If you’ve owned your business for a while, you’ve probably learned a lot about mistakes - the early ones, the expensive ones, the ones that taught you something you still use today.
But here’s the thing: when it comes to selling a business, even smart, successful owners can stumble. Not because they’re careless, but because this process is different from anything else they’ve done before.
Selling a company is part financial transaction, part emotional transition, and part strategy. And when you’re too close to it, it’s easy to overlook details that can make a big difference.
So, let’s talk about the most common mistakes I see owners make when selling and, more importantly, how to avoid them.
Mistake #1: Waiting too long to prepare
By far the most common mistake is waiting until you’re ready to sell to start preparing.
The truth is, the best time to start preparing is when you start thinking about selling, not when you’ve already decided.
I meet owners all the time who say, “I wish I’d started this process a year ago.”
They’re often frustrated because they’ve built a valuable company, but things like disorganized books, customer concentration, or dependency on the owner lower their valuation or slow down the sale.
The reality is, a business that’s ready to sell is often a business that’s simply well run. The same things that make it attractive to buyers such as clean records, clear processes, good people, stable revenue, also make it easier to operate day-to-day.
So even if you’re not planning to sell for a while, start preparing now. It’s not about rushing, it’s about being ready when opportunity shows up.
Mistake #2: Overpricing the business
This one is tough because every owner is proud of what they’ve built, and rightfully so.
But pride and price don’t always match.
Many owners set their asking price based on what they want or need to retire, instead of what the market will realistically pay.
Buyers aren’t trying to undervalue your business, they’re simply looking at it through the lens of risk and return.
An overpriced business sits on the market, gathers dust, and eventually becomes harder to sell, even if it’s strong. Buyers start to wonder what’s wrong with it.
Pricing too high doesn’t create leverage, it creates hesitation.
The best strategy is to price fairly and confidently. When your asking price is grounded in solid financials and realistic expectations, you attract serious buyers faster and often end up with better offers.
Mistake #3: Focusing only on price, not terms
It’s easy to fixate on the sale price, but deals are made or broken in the terms.
Here’s what I mean:
Two offers might look identical on paper - same price, same basic structure - but one could leave you in a much stronger position.
For example, one buyer might offer full cash at closing. Another might offer a slightly higher total price, but with payments spread out over several years.
Sometimes, the lower offer is actually better once you factor in certainty and timing.
The key is understanding that structure matters: cash vs. financing, timing of payments, transition period, and contingencies all affect what you truly walk away with.
A seasoned broker helps you see the real value behind the headline number.
Mistake #4: Letting emotions drive decisions
Selling your business is emotional. There’s no getting around it.
You’ve poured yourself into it. It’s part of your identity. So when a buyer starts questioning decisions, asking tough questions, or negotiating aggressively, it’s natural to take it personally.
But emotions can cloud judgment.
I’ve seen deals fall apart because an owner got frustrated and walked away over something small, only to regret it later.
That’s one of the biggest reasons to have a professional buffer between you and the buyer. A broker isn’t emotionally attached, so they can navigate the tension while you stay focused on the big picture.
Remember: this is business, not personal. The buyer isn’t criticizing your life’s work, they’re just doing their due diligence.
Mistake #5: Not keeping the business running strong during the sale
Selling a business can be distracting. There are calls, meetings, documents, negotiations, and it’s easy to take your eye off daily operations.
But here’s the hard truth: buyers judge your business by its most recent performance.
If sales dip or costs climb during the selling process, it can lower your value or give the buyer leverage to renegotiate.
The best thing you can do while selling? Keep running your business as if you’re not selling.
Deals that close smoothly are the ones where the business stays strong from listing to closing.
You don’t want to limp to the finish line, you want to sprint through it.
Mistake #6: Telling employees or customers too early
Confidentiality is everything in this process.
The moment rumors start, people get nervous. Employees worry about their jobs. Customers wonder what’s changing. Competitors start sniffing around.
Even if your intentions are good and you want to be honest or transparent, it’s best to wait until the right time to share the news.
Handled correctly, those conversations can actually strengthen relationships rather than create anxiety. But timing and messaging are everything.
A broker will help you navigate those conversations so you protect your people and your business.
Mistake #7: Trying to do everything yourself
It’s tempting to try. You’ve built your company by being resourceful, independent, and in control.
But selling a business isn’t like running one. It’s a different skill set.
You need legal guidance, financial review, marketing, negotiation, and deal management, all happening at once.
When you try to handle it alone, you risk missing things, undervaluing your business, or burning out midway through the process.
A good broker coordinates everything, keeps the deal on track, and shields you from the noise so you can stay focused on your business.
Mistake #8: Ignoring deal structure risks
Some owners are so eager to close that they agree to terms they don’t fully understand, things like seller financing, earn-outs, or personal guarantees, without realizing the long-term implications.
These tools can be smart and mutually beneficial, but they have to be structured carefully.
Always review the details with your broker, CPA, and attorney. Know exactly what happens if payments are delayed or targets aren’t met.
The best deals are fair to both sides, but they’re also crystal clear.
Mistake #9: Choosing the wrong buyer
Not every buyer is the right fit, even if the price looks good.
The right buyer isn’t just someone with the funds; it’s someone who shares your values, respects your team, and understands your business.
When a buyer is a bad cultural or operational fit, transitions get messy. Employees leave. Customers get confused. And what you built can unravel.
Take the time to evaluate buyers, not just their offers. A deal that feels right on paper but wrong in your gut is rarely worth it.
Mistake #10: Underestimating the time and energy involved
Selling your company takes patience. Even in the best circumstances, it’s a six- to twelve-month process filled with highs, lows, and lots of waiting.
Owners who expect a quick, simple sale often feel discouraged when it doesn’t happen immediately.
That’s why setting realistic expectations early makes such a difference.
When you know what’s coming, you can pace yourself, stay calm, and keep perspective.
The truth about mistakes
Every business owner makes mistakes, in operations, in hiring, in strategy. It’s part of growth. But when it comes to selling, the cost of mistakes can be higher because you only get one shot.
The good news? Every single one of these pitfalls is preventable with the right guidance.
You don’t have to be perfect, you just have to be prepared.
Final thought
Selling your business isn’t about perfection, it’s about preparation, patience, and good advice.
If you can avoid the common traps, you’ll not only protect your value, but you’ll enjoy the process more. Because selling your business shouldn’t feel like a burden, it should feel like the reward for years of hard work.
If you’re thinking about selling
If you’re starting to think about what a sale might look like, whether that’s this year or sometime down the road, I’d be happy to talk with you about how to prepare and avoid these pitfalls.
A few good decisions now can make all the difference later.