Start by defining the mandate, not the person
Before you evaluate anyone, write down what you actually need. A seed round with a target list of 40 funds, a Series B where the lead is already circling, a sale process with three likely strategic buyers and a private equity option: these are different jobs requiring different people.
Write two or three sentences covering the objective, the timeline, the internal capacity you already have, and the parts of the process you want to keep in-house. Founders who skip this step tend to hire generalists for specialist problems, then discover the gap in month three when the work gets hard.
The mandate definition also gives you a fair basis for comparison. If every advisor is answering the same brief, differences in their answers are informative rather than a function of what each person chose to talk about.
Comparable transactions come first
The single most useful filter is whether the advisor has completed transactions comparable to yours. Comparable means several things at once: similar transaction size, similar industry and business model, similar company stage, similar geography, and a similar counterparty group.
An advisor with 40 completed deals in industrial services has strong experience that may transfer poorly to a Series A for a developer tools company. Conversely, someone with six relevant software deals in the past three years may be a better fit than a banker with a much longer list drawn from a different part of the market.
Ask for a list of the transactions the advisor considers most comparable to your situation, and why. The reasoning matters as much as the list. See our deeper treatment in the guide on why comparable transactions matter when selecting an advisor.
Separate the firm's track record from the person's
Firms present institutional credentials. You are hiring individuals. Find out who will run the day to day work, who attends the investor or buyer meetings, and who writes the materials.
For each transaction the advisor cites, ask what their personal role was. Lead advisor, supporting team member, specialist on one workstream and internal reviewer are very different levels of involvement. None of them is disqualifying, but they tell you what the person has actually done rather than what their employer has done.
A useful question: which parts of that process did you personally negotiate, and which did a colleague handle?
Test the network claim
Every advisor says they have a network. Test it by being specific. Ask which funds or buyers they would approach for your situation, in what order, and what they know about each one's current appetite.
Strong answers include recent, concrete detail: which partner covers your sector, what that fund passed on last year and why, which strategic buyer has an active acquisition programme, which lender is still writing venture debt at your revenue level. Weak answers stay at the level of firm names.
You are also testing whether the relationships are current. A network built five years ago at a different point in the cycle is less valuable than a smaller list of live relationships.
Check references properly
Ask for two references from completed processes and, if possible, one from a process that did not close. The second type is more revealing. Deals fail for many reasons, and how an advisor behaves when a process stalls tells you more than a success story.
Useful reference questions: How present was the advisor once the process got difficult? Who did the work? Did the fee structure create any tension? Would you hire them again for the same job, and for a different job?
Speak to the founder or CFO directly rather than accepting a written testimonial. Ten minutes on a call surfaces more than a page of quotes.
Availability and capacity
Experience is only useful if the person is available. Ask how many live mandates the advisor is running, what stage each one is at, and what happens to your process if another deal reaches a critical point at the same time.
Fundraising and sale processes have peaks. Diligence weeks and negotiation weeks require daily attention. An advisor with four concurrent processes may still be the right choice if the team behind them is real, but you should know that before you sign, not during due diligence.
Fees, incentives and independence
Understand the whole economic package: retainer, any fixed project fee, success fee, the events that trigger it, the base it is calculated on, expenses, exclusivity, duration and termination terms.
Look at what the structure incentivises. A pure success fee rewards closing something, which is aligned when your goal is to close and less aligned when the right answer might be to wait. A retainer-only structure removes that pressure but places more of the risk on you. Hybrid structures are common for exactly this reason.
Independence matters too. Ask whether the advisor has commercial relationships with any of the investors or buyers they propose to approach. Disclosure is normal and manageable; discovering it later is not. Our guide on how advisor fees work covers retainers and success fees in more detail.
Working relationship and communication
You will spend four to nine months in close contact with this person, often under pressure. Chemistry is not a soft criterion in that context.
Practical signals: does the advisor tell you things you did not want to hear during the pitch process? Do they push back on your valuation expectations with reasoning rather than flattery? How quickly do they respond, and in what form? Do they explain their thinking, or just present conclusions?
The best working relationships involve some friction. An advisor who agrees with everything you say in the first meeting is unlikely to defend your position well in the third round of negotiation.
Run a short, structured selection process
Speak to three or four advisors, not one. Give each the same written brief. Ask each for a short view on positioning, likely counterparties, realistic timeline and fee proposal.
Compare the substance of what comes back: how differentiated is the counterparty list, how realistic is the timeline, how well does the positioning reflect what your business actually does. Then weigh that against fees rather than looking at fees in isolation.
The process takes two to three weeks and materially improves the odds of a good outcome. When you are ready to build a shortlist, browse advisors on CAPLINK and filter by advisor type, skills, industry experience and location.