Most people choose a consultant the way they choose a caterer: on the pitch, the deck, and how the person made them feel in the room. None of that tells you what the relationship will actually be like once the contract is signed and the first hard conversation arrives.
The right consultant is not the one with the smoothest pitch. Ask what they would change first, who actually does the work, and what happens if you disagree with their advice. A straight answer is worth trusting. A vague one is telling you exactly how the engagement will go.
I'm the one being asked these questions here, not the one asking them — fair reason to read this list with some skepticism. But I spent a good part of my career on the other side of the table, asking these same questions of consultants. So take it as what I'd want to know, and what I'd expect to be able to answer myself. My rule: ask the uncomfortable question first, not last. The answer to that one tells you more than the rest of the pitch combined.
Ask before you sign, not after
A pitch is a performance, and a reasonably good one is not hard to give. What is harder to fake is a straight answer to a specific, slightly awkward question asked in the first or second meeting, before anyone has signed anything and before the relationship has a reason to be polite.
These are the ten I would ask, and they cluster around the three things I think are easiest to leave vague: who is actually doing the work, what happens when things get difficult, and what you are left with at the end. None of them are trick questions. A good firm should be able to answer all ten without flinching, because the honest answer is the same one it would give a colleague. What I am really testing for is a mismatch nobody names at the start, which in my view does more damage than bad advice ever does: a junior team where a senior partner was promised, a diagnostic that never turns into a decision, an engagement that drifts into permanence because nobody agreed what "finished" would look like. Every one of the ten is aimed at surfacing that while walking away is still easy.
The ten questions worth asking before you commit
Who exactly will do the work? A good answer names a real person, their seniority, and roughly how much of their week sits on your account. A deflection talks about "the team" or "our people" without naming anyone, because the senior partner who sold you the engagement is not the person who will be running it.
Will the person who sold us on this still be in the room next month? A good answer says yes and explains how, or says no and tells you plainly who takes over and when the handover happens. A deflection changes the subject to methodology or "the wider bench," because naming the handover honestly would have cost them the meeting.
What is the first thing you would look at, and why? A good answer names something specific, a margin, a bottleneck, a pattern in the numbers, drawn from what they can already see, and says clearly what still needs proper discovery before they would recommend action. A deflection either claims certainty about a business it has not yet examined, or refuses to name anything at all until a lengthy diagnostic has been commissioned.
What do you need from us that we're probably not going to want to give? A good answer names something uncomfortable: real access to the numbers, time with the founder rather than a deputy, the authority to say no to a pet project. A deflection says "just your trust," which sidesteps the question rather than answering it.
What happens if we disagree with your recommendation? A good answer describes an actual process: they make the case once, plainly, and respect the decision, or push back a second time if the stakes genuinely warrant it. A deflection promises they will always defer to the client, which sounds respectful but means what you get is validation rather than judgement.
How will we know if it's working, and how often will you tell us? A good answer names a cadence and a measure tied to a commercial outcome, built into the engagement from the start rather than saved for a final report. A deflection talks about "regular check-ins" with no fixed rhythm and no stated measure attached to any of them.
What have you said no to, and why? A good answer names a type of engagement, a request, or a client it has turned away, and the reasoning holds up under a second question. A deflection claims to take on everything that comes through the door. A firm with a genuine specialism can point to work it deliberately does not do.
What have you got wrong before, and what changed because of it? A good answer names a real misjudgement, what it did to the work, and what the firm does differently now as a result. A deflection produces a story in which the mistake turns out to have been someone else's, or a lesson so general it could belong to any engagement. Nobody with a real body of work behind them has a clean record, and a firm that presents one is telling you it does not examine its own.
What happens when the engagement ends? A good answer describes what stays inside your business afterwards: a process, a capability, a person now trained to run something without outside help. A deflection assumes you will simply renew, because the model depends on the relationship never quite finishing.
What is outside your specialism, and who would you send us to instead? A good answer names a real boundary and, ideally, the type of specialist you should be speaking to instead. A deflection claims to cover everything a growing business could need. Nobody credible is expert in everything, and the claim that they are is itself the more useful answer.
None of this is about catching anyone out. It is about watching how a consultancy behaves when a question is fair and the honest answer is slightly inconvenient to give.
Before you commit
If what you actually need at this stage is a sounding board rather than a full engagement, worth naming that to yourself before you start interviewing anyone: outside judgement without a scope document is a different arrangement to a structured project, and asking these ten questions of the wrong kind of relationship will just produce confusing answers.
Take this list into three conversations before you decide anything. The firm that answers plainly, not persuasively, is the one worth trusting with the work.
Ask us the same ten questions, in whatever order you like. If an answer sounds rehearsed, you already have useful information. If it does not, start the conversation and see where it goes.
Frequently asked questions
How many consultants should you actually speak to before deciding? Three is usually enough to see a genuine pattern without the search itself becoming the delay. Speaking to only one gives you nothing to compare against; speaking to six mostly just tires you out before a decision gets made either way.
What if a consultant needs time to think before answering one of these questions properly? That is different from evasion, and worth telling apart. A consultant who says "let me look at your numbers before I answer that one properly" is being careful. One who gives the same vague answer regardless of what they have actually seen of your business is being evasive. The tell is whether the follow-up answer gets more specific once they have looked, or stays exactly as vague as the first one.
Should the questions change if you're hiring for a single project rather than an ongoing relationship? The ones about disagreement and about what sits outside their specialism still apply in full. The ones about who does the day-to-day work and what happens when it ends matter even more on a shorter project, because there is less time to notice a mismatch before the work is finished.
Is a consultant who has never turned a client away automatically a bad sign? Not automatically. Someone newly independent may genuinely not have turned much away yet. What matters more is whether they can describe the kind of work they would decline if it came up, rather than whether they already have a list of past refusals to point to.
Does it matter if a consultant asks you hard questions back? It matters a great deal, and it is a good sign rather than a bad one. Someone worth hiring should want to understand your numbers, your team and your real constraints before agreeing to help, not simply nod along to whatever you say you need. A consultant who asks nothing back is either being polite at the wrong moment, or has not yet worked out what your business actually requires.
Kirsty Newman is Founder of The Boutique Consultancy. She spent almost two decades at some of the largest corporate powerhouses in beauty and luxury, including YSL Beauty, Giorgio Armani Beauty, Lancôme and Rimmel (L'Oréal Group and Coty). She went on to work with a number of startups as they scaled, before striking out on her own. Across this time, she has run seven-figure P&Ls and teams of 16, with direct engagement in venture capital funding and expansion.