10 Top Deal Killers in Business Sales - and How to Avoid Them

Selling a business isn’t easy. There are a lot of moving parts, and even good deals fall apart for reasons that could’ve been avoided. I’ve seen it too many times - and it’s never about one big thing. It’s usually a mix of small issues that snowball and derail the deal.

If you’re thinking about selling - or already in the process - here are some of the most common deal killers I see and how to stay ahead of them.

1. 📊 Messy Financials

This is a big one. If your books are disorganized or full of unexplained “add-backs,” it creates doubt. Buyers (and their lenders) need to understand your numbers - not try to decode them.

How to fix it:
Get ahead of it early. Clean up your P&L. Separate out personal expenses. Work with your CPA or broker to make sure things are dialed in. Sloppy numbers kill trust.

2. 🧨 Surprises During Due Diligence

Buyers dig deep - especially if they’re using financing. If something pops up late in the process (a legal issue, missing license, hidden debt), it can spook them fast.

How to fix it:
Be upfront. The more transparent you are early on, the better. A good broker will guide you on what to disclose and when - and how to frame it properly.

3. 💰 Overpricing the Business

This one hurts. A lot of sellers get anchored to a number - usually based on emotion or what they need to walk away with. But that’s not how deals get done.

How to fix it:
Know the market. Price based on real comps and deal structures, not what another broker promised you or what you saw on a listing site. Price it to sell - not sit.

4. 🏢 Landlord Problems

This one blindsides people. You get a buyer, you agree on terms… then the landlord blocks the lease assignment or drags their feet.

How to fix it:
Loop the landlord in early. Understand what they’ll need. If they’re difficult, get ahead of it - don’t wait until the eleventh hour.

5. 🤷‍♂️ Inflexibility

Deals involve some give-and-take. Whether it’s a seller note, training period, or small concession, buyers want to feel like you’re working with them.

How to fix it:
You don’t need to roll over, but a little flexibility goes a long way. The best deals happen when both sides are motivated and collaborative.

6. 🕒 Losing Momentum

Deals thrive on momentum. When things drag - unreturned emails, missing docs, slow responses - buyers start to second-guess.

How to fix it:
Stay engaged. Respond quickly. Keep the process moving. A good broker will help drive the timeline, but sellers need to stay plugged in too.

7. ⚖️ Attorneys Who Don’t Do M&A

Sellers or buyers sometimes bring in a lawyer they’ve used for years - a generalist, real estate attorney, or litigator - and that’s where the deal starts to unravel.

What goes wrong:
They over-negotiate standard terms, miss key deal points, and kill momentum. Worse, they treat it like a court case instead of a transaction.

How to fix it:
Use an attorney who specializes in M&A - ideally small business sales. It saves time, stress, and money. If you need a referral, I’ve got you covered.

8. 💼 SBA Inexperience

If there’s SBA financing involved (and there usually is), everyone on the deal -  buyer, seller, broker, lender, attorney - needs to understand the process. When they don’t, things get complicated fast.

What goes wrong:
Missing forms. Misunderstood timelines. Delayed approvals. And attorneys trying to negotiate SBA loan docs that aren’t negotiable.

How to fix it:
Work with people who’ve done SBA deals before. Not every lender is the same, and not every lawyer understands how SBA-backed transactions work. Experience matters here.

9. 🧭 Choosing the Wrong Broker

Not all brokers specialize in business sales. I’ve seen sellers work with residential real estate agents, friends with licenses, or advisors who don’t understand how to structure and navigate a deal - and it shows.

What goes wrong:
No pricing strategy. No buyer screening. No confidentiality. No deal flow. No ability to manage the financing process, due diligence, or lease assignment. Deals fall apart fast.

How to fix it:
Hire someone who lives and breathes small business M&A. This is a different skill set - you need someone who can guide the process, control the narrative, and solve problems before they blow up a deal.

10. 📉 Declining Revenues

This one doesn’t always get talked about - but it absolutely matters. If your numbers are trending down, buyers (and lenders) start to question the viability of the business.

What goes wrong:
Lenders get spooked. Buyers ask for price reductions. Or they walk away altogether, thinking they’re catching a falling knife.

How to fix it:
If revenue is dipping due to temporary reasons - seasonality, staffing, one-time loss - be prepared to explain it clearly. If it’s a longer trend, pricing and deal structure need to reflect that. Don’t ignore the trajectory - address it head-on.

Final Thought

Most deal killers are preventable. The more prepared you are - with clean numbers, realistic expectations, and the right people in your corner - the better your chances of getting to the finish line.

If you're even thinking about selling, let's talk. I’ll walk you through what’s working, what could be a red flag, and how to set the deal up right from the start.

📩 Reach out anytime. You don’t have to navigate this alone.