Why the choice matters more than founders expect
For many founders, selling a company is a once-in-a-lifetime event; for many buyers, it is routine. The adviser you pick decides who sees your business, in what order, under what confidentiality, and with how much competition at the table. In our experience, those four things shape the final price as much as anything you can still change in the business in the last few months.
Titles do not help much. In our view, “broker”, “adviser”, “corporate finance” and “M&A boutique” are used loosely. The questions below cut through the labels.
1. How do you protect confidentiality during the process?
Good answer: NDA first. Information is released in stages, and only to screened buyers. No mass marketing.
Red flag: “We list your business on public marketplaces. Confidentiality is your responsibility.”
Why it matters: the fastest way to damage a business is for staff, customers or competitors to hear it is for sale before the deal is real.
2. How do you create competitive tension?
Good answer: Running three to five qualified buyers in parallel, on a structured timeline with clear milestones.
Red flag: “We find one buyer and negotiate.”
Why it matters: a single bidder sets the price. Several credible bidders on the same timetable let the market set it.
3. What is your anti-retrade strategy?
Good answer: A structured diligence process, momentum kept high, the psychology of the deal managed, and protective provisions written into the letter of intent.
Red flag: “Retrades happen sometimes. We negotiate when they occur.”
Why it matters: a retrade is a buyer cutting the agreed price after you have stopped talking to everyone else. In our experience, it is one of the main ways a good headline offer turns into a disappointing cheque, and it is far easier to prevent than to fix.
4. How do you qualify buyers before approaching them?
Good answer: Verifying financial capacity, assessing strategic fit and reviewing each buyer’s acquisition track record before anyone sees your name.
Red flag: “We contact as many buyers as possible and see who responds.”
Why it matters: every unqualified buyer who sees your information is a confidentiality risk and a distraction from the ones who can actually close.
5. What is your fee structure and alignment?
Good answer: Retainer-only, or retainer plus success fee. Skin in the game. Performance guarantees available.
Red flag: Success fee only. No upfront commitment. A percentage of any deal.
Why it matters: fee structure shapes behaviour. Ask what the adviser is paid for, and what happens if they cannot produce a qualified offer.
A simple way to use these questions
Ask all five in your first meeting with every adviser you are considering, and write down the answers word for word. In our view, vague answers to questions one and three deserve the hardest follow-up: confidentiality and retrades are where a well-priced sale is most exposed.