Three categories of advisor serve business owners who are thinking about selling. Business brokers typically handle companies with transaction values under two million dollars, and their practice is built around running a process that connects individual buyers to individual businesses. M&A advisors generally take on transactions from roughly five million to a hundred million in deal value, and their work looks more like an investment banking engagement with a managed auction, buyer outreach, and negotiated deal terms. Exit planners focus on readiness rather than transaction execution, and their work often begins years before a sale is even on the calendar.
The first question a founder should ask is which category fits the size and complexity of the business. A founder running a six million dollar revenue company will be poorly served by a broker whose median deal is under a million, and equally poorly served by a banker whose median deal is fifty million. Matching advisor practice size to deal size is the single largest driver of whether the advisor's process will actually fit the business.
The second question is about buyer access. An advisor's value is largely in the buyers they can reach. That includes strategic acquirers with active acquisition mandates, private equity firms with platform companies in the sector, family offices with patient capital, and occasionally high net worth individuals with relevant backgrounds. Ask for the list of buyers the advisor has successfully sold to in the last three years. A working advisor will have that list ready. One who does not is not one to hire.
The third question is about the sector. Healthcare sells differently than light manufacturing. Professional services sells differently than distribution. An advisor whose last five closings were all in one sector brings relationships, comparable transaction data, and buyer insight that a generalist cannot match. That specialization is worth paying for in most cases.
The fourth question is about references. Ask for the names and phone numbers of the founders whose businesses the advisor has sold in the last eighteen months. A serious advisor can produce those references without hesitation. When the founder calls those references, the question to ask is not whether the advisor is good. The question to ask is what surprised them about the process, what they would do differently, and whether the advisor told them the hard things they needed to hear rather than the things they wanted to hear.
The fifth question is about fees. Engagement fees, success fees, minimum retainers, and the structure of what is earned if the business does not sell are all negotiable in most markets. Read the engagement letter slowly. The economics of the relationship should be clear on the face of the document. If they are not, negotiate until they are, or hire someone whose terms are simpler. The best advisor relationships begin with alignment on how the advisor gets paid.