs is not retained. They are captive. And captive executives do not produce the value that justified hiring them in the first place.

They show up. They protect themselves. They count vesting dates.

And the moment they have a viable alternative, they leave—loudly—and tell every peer and every future employer exactly what your structure felt like from the inside.

I’ve had clients leave $2M on the table to escape a structure that felt like a cage. Two million dollars—forfeited—because the psychological cost of staying exceeded the financial cost of leaving. The equity was designed to vest on a calendar, not on performance.

The only thing keeping them was the clock.

When your retention architecture is built on penalty rather than reward, you don’t retain your best people. You retain the ones who can’t afford to leave.

They often check out and perform worse as a result. The damage a checked-out leader wreaks on a company is difficult and expensive to reconcile.

Your best-case scenario is that they walk away from the handcuffs early—and take the damage with them.

Compounding upside changes that equation.

Milestone triggers that make leaving economically irrational—not because you’ve locked them in, but because the deal keeps getting better every year.

• Year one, the trigger is tied to the strategic initiative you brought them in to execute.

• Year two, it’s tied to the revenue that initiative generated.

• Year three, it’s tied to the margin expansion that revenue produced.

Each milestone builds on the last. Each payout is larger than the one before. The executive who delivered all three is now the most expensive person to replace on your team—and the least likely to leave.

When the next milestone is always more valuable than the last, you’ve created a self-reinforcing loop.

The executive stays because staying is winning. Not because leaving is losing.

That is the difference between a captive workforce and a committed one.

The Architecture

Six mistakes. Six structural failures. And in each one, a principle that fixes it.

Those principles aren’t random. They’re an architecture I’ve built from the other side of the table across thousands of negotiations.

I call it SIGNAL™

S — Structure the Outcome, Not the Seat. Design compensation around what the executive will deliver, not what the role title pays at benchmark.

I — Incentivize Alignment Across Stakeholders. The executive, the board, the investors, and the team should all win when the same things happen.

G — Govern with Transparency. Make performance triggers visible, comprehensible, and articulable to every party from the candidate to the boardroom.

N — Navigate Stakeholder Dynamics Collaboratively. Treat comp design as mutual architecture, not adversarial negotiation.

A — Attract Talent Through Compensation Architecture. Your offer is a signal to the market. Performance-aligned structures attract executives who want to bet on themselves.

L — Lock In Value for All Parties. Create positive retention through compounding upside. When the next milestone is always more valuable than the last, the executive’s best decision is always to stay and deliver.

This is not a theory.

This is what I see working—right now, in real deals, across the market. The companies that adopt this architecture don’t just hire better. They retain longer, align faster, and build teams that compound performance instead of managing turnover.

This shift needs champions.

Not the firms clinging to retained search as a commodity—the ones still running the operating model from 2005. The firms that will define the next era of executive placement are the challenger brands.

The ones with leadership that left the big three because they saw the old model breaking.

The ones willing to tell their clients the uncomfortable truth about why they keep losing the executives they just placed.

The ones building a company-side practice around performance and alignment instead of benchmarks and bands.

If you're one of those firms—you already know who you are.

The market will reward you for moving first.

Both Sides of the Table

I’ve spent my career on one side of this table.

Over 40,000 executive consultations. More than a million text exchanges since 2020. A career built on the belief that no negotiation is predetermined—and that seeing the system is the first step to rewriting it.

The real leverage isn’t in the negotiation.

It’s in the architecture.

When a company builds a performance-based structure—before the candidate even walks in—the negotiation changes.

It gets faster. More collaborative. More honest.

The adversarial dynamic dissolves because both sides are already building toward the same outcome.

The executive doesn’t need to fight for alignment. It’s already in the structure.

The company doesn’t need to worry about overpaying. Every premium dollar is funded by value creation.

And the board doesn’t need to debate whether the package was justified. The milestones answered that question before it was asked.

I wrote this one for the companies with the courage to break out and challenge the market—or be prepared to negotiate with an executive leader who is.

Because when both sides build toward the same architecture, everyone wins.

The talent gets better. The alignment gets tighter. The outcomes get bigger. And the negotiation—the part everyone dreads—becomes collaboration, not confrontation.

The truth is, there aren’t really two sides to this table.

There’s the executive. The CHRO. The hiring manager. The recruiter. The board. The comp committee. The investors. Every one of them carrying their own risk, their own incentives, their own reputation on the line.

The metaphor of “two sides” is useful shorthand, but it’s also what keeps the room adversarial. It frames every conversation as a wrestling match with unfair advantages and shifting leverage—as if somebody has to win and somebody has to lose.

That’s not the work. The work is locking arms.

Everyone in the room building toward the same outcome because the structure lets them. Because the architecture rewards the same behaviors the business rewards. Because the milestones are legible to everyone and the incentives compound for everyone.

Nobody has to give up ground. Nobody has to concede.

The pie gets bigger because the structure makes it bigger—and everyone at the table shares in the growth because the design made sure they would.

If your team is rethinking how it designs executive comp, that’s the conversation I’d most like to have. Book a strategy session.

Stay fearless, friends.

Let me tell you about a deal I almost broke.

A near miss that frustrated everyone.

I was advising a CRO candidate—mid-cap SaaS, $3B valuation, strong growth. The offer was objectively competitive. Top of the band.

Strong equity. Solid bonus target. By every “objective” benchmark, it was a good deal.

She looked at it and said something I’m hearing more and more:

“This comp is built for whoever fills this seat. It’s not built for me or what I’m going to do in it.”

We talked it through.

The deal felt more extractive than creative. It was structured to protect the company’s downside, not to reward her upside.

She knew—because she’d done it twice before—that she could double their annual recurring revenue in 18 months. She had the playbook, the industry-specific relationships, and the track record.

But the offer in front of her priced the role at market rate, not the outcome she’d produce. And it gave her pause.

She wanted a structure that reflected her actual contribution. I agreed. Seems pragmatic.

Long story short—the company lost the candidate.

This is a problem.

The company has spent hundreds of thousands in recruiting costs. Dozens of hours from their most senior leaders. The talent consultancy has spent months building the right slate and guiding the company to their best candidate.

And now—at the finish line—everything stops.

When Cinderella is about to get her slipper, the whole room seizes up.

Buzzkill.

She didn’t know how to advocate for what she needed without sounding like she was asking for a favor—or worse, being combative or difficult.

She had the confidence to deliver a $65M revenue lift but not the language to propose tying her comp to it.

When I offered to create a value-based proposal—she responded with

“What, how? You can do that?”

That gap—between knowing your value and having the words to structure it—is what kills more deals than lowball offers ever will.

Is this a failure in the candidate?

The talent consultancy?

The company?

All three—and it creates a system full of friction that we dismantle one deal at a time.

I’ve watched it happen hundreds of times.

Senior leaders who know they can transform a business but default to “can we bump the base and equity?” Because what else are you supposed to do when everything is locked to band and precedent?

Nobody ever showed them a different frame.

Here’s how deep this goes—when I was researching this article, the AI I use for research and ideation actively discouraged me from challenging standard comp structures.

It kept steering me back toward conventional negotiation tactics. Because the training data is the system—and the system doesn’t have examples of what we’re about to do.

That’s how I know we’re in the right territory.

Creativity doesn’t blossom in the 11th hour when pressure is highest.

And honestly—early in my career—I let a few of those moments pass too, before I understood that the language matters as much as the leverage.

This article is about the language.

If you read the piece two weeks ago, you know what The Performance Signal is—the moment you stop negotiating like an employee and start negotiating like an asset.

If you read last week’s Severance Playbook, you know how to protect the downside before you sign.

This is the how.

The exact scripting, positioning, and tactical framework for proposing milestone-based comp that benefits everyone at the table.

Read the Room Before You Play the Card

Not every company can do this. Not every candidate can pull it off.

And knowing who can is half the battle.

Performance-based comp structures require flexibility—in how the offer is designed, how the board approves it, and how the company thinks about talent as an investment rather than a cost line.

Here’s where this approach has the most traction:

PE-backed portfolio companies. Operating partners think in returns. A comp structure tied to value creation milestones speaks their language. They’re already measuring the executive against a thesis—you’re just asking to participate in the upside when the thesis proves right.

Pre-IPO and high-growth companies. Equity is the currency, milestones are the culture, and the company is actively building the story that makes the stock worth more. Performance-loaded comp is native to how these businesses already operate.

Founder-led companies making their first senior hires. Founders understand betting on yourself. When you say “tie my upside to outcomes,” a founder hears a kindred spirit.

A comp committee at a Fortune 100 hears a headache. (Though we’ve won these over too, they are a pain in the ass and can drag for months. We've got deeper frameworks for navigating the layers here—but that's a longer conversation.)

Companies where the hiring manager or CEO is driving the offer—not just HR. When you’re negotiating with someone who has P&L accountability for the outcomes you’ll deliver, they can see the math. When you’re negotiating with someone whose job is to stay inside the band, the math doesn’t matter.

The following signals tell you the company has flexibility.

• The recruiter mentions equity as a conversation rather than a fixed number. The best will do this.

• The hiring manager talks about what success looks like in the first year.

• The CEO asks what it would take to get you excited.

• Board members are involved in the process.

The following signals tell you to tread carefully and build the case over time. Information gathering through curiosity, patience, and timing control become your #1 priority.

• Rigid comp bands referenced early and often.

• A corporate recruiter who quotes Radford like scripture.

• Proxy statement constraints mentioned in the first call.

• A process that feels administrative rather than consultative.

• “We’re just a startup, you see…”

This isn’t a reason to walk away from those companies.

It’s a reason to negotiate differently—win the base and equity conversations first, then propose what it takes to create a no-brainer after you’ve established your value and the company feels the pull of losing you.

You’re not asking them to break the system.

You’re proposing a pie-expanding opportunity that all parties contribute toward.

But know this—if the execution isn’t precise, this can be reputationally damaging.

You need momentum.

You need to carry learnings from early in the process to substantiate your value proposition.

This isn’t a Hail Mary.

It’s a closing argument built on evidence you gathered from the first conversation forward.

So when the room is right—when do you actually play your hand?

When to Play It

Timing is everything. And the timing is not when most people think.

You don’t introduce milestone-based comp in round one.

• Not when you’re expressing your value to the organization.

• Not when you’re selling the vacation.

• And definitely not as a counteroffer to an unexpected lowball.

You introduce it after three things are true:

The company has committed to you. Not “you’re a strong candidate.” Committed. They’ve told you you’re the one. They’ve asked about your timeline. They’ve introduced you to the board or the team. The emotional investment has been made—and reversing course would cost them more than accommodating your proposal.

You’ve received an initial offer that anchors the base. The base number is on the table. You know their range. You know what they’ve committed to in guaranteed dollars. This matters because the milestone proposal comes as an additive layer—not a replacement for the base, but a structure that sits on top of it.

You’ve already asked the question. Earlier in the process—during the interview dynamic, when information flows freely—you asked: “What are the three outcomes that would make the board consider this hire a home run twelve months from now?”

You documented those answers. Because when the comp conversation arrives, those answers become your milestone architecture.

The sequencing sounds like this:

“I appreciate this offer—it’s competitive, and I respect the structure you’re working within. I look forward to joining you. What’s the chance we can adjust the base and equity? And I’d also love to pair that with a performance structure that makes the overall deal stronger for both of us. I’m no stranger to tying my upside to outcomes—and I suspect that’s one of the reasons we’re all so aligned. Let’s build something neither of us came in expecting.”

You’re not choosing between countering and accepting.

You’re doing something more sophisticated—making reasonable asks on the guaranteed side while simultaneously opening a second lane that makes the total package bigger than a typical negotiation conversation ever could.

The base conversation is familiar territory.

The company expects it.

The milestone proposal is where you change the shape of the deal entirely.

You’re not countering. You’re building. The base adjusts. The milestones are additive. And the first words out of your mouth are acceptance and appreciation—not dissatisfaction.

We’ve made clients millions more per year—and helped companies accelerate their most important initiatives, simply by inviting more creativity and alignment into the negotiation.

And yes—we have a repeatable framework to align all parties.

More on that next week.

Milestones Are Designed Together

A milestone proposal built around your own ambitions looks like a bonus request.

A milestone proposal built around the company’s priorities—informed by everything you learned through the interview process—looks like alignment.

A milestone architecture designed together becomes partnership.

That’s the progression.

And most senior leaders never get past step one. Or really try in the first place.

If you walk in with milestones you invented in a vacuum—revenue targets you’re confident you’ll hit, product launches you were already planning—the comp committee doesn’t see confidence.

They see a rigged game.

You’re asking for a premium on outcomes that were already priced into the role.

But if you walk in with nothing—waiting for the company to hand you the targets—you’ve surrendered the frame. You’re asking them to do your thinking for you.

The move is to propose milestones rooted in what you heard during the process.

• The outcomes the CEO kept circling back to.

• The board priorities that surfaced in your conversations.

• The gaps the hiring manager described when they explained why they needed someone at your level.

You listened.

Now you demonstrate that listening by building a comp structure around what they told you matters most.

“Based on our conversations, it sounds like getting this platform to $150M ARR by Q4 next year is the outcome that matters most to the board. I’d like to propose that if we hit that target together, an additional equity tranche vests. And I’d love your input on refining those milestones so they reflect exactly what success looks like from your side.”

You didn’t invent the goal.

You didn’t wait for them to hand it to you.

You proposed something informed—and then invited them to build it with you.

That’s partnership.

And it’s the moment when people realize that negotiation is not adversarial and scary—but energetic and collaborative.

Does this make the process slower?

Yes.

But it makes the outcome dramatically better—for everyone.

The alignment work that happens in milestone design is due diligence that most hiring processes skip entirely.

You’re pressure-testing expectations, defining success in concrete terms, and surfacing misalignment before day one instead of discovering it at the first performance review.

The companies that complain about a longer hiring process are often the same ones running a replacement search eighteen months later.

This isn’t simply a performance strategy—it’s a retention strategy for both parties.

Double the comp, fired in ten months, eighteen-month search—repeat.

The math doesn’t math—and both sides lose.

You’d have been better off taking half the money at a company that was actually set up for you to succeed.

Getting the job is one thing, keeping the job is another—and conversely—finding high-performing senior leaders is one thing, properly aligning, incentivizing, and retaining them is another animal.

Script A vs. Script B

Let’s make this more tangible.

Script A — What Most Executives Say:

“The offer is solid, but honestly, it’s below what I think I can contribute. I’ve done this before—I took my last company from $60M to $200M in two years. I think my track record justifies a higher number, and I’d like to see the base come up to at least [X] with a stronger equity package.”

This isn’t wrong. It’s what the system taught you to do. And I applaud your courage to push.

But listen to what the comp committee hears.

A candidate who values themselves based on past performance at a different company, asking for more guaranteed dollars with no structural link to future outcomes.

The request is about you—your track record, your self-assessment, your number.

Worse—you’ve got a finger in the air guessing at a higher anchor.

Why that number?

Where did you get it?

If you deliver 2x the revenue for the entire organization, why bump a number up 20-40%? Just cause? That’s not aligned to value creation, that’s only increasing the company’s risk.

Because every candidate they talk to thinks they’re top talent—somebody has to be wrong.

You all can’t be the prettiest girl at the prom.

Value is ultimately subjective.

You want more because you’re supposed to ask for more. And more is better. Right?

And usually you’ll get more because comp committees expect this and budget that into their initial ask in many cases. You’ll just never find the ceiling—so don’t pat yourself on the back too soon.

But the senior leaders who are satisfied with the traditional back-and-forth aren’t the ones reading this.

Another exec who thinks they’re special. We’ve heard this before.

Script B — The Commitment Play:

“I appreciate this offer—it’s competitive, and I respect the structure you’re working within. I’d love to discuss a modest adjustment on the base and equity—and pair that with something I think makes the overall deal stronger for both of us. I’d like us to define 2–3 milestone triggers tied to the outcomes you’ve told me matter most. If we hit $150M ARR by Q4, an additional equity tranche vests. If we close the European expansion ahead of timeline, a cash bridge activates. Your guaranteed cost stays close to where it is. But if I deliver outcomes above the benchmark, the comp reflects that — funded by the value creation, not the budget.”

Script B does something Script A fundamentally cannot.

It accepts the offer.

It signals commitment—gratitude, enthusiasm, intent to join.

You’re not threatening to walk. You’re not manufacturing hesitancy to create pressure. You’re telling them you’re in.

And that’s precisely what makes the milestone proposal so powerful.

You’re making it at the moment of maximum leverage—and using that leverage for alignment instead of extraction. The company isn’t bracing for a fight. They’re leaning in because you just told them you want to be there.

You can still decline later if the structure doesn’t come together—gracefully, professionally, with the relationship intact.

But in this moment, you’re doing something most candidates never do: you’re using your strongest negotiating position to build something collaborative rather than to squeeze.

That alone shifts the dynamic.

You’re not in conflict.

You’re in collaboration—proposing a structure that demonstrates you think like an owner, not an employee negotiating a raise. You heard their priorities and built an architecture around them.

Script A says: “I’m worth more. Pay me more.”

Script B says: “I’m worth more. Let me prove it. And let’s build a structure where proving it benefits all of us.”

One is a negotiation. The other is a business case.

Who would you rather work with?

When They Push Back

They will push back.

Count on it.

Here’s what you’ll hear—and what to say.

1. “We don’t do that here.”

Most companies will say this first. It’s reflexive, not final.

“I understand that’s not standard—thank you for brainstorming and considering this path with me. I can’t help but feel that the standard structure is designed for a different market. I propose we build something that works to reduce the company’s risk while giving me the opportunity to earn more when we deliver. You pay the premium only in the scenario where we’ve created the value that funds it. In my experience, aligning these milestones across the company incentivizes all teams to perform better—that’s our competitive advantage.”

You must reframe.

You’re not asking them to break precedent. You’re proposing a structure that’s more aligned with the company’s success. It will send ripples through all departments and every high-potential or overachiever will lock in and drive the company forward—because every incremental dollar is performance-contingent.

2. “Our comp bands don’t allow it.”

“I hear you. What if we stay within the band and structure the performance component as a supplemental agreement? This will give us an opportunity to further align and turn a good deal into a great deal that’s better for everyone.”

The key word is supplemental.

You’re not asking them to violate their comp architecture—or asking them to stick their neck out for someone they just met. That political capital is hard earned and most are not willing to lose it to help you break precedent.

Rather, you’re asking to build an addendum that sits alongside the standard.

Most comp committees have more flexibility in supplemental agreements than they do in base comp—because the supplemental doesn’t set precedent for the rest of the organization.

If you’re worried about being the tall poppy—about being perceived as aggressive or asking for too much—the supplemental path lets you be ambitious without being threatening.

3. “We’d have to get board approval.”

This sounds like a wall. It’s actually a door.

“That’s a great sign—it means the board would see that I’m willing to bet on myself in ways that help you and them get what they want too. I welcome that conversation.”

A comp committee that brings your proposal to the board is a comp committee that’s already advocating for you.

They wouldn’t surface it if they didn’t want it approved.

The board conversation itself becomes your signal—it tells the entire governance structure that this executive showed up with a business case, not a demand.

4. “What if you miss the milestones?”

“Then I earned exactly what the original offer proposed—and you got me at market rate. The only scenario where you pay above benchmark is the one where I delivered above-benchmark results. That’s the whole point. Neither of us intends to miss—or we wouldn’t have made it this far in the first place.”

This is the strongest response in your arsenal.

It neutralizes the risk objection completely. Every dollar above the base is funded by outcomes.

The company’s downside is exactly what they were prepared to pay anyway.

If I perform average, pay me average.

If I break the mold, break the mold with me.

Kill the “At Discretion” Bonus

While we’re here.

If your offer includes a performance bonus described as “up to X% of base salary, at the discretion of the board” —you’re holding a coupon that may never be redeemed.

It sounds like a sure thing at signing—but it certainly is not.

You must take this seriously.

When I advise clients on their comp, I include discretionary bonuses in my own fee structure. Real skin in the game. Because the moment your bonus is something we both have a stake in, you start asking the right questions—the due diligence that most candidates gloss over because the bonus feels like a guaranteed add-on.

It’s not.

These are real dollars that real people depend on. And they deserve more than “at discretion.”

Discretionary bonuses give the company maximum flexibility and you maximum uncertainty.

A banner year where you crushed every metric?

“We’re being conservative with bonuses across the organization.”

You’re kidding me—again?!

You’ve lived this. We all have. We’ve grown to expect it.

The fix isn’t a higher discretionary percentage. It’s replacing “at discretion” with defined triggers.

“I appreciate the bonus structure. Can we define 2–3 specific outcomes that qualify for the full payout? That way we’re both clear on what success looks like—and neither of us is guessing.”

You’re not attacking the structure.

You’re upgrading it from an ambiguous promise into a contract.

And most comp committees want this—defined triggers make their job easier when justifying the payout to the board.

Discretionary bonuses persist not because companies prefer ambiguity—but because nobody asked them to be specific.

The senior leaders who ask are the ones who collect.

The Lowball Application

What about when the offer isn’t competitive?

When the number is genuinely below market and you know it?

The milestone architecture becomes even more powerful.

Most executives respond to a lowball one of three ways. They walk. They swallow it and resent it. Or they go fractional— “If you can only pay me X, I’ll give you X worth of effort.”

I’ll sometimes advise this path when the fit is right.

But it’s trickier than it looks.

Go fractional without precision and you’ll be perceived as a contractor—a mercenary for hire. You’ve capped your ceiling.

You’ve given them permission to treat you as an operating expense instead of a capital investment—and guaranteed that every conversation about your contribution will be measured in hours or billable days instead of outcomes.

The commitment play works differently.

Accept the lower number—if palatable—and propose milestone triggers that bridge the gap between their offer and your real value.

“I understand the range you’re working within. I’ll accept the guaranteed comp as structured. But I’d like to propose that we tie an additional tranche to the outcomes we’ve discussed. If I deliver [specific board priority], the milestone tranche brings my total comp to where I believe it should be — funded by the value I created, not additional budget.”

You just turned a discount into an accelerator.

You absorbed uncertainty the company would otherwise need to resolve with higher guaranteed dollars. That risk transfer earns a premium. The milestone tranche shouldn’t just close the gap—it should exceed it by 25–50%.

Because you made their economics better in every scenario. And the only scenario where they pay the premium is the one where you massively overdelivered—which means they’re thrilled to write the check.

This Structure Is a Filter

Let’s be honest.

This isn’t for everyone. It’s meant to be a filter.

The executive who proposes milestone-based comp has to deliver.

The structure exposes you if you can’t.

It’s not simply naive confidence.

There’s no hiding behind a guaranteed package when your incremental comp is tied to outcomes with deadlines and dollar values attached.

The same filter works on the company side.

A business that accepts a milestone proposal has to be sophisticated enough to define meaningful targets, measure them honestly, and honor the triggers when they’re hit.

The executives who propose this signal to the market: I perform.

The companies that embrace this signal to the market: We reward performance.

When those two signals meet, you get something neither side can achieve alone—a comp architecture that attracts, retains, and motivates at a level that benchmark-driven competitors cannot match.

That’s not a negotiation.

That’s a competitive moat—for both sides.

Your Move

If you’ve followed this series the last three weeks, you now have the architecture—why the market is shifting, how to protect the downside, and now the language to propose the upside.

If you’re heading into a negotiation in the next 90 days: ask the question early.

• Document what the board considers a home run.

• When the offer arrives, counter with a structure, not a number.

• Frame it as alignment.

• And negotiate the severance before you sign.

Your career is the largest financial asset you’ll ever manage. Build the deal accordingly.

And when you’re sitting across from the comp committee, remember—you’re not asking them to bet on you.

You’re showing them what it looks like when someone bets on themselves.

Everything I’ve written in this series has been for you—the senior executive.

But here’s what I’m increasingly hearing from the other side of the table:

The compensation conversation is shifting.

The smartest companies are figuring this out.

They’re redesigning compensation architecture not simply because they’re losing top talent—but because they’ve realized that performance-based structures attract better talent, retain them longer, and align every stakeholder around the same outcomes.

Next week, I’m writing a piece for the companies. Because the executives who read this aren’t the only ones who need to hear it.

When both sides build toward the same structure, everyone wins.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

Nick Richtsmeier runs a podcast called Damns Given, and he asked the kind of questions that make you forget there’s a microphone.

No pre-approved talking points. No safe lanes.

We went places I didn’t expect the Discover Podium origin story, walking away from a $4–5M acquisition, the addiction behind the hustle, why I permanently deleted LinkedIn, and what fatherhood broke open in me that the algorithm never could.

Nick did that.

🎥 Watch on YouTube 🎧 Listen on Apple Podcasts 🎧 Listen on Spotify

Something We Didn’t Get To

Many of you already read Why I Finally Called It Quits With LinkedIn — the most-read, most-shared piece in this newsletter’s history. The podcast with Nick is the unfiltered backstory behind that article—every detail I couldn’t compress into the written version.

But in both the article and the conversation, I circled something I never said directly.

The platform that rewards you with attention is not the platform generating your revenue. And most of us confuse applause for pipeline until the math forces the question.

I built a company on LinkedIn. Scaled it past a million in year one.

Spent five years refreshing ProFinder leads at 3 AM so my team could eat.

And when I finally audited where my actual revenue came from, the deals that changed my life, the clients who stayed, the engagements worth six and seven figures—almost none of it traced back to the LinkedIn feed.

The executive who hires me at that level doesn’t scroll.

They’re not in my DMs. They heard my name from a board member over dinner—or a peer who dropped it in a private Slack thread I’ll never see.

Usually it’s just a text message, “Call Jacob, trust me.”

Meanwhile, the algorithm kept feeding me attention from a room that felt like my market but wasn’t. Every hour I spent performing for that room was an hour I wasn’t in the room that mattered.

This isn’t just a LinkedIn problem. It’s a clarity problem.

If you’re spending four hours a day somewhere—ask yourself where your last three best clients came from.

If the answer isn’t that platform, you’re not building. You’re performing.

The exit isn’t always deletion. Sometimes it’s just proportion. But you have to see it first.

I wrote about this from the inside out—the revenue data, the addiction, the family cost—in Why I Finally Called It Quits With LinkedIn. If you haven’t read it yet, start there. It’s an important piece in the archive.

New Here? Start With These

60+ articles deep. If you want the concentrated version of what this newsletter is about, these five will get you there:

Why I Finally Called It Quits With LinkedIn — The piece behind the podcast. Why I permanently deleted my profile—and what the revenue data actually revealed.

How to Network Without Becoming a LinkedIn Influencer — How to build a high-leverage network without posting “thought leadership,” sending spam, or eating bad cheese at networking events.

Why Executives Leave Millions on the Table: The Werewolf Game Theory of Negotiation — Why most leaders negotiate like villagers instead of winners—and what information asymmetry has to do with it.

Executive Loneliness: Why Climbing Higher Means Feeling Lonelier — What happens when the ladder narrows your world—and how the most effective leaders are reclaiming their humanity.

How Senior Leaders Build Strategic Networks That Create Executive Opportunities — You don’t have a marketing problem. You have a sales problem. This is how real leverage actually moves.

Work with me directly. Every session credits toward representation.

Stay fearless, friends.

Too many senior leaders only think about severance when they’re already out.

The conversation usually starts like this: “Jacob, I just got let go. What can I do about my severance?”

And the answer, usually, is—not much.

We often get something.

But never as much as we could have—and never without the emotional wreckage that follows the deed being done.

The time to negotiate your safety net is before you need one.

• Before you’ve signed anything.

• Before you’ve emotionally committed.

• Before the company knows you’re a sure thing.

Negotiate the terms of your divorce before getting married—when everyone is supportive and full of love.

Because the moment you sign that DocuSign, you’ve surrendered the single greatest source of leverage you’ll ever have in that relationship—the ability to walk away.

I’ve learned across thousands of negotiations that severance isn’t a perk.

It’s a risk mitigation strategy—because you typically pay the brunt of the reputational and financial hardship post termination.

Far more than your organization does.

Especially if you were recruited away from a role where your livelihood and career were relatively safe.

Severance is a structural component of any serious executive compensation package. And the executives who treat it that way—who expect it rather than ask for it—are the ones who walk away protected when the inevitable happens.

And the inevitable always happens.

Why Nobody Talks About This

You just got the offer. The title is right. The comp looks strong.

Your brain is doing what it does after every win—flooding you with the same chemistry that makes you feel invincible after closing a major deal or nailing a board presentation.

Bringing up severance in that moment feels like handing your fiancé a prenup at the rehearsal dinner.

So you don’t.

And that’s exactly what the system is counting on.

Companies aren’t being malicious.

But they understand something you don’t in that moment—that the emotional high of a new offer is the worst possible time for rational financial planning.

The part of your brain responsible for long-term strategic thinking goes quiet when the part responsible for “they picked me” is running the show.

Especially in an employer market.

This is Institutional Homeostasis doing what it does best.

The organization’s immune system resists building protections for your departure during the same conversation where they’re investing in your arrival. It introduces friction. It forces both sides to acknowledge something uncomfortable—that this might not work out.

But here’s what separates the executives who walk away whole from the ones who call me too late—the willingness to have the uncomfortable conversation while everyone is still in love.

Because we’re all adults here.

And adults who’ve led organizations and made decisions that affect thousands of people can handle an honest conversation about protection.

The Leverage Curve

Severance isn’t one-size-fits-all.

There’s a curve—and the more senior you are, the steeper it tilts in your favor.

• At the Director level, 3 months is standard.

• VPs should target 6 months as a baseline—and push for it without hesitation.

• C-suite executives should be looking at 6 to 12 months.

And in the right circumstances—particularly when you’re being recruited away from a stable, high-paying role—we’ve secured 18 to 24 months.

These numbers are generalities—I’ve seen directors get a year and C-suite get 10-year early pension packages.

Never use these as a reason to avoid getting creative.

I’ve also seen leaders negotiate a clause that reads: 6 months of guaranteed severance with 1 additional month added for every year of continuous employment with the company.

The logic is straightforward.

The more senior the role, the harder the landing if it doesn’t work out.

A CMO who gets let go 10 months in doesn’t just lose hundreds of thousands in income.

• They lose 10 months of career momentum.

• They lose the equity they left vesting at their previous company.

• They lose the reputational capital that comes with stability—and inherit the reputational tax that comes with a short, unexplained tenure.

That’s not a one-month-of-base-salary problem.

And this is where most senior leaders get the math wrong.

They think about severance as a function of their new role. It isn’t.

Severance is a function of what you’re leaving behind.

If you’re sitting in a stable position—equity vesting on schedule, bonus trajectory known, institutional credibility compounding—and a company asks you to walk away from all of that, they’re asking you to absorb risk.

Real, measurable, career-altering risk.

Add a cross country move or pulling you into the office full time and we’ve got a lot of life altering changes to consider.

The signing bonus is supposed to bridge that risk.

But most executives treat it like a gift instead of what it actually is—an insurance premium on the career capital you’re forfeiting to take the bet.

Most senior leaders fail to win a signing bonus in the first place. That’s a problem worth its own piece.

The severance package is the backstop.

It’s the thing that ensures you’re not financially devastated if the bet goes wrong—not because you failed, but because the board shifted strategy. Or the CEO who recruited you left a week later. Or the company got acquired and your role was eliminated before you finished onboarding.

I’ve watched all three happen in the last 12 months. To people who are very good at what they do.

The risk isn’t theoretical. The protection shouldn’t be either.

Here’s exactly what to do to win.

The Expectation Play

Make this seemingly counterintuitive move next time.

You don’t ask for severance. You expect it.

In practice, this means you negotiate every other component of your package first. Base. Bonus. Equity. Signing bonus. Title. Reporting structure. Start date. Relocation.

Get all of it where it needs to be.

Then—and only then—when you’re ready to sign, when the company is emotionally and organizationally committed to you as their person, you say something like this:

“Everything looks great. I’m excited to get started. Before I sign, can you forward the severance terms? I’m sure at this level there’s a standard separation agreement—I just want to review the policy and make sure we’re aligned.”

Read that again.

You didn’t ask “Can I get severance?”—which positions it as a request and invites a no.

You asked them to forward it—which positions it as something that already exists. Something everyone at your level gets. Paperwork you’re simply waiting to review.

You control the frame.

The company is now responding to your assumption, not evaluating whether you deserve protection.

Compare that to what most people say:

“I was also wondering—is there any possibility of including some severance language in the offer?”

That’s a request. It signals uncertainty. It tells the company you don’t expect it—which means they don’t have to give it. You’ve handed them the frame, and the frame says this is optional.

It isn’t optional. Not at your level.

The difference between those two scripts isn’t confidence. It’s positioning. The first version assumes the world you want to live in. The second asks permission to enter it.

And adults who’ve led organizations, managed P&Ls, and made decisions that affect thousands of people don’t ask permission to review the terms of their own protection.

They expect them on the table. Because that’s where they belong.

When They Don’t Have It

Often—they don’t have a standard severance policy for your level. Or at all.

Especially at growth-stage companies, mid-market firms, and organizations that haven’t had enough senior turnover to formalize one.

This is not a problem. This is the best possible outcome.

Because now you’re not negotiating against an existing policy.

You’re building one together.

When they come back and say “We don’t have a formal severance policy for this level”—and they’ll usually say it like it’s an apology—you pivot:

“That makes sense. A lot of companies haven’t formalized this yet. Why don’t we build something together that works for both of us? A clean separation framework protects the company just as much as it protects me—it ensures a smooth transition, preserves institutional knowledge, and gives both sides clarity if things ever change. It’s best we set these terms now while we’re aligned—and it will help us attract top talent as we continue to grow.”

Notice what you just did.

You didn’t flinch. You didn’t treat their lack of policy as a dead end.

You treated it as a drafting session—one where you get to hold the pen.

You reframed severance from a personal demand into a joint business decision. A sign of organizational maturity. A retention tool. A talent acquisition strategy.

You’re not winning an argument. You’re helping the other side arrive at a conclusion that happens to serve you both. You also show the maturity that they expect when hiring a top senior leader.

And the institutional reader should be paying close attention here—because formalizing executive severance protections reduces flight risk, increases the caliber of candidates willing to leave stable positions, and signals to the market that your organization takes senior leadership transitions seriously.

The companies winning the war for senior talent aren’t always the ones offering the highest base. They’re the ones offering the most sophisticated deal architecture—upside and downside, both structured before anyone signs.

If a candidate walks you through this conversation, you didn’t just find a good executive. You found someone who thinks like an operator.

Hire them faster.

Companion Architecture

If you read last week’s piece, you saw the upside—how milestone-based comp structures are letting the best executives capture the value they actually create rather than waiting on a board’s discretion.

This is the other half of the equation.

Upside without downside protection is a bet.

And most executives are making that bet without realizing it—signing offers that reward them handsomely if everything goes right and leave them exposed the moment anything doesn’t.

The best-architected deals I’ve negotiated in the last year all share the same DNA:

Upside—milestone-based comp that rewards value creation. Performance triggers. Equity acceleration tied to outcomes you control.

Downside—severance protections that acknowledge career risk. Structured before you sign. Compounding over tenure.

Bridge—signing bonuses that compensate for the guaranteed value you left behind. Not a gift. An insurance premium.

If you’re only negotiating the base-bonus-equity standard, you’re playing half the board. You’ve optimized for the scenario where everything goes perfectly—which, if you’ve been in the game long enough, you know is not the scenario you should be designing for.

I’m not telling you to be pessimistic. I’m telling you to be an architect.

• Every sophisticated financial arrangement accounts for downside risk.

• Every real estate deal has contingencies.

• Every M&A transaction has termination fees.

• Every insurance policy exists because smart people plan for what they hope never happens.

Your career is the largest financial asset you’ll ever manage. Treat the deal accordingly.

The company isn’t going to build this architecture for you.

They’re not evil—they’re just optimizing for their side of the table, which is exactly what we should be doing for yours.

1. Expect the severance.

2. Frame it as standard.

3. Build it together if it doesn’t exist.

4. Add the compounding clause.

5. And sign with the confidence that comes from knowing both sides of your deal are covered.

Create a stronger precedent for all of the leaders who come after you.

The Real Question

Severance negotiation isn’t about pessimism.

It’s about professionalism.

If you want help building this architecture into your next deal—or if you’re already in a negotiation and realize your downside isn’t covered—that’s exactly what I do.

Book a strategy session here.

Stay fearless, friends.

The senior leaders making the most money right now are the ones who asked to get paid less.

Less guaranteed, that is.

From the massive bull market push from ‘08 to ‘20—the COVID hiccup—to the frenzy of inflated activity from ‘21 to ‘24—executive compensation rode a wave that made everyone feel like a genius.

Packages went up because everything went up.

That wave broke.

The last two years have presented a split I’m watching play out in real time across my client base.

On one side—many leaders are feeling defeated and accepting the downward pressure. Settling for deflated packages. Negotiating the same base-bonus-equity structure they’ve always negotiated, just with smaller numbers.

The echo chambers in leadership communities have grown deafening—the downtrodden reinforcing the narrative that this is just what the market pays now.

On the other side—confident senior leaders who get creative.

Who stop negotiating the number and start negotiating the structure. Who propose tying their comp to milestones—and end up making more than they would have in the bull market.

Assuming, of course, that they are as capable as they purport to be.

In a market anticipating poor performance and reducing pay because of it—the true A+ talent is willing to bet on themselves.

I recently helped restructure a Fortune 500 leadership team’s compensation—multiple senior leaders—where we lifted their combined comp north of $10M annually around this exact model.

The old structure was failing everyone—and made top senior leaders ripe for poaching by the competition.

And the competition came aggressively knocking, right after the CEO made public announcements during quarterly earnings calls.

A cutthroat trend that’s increasing during the nuclear arms race to see who wins these AI dollars.

The new structure saved the company between $300M to $500M in value that would have evaporated if even one of those leaders walked during a critical period—and stripped the team out with them—and it put life-changing money in my clients’ pockets.

But this only works if you understand why the traditional structure is designed against you in the first place.

Traditional Structures Fail Everyone

Most people don’t realize that the standard executive comp package is not designed to reward performance. It’s designed to reduce uncertainty and get the deal done quickly.

Base. Bonus. Equity. Four-year vest.

That structure optimizes for presence. Not impact. Not value creation.

For the senior leader:

Every leader walking into a negotiation believes they’re top talent. Very few are willing to back that up with their comp structure. They’d rather take the guaranteed package—higher base, predictable (ish) bonus, time-based equity—and avoid the risk of being measured.

I get it. That instinct is human. Your nervous system doesn’t want uncertainty attached to your paycheck. It wants safety.

But here’s what that safety costs you.

When you crush it in Year 1—when you drive $50M in new revenue or turn around a failing division—what changes in your comp?

Almost nothing.

Your bonus might tick up. Your equity continues its glacial four-year vest. The value you created is captured by the company instantly while you wait years to see a fraction of it.

You’re bearing the execution risk with almost none of the execution upside.

And when it doesn’t work out—when the organization wasn’t ready for what you were hired to do, when the board shifts strategy six months in, when the culture rejects the change agent they recruited—you’re the one explaining a short tenure on your resume.

The guaranteed package didn’t protect you. It just made the failure more expensive to unwind.

For the company:

Hiring the wrong senior leader is one of the most expensive mistakes an organization can make. And the traditional structure makes that mistake maximally painful.

You’re paying full freight from Day 1—guaranteed base, sign-on bonus, equity grants—before you have any evidence the person can deliver in your specific environment.

If it doesn’t work out in 10 months, you’re not just out their comp.

You’re out the recruiter fees, the onboarding cost, the teams they hired who may not survive the transition, the strategic initiatives that stalled, the institutional knowledge that walked out with the predecessor they replaced.

Average executive tenure is shrinking. The cost of a miss is going up. And in this market—where the margin between winning the AI race and becoming irrelevant is measured in quarters, not years—a bad senior hire isn’t just expensive. It’s existential.

The traditional package absorbs none of that risk. It front-loads cost and back-loads accountability.

For the talent firms who place them:

When a firm places a senior leader into a role and that leader doesn’t work out—the firm doesn’t just lose a fee. They may lose the relationship.

Many executive search firms guarantee placements for 12 months. A miss means running the search again on their own dime. But the real cost isn’t the redo—it’s the reputational damage.

The board remembers who brought them the wrong person. Future mandates dry up. Referrals disappear.

A milestone-based structure changes that math.

When all sides define what success looks like before the offer letter is signed—when comp is tied to specific outcomes—the quality of the match goes up. The risk of a bad placement goes down.

There’s a reason advisory firms are circling this space right now. The model is shifting—and the firms that help architect these structures will own the next era of executive placement.

Counterpoint—And Why It’s Actually the Point

The objection I hear most from HR leaders and comp committees is that milestone-based structures take longer to negotiate.

More conversations. More alignment. More complexity.

They’re right. It does take longer.

That is exactly the point.

Companies and senior leaders need to have smarter conversations about what they actually need.

Not vague job descriptions and “at discretion” performance bonuses that nobody can define. Real alignment on what value looks like, what the milestones are, what triggers the upside.

When someone has a meaningful portion of their compensation tied to specific outcomes, they care more about performing. If they don’t perform, the company pays less. If they over perform, the company pays more—and gets dramatically more in return.

This isn’t a new concept.

It’s how every sales organization on earth works.

Close the deal, earn the commission.

But this isn’t commission. Commission rewards transactions. What I’m talking about is rewarding value creation—strategic outcomes, not activity.

We’re not building coin-operated executives.

We’re building compensation architectures where both sides have skin in the game and the incentives are aligned to real value—not a legacy model that persists because that’s the way it’s always been done.

The system resists change—including paying you differently—because the system is designed to protect itself.

That’s Institutional Homeostasis.

And the executives and companies breaking out of that model are the ones winning right now.

The Proof Is Already Here

If you think milestone-based comp is experimental, you haven’t been paying attention.

The Brady Model

When Tom Brady left the Patriots in 2020 and signed with Tampa Bay, the contract was a two-year deal worth $50 million—fully guaranteed. No-trade clause. No franchise tag.

He could have stopped there. He was 42 with six Super Bowl rings. Nobody would have questioned a straight guaranteed deal.

But Brady volunteered to tie an additional $9 million to performance incentives. Up to $4.5 million per year—triggered by top-five finishes in passer rating, touchdowns, yards, completion percentage. Separate triggers for playoff appearances and the Super Bowl.

A player with maximum leverage chose to make part of his compensation contingent on outcomes.

Why?

Because Brady understood something most don’t. When you tie your comp to performance, you aren’t taking a risk.

You’re sending a signal.

You’re telling the other side: I’m so confident in what I’ll deliver that I’ll let you pay me based on results.

The Buccaneers didn’t hear “discount.”

They heard “all in.”

Brady also has the personality to put big hairy goals out there to stay driven—to fuel heavy workouts while his bones beg for him to do anything else.

He won the Super Bowl in Year 1.

Collected the max.

But the incentives weren’t about the money. They were about positioning—telling the organization and the league that he was playing to win, not playing out a contract.

The $250M AI Researcher

Now look at what’s happening in tech.

Meta offered a 24-year-old AI researcher a package worth $250 million over four years—with the potential to earn $100 million in Year 1 alone.

Multiple researchers moving from OpenAI to Meta’s Superintelligence Labs are getting packages in the $100M to $250M range—structured not as salaries but as layered deal architectures with performance conditions, milestone payments, and retention triggers tied to what they actually deliver.

These aren’t comp packages. They’re talent deals.

The stakes are big time right now.

This is how Hollywood has structured talent for decades. How professional sports contracts work. How producers, show runners, and A-list performers get paid—not a flat salary, but a layered architecture of guarantees, bonuses, backend participation, and milestone triggers.

And it’s migrating into the corporate executive suite.

The Rise of Executive Representation

I’m seeing a growing number of executives hand off their negotiations to employment lawyers, advisors, and—in some cases—what can only be described as agents.

Not just for severance. For the entire deal structure.

This is a tectonic shift.

Employment lawyers are the downside folks.

They’re thinking about the divorce—severance protections, termination clauses, non-competes, what happens when things go wrong.

That work matters. Every executive should have it covered.

But most executives stop there.

What I do is the upside.

I’m thinking about the marriage—how to structure the deal so that when things go right, you capture the value you created. Milestone triggers. Performance-based equity acceleration. Comp architectures that reward outcomes, not just presence.

For the talent. For the company. For the talent firm.

I’d argue that you should think this way as well. It’s a much more collaborative and “pie enhancing” mindset.

The downside folks protect you from losing.

The upside folks help you win.

When a senior leader says “let my team handle the details”—they’re not being lazy. They’re being strategic.

They keep their hands clean with the future employer. They maintain the relationship. And their representation fights for protections, milestones, and guarantees that the executive would never ask for directly.

It’s the same reason every professional athlete and A-list entertainer has an agent and a lawyer. The talent focuses on the work. The team architects the deal.

The Fortune 500 is starting to operate the same way.

The Structure Is the Strategy

There’s a name for what happens when you propose tying your comp to outcomes.

I call it The Performance Signal.

It’s the moment you stop negotiating like an employee and start negotiating like an asset.

When you ask for a bigger base, the company hears cost.

When you propose milestone triggers, the company hears confidence.

Same financial outcome. Completely different narrative.

The market is moving here whether you are or not.

• AI talent contracts that mirror Hollywood deal structures.

• Executives bringing in advisors to architect their deals.

• Comp committees experimenting with trigger-based equity because the old model isn’t retaining anyone worth keeping.

The only question is whether you move first—or spend another cycle negotiating base salary increases that don’t compound and equity grants that vest on a calendar, not on value.

I touched on this briefly in my conversation with Lenny Rachitsky.

In the coming weeks, I’ll break down the exact playbook—how to identify the right milestones, how to propose them without sounding like you’re gambling, and how to build a comp architecture that rewards what you actually deliver.

For now, sit with this question:

If you’re not willing to bet on yourself—why should the company?

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

A lot of you are new here.

Good timing.

This past Sunday, I sat down with for a nearly two-hour conversation about compensation negotiation, career leverage, and why the smartest people in tech consistently leave the most money on the table.

If you haven’t listened yet—or want to revisit it—here’s where to find it:

🎥 Watch on YouTube 🎧 Listen on Apple Podcasts 🎧 Listen on Spotify

To the hundreds of new subscribers—both free and paid—who showed up this week: thank you.

Genuinely.

And to —thank you for the platform, the preparation, and the trust. That conversation doesn’t happen if you don’t create the space for it and take a chance with someone new. <3

Now let me earn your attention.

Something We Didn’t Get To

In the podcast, we talked about why sharing your number too early is dangerous. Why the first figure on the table tends to become the ceiling. Why information and timing create power.

But we didn’t get to name the mechanism underneath all of it.

I’ve been trying to articulate this for a while. The best term I’ve landed on is

The Zombie Number.

Here’s what I mean.

Your last compensation figure—whatever you earned at your previous role—doesn’t die when you leave.

It follows you. (Especially if you let it).

It shuffles from recruiter database to recruiter database, from reference check to “market calibration,” from one offer conversation to the next throughout your network.

It’s dead information—no longer reflective of your value, your trajectory, or the scope of what you’re walking into—but it keeps showing up at the table like it has a seat.

You could be worth $2M.

But if your last package was $800K, the system doesn’t see your potential. It sees your price tag.

And every future offer gets quietly calibrated against a number that was set under completely different circumstances—a different company, a different scope, a different market.

That’s the zombie. The dead following you around. And sometimes we do it to ourselves and believe it about ourselves.

It’s dangerous.

You often don’t know it’s in the room. Nobody tells you that the recruiter already pulled your comp history. Nobody tells you that the “generous” offer they just extended started from your old number and worked up 15%—not from the actual value of the role and worked down to fair.

You think you’re negotiating fresh. You’re negotiating against a ghost.

How to kill it:

Control what comp data exists about you and how people think about you before you ever enter the room.

If you’ve ever posted overly tactical or junior milestones or hot takes on LinkedIn, shared salary details with a recruiter “just to get the conversation started,” or answered “what are you making now?” — you’ve fed the zombie!

I wrote about this dynamic early on in this newsletter—Leaders Share Selectively on LinkedIn—and it’s one of the most important pieces in the archive to understand my mindset about this.

When asked about current comp, redirect: “I’d rather focus on the scope of this role and what a fair package looks like for the outcomes you need. What range are you working with?”

Kill the zombie before it sits down at the table.

Because once it’s there, you’re not negotiating your value. You’re negotiating against a past version of yourself.

And we’re not going back there. Are we?

New Here? Start With These

58 articles deep and counting. If you want the concentrated version of what this newsletter is about, these five will get you there:

Why I Finally Called It Quits With LinkedIn — The piece that went viral. Why I permanently deleted my profile, what the math actually looked like, and what it revealed about the gap between clout and cash.

27 “Offensive” Interview Questions That Flip the Dynamic — Stop auditioning. Start auditing. These are real questions from real clients that changed the power dynamic before the offer ever landed.

The 7 Habits of Highly Toxic Companies — Satirical, pointed, and unfortunately accurate. If you’ve ever worked somewhere that “celebrated transparency” while hiding everything, this one’s for you.

How Senior Leaders Build Secret Hype Networks — You don’t have a marketing problem. You have a sales problem. This is how I actually run my business—and how my best clients run their careers.

The Ultimate Guide to Negotiating Your Comp — The comprehensive GAINS framework walkthrough I wrote for Lenny’s newsletter. If the podcast was the overview, this is the operating manual. Give Lenny some love—he took a bet on this topic before anyone else at his scale did.

Thank you for being here.

Whether you found this newsletter yesterday through Lenny or you’ve been reading since Article 1—I don’t take your attention lightly.

The goal hasn’t changed: give you the intelligence, the frameworks, and the language to capture what you’ve already earned.

More soon.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.

Today is an important personal reflection for yours truly—but first, let me tell you what I’m seeing with top senior leaders in the market—and humbly add deeply intentional perspective.

There has been a shift in tone across my client base the last few months.

A shift I can’t ignore.

The anxiety hits different.

A more palpable tension.

It’s not the usual pre-negotiation nerves or the restlessness of being underpaid. Or the annoyance of corporate bureaucracy—or even the always stressful escalation of performance expectations in a tight market.

It’s deeper and heavier. It’s hitting you square in the jaw.

I’m working with leaders running nine-figure P&Ls who can’t sleep. Executives who’ve navigated three recessions and two IPOs—and are telling me, for the first time, that they feel stuck.

Others have nagging health concerns and family challenges they’ve been avoiding during the rut of the grind post pandemic.

Not just stuck in their careers.

Stuck in their lives.

The white collar tech market isn’t providing optimism. And it’s got a compounding effect.

The weight of an economy that can’t decide if it’s recovering or collapsing.

The geopolitical tension that makes every headline feel like a countdown. AI threatening to reorganize your entire industry before you finish reading about it.

And that’s just the macro.

Zoom in and it gets heavier.

• Aging parents who need more from you.

• Kids navigating a school system that feels like it’s failing them.

• A spouse you barely see because you’re both in the trenches battling to combat endless rising costs of living.

• A body that’s trying to tell you something you don’t have time to hear.

And through all of it, you’re expected to lead with poise, negotiate with precision, and show up like nothing is wrong.

And here I am, telling you to share your cards more strategically to maximize your earnings and leverage—which some misinterpret as hiding your true self, being disingenuous, or manipulative.

I get it. I really do.

Because here’s one thing I’ve learned after 15 years and tens of thousands of conversations with leaders: most of what we focus on could be categorized as “champagne problems.”

They are great problems to have.

• We discuss negotiating between two seven-figure offers, not choosing between rent or groceries or gas.

• We debate whether to take the CEO seat or stay as president, not whether you’ll be employed next month.

• We talk leverage—not navigating a child with special needs or caring for a parent in hospice.

But champagne problems still weigh something.

And when you stack them on top of everything else—the real stuff, the human stuff—that weight can metastasize in something unrecognizable and ugly.

So today I’m not writing about negotiation tactics or comp architecture.

Nothing fantastical or seemingly out of reach.

Today I need to go somewhere more important.

Less

We are not dissimilar you and I. And your boss, competitor, or that investor are not all that dissimilar either.

We all have personal motivations and drivers—and we all face the short end of the stick from time to time. Frank Sinatra simply bellows, That’s Life.

I’ve noticed that the people who best navigate all life throws at them and still seem to have their feet under them appear to have a different point of view.

A sort of effortless poise that’s tricky to place your finger on. A collective confidence that I aspire toward. And it’s not luck or that weird hyper optimistic personality that is more annoying than motivational.

And they don’t have some secret to life.

No, they don’t do more. They don’t have more. They don’t know more.

They do less.

They stop trying to optimize every variable and start asking a harder question—one that most people are often terrified to sit with. Especially in a society that idolizes keeping up with the Joneses.

What would your life look like with less?

Less scrolling. Less performing. Less saying yes to things that don’t compound in the direction you actually want to go. Less carrying weight that was never yours to carry.

Not necessarily less work. Less noise.

Less work saying yes to things that compound in the wrong direction.

I call this The Subtraction Premium.

Can you automate it? Can you delegate it? Can you delete it?

Every framework in the business world is additive.

Add a skill. Add a credential. Add a board seat. Add another zero to the comp package.

I recognize the hypocrisy in me of all people writing that. I’m the guy you call to prioritize and accomplish all those things—and am guilty of going overtly “try-hard” to perhaps overcompensate for past sins.

The entire system is designed to make you believe that the next addition is the one that finally makes you feel like you’ve arrived.

But the leaders I admire most—the ones who actually enjoy the lives they’ve built—got there by removing things. Not adding them.

Maybe you feel this way too.

• They remove the toxic board seat that eats their weekends.

• They remove the “necessary evil” of platforms that tax their nervous system.

• They remove saying yes to every introduction, every favor, every ask that comes dressed as opportunity.

While some express boredom in the early weeks following their scale back efforts—as I check in over time, anxiety doesn’t just decrease—clarity compounds.

You ever hear from folks that say, “I don’t think I could ever fully retire and just fish all the time, it would drive me nuts…?”

I’m not suggesting an extreme elimination diet here—although minimalism is a helluva liberating drug. I’m suggesting measured cuts that you can sit with to bring your world into view—into the present.

Subtraction doesn’t just free up time.

It frees up the cognitive bandwidth your brain needs to make the decisions that matter most.

The ones about your family. Your health. Your next move. Your life.

Too often we spend our careers proving we can add value. But I reckon once you’ve climbed the ladder, the harder skill—the one that separates the executives who are successful from the ones who are successful and at peace—is knowing what to subtract.

Staying

The biggest subtraction I ever made wasn’t a platform or a board seat.

It was subtracting the belief that the world would be better without me in it.

I don’t talk about this often—not because I’m ashamed, but because the gravity of it doesn’t fit neatly into a newsletter about executive compensation.

But today it fits. Today it’s the whole point.

There was a version of me—mid-twenties, broke, homeless, sleeping in a skatepark in Roseville, California—who couldn’t see past the next hour.

A version who drank to disappear.

Who used substances—and fast flings—not to feel good but to feel less. Who convinced himself that the people around him would recover faster from his absence than from his presence.

I often contemplated suicide—hovering the safety on a firearm and standing on the sun bleached green railing of the Foresthill bridge.

But I’m still here.

That’s not a sentence I write for sympathy.

I write it because everything—everything—that I’ve built, every client I’ve served, every framework I’ve developed, every word of this newsletter, my wife, my boys, and our future—exists on the other side of a decision I almost didn’t make.

The decision to stay.

There was no dramatic turning point.

No rock bottom movie scene. Just a slow, stubborn, unglamorous choice to keep going. I will say, a timely flip on the radio to Tim McGraw’s “Let It Go” changed my decision one fateful afternoon—and now every time I hear it you can queue the waterworks.

Then I kept choosing it again the next day. And the one after that.

Then I met Mary.

She came from circumstances as brutal as mine—worse even—and had every statistical reason to accept a predetermined future.

But she refused. She had faith—the kind that rebuilds a life from the studs. She had agency and conviction about what her life would be, and she wasn’t afraid to ask for it.

And she had it at twenty years old. Good grief.

She showed me that the story I’d been telling myself—that my future was already written—was a lie.

I’ll write more about this in my upcoming book. But the short version is: Mary showed me I had the agency to save myself.

That changed everything.

On January 1st, 2022, I made another subtraction as Mary and I got serious about having children. I stopped drinking entirely.

Raising children forces you to relive past trauma—but in experiencing your babies grow—the experience matures and heals your trauma. You didn’t deserve that pain, you were just a kid.

I never want my children to experience how substance abuse and domestic violence will slowly rip a family apart.

As I write this, I’m over 1,500 days sober.

However, I didn’t get sober because I had some profound revelation.

I got sober because I finally understood that alcohol was compounding in the wrong direction. Every drink borrows clarity from tomorrow. The interest rate is brutal.

Sisyphus had better odds.

My faith deepened in this season.

I started to see the evidence of something deliberate in my life. Too many close calls. Too many doors that opened when every logical outcome pointed to a dead end. At some point, coincidence stops being a satisfying explanation.

Sobriety didn’t add anything to my life. It subtracted the thing that was blocking everything good from getting in.

And what rushed into that space—once I stopped filling it with noise and poison—was gratitude.

Not the motivational poster kind. Not the “write three things in your journal” kind. Just the peace of knowing how a few key decisions and my present reality would be an unattainable dream otherwise.

The kind where you’re sitting on a porch in Montana with your beautiful partner and two boys and the spring air hits your face and you think—God, thank you—I almost didn’t get this.

Any of this.

That kind of gratitude simply needs space to exist.

And space only comes from subtraction.

Your Brain Can’t Hold Both

Mary told me something years ago that I didn’t believe at first.

I was spiraling—monologuing about how the weight of everything was getting to me as the CEO of Discover Podium.

How I wasn’t sure what to tell my staff who were drowning in the same anxiety I was feeling. You know, small businesses surviving COVID stuff.

She listened, then said two words.

Be grateful.

I pushed back. No way.

She didn’t flinch. “Your brain cannot process anxiety and gratitude at the same time. So be grateful.”

I fat-fingered a Google search to prove her wrong. Harvard agreed.

She was right. A comment I did not mutter vocally.

Here’s why this matters for you—not as a platitude, but as a biological fact.

When anxiety takes over, your brain shifts into threat mode.

The same system that kept your ancestors alive when a predator was circling now fires when you open your inbox, read a headline about tariffs, or sit across from a CEO who’s about to discuss your future.

Your heart rate spikes and your thinking narrows.

The part of your brain responsible for strategic decision-making—the thing you’ve spent your entire career sharpening—goes quiet at the moment you need it most.

You’ve felt this.

The moment a comp offer slides across the table and your mouth says “that sounds fair” before your brain catches up. The meeting where you had the perfect response rehearsed and forgot it the second the room got tense. The Sunday night dread that eats your evening before Monday even arrives.

That’s your chemistry.

But gratitude—real, deliberate gratitude—interrupts the loop.

It activates a different system entirely. One that lowers cortisol, restores clarity, and gives your prefrontal cortex back the oxygen it needs to function.

• You can’t white-knuckle your way out of anxiety.

• You can’t think your way past a threat response with more thinking.

• You can’t simply be tougher and more disciplined—which is likely how you’ve overcome most other things that get in your way. What got you here, won’t get you there.

However, you can replace it.

Gratitude isn’t the absence of anxiety. It’s the antidote.

This is why subtraction matters beyond your calendar and your commitments.

When you subtract the noise—the doom scrolling, the performative obligations, the relationships that drain you, the LinkedIn humblebragging—you create space for gratitude to do its work.

And when gratitude is running the show instead of anxiety, you make better decisions.

You lead with more clarity. You show up for your family without the static in the back of your head.

You no longer have to do challenging things; you get to do challenging things.

For them.

If you think back on how you’ve gotten to where you are today, you can objectively say that in most cases you make great decisions.

If you’re reading this article today, you are already performing in the top percentile of people globally—at least according to what our society tends to value.

Trust yourself to continue—and that your champagne problems are a reason to celebrate.

Gratitude is not soft.

It’s the hardest reframe most leaders will ever attempt.

Because it requires you to stop focusing on additive performance long enough to feel something real.

When your clarity becomes abundant—your ability to negotiate for your life becomes second nature. You won’t even need to call me.

What Would Your Life Look Like With Less?

I ask my clients this question more than any other.

More than “what’s your target comp?” More than “what’s your walkaway number?”

Because the answer reveals everything.

About a decade ago, I worked with a couple in Los Angeles. Husband—a high-profile HBO executive, early fifties, making $1.2M a year. Wife—a CMO in Orange County, earning around $900K.

No children. Eight figures in the bank.

The husband was diagnosed with stage one cancer. His doctor warned that the stress of working would likely kill him—but he was three years short of full pension.

The wife, meanwhile, was laser-focused on landing a higher-paying CMO role. When I pressed on why, the answer was simple—she wanted to finally out-earn her husband. Perhaps to give him permission to stop. But neither of them needed to work. They didn’t even need to live in Los Angeles.

What do you think their life would look like with less?

When she asked what she should do, I told them to take four weeks of PTO in Hawaii and leave their phones behind.

They chose to retire on the flight home.

They’re both still enjoying themselves today.

Most executives only consider what less looks like near the twilight of their career.

They’ve optimized relentlessly—for title, for comp, for prestige, for the next rung—but too many have never stopped to ask whether the ladder is leaning against the right wall.

And in chasing their maximum potential—they often forget to live in the moment. Or worse—they live for someone else’s moment.

Money decreases in value as we age. It’s taxed. Inflated. Stripped away.

Yet time increases in value as we age. It grows scarce.

We’re quick to lose every negotiation by trading time for money.

So, I ask: what would your life look like with less?

When I ask, the room usually goes quiet. Not because you don’t know the answer. Because you do—and you know you can do something about it.

It’s some combination of less.

Less obligation. Less performing. Less carrying the expectations of people who wouldn’t carry yours.

• Sometimes the answer is cutting a board seat you’ve been dreading for two years or quitting a toxic, unethical, or misaligned company.

• Sometimes it’s leaving a city you hate living in.

• Sometimes it’s ending a relationship you’ve outgrown but maintain out of guilt.

• Sometimes it’s tossing the device in your pocket that steals more than it gives.

• Sometimes it’s deleting all social media accounts and becoming a digital ghost.

• Sometimes it’s removing addictive highly processed food, seed oils, sugar, alcohol, and substances.

The answers are always specific. And they’re always obvious—in hindsight.

This week, consider a strategic audit of your life.

Write down three things you’re carrying that aren’t compounding in the direction you want to go.

Be honest. Nobody sees this list but you.

Then ask yourself—for each one—can I automate it, delegate it, or delete it?

You don’t have to act on it today. Just name it. Because the act of naming it—of pulling it out of the background static and putting it on paper—is itself a subtraction.

You’re taking something that’s been quietly taxing your nervous system and forcing it into the light where it loses half its power.

And then write down three things you’re grateful for.

Not the things you think you should be grateful for. The real ones. The ones that hit you in the chest when you’re not performing for anyone.

Your kid’s laugh at dinner. Waking up healthy. A partner who sees through your armor and loves what’s underneath. The career you’ve built—even when it’s heavy—because you built it. That’s yours.

Hold both lists.

The things to subtract. The things to protect.

That’s your compass. Not your comp band, not your title, not the market—that list is your compass.

There's a rule in aviation—if a plane is off by a single degree at takeoff, it drifts one mile for every sixty flown.

The pilot doesn't feel the error. The passengers don't feel the error.

But after enough distance, the plane lands somewhere it was never meant to be.

This is why the audit matters.

You're not looking for catastrophic misalignment. You're looking for the one-degree drift—the thing that feels small today but is quietly compounding you toward a destination you never chose.

Consider:

• A 12 ounce soda a day is 10lbs of extra calories a year.

• 30 minutes of lost sleep every night is a month of sleep debt a year.

• Sitting an hour longer every day increases cardiovascular risk 14%.

I spent the first half of my life adding—clawing, building, chasing, numbing, performing. I spent the second half learning that the things I subtracted gave me more than anything I ever earned.

Sobriety gave me more than any deal I’ve closed. Faith gave me more than any framework I’ve named. My family gives me more before 7 AM than my career gives me all year.

Trust me.

And gratitude—the simple, stubborn, daily practice of noticing what’s already here—gave me back a life I almost threw away.

You don’t need more.

You might just need less.

Ready to discuss your career? Book a strategy session.

Stay fearless, friends.