I have asked founders about their exit for twenty years, in boardrooms, in due diligence, and across kitchen tables at the point where a deal is either happening or falling apart.
The pattern is consistent. Ask about the next twelve months and you get precision: the pipeline, the hires, the margin target, the two things keeping them awake. Ask about the end and something changes in the room. The answer gets shorter and more general. "At some point I'd like to step back." "There's no rush." "I'd take the right offer."
None of those are answers. They are ways of not answering, and I say that without judgement, because the questions underneath are genuinely difficult and nobody schedules time for them.
So here are ten, in the order I ask them. They are deliberately uncomfortable. The comfortable versions have been asked for years and have not produced answers.
Answer them alone first. Write the answers down. Then find somebody who will argue with you.
01What number, after tax, would be enough?
Why it matters. Almost every founder has a figure in mind and almost none have tested it. Tested means: subtract tax, subtract what is owed, subtract what you have promised others, then check the remainder against the actual cost of the life you intend to live for thirty years.
The arithmetic frequently produces a surprise, in both directions. Some founders find the figure they have been grinding towards is well beyond what they need, and they have been taking risk for a margin that does not buy them anything. Others find the number is meaningfully higher than they assumed, which is unwelcome but far better learned now than during a negotiation.
A poor answer sounds like: "Enough to be comfortable." Comfortable is not a number.
02By when?
Why it matters. A date is what converts intention into sequence. Without one, the work that only pays off in three years never starts, because there is always something with a nearer deadline.
The date does not have to be right. It has to exist, and you have to have said it out loud to at least one other person, because unspoken dates move silently.
A poor answer sounds like: "In the next five years or so." That is a way of saying not this year, repeated annually.
03What are you doing on the Monday after?
Why it matters. This is the question that catches people, and it is the one most correlated with whether a founder is happy eighteen months after a deal. Running a company is a structure: it fills the diary, provides the identity, and answers the question of what today is for. Removing it without a replacement is a much bigger event than the financial one, and almost nobody prepares for it.
It is also a commercial question. If you have no answer, you will be more willing to accept a long earn-out and a three year tie-in, not because it is a good deal, but because it postpones the problem.
A poor answer sounds like: "Take some time, travel a bit, see what comes up." Everybody says this. Very few enjoy month four.
04If you stopped tomorrow, what actually happens?
Why it matters. Not the money. The business. Who makes the decisions you make, who holds the relationships you hold, and how long before somebody notices.
The gap between the answer to this question and the answer you would want a buyer to hear is the size of the work in front of you, expressed in months.
A poor answer sounds like: "It would be difficult for a while, but they'd cope." Difficult for a while, priced by a buyer, is a deferred consideration structure.
05What proportion of revenue would leave with you?
Why it matters. Founders systematically underestimate this. The relationships you consider institutional are frequently personal, and the test is not whether the customer likes the company. It is who they ring when something goes wrong.
Work through your top ten accounts by name and be honest about each. The number that comes out is one of the two or three most important figures about your business, and most founders have never calculated it.
A poor answer sounds like: "They buy from the business, not from me." Occasionally true. Usually the thing people say before diligence proves otherwise.
06Which form of exit are you actually building for?
Why it matters. A trade sale, a private equity deal, a management buyout and an employee ownership trust all want different businesses. A trade buyer wants something that slots into their operation. Private equity wants a management team that can run without you and a credible growth story for the next holder. A management buyout wants managers who want it, and funding. An EOT wants stable profitability and a genuinely independent operation.
Building for all four means building for none. It is the strategic version of hedging, and it produces a company that is slightly wrong for every buyer.
A poor answer sounds like: "Whichever gets the best price." That is a preference, not a plan, and the price will be worse for it.
07What do you want to happen to the people?
Why it matters. It matters commercially, because the answer constrains which buyers you can work with, and it matters personally, because this is the thing founders find hardest afterwards.
If the honest answer is that you want the team protected, that rules out certain buyers and certain structures, and it will cost you something. That may well be the right trade, but make it deliberately and early. Making it late, during a process, is how good people end up making bad decisions under time pressure.
A poor answer sounds like: "I'd want a buyer who values the culture." Everybody says that in the first meeting. Ask what you would give up for it.
08What would you not accept, at any price?
Why it matters. Knowing your limits before you are tired is the most useful preparation there is. Processes are long, and by month seven the desire to be finished exerts a real force on judgement.
Write down two or three things you will not do: a structure, an outcome for a particular person, a buyer you would not sell to. Give the list to your adviser. It is much easier to hold a line you wrote down when you were fresh.
A poor answer sounds like: "It depends on the number." For some things that is genuinely true. If it is true for everything, you have no floor, and you will find out where it should have been afterwards.
09Who else does this decision affect, and have you asked them?
Why it matters. A partner who assumed you were selling in two years, a co-founder with a different timeline, an adult child who thought they might one day run it. Every one of these is capable of stopping a deal late, and every one is easy to resolve years early.
The conversation is usually shorter and less fraught than the founder fears. The version that goes badly is the one that happens in week nine of a process, when positions have hardened and there is money on the table.
A poor answer sounds like: "They'll be fine with whatever I decide." Perhaps. Ask.
10What would have to be true, in three years, for the answer to question one to be achievable?
Why it matters. This is where the previous nine turn into work. Take the number, apply a realistic multiple for a business of your type and quality, and see what profit that implies. Then look at the gap between that and where you are.
Sometimes the gap is modest and the plan is essentially to keep going while fixing two structural issues. Sometimes the gap is enormous, and the honest conclusion is either that the timeline is wrong, the number is wrong, or the business needs to become a different business. All three of those are workable conclusions. What is not workable is not knowing.
A poor answer sounds like: "Keep growing and see where we get to." That is the plan that produced the current position.
What to do with your answers
Do not try to resolve everything. Look for the two questions where your answer was vaguest, because vagueness is the actual finding, and start there.
Then put the answers somewhere you will find them, and diarise a date twelve months out to do it again. The answers will move. That movement, year on year, is one of the more informative things you can know about your own business, and about yourself.
The founders who do this are not more decisive by temperament. They have simply made the questions routine, so that answering them stops being a moment of reckoning and becomes something that happens every January, in about ninety minutes, with a coffee.