Boutique advisory firms are easy to assess because there are few enough people that the answers are specific. Five questions get you most of the way, and the quality of the answers matters more than their content.
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Questions one and two: the record and the team
Which businesses like mine have you sold in the last two years, and may I speak to two of those sellers. Who by name will do the work, and how many live mandates do they carry right now. A firm that answers both precisely is a firm that expects to be checked; vagueness here predicts vagueness later.
Questions three and four: the buyers and the fee
How many buyers will you approach, and how many of those have you closed with in the last two years. What is the fee, the minimum, the tail and whether the retainer is credited at closing. Ask for a worked fee example at three prices, because a scale is easy to describe and harder to apply.
Question five: the awkward one
What would you do if I insisted on a price you thought was too high. A firm that says it would take the mandate anyway is telling you it will let the market educate you at your expense in time. The answer you want is that they would say so, in writing, and show you the evidence.
Questions people ask about boutique M&A advisory firms
How many boutiques should I approach?
Three, with the same written questions, which is enough to see the spread without the process leaking.
Do boutiques have real buyer lists?
In their sector, often better than a larger firm's. Outside it, frequently not, which is why sector fit is the first filter.
Is a retainer normal?
Yes at this level, because the preparation work is real. Ask whether it is credited against the success fee and what happens if you withdraw.