(And how to avoid learning them the hard way)
For most founders, selling a business isn’t a repeatable skill. You build once, you exit once—and the stakes are usually life-changing. That’s exactly why so many good businesses leave money on the table or see deals collapse late in the process.
After watching dozens of transactions up close—good ones, bad ones, and a few that blew up at the finish line—certain patterns show up again and again. The mistakes aren’t dramatic. They’re subtle. And they’re avoidable.
Here are the big ones I see business owners make when entering an M&A process.
1. Treating exit planning like a “future problem”
Most owners are buried in operations and assume exit planning can wait. It can’t. A well-run process starts years before a deal, not months. Succession, governance, ownership alignment, and contingency planning all affect value—whether you plan for them or not.
2. Thinking you can run the process alone
Interest from buyers doesn’t mean you’re close to closing. It usually means the hard part is just beginning. A strong M&A advisor does more than market a business—they pressure-test valuation, anticipate diligence issues, negotiate terms you didn’t even know existed, and keep deals alive when they wobble.
3. Forgetting that employees drive value
Culture isn’t a soft metric in a transaction. Buyers notice disengaged teams immediately. Strong leadership alignment, retention, and morale aren’t just “nice to have”—they directly affect sustainability, risk, and price.
4. Keeping all your wealth trapped in the business
Many owners delay diversifying because they feel most in control inside their company. The irony is that concentration increases personal risk and reduces flexibility at exit. Owners with outside liquidity have more options, including alternative buyers and smoother transitions.
5. Going to market with messy financials
Buyers don’t just look at earnings—they look for credibility. Clean books, consistent reporting, clear revenue recognition, and organised records reduce friction and increase trust. Sloppy financials invite discounts, delays, or worse.
6. Stretching EBITDA adjustments too far
Addbacks need evidence, not optimism. Unsupported adjustments erode trust fast and often widen valuation gaps. Serious buyers expect discipline and documentation, not “pro forma storytelling.”
7. Letting bias dictate who you’ll sell to
Strategic buyers aren’t always the answer. Private equity isn’t inherently destructive. Family offices aren’t automatically patient. Independent sponsors aren’t unsophisticated. Every buyer type has trade-offs. Rigid thinking limits outcomes.
8. Withholding “minor” historical issues
Nothing kills momentum faster than a late discovery that should’ve been disclosed early. Even immaterial issues can derail a deal if they appear hidden. In modern diligence processes, everything surfaces eventually. Transparency protects credibility.
9. Ignoring chemistry
Price matters—but alignment matters more. You may be working with the buyer for years post-close. How decisions get made, how people communicate, and how conflict is handled will shape your experience far more than the headline number.
10. Obsessing over price and ignoring terms
Cash vs. equity. Earnouts. Representations. Employment agreements. Stock protections. These details often matter more than the top-line valuation. A “higher price” can easily become a worse deal if the structure is wrong.
11. Not doing diligence on the buyer
Sellers scrutinise buyers—but often not deeply enough. Earnouts, incentives, and post-close governance only work if the buyer’s behaviour, capital structure, and operating philosophy support them. Assume nothing. Verify everything.
12. Underestimating post-close integration
Integration is where most deals quietly struggle. Even aligned partners face change fatigue, role confusion, and cultural friction. Clear communication, defined responsibilities, and realistic timelines are essential to preserving value after the ink dries.
Final thought
M&A isn’t just a financial transaction—it’s a leadership transition, a cultural shift, and often a personal reckoning. The biggest mistakes rarely come from lack of intelligence. They come from lack of preparation, overconfidence, or misplaced focus.
If you’re a founder thinking about an exit—even if it’s years away—the smartest move you can make is to start treating the process with the same discipline you applied to building the business in the first place.
That’s how good companies become great exits.