Questions to Ask a Business Advisor
Questions to ask a business advisor in a first meeting, before you commit to a retainer or a project. They cover how the advisor is paid, whether anything they recommend earns them a commission, what the engagement produces, how much of their time you get, and how the relationship ends.
The questions
Open any question for the note
What would you want to look at first in a business like mine, and why that?
Why ask it
This exposes their default lens within a minute. Some go to cash and margin, some to pipeline, some to the founder's calendar. All three can be right, but you want to know which one you are hiring, and whether they chose it for your situation or apply it to everyone.
What is the smallest and largest business you have advised, and where do I sit?
Why ask it
Advice designed for a fifty-person company breaks in a four-person one, mostly because it assumes someone exists to carry it out. If you are at the edge of their range, ask what they would have to do differently for you.
Have you run a business yourself, and how did it end?
Why ask it
Neither answer disqualifies anyone, but the second half is the useful part. Someone who sold, closed, or ran out of money and can describe what they learned is more useful than someone whose only experience is advising, and both are more useful than a vague reference to entrepreneurial background.
How are you paid: hourly, monthly retainer, project fee, or equity?
Why ask it
Each structure pushes behaviour a different way. Hourly rewards meetings, retainers reward staying, project fees reward finishing, equity ties them to an outcome years out. Ask which they prefer and why, then ask what a realistic first-year total looks like.
What else do you sell, and how much of your income comes from advising?
Why ask it
Many advisers are also selling software, bookkeeping, recruitment or a course. That is not disqualifying, but you need to know before you receive a recommendation. If advising is a small share of their revenue, it may be a route into the larger sale.
Do you receive referral fees or commission from anyone you would refer me to?
Why ask it
Ask it plainly and watch the pause. Lenders, brokers, insurers and software vendors all pay for introductions in some markets. The right answer is either a clear no or a clear disclosure with the amount, and anything less specific is an answer in itself.
What does the first ninety days look like, and what exists at the end of it?
Why ask it
You want something you could hold: a written diagnostic, a cash model, a hiring plan, a priced list of options. Engagements that produce only meetings and encouragement are the ones people quietly cancel in month five.
How many clients do you have right now, and how many hours a month would I get?
Why ask it
Ask for both numbers and do the arithmetic in front of them. Advisers with twenty retained clients are running a portfolio, which is fine for a monthly review and no use in a crisis week.
Who else would work on my account, and who would I actually be talking to?
Why ask it
Firms sell the senior person and staff the work junior. Ask who attends which meetings and who does the analysis. If the person in front of you would appear monthly at best, price the engagement on the person who shows up weekly.
What will you need from me each month, in hours and in documents?
Why ask it
Advice fails more often through client capacity than adviser quality. A good answer is specific: monthly accounts by the tenth, two hours of your time, access to your team. If they say almost nothing is needed from you, they are selling comfort.
What will you not do?
Why ask it
You are checking the boundary between advice and delivery. Advisers who will not implement anything leave you with a plan and no capacity to run it, and advisers who will do everything are becoming a dependency. Either can work, but only if it is stated.
What would you want to see in my numbers before our first working session?
Why ask it
A specific list, twelve months of profit and loss, the balance sheet, aged receivables, a payroll summary, shows someone who works from evidence. An adviser who does not ask for financials will be advising on your description of the business rather than the business.
How would we know in six months whether this was worth it?
Why ask it
Push for something measurable, even if imperfect: days of cash, gross margin, hours you personally spend on the thing you hired them to fix. Advisers who resist any metric usually have a renewal conversation planned around goodwill instead.
If you and my accountant or lawyer disagree, how do we settle it?
Why ask it
This happens over tax structure, valuations and employment decisions. Good advisers will say plainly where their opinion stops being professional advice, and will offer to speak to the other adviser directly rather than through you.
Have you worked with a competitor of mine, and how do you handle that?
Why ask it
Sector experience and conflict of interest come from the same place. Ask what they would decline to advise on and whether they would tell you if a competitor approached them. Assurances of confidentiality without any restriction on taking the work are worth little.
Who owns the work when we are finished?
Why ask it
Models, forecasts, templates and process documents are often built on the adviser's proprietary material and licensed rather than transferred. Ask what you keep and in what format, because a spreadsheet you cannot use after they leave is not an asset.
How does this end? What notice do we each give, and what happens to work in progress?
Why ask it
Ask before you start, when it is an administrative question rather than an argument. Look for a short notice period on both sides and no fee for stopping. Long lock-ins for advisory work are a sign of how their renewals usually go.
Tell me about a client where your advice did not work.
Why ask it
Everyone with a real track record has one. Listen for whether they take any share of it, and whether the diagnosis was wrong or the execution failed. An answer that blames the client entirely tells you what they will say about you.
What kind of client do you do your worst work with?
Why ask it
This produces more honesty than asking about their ideal client. If the profile they describe sounds like you, take that seriously; they have just told you the engagement will be a struggle for reasons neither of you can fix.
What are you seeing in businesses like mine that I would not see from inside my own?
Why ask it
This tests whether their cross-client view is real. Specifics about pricing, hiring or how customers are buying now are worth a lot; general observations about uncertainty and change are available for free and suggest a thin client base.
From what you have heard so far, what would you tell me to stop doing?
Why ask it
A closing question that asks for a real opinion before any money changes hands. Advisers who give you one concrete thing have shown you how they work; those who defer entirely to a paid diagnostic have also shown you something.
Hiring and using a business advisor
Practical guidance for the conversation itself
Get the engagement clear before you sign
Name the problem in one sentence
Write down what you want different in six months before the first meeting: margin, cash, a hire, a decision about selling. Advisers will happily fill an unclear brief with their own specialism, and the work then becomes hard to judge.
Start with a small paid piece of work
A short diagnostic or a single project tells you how they think, how they write, and whether they hit deadlines, at a price you can walk away from. Retainers are easier to enter than to leave.
Insist on something written
Meeting notes with owners and dates, at minimum. Verbal advice is impossible to review later, and the discipline of writing it down catches the recommendations that only sounded good out loud.
Check them with someone who stopped using them
Ask for a client whose engagement ended and find out why. Advisory relationships usually end from drift rather than disaster, and hearing how the drift happened tells you what to watch for in yours.
Two short sequences
First meeting, deciding whether to continue
- 1What would you want to look at first in a business like mine, and why that?
- 2How are you paid: hourly, monthly retainer, project fee, or equity?
- 3Do you receive referral fees or commission from anyone you would refer me to?
- 4What does the first ninety days look like, and what exists at the end of it?
Before signing a retainer
- 1How many clients do you have right now, and how many hours a month would I get?
- 2What will you need from me each month, in hours and in documents?
- 3How would we know in six months whether this was worth it?
- 4How does this end? What notice do we each give, and what happens to work in progress?
Warning signs
A diagnosis before any numbers
An adviser who knows what is wrong with your business in the first meeting, before seeing a single financial statement, is describing their standard product. Ask what evidence would change that view.
Promised outcomes with a percentage attached
Specific revenue or margin guarantees are not something an outside adviser controls. Confident ranges based on comparable clients are fine; a promised number is a sales tactic and usually appears alongside a long contract.
Fees that scale with a decision they influence
Being paid more if you raise capital, sell, or buy a particular system creates a pull on the advice. If the structure is unavoidable, get the conflict written down and take the actual decision to someone with no stake in it.
No willingness to disagree with you
You are paying for the sentence you do not want to hear. An adviser who agrees with everything in the first meeting will agree with everything in month nine, which is the same as having no adviser at a higher cost.