Exit Preparation Isn't About the Deal—It's About Building Options
How to prepare your business so you can sell when you want, not when you have to.
A founder I was coaching came to me with what he thought was good news. He'd received an offer for his company—an offer that exceeded his target EBITDA multiple by almost a full turn. On paper, it looked like everything he'd been working toward.
But as we dug into the details, problems emerged. The deal included a three-year earnout with aggressive performance targets tied to metrics he couldn't fully control. He'd be required to stay on as CEO, reporting to a private equity board with a very different operating philosophy than his own. The buyer wanted to aggressively cut costs in ways that would affect long-tenured employees. And the timeline was compressed—close in ninety days, or the offer disappeared.
He was torn. The price was exceptional. But the terms would lock him into a situation misaligned with what he actually wanted from his exit. He'd spent years imagining a clean transition that freed him to pursue new ventures. This deal would do the opposite.
The problem wasn't the buyer or the offer. The problem was that he'd never defined what his exit was supposed to enable. He'd optimized for maximum valuation without clarifying what kind of exit would actually serve his life.
I call this the Transaction Trap—the pattern where founders focus so intensely on deal mechanics that they lose sight of what the deal is supposed to accomplish. It's one of the most common mistakes I see when coaching founder-CEOs through exit planning, and it leads to some of the worst outcomes.
When Optimizing the Deal Means Losing Sight of the Goal
The Transaction Trap shows up in predictable ways. Here's how to recognize it:
Your exit planning conversations focus almost exclusively on financial optimization. You spend hours discussing EBITDA adjustments, comparable transaction multiples, and tax structuring. But questions about post-close involvement, buyer culture fit, or how the deal serves your longer-term vision receive minimal attention—maybe a few minutes at the end of a meeting, treated as soft considerations rather than strategic requirements.
You're primarily evaluating buyers by price. When multiple offers come in, the ranking is determined by purchase price and deal certainty. Factors like how the buyer will treat your employees, whether their values align with yours, or what role they expect from you post-close are acknowledged but not weighted heavily in the decision.
You haven't written down what you need from this exit beyond financial terms. There's no document that says "For this deal to be successful, it must include X, Y, and Z" where X, Y, and Z go beyond price. You're optimizing a single variable rather than solving for a multi-dimensional outcome.
The urgency feels one-directional. You're pushing toward a transaction without a clear answer to why now and why this deal. The pressure comes from the process itself—advisors with engagement timelines, buyers with competing priorities—rather than from a genuine strategic imperative tied to your life goals.
Why Transaction Thinking Takes Over
Founders don't fall into the Transaction Trap because they're unsophisticated. They fall into it because the conventional approach to exit planning pushes them there.
First, the advisory ecosystem is transaction-focused by design. Investment bankers earn fees when deals close. M&A attorneys optimize deal terms. Accountants minimize tax exposure. These are valuable services, but they're all oriented toward getting the transaction done, not toward ensuring the transaction serves your broader goals. The question "Does this deal make sense for your life?" isn't typically part of their scope.
Second, "maximize valuation" is the default objective. It sounds rational—who wouldn't want the highest possible price? But maximizing a single variable often requires trading away other things that matter. A higher price might mean more earnout risk, longer post-close involvement, or a buyer whose approach will damage the culture you built. Without clarity about what you'd trade for what, you default to optimizing the most measurable number.
Third, exit planning typically starts too late. By the time most founders engage seriously with exit preparation, they're already in a deal process or close to one. At that point, there's pressure to move fast and keep momentum. The deeper work of clarifying what the exit should enable gets compressed or skipped entirely—it feels like a luxury when term sheets are in motion.
Fourth, personal readiness work is uncomfortable. Thinking through what you want from your life post-exit requires confronting hard questions about identity, purpose, and legacy. Many founders would rather focus on spreadsheets than sit with questions like "Who am I when I'm not the founder?" The Transaction Trap lets you stay busy with deal mechanics instead of doing that harder work.
The Price of Chasing Valuation Without Vision
The costs of the Transaction Trap often don't become visible until after the deal closes—but by then, it's too late to do anything about them.
You accept terms that conflict with your actual goals. The founder I mentioned earlier eventually walked away from that initial offer. But many founders don't. They accept earnouts that keep them trapped in roles they wanted to leave, agree to non-competes that block ventures they wanted to pursue, or choose buyers whose operating approach makes their final years at the company miserable. These aren't failures of negotiation—they're failures of clarity about what to negotiate for.
You leave money on the table in less obvious ways. A founder with clear criteria can negotiate more effectively because they know what they're willing to trade. They can offer concessions on terms that don't matter to them in exchange for terms that do. Founders without that clarity give up value without realizing it, accepting compromises on things that turn out to matter deeply.
You experience post-exit regret even when the deal succeeds financially. The 75% regret statistic among founders within a year of selling isn't driven primarily by bad deals. It's driven by deals that didn't align with what founders actually wanted. They got the number but not the outcome. The money landed and they discovered it wasn't enough—not because the amount was insufficient, but because money alone doesn't create meaning, purpose, or satisfaction.
The personal cost extends beyond the founder to families, teams, and communities. A founder who's miserable in a post-close role brings that energy home. A founder who sold to a buyer that gutted the culture has to watch former employees lose their jobs. A founder who took the money but lost their sense of purpose may struggle for years to find footing. These are real costs, even if they don't appear on any closing statement.
Building a Business That Sells on Your Terms
Founders who navigate exits well do something fundamentally different: they start with an Exit Blueprint that defines what success looks like before engaging with the transaction process.
The Exit Blueprint has three components. First, a Post-Exit Plan that articulates what you want your life to look like after the transition—not vague aspirations, but specific answers about what you'll do, what relationships and activities will structure your time, and what accomplishments would make the next chapter meaningful. This is the destination that the exit should transport you toward.
Second, a Pre-Exit Plan that identifies what needs to happen in your business and your life before you can execute the exit effectively. This includes operational improvements that increase valuation, personal readiness work that prepares you for transition, and timing considerations that align the exit with your broader plans.
Third, a Deal Evaluation Framework that specifies your criteria across multiple dimensions—not just price, but also post-close involvement requirements, cultural alignment needs, employee treatment expectations, and timeline constraints. This framework gives you a rubric for comparing offers that goes beyond the single dimension of purchase price.
The Exit Blueprint serves as a filter for every decision during the exit process. When you're evaluating buyers, you assess them against your criteria, not just their financial offers. When you're negotiating terms, you know which elements are essential versus tradeable because you've defined what the deal must enable. When you're making trade-offs, you can make them deliberately rather than reactively.
The underlying mindset shift is crucial: instead of asking "How do I maximize valuation?" you ask "What does this exit need to enable?" That question puts your goals at the center rather than treating them as an afterthought.
This leads to what I call the Sell-Keep Mindset: run your business as if you'll own it forever while ensuring it's structured to sell at any time. Always ready, never desperate. This mindset creates optionality. You're not running toward an exit out of necessity—you're building a business that could sell when the right opportunity aligns with your goals, or could continue thriving if no such opportunity appears.
Assessing Your Own Exit Readiness
Here's how to assess whether you're approaching exit planning with an Exit Blueprint mindset:
Write down, in specific terms, the five criteria that any acceptable deal must meet beyond a minimum price. If you struggle to articulate five non-financial requirements, you haven't developed a comprehensive deal evaluation framework. You're evaluating on a single dimension.
Consider the last three strategic decisions you made about your business. For each one, ask: Did I make this decision thinking about how it serves a potential exit, or did I make it thinking about how it serves the business long-term? If your answers are inconsistent, you may be oscillating between "optimize for sale" and "optimize for operations" without a unifying strategy.
Imagine receiving two offers tomorrow—one offering your target price but requiring significant post-close involvement, another offering 15% less but providing a clean break with no earnout. Would you know immediately which to prefer? If you'd need extended deliberation, you haven't clarified what you're actually solving for in an exit.
Finally, ask yourself: Am I pursuing an exit because it aligns with my life goals, or because external pressures are pushing me toward a transaction? If the answer is the latter, you may be entering a process prematurely—and the Transaction Trap becomes much more likely.
Where to Start
Begin by separating exit planning from transaction planning. Exit planning is the strategic work of clarifying what you want, preparing your business, and developing your criteria. Transaction planning is the tactical work of engaging buyers, negotiating terms, and closing deals. Most founders jump straight to transaction planning. Doing the exit planning work first makes everything downstream clearer and more effective.
Block dedicated time to develop your Exit Blueprint. Start with the Post-Exit Plan component—what you want your life to look like after the transition. Write it down. Be specific. This isn't a one-hour exercise; it may take multiple sessions over weeks. But this clarity becomes the foundation for everything else.
Have honest conversations with people who know you well—not your transaction advisors, but trusted friends, mentors, or coaches who can challenge your thinking. Share your Post-Exit Plan and ask them whether it aligns with who they observe you to be. Often, others can see blind spots in our self-perception.
Assess your current business through the lens of the Sell-Keep Mindset. What would need to be true for your business to be attractive to buyers at any time? What operational improvements would increase both current performance and eventual exit value? Building this way creates optionality rather than forcing premature decisions.
Finally, don't wait for an imminent transaction to do this work. The best time to develop an Exit Blueprint is when you're not under pressure—when you can think clearly about what you want without the distortion of active deal dynamics. If you're already in a process, carve out time to do this work anyway. It's not too late, and the clarity will improve your decisions even under time pressure.
Questions for You and Your Team
Before moving on, take a few minutes to reflect on these questions. The goal isn't to have perfect answers—it's to surface whether the Transaction Trap might be shaping your exit planning.
If you received your target price tomorrow but the deal terms made the next five years of your life significantly worse, would you still take it? What would make you walk away? This question forces you to quantify what you'd trade for money and what you wouldn't.
Can you articulate, without hesitation, what your exit needs to enable beyond financial liquidity? If the answer takes more than a few sentences, you may need to do more work clarifying your Post-Exit Plan.
Are you building a business you'd be happy to keep owning indefinitely, or are you building specifically toward a sale? The Sell-Keep Mindset says these shouldn't be different. If they are, you might be forcing yourself toward a transaction that isn't right.
Take the Next Step
If you want to see where your business stands on the dimensions buyers scrutinize most closely, take the Exit Readiness Assessment. It's a free 15-minute diagnostic that scores your business across six dimensions—and helps you understand what would move your valuation.
Take the Exit Readiness Assessment
If you'd like help developing your Exit Blueprint—whether that's clarifying your Post-Exit Plan, building your Deal Evaluation Framework, or preparing your business for eventual transaction—I offer a free 60-minute consultation.
The Exit Planning Book for Founder-CEOs
Why do 75% of founders regret their exit within a year—even when they hit their number? Because most exit planning ignores what actually matters: personal readiness, life after the transaction, and building a business that sells on your terms.
SPRINGBOARD: A Founder's Guide to Selling Your Company With Purpose, Clarity, and a Vision for What's Next provides a comprehensive framework for planning exits that serve your life goals, not just your financial targets. It covers the four phases most founders miss: preparing yourself, preparing your business, executing the transaction, and navigating what comes next.
The first three chapters are available now.
About the Author
Bruce Eckfeldt is a strategic business coach and exit planning advisor who helps founder-CEOs of growth-stage companies scale systematically and exit successfully. A former Inc. 500 CEO who built and sold his own company, he brings real-world operational experience to strategic planning and leadership development. He's a certified ScalingUp and 3HAG/Metronomics coach, Certified Exit Planning Advisor (CEPA), an Inc. Magazine contributor, and host of the "From Angel to Exit" podcast. Bruce works with growth companies in complex industries, guiding leadership teams through growth challenges and exit preparation. Reach him at bruce@eckfeldt.com with any questions or if you want more information or to book a call with him.
