You're thinking about hiring a consultant. Before you do, here are the questions I think you should ask. Any consultant, including me. Especially me, actually, since I'm the one telling you to ask them.
I'm organizing these by what you're really trying to learn, because the questions only matter if you know what a good answer sounds like.
"What exactly will I get?"
You're trying to learn whether the consultant has a clear picture of what they'll deliver, or whether they're winging it.
Ask it directly. What are the deliverables? What will I have in my hands at the end of this engagement? Can you describe the output in specific terms?
A good answer sounds like: "You'll receive a written report that includes a map of your core processes, a list of identified bottlenecks with analysis, and a prioritized set of recommendations with estimated impact. We'll walk through it together in a 90-minute session."
A bad answer sounds like: "We'll work together to develop insights about your business." That's not a deliverable. That's a fortune cookie.
"Who does the actual work?"
At larger firms, the person who sells you the project is often not the person who does the work. You meet a senior partner, get impressed, sign a contract, and then a team of junior people shows up on Monday.
For a solo consultant like me, this isn't an issue. I'm the person who scopes it, sells it, does it, and delivers it. Same person all the way through. But if you're talking to a firm, ask. You deserve to know who's actually going to be in the room.
Follow up with: what's their experience? Have they worked with businesses like mine? Can I meet them before I commit?
"How is pricing structured?"
You're trying to understand what this will cost, but also how the incentives work.
Is it hourly? Fixed price? Retainer? Value-based? Each structure has implications. Hourly means you don't know the final cost. Fixed price means you do. Retainer means you're paying for availability. Value-based is often a fancy way of saying "expensive."
Whatever the answer, follow up with: what does this typically cost for a business like mine? Can you give me a range?
If they dodge the question, that's information. Pricing shouldn't be mysterious. You're not buying a house at auction. You're hiring professional services. The price should be clear before you sign anything.
"What happens if it doesn't work?"
This question makes some consultants uncomfortable, which is exactly why you should ask it.
What if the recommendations don't produce results? What if the implementation hits a wall? What if we get halfway through and realize the problem was different than we thought?
A good consultant has thought about this. They'll talk about how they adjust course mid-project, how they handle scope changes, what their follow-up looks like. They won't guarantee results, because nobody can guarantee results in a complex system, but they'll have a plan for when things don't go as expected.
A bad answer is any variation of "that won't happen." It will happen. Something will go differently than planned. The question is how they deal with it.
"Do you implement, or just advise?"
This is a big one. The consulting industry has a long history of producing beautiful recommendations that nobody implements. The report sits in a folder. Nothing changes.
If a consultant only advises, that's not necessarily a deal-breaker. But you need to be honest with yourself about whether you have the bandwidth and capability to implement on your own. If you do, advisory-only might be fine and cheaper. If you don't, you need someone who'll stick around for the messy part.
Ask: what does implementation support look like? How involved are you in making changes happen? At what point do you hand things off?
"What does the handoff look like?"
You're trying to learn whether you'll be able to sustain changes after the consultant leaves, or whether you'll be dependent on them.
Will there be documentation? Who gets trained? What does ongoing support look like? Is there a follow-up period?
The best answer includes specifics about how knowledge gets transferred to your team. The worst answer is a blank stare, which tells you they haven't thought about it, which tells you they've probably left a trail of clients who reverted to old habits the moment the engagement ended.
"Can you describe a project that didn't go well?"
This one catches people off guard. Everyone has success stories ready. But a consultant who can openly discuss a project that struggled, what went wrong, what they learned, and what they'd do differently, is someone with self-awareness and integrity.
If they claim nothing has ever gone wrong, either they're lying or they haven't done enough work to have encountered real complexity. Both should concern you.
"What's your experience with businesses like mine?"
This doesn't mean they need to have worked with your exact industry. Operational problems are similar across a lot of different businesses. But they should have relevant experience at your scale, your stage, and your general type of work.
A consultant who has only worked with venture-funded tech startups might not understand the constraints of a bootstrapped service business with eight employees. The skills overlap, but the context matters.
Ask for specifics. Not just "I've worked with small businesses" but "I worked with a professional services firm with about your headcount that was dealing with a similar growth transition. Here's what that looked like."
"Why should I hire you instead of someone else?"
This is uncomfortable to ask but useful to hear the answer.
A good consultant won't trash-talk competitors. They'll tell you what's specifically different about their approach and let you decide if that difference matters for your situation. They'll also be honest about the cases where they're not the best fit.
If the answer is all about credentials and no about approach, that's a yellow flag. Credentials tell you where someone went to school or which firms they worked at. Approach tells you what it'll actually be like to work with them.
Using the answers
You now have a set of questions and a sense of what good answers sound like. But the most important thing isn't any single answer. It's the overall pattern.
Did the conversation feel like a pitch, or like a genuine exploration of whether you're a good fit? Did they ask you as many questions as you asked them? Did they seem more interested in closing you as a client or in understanding your situation?
The best consulting relationships start with mutual honesty. If the initial conversation doesn't feel honest, the engagement won't either.
If you want to try these questions on me, I'm happy to sit for the exam. Grab a time for an intro call and ask away.