The Unspoken Deals That Kill Your Business Exit: A Cautionary Tale for Business Owners
The Deal That Should Have Changed Everything
The day he sold his company was supposed to be the victory lap.
After years of late nights, missed vacations, and payroll close calls, the wire finally hit his account. The numbers on the screen looked unreal. He took a breath he felt like he’d been holding for a decade.
Three days later, an email arrived from an attorney he didn’t recognize.
The subject line mentioned the name of a long-time employee and the words “5% ownership interest.” The letter claimed that years earlier, in a conversation after a big client win, he had promised this employee “5% of the deal” when he eventually sold.
In his mind, it had been a generous, casual thank-you. In their mind, it was a binding commitment.
Then came the real question: Five percent of what?
The original sales price?
The final adjusted price after negotiations?
The amount left after paying off debt?
The actual cash he took home?
By the time it was over, that vague promise cost him $3 million.
Rewinding the Story – How Simple Favors Become $3M Problems
That “5%” conversation didn’t happen in a boardroom.
It was after a long week, when a key team member had just pulled off something big for the company. They’d stayed late, smoothed over a frustrated client, and helped land a renewal that kept the business afloat.
The owner was grateful and tired. He wanted this person to know they mattered.
“Listen,” he said, “when I sell this thing someday, you’ll get 5% of the deal. You’ve earned it.”
In his head, it was a rough idea. A future bonus. A way of saying, “You’re part of this.”
What never happened next was the important part.
They didn’t define what “5%” meant.
They didn’t put it in writing with clear terms.
They didn’t ask a CPA what that would look like on the books, or how it would work when he finally figured out how to sell the business.
Years later, those missing details turned one kind promise into a multi‑million‑dollar problem.
The Hidden Web of Side Deals in Many Businesses
Here’s the hard truth: that owner’s story isn’t unusual.
When I sit down with business owners who are starting to think about business exit planning or a broader business transition planning process, I almost always find a web of side promises underneath the surface.
A quiet “you’ll get a piece when I sell” to the right-hand employee who stayed through the hard years.
A handshake agreement with a consultant who “helped grow the business” and was told they’d share in the upside.
A long-time client who believes they were promised a percentage if they made an introduction that led to a future buyer.
Sometimes these deals are half-written in old emails. Sometimes they’re completely verbal. Almost always, they mean different things to different people.
When the time finally comes to figure out how to sell a business, those same people step forward expecting their version of the deal. Buyers notice.
Attorneys start asking questions. And what should have been a clean exit suddenly feels crowded, tense, and risky.
Where Deals Go Off the Rails – When Legal and Financials Don’t Match
Once these promises surface, the first move is usually to “get something in writing.”
An attorney steps in and drafts an agreement to reflect whatever everyone thinks the deal was. On paper, it might look fair. The language sounds formal and polished. People feel relieved that it’s finally documented.
Then the numbers hit the books.
This is where things often break. The CPA has to ask questions like:
How do we record this?
Is this a liability? A bonus? Equity?
What happens to your taxes if we do it this way?
Does this destroy the profitability the buyer thought they were getting?
Just because an agreement can be written in legal language doesn’t mean it works financially.
I’ve seen beautifully drafted side agreements that were impossible to book cleanly, created tax surprises, or quietly erased a meaningful chunk of the owner’s net proceeds from the sale.
How a CPA Brings Clarity to “Unspoken Deals”
This is where having a CPA deeply involved in your business exit strategy is essential, not optional.
When I’m brought into an exit where side promises exist, my first job is to surface them all. I’ll ask questions like, “Who else believes they’re part of this sale?” and “Have you ever told someone they’d get a piece when you sold?” It’s amazing what owners remember once they feel safe enough to say it out loud.
From there, we get specific:
If you promised “5%,” we define 5% of what. Gross sale price? Net after debt? Profit over a certain threshold?
We model the different interpretations in actual dollars so you can see the real impact.
We check if the deal can be recorded correctly in your financials and what it does to taxes and cash flow.
Then we work with your attorney so the legal language and the financial reality actually match.
This process doesn’t just protect the owner. It creates clearer, fairer expectations for the people you’ve promised to take care of.
Practical Strategies for Owners – Before You Even Think About Selling
You don’t have to be at the closing table to start cleaning this up. In fact, the best time is years before you seriously look into how to sell your business or what your business exit planning should look like.
Here are a few steps you can take now:
Make a promise list.
Take ten minutes and write down every person you’ve ever told, “You’ll share in the sale someday,” or “I’ll take care of you when I sell.”Write down what you think you meant.
For each promise, jot a simple note: “I meant a one-time bonus,” or “I meant a percentage of what I actually take home.”Clarify the base.
If you’ve used percentages, define the base: sale price, net after debt, or profit. This is where “5% of what?” becomes real.Loop in a CPA early.
Ask a CPA who understands business transition planning to review your list. The key question is, “Can we actually record this in a way that works?”Clean up before you go to market.
Resolve, update, or renegotiate vague deals long before buyers and their advisors start digging.
A few small conversations now can save you from very big, very expensive conversations later.
Closing – Protecting the People and the Legacy You Care About
Most “unspoken deals” don’t start from greed. They start from loyalty.
Owners make these promises because they care about the people who helped them build the business. They want their team, their partners, and sometimes their clients to win alongside them.
The goal isn’t to stop being generous. The goal is to make your generosity clear, documented, and workable so it doesn’t come back to tear apart the moment you’ve been working toward for years.
If you’re even casually wondering how to sell a business in the next few years, this is a powerful place to start: list your promises, define what you mean, and sit down with a business exit plan consultant who understands how to sell your business.
That way, the day you sell really can be the celebration you imagined, without unspoken deals waiting in the background to rewrite the ending.
Ready for that next step? Learn more about my Exit Planning Strategies through the SCOTT Method. Or schedule a complementary consultation with me to review where you’re at! Need to better understand where you’re at? Take my free, 10-minute business exit planning assessment!