When was the last time they went on vacation... will tell you a lot not only about the middle management layer, but also about the seller's leadership style and if the business can do without them.

Hi ^redacted‌. The key thing to remember is that first calls aren’t about due diligence, they’re about psychology, positioning, and signal-gathering. Your goal is not to interrogate, it’s to make the seller feel like you get them by asking thoughtful, open-ended questions. Some of my favorite angles: -Origin story. Ex: “How did you start the business, and what’s kept you going this long?” -Motivation check. Ex:“What does an ideal next chapter look like for you once you step away?” -Pride points. Ex: “What are you most proud of building here?” -Future vision. Ex: “If you had another 5 years, what would you double down on?” -Transition clarity. Ex: “What would make you feel confident about handing this business over to the right buyer?” -Management & systems. Ex: “How involved are you today in daily operations? What systems or automations already run without you?” -Post-sale goals. Ex: “Once the business is sold, what do you see yourself doing next? Travel, another venture, family time?” -Timing lens. Ex: “Why sell now versus 5–10 years from now?” When you weave these in, sellers open up about more than just numbers, they share their pride, fears, goals, and vision. That’s gold, because the more you uncover early, the more you can tailor future negotiations and structure a deal that speaks directly to their dream outcome. We also have briefing decks and call scripts but I can't share those unfortunately as it's only for in house members only, I hope you had some value with the topics above and feel free to send me a dm if you need more help and advice.