Owners tend to think the dangerous part of a sale is finding the buyer. It is not. The mistakes owners make before a business goes to market are well documented; the ones that come after a buyer is at the table are discussed far less, and they cost more — because by then the number is real and every point given back is measurable. Here are the five ways owners hand value back once the process is underway. Each is common, and each is avoidable.
1. Negotiating alone with the first buyer
An offer arrives and the owner starts talking. A few weeks later there is a number on the table, a relationship with one buyer, and no way to know whether the number is strong or light. The buyer, meanwhile, knows exactly what they are competing against: nothing. The mistake is not engaging — it is engaging before there is a process around the conversation. A serious approach is a reason to get organized, quietly bring other qualified buyers to the same table, and let the first buyer earn the deal against a market rather than against your own uncertainty.
2. Signing the letter of intent for the number and not the terms
The letter of intent is where most owners stop reading closely, because the headline price is finally on paper. But the LOI also sets the structure — how much is cash at close, what is deferred, where the working capital target sits — and it almost always grants the buyer exclusivity. From the moment it is signed, the competition you built is gone and every remaining point is negotiated one-on-one. A vague LOI is the buyer's best friend: whatever it leaves open gets settled later, when your leverage is at its lowest. Pin the terms down before you sign, not after.
3. Taking your eye off the business during diligence
Diligence takes months, it is exhausting, and it pulls the owner into data requests and management meetings at exactly the moment the business needs them most. A soft quarter inside that window is not a footnote. The buyer is re-measuring trailing earnings the whole time, and a dip becomes a price reduction or a shift of cash into an earnout. The owners who close at their number are the ones who kept running the company as if no sale were happening, and let their advisor and their team carry the process.
4. Leaving a known problem for the buyer to find
Every business has something — a customer that is wobbling, a lawsuit that went nowhere, a contract with a change-of-control clause, a key manager who is thinking of leaving. Owners often hope it will not come up. It comes up. And when the buyer finds it themselves, they discount twice: once for the problem, and once for the fact that you did not mention it, which makes them wonder what else is there. Disclosed early and framed honestly, the same issue is a line item with a plan attached. Discovered late, it is a reason to reopen the price.
5. Negotiating personally
Buyers probe. They question the add-backs, the concentration, the depth of the management team, and they do it deliberately. Owners who spent decades building the company hear that as an insult and answer it as one — digging in on points that do not matter, walking out over tone, saying things in a meeting that cannot be walked back. This is what an advisor is for: a layer between you and the buyer that lets hard positions be taken without damaging the relationship you will need after closing. The owner should be the person the buyer likes. The advisor can be the one they argue with.
The takeaway
Getting a buyer to the table is not the finish line — it is where the expensive mistakes begin. Run a process instead of a conversation, sign an LOI for its terms and not just its price, keep the business performing through diligence, put your problems on the table before the buyer finds them, and let someone else do the arguing. Do those five things and the number you agreed to has a far better chance of being the number you receive.
