One of the hardest things to assess early on is fit. The financials might check out. The business might fall right in your target industry. But if you don’t mesh with the seller—or their vision—the deal can quietly unravel.
When I first started taking seller calls, I focused a lot on the numbers. Revenue. Margins. Customer mix. I had my checklist, and I wanted answers. But over time, I realized I was missing something more important: the tone of the conversation. The comfort (or discomfort) between us. The vision match—or mismatch—that shaped every other topic.
Some of the strongest calls I’ve had weren’t with the best businesses—they were with the best people. Sellers who were honest about the hard parts. Who asked about me, not just my capital. Who wanted to understand what kind of operator I’d be.
If you’re trying to spot fit, here’s what I’ve learned to look for:
- The seller is open—not just in what they share, but how they share it
- You both see a similar path for the business post-transition
- They’re curious about you, not just your funding
- You feel the conversation is two-sided, not just informational
And on the flip side, here are a few signs that usually mean friction:
- Defensiveness or sugarcoating around tough topics
- A total absence of interest in who you are as a buyer
- Avoidance when you bring up transition, team, or handoff plans
These calls aren’t just about data—they’re about trust. Listen to what’s said, and how it’s said. Trust your gut. If the energy feels off, it probably is.
The numbers matter. But so does the relationship. And when you find a seller you actually connect with, it makes the entire deal process smoother.
