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What does the buyer actually do, and why do they want this?
Before the number, understand the model. A trade buyer in your sector is usually buying your customers and will fold the rest in. A private equity buyer is buying a return on a timetable and will need an exit inside five years or so. An individual buyer is often buying themselves a job. A group like mine is buying an operating business it intends to keep and grow.
None of those is wrong. They just produce completely different outcomes for the name over the door and the people who work under it. Ask directly what the plan is for the brand, the premises and the team, and ask what the last three businesses they bought look like now. That last question is the one that separates a plan from a pitch.
Is there anyone to hand it to?
Succession is the question owners underweight most. A buyer with no management bench needs you to stay, or needs to recruit into a business they do not yet understand. Both are risks you carry, because both show up in the earn-out, the handover period and the deferred element of your consideration.
A buyer who already runs comparable businesses can absorb yours without needing you there on the Monday. That is worth real money to you, and it is usually invisible on the offer letter.
Does the culture survive contact?
More deals disappoint on culture than on price. Look at how the buyer treats the companies they already own. Are those brands still trading under their own names? Are the original owners still involved, or did they leave inside a year? What do people who have worked for them say when the buyer is not in the room?
Your staff and your customers will read the answer to that question long before you announce anything. In a trade sector, they will hear about it from a competitor first.
The structure is part of the answer
You do not have to choose between the best price and the right home. A partnership sale, where the buyer takes 40% to 80% and you keep the balance, means you are not handing over a legacy at all. You still own part of it, you still have a say, and you take a second payday when the group grows. That is the structure I recommend in most deals, and it exists precisely because the all-or-nothing choice is a false one.
I buy companies directly and I keep the name over the door. So take the above as coming from an interested party rather than a neutral one. The three questions still work, including when you point them at me.