Most sellers spend months preparing their business for a buyer’s scrutiny — clean financials, tidy contracts, a story that holds together under questioning. Fewer spend five minutes preparing their own questions for the buyer sitting across the table. That’s backwards. You’re not just being evaluated here. You’re evaluating right back, whether anyone says so out loud or not.

Here are ten questions worth asking before you sign anything, and what a confident buyer’s answer should sound like.

1. What happens to my team on day one? A buyer with a real plan will tell you specifically. A buyer who gets vague is telling you something too.

2. How many deals like mine have you actually closed? Enthusiasm is common. A track record of closed MSP transactions is not, and it’s the difference between a buyer and a buyer-shaped idea.

3. What does your typical hold period look like? This tells you whether you’re joining a five-year growth story or a two-year flip, and both can be fine — as long as you know which one you signed up for.

4. Who exactly makes the final call on this deal? Every buyer has a real decision-maker. Finding out now saves you from negotiating with someone who has to check with someone else at every turn.

5. What’s your integration philosophy — absorb or preserve? Some buyers fold you into one unified brand. Others let you keep your name and your culture with back-office support underneath. Both are legitimate strategies; you just want to know which one you’re getting.

6. How does your earnout actually get calculated? Ask for the formula, not the summary. The summary is marketing. The formula is the deal.

7. What happens if we miss a projection by a little? A buyer’s answer here tells you how much good faith is built into the structure — and how much of your future payout rides on things outside your control.

8. Can I talk to a founder you’ve already acquired? A buyer confident in their own track record will connect you. Hesitation here is data.

9. What’s your timeline from LOI to close, realistically? Ask for the version that accounts for the diligence surprises that always show up, not the version from the pitch deck.

10. What does success look like for you a year from now? This is the question that tells you whether your goals and theirs are actually the same shape, or just pointed in the same general direction for now.

None of this is about grilling a buyer like a hostile witness. It’s about walking into the biggest financial decision of your career with your eyes as open as theirs are. The best buyers expect these questions and respect them. The ones who don’t just told you something worth knowing before the ink dries.

This is a lot of what Transaction Therapy actually is in practice — not just closing a deal, but making sure the seller has someone in their corner asking the sharp questions before, not after.