10 Questions to Ask Before Hiring an M&A Advisor (and the Answers That Matter).

By Lane Gordon, 733Park. Updated September 15, 2026.

733Park's rule of thumb: the right M&A advisor for a lower-middle-market company can name your three most likely acquirers on the first call, will personally run your process from pitch to close, and can tell you how many engagements taken to market actually closed; if any of those three answers is vague, keep interviewing.

Most founders hire an M&A advisor once. The firm you pick has done it hundreds of times, and it will be very good at the pitch. These ten questions cut through the pitch. For each one, the good answer and the bad answer, then a scorecard to run across every firm you interview.

The ten questions

1. Which buyers have you sold companies to in my category? Good: names, deals, and why each buyer bought. Bad: "we have a great network."
2. Who are the three most likely acquirers of my company, and why? Good: an immediate, specific answer with a reason for each. Bad: "we would run a broad process and see who responds."
3. Who will run my deal day to day? Good: the person in the room, from pitch to close. Bad: a senior pitch and a junior team you have not met.
4. How many engagements taken to market actually closed? Good: a number, and the reasons for the ones that did not. Bad: a logo wall.
5. How many deals is your team running right now? Good: few enough that yours gets attention. Bad: a number that makes you a line item.
6. What size deals do you do, and where does mine sit? Good: your deal is in the middle of their range. Bad: you are the smallest or the largest they have done.
7. How will you position my company, and to whom first? Good: a point of view on the buyer order and the story. Bad: a generic teaser and a blast.
8. What will you need from me, and when? Good: a preparation list and a timeline. Bad: "just send us the financials."
9. What happens if we get an inbound offer during the process? Good: a plan for using it as a floor without losing the other bidders. Bad: surprise.
10. What is the engagement structure, in writing? Good: a clear scope and term, in writing, before work starts. Bad: vague.

The scorecard

Weight buyer relationships and senior attention most heavily. Those two decide the outcome; everything else is hygiene. Run the same card on at least three firms.

Boutique or bank

For a company between $5M and $100M of enterprise value, a sector boutique usually wins on all three of the answers that matter, because the senior partner runs the deal, the buyer relationships are specific to your category, and your deal is not the smallest in the building. Above that range, or for a public-company sale, a bank's balance sheet and coverage start to matter. The fuller comparison is in investment bank vs boutique M&A advisor; the payments-specific version of this checklist is how to choose a payments M&A advisor.

About 733Park

733Park is a boutique M&A advisory firm for payments, fintech, AI and SaaS companies, with 25 years of payments M&A expertise, 200+ closed transactions and $10B+ in transaction volume. Clients have enterprise values of $5M to $350M and work directly with Lane Gordon and the principals, not junior associates. 733Park provides sell-side advisory, buy-side advisory and consulting on growth strategy and exit readiness, with roots in merchant portfolios and ISOs.

Frequently asked questions

What questions should I ask before hiring an M&A advisor?

Which buyers they have sold to in your category, who your three likely acquirers are, who runs the deal day to day, how many engagements taken to market closed, how many deals they are running, where your deal sits in their range, how they will position you, what they need from you, how they handle an inbound offer, and the engagement terms in writing.

How do I choose the right M&A firm?

Interview at least three firms and score them on the same ten questions, weighting buyer relationships in your category and senior attention most heavily; those two decide the outcome.

Should I use a boutique or an investment bank?

For most companies between $5M and $100M of enterprise value, a sector boutique, because the senior dealmaker runs the process and the buyer relationships are specific.