Beyond Price: 11 Questions to Keep on the Table When You Sit Down with a Seller

Quick story for context. Three years ago I met a founder who opened our first meeting dreaming out loud about retirement on a sailboat. Four weeks later he was dodging calls. When we finally talked it through, his real worry surfaced: he was the town’s unofficial mayor. If he sold, neighbors might lose jobs, his kids’ stature could slip, and his legacy would feel tarnished. Once we understood that, we reframed the deal around job-security guarantees and a community-reinvestment fund. The conversation unlocked again. That experience reminded me why the questions below matter. What truly motivates the seller? Legacy, community standing, or family reputation often outweigh simple price. Identify those drivers early so your terms solve real needs, not imagined ones. Is the market expanding or quietly shrinking? A contracting TAM compresses multiples and shifts leverage toward buyers. Invite the owner into the macro view; it moves the dialogue from yesterday’s EBITDA to tomorrow’s resilience. Who owns the customer relationships after closing? If goodwill lives in the owner’s personal touch, plan for a structured hand-off period or consulting role before it disappears. Is the reported EBITDA repeatable? Normalize for one-offs, deferred maintenance, and owner perks. Position this as joint risk management rather than a price-cutting exercise. What is a fair working-capital peg? Agree on target WC, collar ranges, and a true-up mechanism before the LOI. Clarity now prevents emotion later. How sticky is the talent bench? Use retention bonuses, stay interviews, or option pools to lock in key staff for the first 180 days. Leverage the seller’s influence while you still have it. Are there hidden liabilities on or off the balance sheet? Personal guarantees, pending litigation, or long-term warranties can outlive closing. Map them and decide who carries what. What role, if any, will the seller play post-close? Advisory gigs, board seats, or phased exits ease transition risk. Put expectations in writing to avoid drive-by management later. How will institutional knowledge transfer? Schedule structured downloads for SOPs, passwords, and vendor nuances. Do not rely on hallway conversations. Do the two cultures fit? Shared communication style, decision rights, and meeting cadence can matter more than another decimal place on valuation. Pilot a joint working session to test cultural chemistry. What is the plan for deal fatigue? Lower-middle-market timelines stretch. Set weekly check-ins, milestone deposits, and mutually agreed quiet periods, such as holidays, to keep momentum and trust intact. These questions are lenses, not checkboxes