Experience and relevance
Which of your completed transactions is closest to my situation, and why? How many transactions have you completed in my size band in the past three years? What was your personal role in each of them? What has changed in this part of the market in the last twelve months? Which parts of my situation are outside your usual experience?
The last question is a good test of candour. Every advisor has boundaries, and the ones who name them are usually more reliable on everything else.
Team and staffing
Who runs this mandate day to day? Who attends investor or buyer meetings? Who writes the memorandum or the deck, and who builds the model? How many other mandates is that person running right now? What happens if they leave the firm during my process?
Ask for the answers to be reflected in the engagement letter. Named team members in a mandate document prevent the most common post-signing disappointment.
Counterparties and network
Which investors or buyers would you approach first, and in what order? Which of them have you spoken to in the past six months? Which are likely to pass, and why? How would you approach a party where you have no existing relationship? Are you working with any of these parties on another mandate?
The final question addresses conflicts. Advisors run multiple mandates, and overlapping counterparty lists are normal, but you should know about them before signing.
Process and timeline
What process would you run for this situation, and why that one? What is a realistic timetable by phase? What preparation work needs to happen before we approach anyone? How do you keep competitive tension once we are down to a small number of parties? What are the two most likely reasons this process does not complete?
The realistic timetable is worth probing. Optimistic timelines are a selection tactic; ask what their last comparable process actually took.
Valuation and expectations
What range do you think is achievable, and what supports it? Which comparable transactions inform that view? What would need to be true for the upper end to be reachable? What in our numbers will attract the most challenge?
Be careful with advisors who quote an attractive number before reviewing your financials. Valuation promises in a pitch meeting are a known way of winning mandates and rarely survive the market.
Fees and mandate terms
What is the full fee structure including retainer, success fee and expenses? How is transaction value defined for the success fee? Is the retainer credited against the success fee? What is the tail period, and how is an introduced party defined? What notice is required to terminate, and what is owed on termination? Is the mandate exclusive, and for how long?
Ask for a draft engagement letter early. Reading it is more informative than discussing it. Our guide on how advisor fees work covers these terms in detail.
Working relationship
How often will we speak, and in what format? Who is my point of contact for day to day questions? How do you handle disagreement with a client about strategy or price? What do you need from us to do this well?
The last question separates advisors who see the mandate as a joint process from those who see it as a service delivery.
After the meeting
Write down the answers immediately and compare them side by side. Look for differences in the counterparty list, the timetable and the valuation reasoning rather than differences in polish.
Then check the references before you negotiate fees, not afterwards. Reference calls sometimes change the ranking, and it is easier to walk away before a fee negotiation has created momentum.