Before the CPA, before the spouse conversation, before any buyer’s coffee, there’s an audit only you can run, alone, with a legal pad and an honest hour. These are the twelve questions we’d want any owner to sit with before starting a process, ours or anyone’s. There’s no scoring rubric and no “mostly B’s” verdict at the end, because readiness isn’t a quiz result. It’s the condition of having real answers where these questions live. Take them in any order. The hard ones will find you regardless.
1. Why now? Not the polished version for buyers, the real one. Health, boredom, a market window, a spouse’s patience, an anchor client wobbling? Every reason is workable when it’s named, and every unnamed reason runs the negotiation from backstage. This is the selling-versus-escaping question, and it goes first because every other answer bends around it.
2. What does the money actually need to do? Not “what’s it worth” but “what do we need”: the retirement arithmetic, the kids, the buffer. Until you’ve computed the need, no offer can be evaluated, because “enough” has no definition. The gap between need and likely proceeds is either your green light, your work plan, or your reason to wait.
3. Do I know what it’s worth, from evidence? A workbook run, a conversation with someone who prices these businesses, anything but the conference rumor and the hoped-for number. Unrealistic expectations don’t just waste your time; they waste your best buyers, who walk early and don’t come back.
4. Could the business run 30 days without me? The vacation test, answered honestly. It measures what a buyer can believe survives your exit, and it measures something more personal: whether what you’d be selling is a company or your own job. One of those has a market.
5. Who on my team am I protecting, and what does protection mean? Names, not sentiment. The lieutenant who’s owed the truth early, the twenty-year tech near retirement, the young one carrying the on-call. What you’d want written into a deal for them, and what you’d trade for it, because you will be asked to price it.
6. Is my house aligned? Has the dinner-table conversation happened, and did it end in a shared direction or a postponed one? Deals negotiated against a divided home fail late and expensively, and “my spouse is fine with it” is an answer that deserves one follow-up: have you actually asked?
7. What would I protect at any price? The name, the office staying open in your town, no layoffs for a year, the anchor client’s service model? Rank them, because a negotiation is coming where they’ll be traded against dollars, and owners who rank under pressure rank badly.
8. What am I afraid the diligence will find? Everyone has a list: the messy 2023 books, the handshake contracts, the license true-up, the client who’s really a friend doing you a favor. Naming yours converts dread into a work plan, and almost everything on it is fixable with runway. The unfixable version is the one discovered by a stranger in month five.
9. Am I prepared to be judged? A sale process is months of strangers grading your life’s work: your margins, your paperwork, your decisions from 2015. Sellers who internalize that the grading is of the asset, not the person, survive it cheerfully. Sellers who can’t are in for a bruising season, and it’s better to know your skin’s thickness in advance.
10. What’s my walk-away, and would I actually walk? A number and a set of terms below which there is no deal, written down, before the first offer recalibrates your sense of normal. The question isn’t whether you have one. It’s whether the person who has spent two years wanting this done would honor it at month five, tired and close. If the honest answer is no, appoint guardians: an advisor with instructions, a spouse with veto power.
11. What is Monday for, after? The question nobody prepares for, asked before it’s urgent. You don’t need the full answer. You need evidence you’ve started: something prototyped, something on a calendar, some structure waiting on the far side. Owners with a Monday negotiate better and land softer, and the ones without one find reasons to blow up good deals.
12. If nothing changed for three more years, how would I feel? The control question, and the quiet tiebreaker for everything above. Relief means you’re not ready, and that’s a fine answer that saves everyone a wasted process. Dread means the timeline is more honest than you’ve been letting it be. Something in between means you’re exactly the owner this whole audit was designed for: not ready today, but ready to get ready, which is the strongest position in this entire subject.
Sit with the twelve, write real sentences under each, and date the page. Owners who repeat the exercise a year later report the most useful part is the diff: watching which answers hardened, which softened, and which question suddenly has a different name in it. When most of the page reads like decisions instead of worries, you’re done auditing, and the first conversation, whenever you choose to have it, will be one you walk into already knowing your own mind. That, more than any multiple, is what ready looks like.