Questions to Ask a Business Mentor
For founders and small business owners who have a more experienced owner willing to mentor them, and who want to spend that time on their own business instead of on the mentor's life story. The questions follow the order these conversations tend to take: a first meeting, then money, customers, hiring and your own time, growth, and the meetings after that. Each has a note on what a good or a worrying answer sounds like, or what to do with it.
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The questions
Each question, and why to ask it
First meeting
What should I be focusing on at this stage of my business?
Why ask it
Describe the stage in numbers first: how long you have been open, what comes in each month, who does the work. A useful answer picks one thing and says what to leave alone for now. If you get a list of six, ask which one they would do if they could only do one.
What are the most common mistakes you see owners make at the stage I am at?
Why ask it
The answer usually arrives as stories about other owners: the one who hired before the cash was there, the one who never raised prices. Follow it with the direct version: which of those can they already see in your business?
What do you wish you had done sooner in your own business?
Why ask it
Answers tend to be about delay more than disaster: charging more, letting someone go, getting the books in order. Ask what held them back at the time, because the same reason is probably holding you back now.
If this were your business, what would you do in the next 90 days?
Why ask it
A time limit turns general advice into a short list you can act on and report back on. Notice whether the plan starts with selling, with money or with getting organized, since that shows what they think the real problem is. Write it down and bring it to the next meeting.
From what you have seen so far, where is my business weakest?
Why ask it
Hold this until they have seen your numbers or visited the business; it is not for the first ten minutes. A specific answer, such as one customer carrying the business or no record of what jobs cost, means they have been paying attention. 'It all looks fine' may only mean they have not looked closely yet, so offer the figures again.
Would you read my business plan and tell me which part you do not believe?
Why ask it
Send it a week ahead and call it a draft, so they feel free to mark it up. Sales forecasts and timelines are where a plan is most often hopeful, and someone who has run a business will know which of yours to question. No written plan? One page on what you sell, to whom and at what price gives them enough to react to.
What do you need to see from me before you can give useful advice?
Why ask it
Every mentor has a few things they judge a business by, and those are rarely what you would have prepared. Expect requests for sales by month, your prices and where customers came from. Send whatever they name before the second meeting.
Which parts of running a business do you know well, and which should I take to someone else?
Why ask it
An owner who built a company on sales may have little to say about staff, and one who ran a shop may never have sold to other businesses. A mentor who draws that line plainly is easier to trust on the rest. For each gap, ask who they would send you to.
Before I share my numbers, do you have any ties to my competitors or customers that I should know about?
Why ask it
Someone who sells to the same customers, owns part of a competitor or might one day want to buy you can still be a good mentor, but you should know before you open the books. A straightforward answer settles it in a minute. If you would like confidentiality in writing, a lawyer or the mentoring program can tell you how that is usually done where you are.
How would you like to use our time: one decision per meeting, or a look across the whole business?
Why ask it
One decision per meeting suits a mentor with an hour a month and gets you an answer you can use. A review of everything suits the first session or two. Agree which it is, and who sends the agenda, so the hour is not spent deciding what to talk about.
Money
How should I be managing cash flow at my size?
Why ask it
Profit on paper and money in the account are different things, and this question is about the second. A practical answer is a habit: a list of what is due in and what is due out over the next couple of months, checked on the same day every week. If you have never kept one, ask to see how they lay out theirs.
Here is what I charge and what it costs me to deliver. Do my prices look right to you?
Why ask it
Count your own hours in the cost, at a rate you would have to pay someone else. A common verdict is that you are too cheap, so the useful part is why: the wrong comparison, a cost left out, or fear of asking. If they say the price is fine, look at your costs next, the other place a margin can come from.
How would you raise prices without losing the customers I already have?
Why ask it
Look for a method you could copy: new customers first, notice given in writing, a date, no apology. Then ask how many customers they lost the last time they did it and whether they missed them.
What do you say when a customer asks for a discount?
Why ask it
You want the sentence they actually use, so write it down. Some owners trade a lower price for something in return, such as payment up front or a smaller job, and some simply say no. Either gives you a line to practice before the next quote.
How much cash should I keep in reserve, and how did you settle on your own figure?
Why ask it
There is no single right number, which is why the second half matters. An answer tied to something real, such as two payrolls or the rent through the slowest season, shows you how to work out yours. Be wary of a round figure with no reasoning behind it.
Which numbers would you look at every week if you were running this?
Why ask it
A short list is the good answer. Cash in the bank, what customers owe you and one measure of new work coming in are frequent picks. If you cannot produce one of the numbers they name, that is your task before the next meeting.
Customers are slow to pay me. What would you change about how I bill and collect?
Why ask it
Take a real invoice and your payment terms with you. Fixes tend to be plain: invoice the day the work is done, ask for a deposit, call on the first day it is late. Late fees and debt collection have rules that differ by location, so check yours before adding a penalty to your terms.
When should I start paying myself a regular amount, and how do I decide how much?
Why ask it
Owners who waited years and owners who paid themselves from the first month will give opposite advice, so ask what each choice cost them. How money you take out is taxed depends on where you are and how the business is set up. Take that part to an accountant and use the mentor for the judgment call.
Which of my costs would you question first?
Why ask it
Hand over a list of what goes out each month and let them point. An outsider spots the subscription nobody opens or the supplier who has not been asked for a better price in years. A good mentor will also name the spending to leave alone because it is what brings the work in.
Is there a product or service I should stop offering?
Why ask it
The line that looks busy and earns little is easier for an outsider to see, provided you can show what each one brings in after its costs and how much of your week it takes. If you catch yourself defending it, work out what would have to be true for it to be worth keeping.
How would you get this business through a slow season?
Why ask it
The answers worth having are things done months ahead: cash set aside in the good months, a cheaper offer that fills quiet weeks, costs that can be paused. The story of the first slow stretch that caught them out is often where the real advice is.
Would you borrow, bring in an investor, or grow on what the business earns?
Why ask it
You will hear the route the mentor took, so ask what it cost them in control, in sleep or in speed. What lenders and investors ask for changes over time and from one provider to the next, and a mentor's experience of it may be years old. Treat the answer as one owner's view and check the current terms yourself.
Customers
Looking at my customer list, who would you say is my best kind of customer?
Why ask it
Add two columns to the list before you show it: what each customer spent and how they found you. A mentor often sees a pattern you are too close to: the same industry, the same size, the same kind of problem. Once it has a name, ask where more of them can be found.
Where would you look for my next ten customers?
Why ask it
Good answers are places and people: a trade association, a business that serves the same customers before you do, the customers you already have. Be cautious if the answer is only to post more online with no idea who would see it. Finish by having them rank the list, so you know what to try this week.
Why would someone choose my business over a competitor, and is that reason strong enough?
Why ask it
Give your own answer first and let them test it. 'Better service' and 'quality' are claims any competitor can make, so a useful mentor will push for something a customer could check: a turnaround time, a guarantee, a specialty. If neither of you can name one, finding it is the next job.
Here is how I describe what I do. What would you change?
Why ask it
Say it exactly as you would to a stranger, then stop talking. If the mentor repeats it back and gets it wrong, the wording is the problem. Have them say it their way and try that version on the next three people you meet.
I spend this much on marketing each month. Which parts would you keep?
Why ask it
This needs two things on the table: what you spend, and whatever you know about where each customer came from. If you cannot connect the two, the first advice will be to start asking every new customer how they found you. Anything they would cut, pause for a month and see whether inquiries drop.
How do I get more referrals and repeat work from the customers I already have?
Why ask it
The useful answers are routines: a call a month after the job, asking for a referral at the moment a customer says thank you, a reminder when something is due again. 'Good work speaks for itself' is a thin answer on its own, since it leaves the asking to chance.
One customer brings in a large share of my sales. How worried should I be?
Why ask it
Put a percentage on it. If they have lost a big account themselves, hear what the following six months were like before it happens to you. Then get their order of work: find a second customer of that size first, or get the terms with the first one in writing.
What do you do when a competitor undercuts you on price?
Why ask it
Experienced owners usually have a view on when to match, when to ignore it and when to let the customer go. Ask about a time they held their price and what happened to that customer afterwards. Advice to win on price alone fits only if your costs really are lower.
What do you do about a customer who takes more time than they pay for?
Why ask it
Describe a real one, without the name. Options you may hear are a higher price, firmer limits on what is included, or a polite ending. If they have let a customer go, ask how they worded it.
How do you follow up on a quote when the customer has gone quiet?
Why ask it
You are after timing and wording: how many days, how many attempts, what the last message says. A mentor with a routine can dictate it to you. Use it on your oldest open quote before the next meeting and report what came back.
Hiring and time
What should my first hire be?
Why ask it
Describe your week before you ask, including what you are good at and what you put off. The mentor may suggest a helper for the routine work so you can sell, or the reverse, and the reasoning matters more than the job title. 'Do not hire yet' is a fair answer too, as long as it comes with what would need to change first.
How will I know the business can afford to hire someone?
Why ask it
What you want is the test they applied: a number of months of pay in the bank, steady work booked ahead, or a role that pays for itself by a set date. An employee costs more than the wage, and how much more varies by location, so get that figure from a local accountant or payroll provider. If they once hired on hope and regretted it, that is the story to hear.
Would you start with an employee, a contractor or an agency for this work?
Why ask it
The mentor can speak to what each was like to manage and what went wrong. Who counts as an employee and what you owe them is set by the rules where you operate. Ask how it works there, and confirm it with someone qualified before you agree to anything.
What am I doing every week that I should stop doing?
Why ask it
Keep a rough log of a normal week and bring it, because memory flatters. The mentor will circle work that someone cheaper could do and work that nobody needs to do at all. Pick one item and drop it or hand it over before you meet again.
When you first handed work to someone else, how did you keep from taking it back?
Why ask it
Plenty of owners took the work back at least once, and one who admits it has the useful answer. Listen for specifics such as a written checklist, a weekly review in place of daily checking, and accepting work that is good enough. How long it took to stop feeling like a risk is worth knowing, so you do not give up in the second week.
How did you get what was in your head written down so someone else could do it?
Why ask it
Some owners record themselves doing the task, some write a one-page checklist, and some have the new person write it as they learn. Any of those beats waiting until you have time to write a manual. Start with the job you most want to stop doing.
What do you do when someone you hired is not working out?
Why ask it
They can tell you how early they knew, what they tried and what waiting cost. Notice whether they spoke to the person plainly and early. Ending someone's employment comes with rules and contract terms that differ by location, so get advice on yours before you act.
How many hours a week should this business be taking from me at this stage?
Why ask it
The number matters less than what an owner who has been through your stage calls normal and what they call a warning. Give your real weekly total, not the one you tell your family. If the verdict is 'too many', go straight to which hours they would cut.
Growth
Is this business ready to grow, or is there something to fix first?
Why ask it
An honest mentor may say fix first, and name it: thin margins, work that depends on you alone, customers who do not come back. Growing with one of those in place makes the problem bigger. A plain 'go' is fine when it comes with what to watch on the way.
If I landed twice as much work next quarter, what would give way first?
Why ask it
The answer points to what to strengthen before spending on marketing. It might be your own hours, cash to buy inventory, a supplier or the way jobs are tracked. Their own weak point was probably found the hard way, and that story is worth the time it takes to tell.
Which of the opportunities in front of me would you turn down?
Why ask it
List them all, including the one you are excited about. A mentor is useful here because they are not flattered by the offer and can see what it would take your attention from. If they would turn down your favorite, hear the whole reason before you argue.
Should I bring in a partner, or keep this in my own hands?
Why ask it
Start by asking whether they have had a partner and how it ended, since strong opinions here often come from one experience. Useful advice covers what to settle first: who decides, who puts in what, and how one of you leaves. Have any agreement drawn up by someone qualified where you are.
At what point is it worth paying an accountant, a lawyer or a consultant, and how do I choose one?
Why ask it
Ask what each one saved or cost them, and which they hired too late. On choosing, a mentor can say what to ask and may know someone who works with businesses your size. Fees and what each one covers vary a good deal, so talk to two or three before you sign with one.
What should I have in writing that I probably do not?
Why ask it
Expect a list drawn from what once went wrong for them: terms of sale, a lease clause, an agreement with a partner or a key supplier. The mentor can tell you what to look at. What the documents need to say is a question for a lawyer who practices where you operate.
What risk in my business do you think I am not seeing?
Why ask it
Outsiders notice dependence: one supplier, one platform, one employee who knows everything, or you. Ask what the month after that one thing failed would look like. Some of these can be insured and some need a backup plan, and which is which is a question for a local broker once you know the risk.
What would tell you this business model is not working, and when would you change course?
Why ask it
It is easier to set the test now than in a bad month. Agree on something measurable, such as a level of sales by a date or a margin that has to hold. If they have closed or changed a business themselves, ask what they ignored for too long.
What could this business realistically look like in three years?
Why ask it
Their picture may be bigger or smaller than yours, and the gap is worth talking about. Some mentors assume every owner wants staff and a bigger space. Say what you want the business to give you, in income and in time, and ask whether the plan fits that.
Later meetings
Here are this month's numbers beside last month's. What stands out to you?
Why ask it
Send them a few days ahead so the meeting starts with their reaction. What they look at first shows what they think matters. If nothing stands out, ask which number they expected to move and why it did not.
I acted on what we agreed and it did not go as planned. What would you try next?
Why ask it
Say exactly what you did, including the part you changed or skipped. Reporting back, even on a failure, is what keeps a mentor engaged. Notice whether they adjust the advice or repeat it: the first means they are listening to your business and not only remembering their own.
What decision do you think I am putting off?
Why ask it
After a few meetings a mentor has heard you circle the same subject more than once. It is often a price rise, a person or a customer. If they name it, set a date for it before you leave.
As the owner, what do I most need to get better at?
Why ask it
The work that started the business and the work of running it are different jobs: selling, reading the accounts, managing people, saying no. Ask which one they see you avoiding. Then find out how they learned it themselves, whether through a course, a hire who covered the gap or a few years of doing it badly.
I am starting to doubt whether this business is worth it. Did you ever get there, and what did you do?
Why ask it
Put it as plainly as that, because a mentor cannot help with a worry they have not been told about. Ask what they checked before deciding to carry on: the numbers, a deadline they had set themselves, what else they could have been doing. If the doubt is really about the figures, go back to the question on what would show the model is not working.
Is there a local owners' group or trade association that would be worth my time?
Why ask it
One mentor is one point of view, and a room of owners at your stage gives you several more. Ask which groups they have belonged to, what the dues bought them and which turned out to be mostly members selling to each other. See whether you can visit as a guest before you pay to join.
Who else should I be talking to, and would you be willing to introduce me?
Why ask it
Go for a named person and a reason, such as an owner one step ahead of you or a supplier worth knowing. Wait until you have shown you follow through, because the introduction spends their reputation. Tell them afterwards how the conversation went.
What would make these meetings a better use of your time?
Why ask it
Mentors rarely complain unprompted, so this is how you find out that they want the numbers sooner or fewer subjects per meeting. Small changes keep the arrangement alive. Ask it every few months, not once.
What should I have done before we meet again?
Why ask it
End every meeting with it. One or two tasks with a date turn a good talk into something that changes the business, and they give the next meeting its opening. If the mentor leaves it to you, say what you plan to do and ask whether it is the right thing.
How to get the most from a business mentor
Practical guidance for the conversation itself
Before you meet
Put the business on one page
A mentor can only advise on what they can see. One page is enough: what you sell and at what price, sales for the last six to twelve months, your main costs, how many customers you have and where they came from, and who does the work. Send it a few days ahead. Rough figures you have now are more useful than tidy ones you promise for next time.
Pick one decision per meeting
An hour disappears quickly. Choose the decision that is costing you the most sleep, whether that is a price, a hire or a customer, and take one or two questions from the matching group. Keep the others as spares in case the first is settled in ten minutes.
Say what you want the business to be
Advice on growth depends on the destination. Tell the mentor whether you want a business that employs people, one that pays you well and stays small, or one you could sell. Otherwise they will assume you want what they wanted.
Agree what stays private
You will be showing figures, customer names and worries you have told nobody else. Say at the start that you would like it kept between you, and ask whether the mentor has any tie to a competitor or a customer of yours. If the mentor came through a program, ask the organizer what its rules are.
In the meeting
Put the figure before the question
A mentor asked 'Are my prices right?' can only guess. Told what you charge, what the job costs you and that about half your quotes are accepted, they can answer. Nearly every question under Money and Customers works better with a real figure in front of it.
Ask what they would do, then ask why
The decision is yours, but hearing what an experienced owner would do in your place is the quickest way to their reasoning. The reason is what you take home, because it tells you whether the advice still holds when your situation differs from theirs.
Ask how it works where you are
Tax, employment, contracts, licenses, lending and insurance differ by country, by state or region and by provider, and they change over time. A mentor can tell you what happened to them and what to look into. For what applies to your business now, go to the accountant, lawyer, agency or provider concerned.
Leave with a task and a date
Before the hour ends, say back what you are going to do and by when. It shows the mentor their time turned into something, and it gives the next meeting a first item.
Weighing the advice
It is one owner's experience
Your mentor built a particular business in a particular trade, place and decade. What worked there may not work for you, and a good mentor will say so. Where the advice surprises you, ask what about their situation made it right.
Good answers have detail in them
An answer with a figure, a customer or a year in it comes from something that happened. 'Focus on value' or 'hire slow, fire fast' could come from anyone. Ask for the occasion behind the slogan before you act on it.
Notice what they keep coming back to
If the mentor brings up your prices in three meetings running, that is their view of the main problem, whatever you came to ask. Either act on it or say why you will not, so the conversation can move on.
Test it small
Much business advice can be tried on a small scale first: a higher price on new quotes only, a contractor for one month, one marketing channel paused. A small test gives you your own evidence to bring back, which is better material for the next meeting than an opinion.
Mistakes to avoid
Showing only the good numbers
It is tempting to impress someone you admire. A mentor who sees only the flattering half gives advice for a business that does not exist. Lead with the figure you are least proud of.
Handing over the decision
A mentor who makes your calls becomes a boss without the responsibility, and it is still your money on the line. Hear what they would do and why, make the call yourself, then report which way you went and how it turned out.
Coming back with nothing tried
Giving the same advice twice to someone who has not tried it is how mentors lose interest. If you decided not to follow something, say so and say why. That is a better meeting than pretending it slipped your mind.
Turning the mentor into something else
Asking a mentor to invest, to become a customer or to open their contact list changes the relationship, and it can end it. If one of those ever makes sense, raise it plainly as a separate conversation and make it easy for them to say no.