"How much money do you want?"

"What's your number?"

"What's it going to take?"

Your answer to these questions can be the difference between zero and $15 million at exit. Between retiring at 45 and never retiring at all. Between your kids attending Ivy League schools or no school at all.

I've led hundreds of negotiations for executives, many with 7 and 8+ figure deltas at stake.

I ran a poll about how to answer the question, "How much money do you want?" — and 77% of executives responded incorrectly.

When 3 in 4 executives answer basic negotiation questions catastrophically wrong, I know there is a significant financial opportunity for you and other Execs and the City readers to grab hold of.  

After all that back-and-forth, one truth remains constant: how you handle compensation questions will make or break your career.

Before you dive into the deeper read, I must note that I am concentrating on number values, as money is the universal language of perceived value.

However, money is simply one negotiation factor.

Negotiating time off, flexible hours, consulting/advisory work, severance, title, role, parental leave, promotions, equity, healthcare, and other benefits may be more important to you than straight cash.

Consider: You can always get more money but can't get more time. Negotiate accordingly.

While you dissect this article, assess what you value most and use your findings to structure the right negotiation strategy.

Today's article isn't just about leaving money on the table. It's about understanding the deeper game—which starts long before anyone mentions numbers.

Why This Question Is More Complex Than You Think

"How much money do you want?" has nothing to do with money.

It's a power play masquerading as a courtesy—the professional equivalent of showing your cards before the first bet.

That warm, helpful recruiter voice asking about compensation "just to make sure we're aligned"?

Pure theater.

They'll tell you it's to save everyone's time. How thoughtful.

But here's what's really happening: you're being asked to anchor your value before anyone's bothered to understand it.

This question appears early—usually in the first screening call—for one reason: to establish dominance.

To get you to anchor low, negotiate against yourself, and thank them for the privilege.

And it works.

Especially on middle managers — but apparently on approximately 75% of senior leaders, too.

Yikes.

After hearing, "How much money do you want?" — how you handle your answer will echo through your career.

Your response doesn't just set the financial trajectory for your next role—it creates the blueprint that future employers will follow.

You're not just having a one-time conversation when you share compensation details with recruiters.

That information lives in their databases and networks, shaping how you're positioned for opportunities years into the future.

Each compensation discussion becomes part of your professional record, influencing the roles and offers that come your way.

Further—every executive who caves early creates a ripple effect, dragging down compensation for an entire generation of leaders.

It's corporate natural selection in reverse—the strong setting the bar low for everyone else.

Here's why I roll my eyes at industry compensation benchmarks, no matter how many fancy logos are on the report.

They're averaging mediocrity.

When approximately 75% of executives negotiate poorly, why would you want their "market rate" to define your worth?

Negotiating well is bigger than your next direct deposit.

When you negotiate from a position of weakness, you're not just leaving your own money on the table—you're building the table everyone else will have to sit at.

Think bigger than your bank account for a moment.

That VP who comes after you? They'll be negotiating against the ceiling you created.

Your compensation negotiation isn't just about you—it becomes a reference point that shapes opportunities for those who follow.

This ripple effect helps explain why pay inequities persist.

If you accept less than your worth, you can inadvertently constrain compensation for your successors, perpetuating historical disparities across entire talent pools.

And years from now, when top talent ghost your job postings, you'll understand why—your compensation ceiling became their floor somewhere else.

Let's get ruthlessly selfish for a moment.

Imagine trying to build a world-class team when your value is capped at 70% of the market.

Are the A-players lining up to work for someone who couldn't negotiate their worth?

No.

Your weak negotiation today becomes your leadership handicap tomorrow.

A rising tide lifts all ships, but right now? You're the captain dropping anchor in the kiddie pool.

Think I'm being dramatic?

Let me paint you a picture: A single fumbled response here can cost the average executive $100,000 annually.

Over a decade, that's a million dollars—before we even talk about equity, bonuses, or compound interest.

A single fumbled response for my average client? It could cost them multiple 7 and 8 figures.

You need to get this right.

Three Levers That Control Your Financial Future

Most executives think negotiation is about tactics and scripts.

They're wrong.

It's about mastering three fundamental principles that determine your fate long before you ever discuss numbers.

Every negotiation hinges on information, timing, and power.

Master these three levers, and you'll control any compensation discussion.

Fumble them, and you'll be playing catch-up from a position of weakness.

The problem is that most executives are already losing the negotiation game before they even know they're playing.

They're reactive instead of proactive, waiting for the negotiation to "start" when it began months ago.

This negotiation blind spot is more dangerous than a mere lack of skill—it's the confident incompetence of executives who don't realize they're playing checkers in a chess match.

Think about it.

Every LinkedIn update, every casual conversation with a recruiter, every industry event you attend—they're all part of the negotiation ecosystem.

The moment you enter the market, whether actively or passively, the game is on.

And that "How much money do you want?" question?

It's where these three levers collide in a perfect storm, separating exceptional executives from the merely qualified.

Let's break down how these dynamics actually work in the real world.

Information: Everything Can And Will Be Used Against You

Let's get clinical for a moment. Negotiation is warfare with information as ammunition.

Every piece of data you share—or withhold—shapes the battlefield.

Think you're just having a friendly chat with a recruiter?

Think again. That casual conversation is reconnaissance.

Your LinkedIn profile? That's your billboard.

Those "quick catch-up" calls? They're intelligence-gathering operations.

Information isn't just what you deliberately share—it's what you're constantly broadcasting:

• Your resume tells a story.
• Your social media whispers your desperation (or confidence).
• Your email response times (and wordy buzzword-laden diatribes) signal your urgency.
• Your network hints at your real value.
• Even your silence speaks volumes.

And let's address the elephant in the room: Your age, gender, race, and even how you look will factor into the equation—whether we like it or not. Pretty privilege is a thing.

Welcome to the real world.

The key isn't to pretend these factors don't exist but to understand how they influence the information game and how you can adapt.

Want to know why long-term employees usually make less than new hires?

Simple: The company already has the most dangerous information possible—proof of what you'll accept.

They know your price, so why would they shop at Neiman Marcus when they've got you at Walmart rates?

Every "getting to know you" conversation is a data-mining expedition.

That recruiter? They're building a dossier that will determine your future earning potential.

Everything you say can and will be used to cap your compensation.

The first rule of negotiation: Information is power.

Timing: When You've Lost Before You've Begun

"When should I start negotiating?"

If you're asking this question, you're already behind. Way behind.

I wish 100% of executives who come to me for negotiation help—came sooner.

They wait until they have an offer in hand, wanting to know if it's fair or how to counter.

By then? I'm not a negotiation coach—I'm running a salvage operation.

As a rule of thumb, you don't get what you're worth—you get what you negotiate. And that's often not fair.

Let me paint you a familiar scene:

"Jacob, I just got an offer. Is it competitive? Should I counter?"

My response is always the same: "What have you already told them?"

And that's when the blood drains from their face.

• They've already revealed their current salary in a "casual" chat.
• They've shared their target range to "save everyone time."
• They've mentioned their urgency to make a move.

Each piece of information, shared at the wrong time, has cut their leverage in half. By the time they reach me, they're negotiating with both hands tied behind their back.

We can still gain 20 maybe 30% in these instances, but not 300% or more like we can with a fully strategic playbook.

This isn't just about poor timing—it's about poor strategy.

Think about it: Would you start a chess match after letting your opponent remove half your pieces? Would you enter a poker game after showing your hand? Yet that's exactly what most executives do when they mistime their negotiation moves.

The most dangerous part? These timing mistakes often feel like the "right" thing to do:

• Being transparent about your current compensation (trap).
• Sharing your expectations early to "be efficient" (trap).
• Mentioning your other opportunities too soon (trap).
• Waiting for the "right time" to negotiate (biggest trap of all).

Remember: There's no such thing as a casual conversation when you're an executive in the market.

Every interaction is part of your negotiation timeline, whether you realize it or not. The competition is too smart for you to be naive.

The best time to start negotiating was a year ago. The second best time is now—but only if you know how to play the long game.

Further—haste equals risk.

Employers will spend months meticulously evaluating executives through endless interviews—then suddenly demand you make a life-changing decision in 48 hours.

This manufactured urgency isn't an accident; it's a negotiating tactic designed to rush you into accepting their first offer. The asymmetry is striking—and strategic.

Why?

Why can't you slow down to improve your due diligence now that you have won the offer and have the leverage?

It's not common precedent to do so—so asking to slow down is uncomfortable.

Most executives rush to close when they receive an offer—eager to end the discomfort of being in the market and start earning again.

But this instinct betrays them at the precise moment their negotiating power peaks. They surrender their strongest position in a hurry to feel settled.

This is backwards.

Consider the dynamics of urgency: Once a hiring manager has mentally committed to you as their candidate—perhaps even announced it internally—walking away becomes incredibly costly.

They'd have to restart a months-long search, explain the failure to their team, and potentially damage their reputation.

Now, imagine you're prepared to walk away because the offer falls short of your minimum.

Which scenario costs the hiring manager more: paying you an additional 20% or admitting defeat and restarting their search from zero?

The truth is, your urgency to close and their urgency to hire are radically different forces.

When you understand this—and more importantly, when you learn to leverage it—you hold unprecedented power in the negotiation.

But you must resist that instinct to rush toward closure just as the game turns in your favor.

Power: The Art of Walking Away

Want to know who has the real power in a negotiation?

It's not who has the bigger title, deeper pockets, or fancier office.

It's who can walk away.

Let me be brutally honest. If you need this job, if this is your only option, if your runway is running out—you've already lost the power game.

You're negotiating with a gun to your head, and the other side can smell it.

Here's what real power looks like:

• Multiple opportunities in play.
• A stable financial position.
• Deep market intelligence.
• The genuine ability to say "no."
• Being selective.

But here's where it gets interesting: Power isn't just about having alternatives—it's about the perception of alternatives.

Think about poker. Who has more power?

The player with a strong hand who looks nervous or the player with a mediocre hand who exudes confidence?

In negotiation, just like in poker, perception often trumps reality.

The most dangerous position?

When they know your alternatives (or lack thereof), but you don't know theirs. That information asymmetry creates a power vacuum that will eviscerate your leverage.

This is why I laugh when executives proudly tell me they're "transparent" about their job search.

Congratulations—you've just broadcast your desperation to the market. That's not transparency; that's surrender.

Real power comes from optionality.

Every additional opportunity you have is another chip in your stack, another card up your sleeve, another reason you can look across the table and say, "No, that doesn't work for me" without your voice shaking.

Further, executives who grow confident in creating optionality for themselves naturally become more assertive negotiators because if they lose a deal, they believe in themselves enough to make another.

Consider a top sales rep with a thriving pipeline.

They've got ten solid opportunities and need just one to hit their quota. When negotiating with their most promising prospect, they can confidently push for better terms because they know nine other deals could close instead.

That's negotiating from strength—when walking away is a real option, not just a bluff. The difference in posture and results is unmistakable.

Remember: The person who cares least about making the deal usually gets the best terms. You have unlimited power simply by saying no.

Compensation Responses To Consider

Let's get tactical.

Below are response templates that have created millions in executive compensation gains by establishing a more respectful foundation to start negotiating.

But remember—it's not just what you say, it's how you say it.

Deliver these with relaxed confidence, as if you're having a casual conversation with a partner.

The Strategic Deflection:

Why this works: It demonstrates strategic thinking while subtly highlighting your value proposition. You're not avoiding the question—you're elevating the conversation.

The Value-First Approach:

Why this works: It frames compensation as a natural outcome of mutual fit, not a barrier to entry. The closing question is particularly powerful—it's hard to argue with reasonableness.

The Sophisticated Package Play:

Why this works: It demonstrates experience while maintaining control. Plus, it often prompts them to share their compensation structure first.

When They Push Back: The Red-Line Responses

Sometimes, they'll insist on a number.

Here's how to handle it without surrendering power:

The Value Flip: "Based on my track record of [specific achievement], what would you consider appropriate compensation for someone who can deliver similar results here?"

The Range Reverse: "Perhaps you could share the range you're working with? I can quickly confirm if we're in the same ballpark."

The Graceful Exit:"I respect your position. Since compensation seems to be a crucial next step for you, and I'm not comfortable discussing it yet, perhaps we should pause here? I'm happy to resume once we've established a mutual fit."

Critical Pitfalls to Avoid

1. Never apologize for deflecting the question.
2. Don't get defensive—stay relaxed and confident.
3. Avoid hypothetical ranges—they become anchors.
4. Never cite your current compensation.
5. Don't rush to fill in silence after your response.
6. Never negotiate against yourself.
7. Never be so sure of your worth that you wouldn't accept more.

The Power Move Nobody Talks About

Ask yourself: If you were in their shoes, wouldn't you want to know the compensation expectations upfront?

Use this perspective to deliver your deflection with authentic empathy:

"If you were in my shoes, wouldn't you want to fully understand the opportunity before discussing numbers? I've found that rushing to compensation often leaves value on the table for both sides. Shall we explore the role's impact first?"

Or

"If you were in my shoes, what would you share?"

This response transforms potential conflict into collaboration. It's not saying no—it's a pattern interruption that forces the other party to think deeply and reveal more information.

Remember — You'll look smarter when you share this article. So be the top executive with all the good tips.

Stay fearless, friends.

Master these principles. Get the complete blueprint in my job search course below.

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