What No One Tells You About Selling Your Business

Selling a business is often seen as a strategic and financial decision—one defined by contracts, valuations, and negotiations—yet it is just as much an emotional and psychological journey.

At EFBC’s February 13th Fireside Chat, seasoned business leaders Jim Flanagan and Mark Wesa shared their firsthand experiences in selling their companies. Jim Flanagan, the former CEO of Nuance Solutions, and Mark Wesa, the former owner of MKD Electric, have both navigated the complexities of business sales in recent years.

Although they anticipated challenges in their M&A journeys, they encountered many unexpected surprises along the way.

Here’s what they—and many other business owners—wish they had known before stepping into the world of mergers and acquisitions.

1. The Emotional Toll is Real

No matter how prepared you are, selling your business isn’t just about the numbers—it’s about identity, legacy, and years of hard work.

Jim and his brother agonized over the decision, asking themselves, “How much risk do we want to take at this point in our careers?” Many business owners face the same struggle: logic vs. emotion, what’s best for the business vs. what feels right personally.

Deanna, EFBC member and chat moderator, summed it up perfectly:
“Deciding to step away from a business is truly a head vs. heart decision.”

The process can be exhausting, and when emotions take over, it becomes harder to stand firm on important terms.

Takeaway: Acknowledge the emotional weight early. Surround yourself with trusted advisors to stay grounded.

2. The Deal Isn’t Final Until It’s Final

A signed Letter of Intent (LOI) does not guarantee a sale.

The speakers recalled “11th-hour” situations where terms were renegotiated at the last minute—even after an LOI was finalized. This happens more often than most sellers expect.

Takeaway: Expect changes. Have a contingency plan, and ensure all verbal promises are put in writing.

3. Trust is Essential—But Not Always Enough

Even well-meaning buyers may struggle to uphold commitments due to market conditions, leadership changes, or financial challenges. Jim put it simply:
“In reality, what’s in writing is just on paper.”

Takeaway: Trust is important, but so is legal protection. Work with experienced advisors and push for contract transparency.

4. Keeping Quiet Can Be Critical

Mark stressed the importance of keeping acquisition talks private until a final decision is made.
“Don’t put your team on the emotional rollercoaster unless you’re certain it’s happening.”

Premature discussions can create unnecessary stress. Employees may start looking for new jobs, clients may get uneasy, and competitors may exploit the uncertainty.

Takeaway: Share information strategically. Until the deal is confirmed, limit discussions to those who absolutely need to know.

5. Define Your Non-Negotiables Early

Having clear guardrails—on culture, employee retention, leadership roles, operating systems or brand legacy—can prevent regret. Jim recalled Mark mentioning this concept at an EFBC meeting, emphasizing how it helped him maintain clarity.

Takeaway: Establish non-negotiables before negotiations start. Write them down and revisit them often.

6. Get Every Verbal Promise in Writing

Many sellers assume that once a deal is signed, everything will go as planned, but that is rarely the case.

Mark admitted:
“If I could do it differently, I would get all verbal promises in writing.”

Jim agreed:
“Same!”

Takeaway: Never assume verbal agreements will be honored. Get everything in writing—and be prepared to hold buyers accountable.

7. Private Equity: A Common Buyer with High Turnover

Many business owners sell to private equity (PE) firms, which are among the most active buyers in the M&A space. But PE firms have high turnover.

Statistically, the people you negotiate with may not be the ones leading the company post-sale—or even through the entire process. This creates unexpected challenges, especially when new decision-makers shift priorities.

This turnover can also mean verbal agreements or assurances may not hold up under new leadership. The individuals who promised to maintain company culture or protect employees might not be around to enforce it later.

Takeaway: If selling to private equity, expect leadership turnover. Get every commitment in writing, and don’t assume the people you’re negotiating with will be the ones executing the plan.

8. EFBC’s Impact: Having the Right People in Your Corner

One of the biggest challenges of selling a business is navigating the unknown. Having a trusted network of advisors and peers makes all the difference.

Mark described EFBC’s impact as invaluable:
“The advice and experience I received from my EFBC forum was very powerful during this time.”

Forum members who had already been through the process helped him anticipate challenges, evaluate offers more critically, and make better decisions.

Takeaway: Surround yourself with a strong support system. Peer networks like EFBC provide real-world insights that can help you navigate both the emotional and strategic complexities of selling a business.

Final Thought: Selling a Business is More Than Just a Transaction

Selling a business isn’t just about valuation and deal structuring—it’s about relationships, emotions, and unexpected hurdles. The more prepared you are for the hidden challenges, the smoother the transition.

If you’re considering selling, learn from those who have been through it. Their experiences might just save you from surprises down the road.

Want to connect with business owners who have firsthand M&A experience?

Join EFBC to gain access to a network of peers who have navigated the same journey.