In a first meeting with a business broker, ask about their experience closing main street deals, how many similar businesses they have sold recently, and how they handle valuation and marketing to attract qualified buyers.

In a first meeting with a business broker, the three most important questions are: How many Main Street deals like mine have you actually closed recently? How do you price and market small, owner-operated businesses in the real world not just on paper? and How involved will you personally be from start to finish? These questions cut through the sales talk and help you feel whether they truly understand the emotional, hands-on nature of Main Street deals or if they’re just chasing listings without real follow-through.

In the first meeting, ask about their track record with Main Street businesses, including recent deals similar in size and industry. Clarify how they source and qualify local buyers to avoid wasted time. Finally, understand their valuation approach and closing process, as experience here often determines a smooth, successful sale.