Most leaders think negotiation starts when the offer lands in their inbox.
They're wrong.
By the time you're reviewing compensation details, you've either built significant leverage or surrendered it entirely.
The painful truth?
The interview isn't just an evaluation—it's the negotiation itself.
I hear about countless leaders coming up #2 again and again—leaving hundreds of thousands on the table and growing more and more frustrated with their careers.
When they finally break through—they'll get blindsided by a lowball offer and start scrambling to maximize value.
Oftentimes, they are so defeated that they only take the deal to live and fight another day.
The pattern repeats with alarming frequency, even among seasoned C-suite leaders. The cost? Often, six or seven figures in lost compensation over a career transition.
It doesn't have to be this way.
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The Invisible Start Line
Repeat after me.
My negotiation doesn't begin with the offer.
It begins with your very first interaction. That LinkedIn message, the first recruiter call, your resume, and yes—even your social media presence.
Every email, every call, and every interview question is negotiation territory. That post you just shared, that comment you left, that recommendation you wrote—all of it shapes your perceived value long before compensation discussions begin.
Hence why, the green "open to work" circle on your profile photo is a death sentence.
The most painful part?
The approach that got you this far—polishing your achievements, enhancing your experiences, scripting answers, and waiting for the next question—is precisely what's holding you back now.
The Back-Foot Trap
Most leaders waste precious interview time trapped on "the back foot."
They arrive prepared to talk about themselves, armed with polished stories of their achievements, expecting to be impressive. However, their focus remains inward rather than outward, reactive rather than proactive, passive rather than strategic.
The conversation typically follows a predictable pattern:
Interviewer: "Tell me about yourself."
You: Delivers rehearsed career summary.
Interviewer: "What's your greatest achievement?"
You: Shares impressive accomplishment.
Interviewer: "Why are you interested in this position?"
You: Offers flattering reasons.
Each perfectly crafted answer leaves you anxiously awaiting the next question, hoping it doesn't catch you off guard.
This defensive posture—constantly reacting rather than leading—undermines your executive presence and surrenders negotiating power before you realize it's at stake.
The Psychology of Power Dynamics
Understanding the psychology behind interview interactions reveals why this approach fails at the highest levels.
Robert Cialdini's principle of authority tells us that perceived expertise dramatically impacts how others value our contributions. But here's the counterintuitive truth—constantly responding to others' inquiries positions you as the evaluated rather than the evaluator.
When you're answering questions, you're implicitly accepting a subordinate position in the power dynamic, regardless of how impressive your answers might be.
This dynamic creates a cognitive frame where you seek approval rather than assess mutual fit. The subtle psychological positioning matters more than most executives realize.
Think about it for a moment.
Who asks more questions in a typical business scenario—the service provider or the client? The vendor or the buyer? The candidate or the decision-maker?
The party with perceived power leads the questioning, while the party seeking approval provides the answers.
Top negotiators understand this dynamic intrinsically.
They don't just answer questions—they transform interviews into consultative discussions where both parties are evaluating fit.
It can be tricky to reverse course and take assertive ownership during stressful interviews, but it's well worth your while.
Transform From Candidate to Consultant
The strongest leaders approach interviews not as candidates seeking approval but as strategic partners evaluating opportunities.
This mental shift—from being interviewed to conducting a discovery consultation—transforms the entire power dynamic. It positions you as a peer rather than a subordinate and creates the psychological foundation for more favorable negotiation later.
The approach is deceptively simple.
- Lead with curiosity rather than credentials.
- Gather information about organizational challenges.
- Explore the motivations of key decision-makers.
- Identify gaps between the current state and desired outcomes.
- Position your expertise as the bridge between problems and solutions.
When conducted effectively, this approach creates what negotiation experts call "expanding the pie"—increasing the perceived value of the relationship beyond the original parameters.
It's your job to identify and create MORE.
Rather than negotiating within the constraints of the defined role, you're reshaping the conversation around the broader value you bring to the organization.
This value expansion drives compensation up—sometimes by hundreds of thousands or even millions of dollars for my clients.
Five Power Questions That Transform Interviews
I believe that the fastest way to determine if someone is the real deal or a fraud is by the quality of the questions they ask.
The questions you ask signal your strategic thinking and reveal more about your leadership than any rehearsed answer ever could.
Here are five high-impact questions that you can use to transform interview dynamics in your favor.
1. The Strategic Challenge Question
Why it works: This question immediately elevates the conversation from role fulfillment to strategic impact. It reveals unstated expectations and positions you as a problem-solver rather than a position-filler.
2. The Previous Leader Question
Why it works: This question uncovers organizational history, potential landmines, and unstated expectations. The response reveals both practical insights and political dynamics that wouldn't emerge in standard interview questions. Plus, you want to know where they are hiding the dirty laundry and how they speak about their former colleagues.
3. The Stakeholder Alignment Question
Why it works: This question exposes potential misalignment among decision-makers and demonstrates your understanding of organizational dynamics. It also helps you identify potential champions and blockers.
This approach also elevates the leader you're speaking with as having their own valued perspective and helps them feel seen.
4. The Forward-Looking Question
Why it works: This question uses future-focused framing to create a shared vision of success. It subtly positions your relationship as a partnership rather than an employer/employee dynamic and provides concrete metrics for success.
You help the team visualize you as the solution to their problems in a future utopia.
We call this selling the vacation.
When they think about you and your competition, they're more likely to think about you positively because you already helped their brain fire the neurons necessary to see you as the winner in your hypothetical utopian scenario.
5. The Missed Opportunity Question
Why it works: This question demonstrates intellectual humility and strategic awareness at the same time. It catches most executives off guard because nobody asks it.
They'll often reveal their deepest organizational challenges, personal concerns, or unspoken expectations that wouldn't surface in structured interviews.
The response typically contains the most valuable information of the entire conversation — the thing they genuinely want you to know but weren't directly asked about.
It creates an authentic moment that shifts the dynamic from formal assessment to collaborative problem-solving.
Often, it will give you enough additional meat on the bone that you'll need another conversation to fully explore the impact of what you learned.
Your only goal is to keep the interview process progressing with you as the leading candidate.
You won't win the deal in a single call.
Your next step is to drive forward and suggest the next step.
Never wait to hear back. Don't wait to "be kept in mind."
If you hear this, you've not done enough to secure the momentum necessary to drive your leverage.
I always recommend that you set the following steps to force them to address their interest in you face-to-face — and — drive a scarcity mindset about how valuable your time is (by not being available again for several days).
These questions don't just gather information—they reshape how the interviewer sees you. They transform you from a candidate to be evaluated into a strategic partner assessing mutual fit.
Red Flags
If you recognize these patterns in your interview approach, you're likely surrendering negotiation power before you realize it's at stake.
You spend more than 70% of the interview talking about yourself rather than exploring their challenges. This mistake positions you as the seller rather than the buyer.
You struggle to articulate the company's core challenges beyond what's publicly available. This signals surface-level research rather than strategic insight and indicates that you need to ask deeper diving questions.
You focus exclusively on your functional expertise rather than broader business impact. This mistake positions you as a skilled executor rather than a strategic leader. Spend more time navigating the cross-functional challenges and advocating for everyone to win together.
You wait for formal negotiations to discuss value creation. By then, you've already established your position in the power hierarchy, and your negotiation power will be severely limited.
You end interviews with logistical questions ("What are the next steps?") rather than strategic ones that advance the relationship.
These patterns don't just impact the offer—they fundamentally shape how you're valued throughout the entire relationship with the organization. They should beg to speak with you again because you've demonstrated so much value in a single call.
The Negotiation Reset
If you're already deep in an interview process where you've been playing defense, don't panic. You can still recalibrate the dynamic.
- Shift your mindset from proving your value to exploring mutual fit.
- Schedule a follow-up conversation specifically to share value and ask more strategic questions.
- Frame the shift as professional diligence.
"I've reflected on our conversations and have some new ideas to share with you—plus a handful of questions that will help me better show up for the team. What's the chance you're open Tuesday afternoon or Thursday morning?" - Come prepared with questions that demonstrate a sophisticated understanding of their challenges.
- Listen for gaps between what they need and what they've asked for in the role. Assess where the misalignment in the executive leadership team is and dare to bring it up and challenge the approach.
Adapting your interviewing methods will signal mature leadership and can reset the negotiation dynamic even later in the process.
The Power of Leading with Questions
Remember, by the time they make you an offer, you've either developed your negotiating power or surrendered it.
The executive who asks sophisticated questions is perceived differently from the one who provides polished answers.
The first is evaluated as a peer, the second as a subordinate.
The first is invited to co-create solutions, and the second is to execute them.
The first negotiates as a strategic partner, and the second as a resource to be acquired.
The difference in compensation outcomes isn't just about negotiation tactics—it's about the fundamental positioning that happens long before the offer letter arrives.
In your next interview, try shifting the balance. Ask more questions, lead with curiosity, and explore both organizational challenges and personal motivations.
You'll find gaps, opportunities, and ways to create value that others miss.
And when the offer finally arrives, you won't be negotiating from a position of weakness—you'll be finalizing a partnership where your value has already been established.
Stay fearless, friends.
