Advice on First Conversation with Potential Seller After Proprietary Outreach?

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June 30, 2025

by a searcher from University of California, Los Angeles - UCLA Anderson School of Management in Santa Monica, CA, USA

Just what the title says. Began proprietary outreach - have a couple meetings on the docket. Potential seller and I have some overlap in backgrounds/interest etc. Wondering if anyone has any good initial strategies and how to approach these initial conversations. Appreciate any advice!
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Reply by a searcher
from University of Edinburgh in Boise, ID, USA
My goal is to lay a foundation of trust. This first meeting is very much like a first date, you will both be trying to determine if you're interested in making some life altering decisions together. I spend as much time as I can learning about the owner, what makes them tick, what is motivating their desire to sell, what's stressing them out, what makes them proud, etc. Finally, I focus on letting them know I want to be a caretaker of their business, building on their legacy (as opposed to simply doing a transaction). This has to be true of course, you can't fake it.
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Reply by a searcher
from St. Cloud State University in Sheridan, WY 82801, USA
Here’s what helped us navigate those early convos:
1. Don’t treat it like a pitch. Ask open-ended questions that pull out their “why now.” Most sellers have a quiet reason they’re taking the call you want that revealed, not resisted.
2. Anchor to legacy early. One phrase that shifted the tone for us:“If we go down this path, I want you to feel proud of how your name lives on after the transition.”That instantly reframed us as legacy stewards, not opportunists.
3. Make it personal, not performative. We had some shared background with the seller too. Rather than over-index on that overlap, we used it to build trust e.g., “Feels like we both saw the same problem from different sides.”
4. Follow-up as a partner, not a suitor. After the call, send a note that recaps key emotional beats and next steps. Keep it short, but signal clarity and care. You’re setting precedent for how this deal will run.
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