Most executives think they're good negotiators.
They're wrong.
The painful truth? Your negotiation skills are likely costing you millions.
I see it constantly at the highest levels.
Recently, a client renowned for being a hellacious negotiator nearly negotiated themselves out of $200,000 in an uncomfortable confrontation with their CEO.
Their mistake?
Being too quick to compromise on a miscommunication.
We caught the error and framed a stronger counter approach that saved my client the cash.
Even those known by peers to be the best negotiators are subject to significant miscues, including yours truly.
The pattern repeats with alarming frequency among seasoned PE partners and Fortune 100 CEOs.
The cost? Often, eight figures in lost compensation over a career.
Here's what most don't realize. True negotiation mastery isn't about the moment of confrontation. It's about what happens long before you ever reach the table.
While average executives polish their LinkedIn profiles, hoping for inbound opportunities, elite leaders are methodically engineering their next three moves.
The difference isn't about skill—it's strategic preparation that meets discipline and habit.
For the sharpest and most desirable leaders, negotiations begin months—or more likely years—before a meaningful transaction.
They create an overwhelming groundswell of unfair advantages through disciplined habits that pay compound interest when the timing is right.
Putting several irons in the fire and stoking them regularly, if you will.
The most painful part? The strategies that got you this far are often exactly what's holding you back now. Your impressive career, built through skill and determination, might work against you.
Your career is no longer about proving you are impressive but delivering returns that only your experience can create.
I've seen a clear pattern after guiding over 3,500 clients and lifting over $300M in compensation gains. Negotiation isn't about talent or credentials. It's about principles and anticipation. It's about seeing around corners and smoothing friction before it becomes problematic.
Hell, I even had a conversation about this on Tuesday with a Hollywood agent where we're anticipating challenges with a new project for Pitt and Clooney—and a second project with Michelle and Barack Obama.
It's important at all levels.
Today's wake-up call is for reactive executives coasting through their careers, waiting for opportunities instead of creating them.
Let's fix that.
The Power Dynamic Reality Check
Most executives approach negotiation like a boxing match that begins with the first offer.
Fatal mistake.
This reactive mindset puts you at a massive disadvantage before stepping into the ring.
More critically, viewing negotiation as confrontation instead of collaboration limits your potential outcomes before you start.
Elite executives understand that true negotiation power is built in the shadows long before the first conversation. They're architects of strategic advantage and masters of proactive opportunity creation. While others wait for the bell to ring, they've already designed the outcome.
Here is a stark example.
I recently watched a Fortune 1000 executive lose a $1.8M+ opportunity through misplaced trust. Despite their experience, track record, and competing offers, they failed to secure their strategic foundations.
Their fatal flaw?
Trusting another leader as their champion without doing the work to ensure they indeed were. That so-called champion later orchestrated their termination instead of supporting their promotion.
Consider these power dynamic indicators:
- When was the last time you expanded your network without an immediate agenda?
- Do you know who calls the shots at your target companies?
- Have you built genuine relationships with company leaders before needing their help?
- Are you cultivating multiple serious opportunities or banking on a single conversation?
- When did you last contribute to your network without expecting anything in return?
- Do you maintain meaningful connections with influential leaders, or only reach out when you need something?
If you're not habitually executing these elements, you're already behind.
But here's the good news—I'm about to share the playbook that has helped my clients secure extraordinary outcomes consistently.
My approach isn't theory or conventional wisdom. It's a battle-tested process that transforms how elite executives approach negotiation.
The difference between good and extraordinary outcomes often isn't skill or credentials—it's strategic preparation and positioning.
Let me show you how to build both.
ThinkWarwick GAINS© Framework
Every successful negotiation begins with establishing meaningful leverage.
Whether you're months away from your next opportunity or actively navigating complex discussions, the GAINS© framework helps identify where to focus your efforts to maximize your position.
Here's a brief overview before we get into the tactical specifics of each phase.
Gather: Build your strategic foundation by deeply understanding the company, key players, and market context before formal conversations begin.
Align: Focus on understanding challenges and demonstrating relevant solutions rather than simply showcasing credentials. The goal is a meaningful connection, not highlighting functional acumen.
Influence: Create advocates by showing how your experience can help solve organizational challenges. Build momentum through consistent demonstration of value.
Navigate: Handle complex discussions with a collaborative mindset. Know when to advance positions and when to focus on relationship building.
Secure: Close agreements effectively while strengthening relationships for future opportunities.
Let's explore how each phase works in practice.
Gather Intel
The most valuable intelligence lives hidden between org charts and public statements.
Elite executives master three domains that create real leverage, while others only scratch the surface.
The first domain is Organizational Dynamics—where true power often defies the formal hierarchy.
I recently watched an SVP candidate torpedo a $2.8M opportunity because they over-indexed on impressing the CEO, missing that the Chief of Staff held unofficial veto power over executive hires.
During their interview with the CoS, they treated it as a formality rather than recognizing it as a critical advocacy point. That mistake cost them millions in lost compensation.
The real power structure in any organization is a web of relationships, favors, and historical alliances that you won't find in any press release. And yes, sometimes nepotism and beyond.
During the Gather stage, ask yourself the following:
- Who do people consult before making decisions?
- Which former executives, failed strategies, or mistakes still shape current thinking?
- Which rising stars have the CEO's ear?
- What are the underlying drivers that aren't often voluntarily shared?
Understanding these hidden power centers isn't just helpful—it's critical to navigating complex organizations and creating unfair advantages.
The second domain is Decision-Maker DNA—because, at the executive level, processes don't make decisions; people do.
One of my clients landed a $3.2M annual package largely because we worked to understand their future boss's pattern of betting big on executives who had survived public failures.
We knew this leader's risk tolerance, what behaviors they rewarded, and most importantly, what kept them up at night. This deep understanding of decision-maker psychology shaped everything from initial conversations to final negotiation.
We used that intel to build advocacy and leverage throughout the entire process. When others saw a standard interview process, we saw a choreographed dance of influence.
The third domain is Market Context—but not surface-level trends anyone can Google.
Elite executives develop an intimate understanding of pressure points that create leverage. They know—or can anticipate intuitively—which divisions are missing their numbers, which critical roles have been open too long, and which strategic shifts are being contemplated in the boardroom.
They track where companies are going, where they've been, and what pain they will feel next. This foresight creates opportunities before others even see them coming.
The Red Flags:
- Your research stops on LinkedIn and in press releases.
- Your network lacks board members and PE partners.
- You're not tracking former executives' moves.
- Your intelligence feels comfortable and obvious.
- You start digging only when you need something.
- You're afraid to ask questions that challenge the status quo.
The difference between good and extraordinary compensation isn't necessarily about having better credentials—it's about knowing which pressure points matter most and how to use them.
While others rely on public data, elite executives build intelligence networks that create real leverage when it matters most.
They're not just gathering information but building the foundation for unfair advantages that compound over time.
Align Authentically
Most executives try to impress in interviews. Elite executives focus on creating alignment.
The difference isn't just semantics—it's a fundamental shift in approach that transforms the power dynamic.
Instead of trying to prove yourself worthy, you're evaluating mutual fit and demonstrating peer-level understanding.
I recently worked with a design leader to convert a standard interview into a 7-figure opportunity by shifting one fundamental dynamic.
Instead of presenting their prestigious big-company accolades (which they had plenty of), we engaged the entire leadership team in an enthusiastic discussion about how the company would be perceived as an industry hero by making a significant investment in innovative design.
The difference?
While other candidates listed achievements, we created authentic alignment through shared problem-solving.
Consider these contrasting approaches I witness every day during executive discussions.
Weak: "I have 15 years of experience leading sales teams and consistently exceeded targets..."
Strong: "Your challenges with sales remind me of a similar situation at [Company]. We discovered that the root cause wasn't our process but our product positioning. I'm curious, how aligned are your sales and product teams on ideal customer profile?"
The weak response positions you as an applicant listing credentials. The strong response establishes you as a peer exploring solutions together.
The difference in perceived value is astronomical.
This transformation happens through three critical elements that elite executives master:
The first is Strategic Storytelling—but not the kind you're likely thinking about. I'm not talking about polished success stories and scripts. I'm talking about raw, relevant experiences that create immediate connection.
A CMO client recently landed a new role by sharing a story about a failed career transition—not to showcase resilience but to explore how that experience shaped their approach to due diligence and their prospective employer's current challenges.
They weren't trying to impress—they were ensuring alignment to avoid another career mistake.
The second element is Authentic Curiosity—not surface-level questions but a genuine exploration of complex business problems.
Kickass questions demonstrate competence and humility—a powerful combination that transforms interviews into strategic discussions.
I watched a COO candidate flip the power dynamic by asking the CEO questions no other candidate dared to ask about their go-to-market challenges.
One was:
That conversation led to landing a big role being created specifically for them at over double their initial target.
The third element is Future-Focused Problem Solving.
Instead of riding on past achievements, elite executives engage in real-time strategic thinking about future challenges. They're not just interviewing; they're already solving problems. I call this selling the vacation.
Instead of waiting to be drilled with questions by a gauntlet of high-profile executives, a recent client turned an intimidating panel interview into a collaborative strategy session about international expansion challenges.
The result?
They created such powerful alignment that the company expanded the scope and compensation.
The Red Flags:
- You spend more time talking than listening.
- Your stories focus on past glories rather than future value.
- You use rehearsed answers instead of authentic responses.
- You try to impress rather than connect.
- You position yourself as an applicant rather than a peer.
The difference between a standard executive interview and a transformative career opportunity often comes down to this.
Are you trying to impress because you don't think you belong in the room—or are you creating real alignment because you know you belong there?
While others rehearse their achievements, elite executives create connections that transform power dynamics into bar-raising outcomes.
Influence Momentum
Elite executives understand that successful negotiation requires more than convincing the hiring manager—you need advocates throughout the organization.
Most executives severely underperform when influencing from the outside—focusing solely on the immediate decision-maker while ignoring the broader organizational dynamics that can make or break their success.
Creating real influence requires a sophisticated understanding of how power flows through organizations.
It's not enough to impress in interviews—you need to generate excitement and advocacy across functions and levels.
The key is understanding that influence isn't about manipulation but creating real value in every interaction.
Elite executives master this through three critical elements.
The first is Strategic Story Selection—which must resonate across functions. Your stories must cater to each person's drivers and demonstrate your understanding of functional expertise and broad business acumen.
For example, I'll return to the sales challenge that was actually a product alignment issue in disguise.
You could raise the story like this.
The second element is Relationship Building—which must create immediate rapport and organic advocates.
Every interaction is an opportunity to build support.
One client turned a potential blocker into her strongest champion by deeply understanding his concerns about the finance transformation and incorporating his insights into her strategy. She didn't just hear him out—she made him part of the solution by using forward language such as, "As we solve this together, what will we tackle next?"
That relationship proved crucial later when compensation discussions hit a snag.
The third element is Value Demonstration—which must generate continuous excitement. Instead of telling people how great you are, show them how you'll improve their lives. Value demonstration creates natural advocacy because people support what they help create.
This approach is most effective in thank you and follow-up emails where you create momentum by teasing ongoing value instead of simply restating why your experience is excellent and looking for guidance on the next steps.
For example.
The Red Flags:
- You focus solely on the hiring manager.
- Your examples don't relate to their specific challenges.
- You talk about what you've done instead of what you'll do.
- You fail to build champions across the organization.
- You miss opportunities to create advocates.
The difference between landing a role and creating a groundswell of support comes down to this: Are you trying to get through the interview process, or are you building momentum that makes you the obvious choice?
While others focus on impressing one decision-maker, elite negotiators create a wave of advocacy that makes their selection feel inevitable.
Navigate Complexity
You're always going to run into complexity.
But since you're already a diehard advocate of Execs and the City—you no longer treat negotiation as a single conversation about compensation. You can better anticipate the sophisticated dance of influence, timing, and strategic pressure.
Too many times, I've watched talented executives destroy multi-million dollar deals by rushing to close, being too quick to compromise, missing signals, and being afraid to confront the uncomfortable.
Hell, this even happens with clients who work with me, most often when haste and stubbornness win over a negotiation's evolving and calculated ebb and flow.
Navigation requires mastering three critical elements simultaneously.
The first is Power Dynamic Management—which must maintain relationships while advancing position. Success isn't about dominance but creating mutual value (expanding the pie, so to speak) while steadily building leverage.
Consider this client example.
A C-suite candidate received an offer they thought was strong. Instead of accepting immediately, they responded with:
This response maintained momentum and signaled that the deal would be accepted while creating space for value creation. We ultimately secured a package 35% above the initial offer.
The second element is Strategic Patience—which prevents value destruction. Rushed negotiations almost always leave money on the table. Haste = risk.
A C-suite candidate in the F1000 I worked with was negotiating with three companies simultaneously.
Instead of jumping at the first solid offer, we used the following:
This approach kept all options alive while building trust (and scarcity) through transparency. The result? A final package we navigated with a multi-seven figure signing bonus.
The third element is Complex Stakeholder Management—which requires sophisticated relationship skills across multiple parties.
One client masterfully managed five stakeholders during their negotiation by:
- Keeping each party updated on progress without revealing specifics.
- Using subtle signals to indicate market interest without appearing mercenary.
- Building genuine excitement about future collaboration.
- Never allowing urgency to override strategy.
The Red Flags:
- You rush to close without complete diligence.
- You become adversarial or defensive.
- You negotiate without alternatives.
- You let emotions drive decisions.
- You damage relationships during negotiation.
The difference between good and extraordinary outcomes often comes down to whether you're flying by the seat of your pants or planning multiple moves ahead.
While others rush to close, elite executives orchestrate sophisticated negotiations that create maximum value for all parties.
Secure Success
Securing isn't just about getting the offer—it's about setting yourself up for sustained success.
Lots of leaders win roles and also get fired within 18 months. While it's not always within our immediate control, we all aim to do better.
I've watched too many executives fumble at the finish line, focusing so intently on immediate gains that they compromise their long-term leverage.
One recent example.
A prospective client of mine was terminated and lost over $20 million by rushing through final terms without proper documentation of their equity acceleration provisions.
Slowing down and legal support could have avoided this gut-wrenching mistake.
Success at this stage requires mastering three critical elements.
The first is Agreement Engineering—which goes far beyond basic offer acceptance. This is about creating crystal-clear alignment that prevents future friction.
At the highest levels of leadership, involving employment attorneys and working through legal is expected. Red lines and clarifications are expected.
Miscommunication and attorneys changing a single word can cost you millions and create uncomfortable tension with you and your future colleagues when you have to find a way to challenge them.
Many executives crumble and compromise instead of challenging the language and broaching any misalignment head-on.
I get it—these are high-stakes moments.
Attorneys are intimidating. CEOs and investors are intimidating. And it always seems like they hold the power to make or break your career with a single misstep.
You must embrace uncomfortable conversations and bring them up. Oftentimes, the solution is to consult your network or an experienced attorney or coach yourself.
Be wary, though. Even those with the best intentions may not know how to help you or miss critical conflict points.
Consider that if you don't know how to bring up a point of conflict, it's not because you shouldn't bring it up; it's simply that you don't know the best approach yet, and you must slow down.
The second element is Value Acceleration—which means you start delivering before day one. Elite executives create momentum during the final negotiation phase throughout their entire tenure.
A recent COO hire masterfully demonstrated this by:
- Sharing relevant industry insights during final discussions.
- Connecting key stakeholders to valuable resources.
- Identifying immediate impact opportunities.
- Setting up informal conversations with future direct reports before their start date.
Their value was evident before officially starting, creating leverage for future negotiations.
Now isn't the time to complain about working for free—which I recognize is dangerous territory, especially for those predisposed to being taken advantage of. Now is the time to drive value—because if you don't—your competition will.
I'm not suggesting that this is a healthy working culture, it's simply reality, and we would be naive to think otherwise.
Further, if you're racking up a seven-figure salary and complaining about this, I'd like to introduce you to the world's smallest violin.
The third element is Foundation Building—which ensures every agreement sets you up for long-term growth.
Years ago, one client delayed their three-week start date to document their performance metrics properly, reporting structure, and future compensation triggers.
That patience paid off with a $1.2M acceleration in their equity vesting when the company was acquired.
Never assume a shared understanding of corporate language—it's a minefield of misaligned expectations.
Misalignment happens constantly with terms like:
- "Significant equity"
- "Performance-based bonus"
- "Growth opportunity"
- "Strategic leadership role"
- "Competitive package"
Each party often interprets these phrases through their lens of experience and expectation.
Instead of assuming alignment, get specific:
Even seemingly straightforward terms need clarity.
A client recently discovered that "fully remote" actually meant "remote until our new office opens next year."
Another found that "change agent" meant, "Please don't change my team if it means firing my friends."
Slow down. Define terms. Get specific.
Your career is too valuable to leave to interpretation.
The Red Flags:
- You focus only on immediate gains.
- You rush through the final documentation.
- You stop networking after securing the role.
- You fail to create precise alignment on expectations.
- You neglect to build your future leverage.
Are you just closing a deal or building a foundation for sustained success?
The Bottom Line
The GAINS© methodology isn't a collection of negotiation tricks—it's a systematic approach to creating unfair advantages through disciplined execution.
Elite executives don't just negotiate better—they create conditions where traditional negotiation isn't necessary.
Their value is so clear, their relationships so strong, and their options so abundant that compelling opportunities naturally flow their way.
Negotiation isn't magic. It's methodical.
It's about showing up differently every single day:
- Gathering intelligence before you need it.
- Creating alignment through every interaction.
- Building influence across organizations.
- Navigating complexity with strategic patience.
- Securing outcomes that compound over time.
The question isn't whether you can negotiate better—it's whether you're willing to work to create genuine negotiation power.
Ready to level up? The time to start is now.
Stay fearless, friends.
