Nobody tells you this, so here it is.
The first call with an owner is not a negotiation and it isn't diligence. It's a fit test, and it runs on a fixed question set that never changes. Same questions, same order, every time.
Fixed beats clever. When the questions are the same on every call, the notes are comparable, nothing gets forgotten, and you stop improvising at the exact moment improvising costs you the most.
Here's the set, why each one is in there, and what to do with the answers.
Before you ask anything
Two moves, in this order, and they take about ninety seconds.
Say who you are. Your name and what you actually are. A buyer. An operator. A firm working for a buyer. If someone else pays you, say so out loud. Owners tell the truth to people who tell the truth first.
Ask permission and hand them the exit. This is the move that makes the whole set work:
"I've got about eighteen questions. Anytime you want, you can say let's wait until an NDA and I'll note it and move on. It's basic stuff about the business, and it tells me whether I'm even the right fit for you. Good to run through them?"
You've reframed the questions as a fit test for them instead of diligence from you, and you've removed the pressure that makes owners stonewall. Offer that door and most of them walk right past it. I've had owners who brought up an NDA before we started answer every single question, margin and earnings included, without ever invoking it.
One note on the count: the sheet actually runs nineteen fields. We say eighteen on calls out of habit. Either is fine. Just don't promise a number and then ask thirty.
The business
1. What does the business do and how does it make money? Listen for how revenue is actually earned, not what the company calls itself. This question surfaces more structural surprises than any other. It's where you find out the target is one of two entities, or that half the revenue comes from a line nobody mentioned.
2. How long have you been in operation? Short question, long answer if you let it run. Owners volunteer pivots, prior raises, model changes. A prior venture raise is a cap table problem you'll want to know about now rather than in month four.
3. How many employees, and what are the key roles? Get a number and get roles. If the number is small, say something nice about it. It costs nothing and it lands.
4. How involved are you day to day? Is there a management team, or does the place depend on you? The most valuable non-financial answer on the sheet. Get hours per week if you can. This one determines what you're actually buying: a business or a job.
The numbers
5. Do you have a sense of your SDE or EBITDA, even roughly? Then immediately: "You don't have to give me a number. Just tell me what you feel would be useful." That softener is what produces the answer. Without it you get a wall.
Never lead the call with this question. Ask it here, fifth, after four easy ones have already gone well.
6. How has revenue trended the last couple of years: growing, holding steady, or pulled back? Give them the three options. A multiple-choice question gets answered. An open one gets a shrug.
7. Are your financials in good shape? Do you have current P&Ls and tax returns? Ask it and then stop talking. This is the one people blow by filling the silence with "I'm sure you do." Now you have no answer on the record.
The sale
8. What's got you thinking about a sale at this point? The answer is usually one word. Take that word and reflect it back in their own frame: "Sounds like you've taken it as far as you want to take it, and you're not in a place where you want to run the next chapter." Owners expand on a reflection far more than on a follow-up question.
9. If things moved forward, what timeline would feel right? If they don't have one, name the stage for them. "You're probably just curious what this could trade for. Early, exploratory." That reframe lowers the stakes and keeps them talking instead of making them commit to something.
10. Do you have a number in mind, or are you open to working through a valuation? Expect the multiple question to come straight back at you. Answer it with a range, attach the range to the buyer, and don't commit to anything. Then stop talking. Owners price themselves out loud more often than you'd expect, but only if you gave the range first and then went silent.
11. Have you talked to any other brokers or buyers? Working with anyone now? Ask about inbound private equity too. Owners who are getting PE calls and refusing them will tell you so, and that answer is a gift.
Operations and risk
12. Is any one customer a big chunk of revenue?
13. Is there anyone on the team the business couldn't run without? If the answer is yes, don't stop at yes. Two follow-ups, both of them: "Tell me about that a bit," and "Do you think they'd stay after a sale?" Then two more people forget: what that person earns, and whether there's an employment agreement or non-compete. Retention cost is a real number and you want it early.
14. Is there a lease? What are the terms and when does it run through?
15. Any legal issues, liens, or anything we should know about? Ask it and wait. This is the second question people answer for the owner. If nobody answers it, write "not discussed." Silence is not a representation that nothing exists, and your notes should say exactly that.
Fit and next step
16. What would the right buyer look like to you? Offer the contrast if they stall. Most owners have strong feelings about who takes over what they built, and many of them have already decided how they feel about private equity.
17. Would you consider an earn-out or staying on for a period, or are you looking for a clean exit?
18. Is there anyone else involved in this decision? Are you the sole decision maker?
19. Not a question for them. It's your call, written down: pursue, hold and develop, or pass.
The four rules that make the set work
Ask, then be silent. If you answer your own question you've lost the field. This costs more than any other mistake on this list.
A non-answer is an answer. "Not stated" is a legitimate entry and a useful one. It tells you what to ask next time.
Never write a number they didn't say. Not in your notes, not in a summary, not in an email to a partner. An estimate you invented becomes a fact three weeks later, and then it's wrong in a model.
When they defer to the NDA, mark it and move on. No push, no "well, ballpark?" Write "to be discussed once the NDA is in place" and go to the next question.
Before you hang up
Full name spelled out. Legal company name. Direct line. Best email.
Sounds trivial. It's the thing everyone skips and then spends an hour recovering afterward.
Same questions, same order, every call. That's the whole game. And it pays to play it right.