The One Question He Wishes He'd Asked His Advisers

Most founders would have done what he did. You assemble your outside help over a decade, one problem at a time, and you never step back and ask whether the group you've assembled can do the thing you're eventually going to ask of it. It's the wrong test, applied for years. Running your business well and selling it well are different jobs. An accountant who closes your books cleanly hasn't necessarily survived a quality of earnings review. A lawyer who handles your contracts hasn't necessarily sat across from a private equity buyer's counsel. The question is a good one because it can't be answered with enthusiasm. Nobody talks their way through "what size exits have you been part of, and whose." You either get a list or you get a pause, and the pause is the answer. It also costs nothing to ask now. Asking during a live process means firing someone in the middle of a deal, which almost nobody does, because the deal is the priority and the adviser is already halfway up the hill with you. This is the cheapest exit preparation there is. No diligence, no consultant, no restructuring. Four phone calls.

List the four outside partners who'd be involved if you sold: accountant, lawyer, banker, whoever else. Send each of them the question. What size exits have you been part of, and who have you taken through one? You're not hiring or firing anyone this week. You're finding out what you've got, while you still have years to change it.