Questions to Ask Business Owners
Good questions to ask a small business owner, for a conversation with someone who runs their own shop, trade or firm, the kind where they still know the customers and sign the cheques. They are grouped by how the business started, the money, the customers, the working week, what could go wrong and where it is all heading, and each has a note on what the answer tells you. Use them as interview questions to ask a business owner for a school, college or business ethics assignment, over a coffee with an owner you admire, or to find out how a small business really works before you start one.
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The questions
Each question, and why to ask it
Starting out
What made you want to start your own business?
Why ask it
Almost any owner has an answer ready for this, which is why it works first. Listen for whether they were pushed or pulled: a redundancy or a boss they could not work for on one side, an idea they could not put down on the other. If it sounds rehearsed, ask what else was going on in their life that year.
How did you come up with the idea for the business?
Why ask it
Few ideas arrive whole. More often the owner saw a gap from inside a job, got tired of something as a customer, or took over what a relative had begun. Ask how far the business has moved from that first idea, since the change is often the more useful half of the story.
What did it cost to get started, and where did that money come from?
Why ask it
Separates a business you can start from savings from one that needs a loan, a lease guarantee or an investor. Ask what they would spend it on if they were starting again, since the answer is rarely the same list.
What was the biggest challenge when you were starting out, and how did you get through it?
Why ask it
The second half is the one to hold on to. A challenge on its own is a story, while the way through it (a loan from a relative, a second job, a landlord who agreed to wait) is something you could act on. If the answer is 'everything', ask which problem kept them awake.
What do you wish you had known before you started?
Why ask it
Hindsight answers are usually small and exact: how slowly customers pay, how quiet the first winter would be, how much of the week goes on things that are not the trade. It is a different question from what they would do differently, because it gets at what nobody told them.
What does the business do, and how long have you been running it?
Why ask it
Ask this first if you are meeting the owner cold, and skip it if their website already answers it, since having looked it up shows you prepared. The number of years matters for everything that follows: advice from year two and advice from year twenty come from different places.
What were you doing before this, and did you quit outright or start on the side?
Why ask it
A previous job in the same trade often means they left with skills, suppliers and a few customers, while a complete change means they learned all of it in public. How they left matters as much: building it on evenings and weekends and resigning on a Friday carry different risks, so ask which they would choose now.
Why this business and not one of the other ideas you had?
Why ask it
Many owners weighed other ideas before settling, and the reasons those lost tend to be practical: too much capital, a crowded street, a licence they could not get. It shows how they judge an opportunity, which asking why they love the work rarely does.
Did you write a business plan before you opened, and how closely did you follow it?
Why ask it
Some owners wrote one only because a bank or a landlord asked, and some never wrote one at all, so there is no right answer to fish for. What you want is the part of the plan that turned out wrong first, which is often the sales forecast or the timeline.
How did you choose the name of the business?
Why ask it
A light question that owners enjoy, and a good one for a school interview. There is often a practical story under it: a name already taken, a web address that was gone, a family name they hesitated to put over the door. Ask whether they would pick the same one again.
How is the business set up legally, and why did you choose that structure?
Why ask it
Sole trader, partnership, limited company, LLC: the options, and what each means for tax and personal liability, differ from country to country, so ask how it works where they are and hear it as their story, not as advice. The interesting part is who told them to do it that way and whether they have changed it since.
How did you get your first ten customers?
Why ask it
The honest answer is usually unglamorous: friends, one old employer, a market stall, knocking on doors. It is far more instructive than a marketing strategy, because it is what actually works before anybody has heard of you.
What did you live on during the first year?
Why ask it
Savings, a partner's income, evening work, a redundancy payment. Founding stories tend to skip this part, and it decides whether the same path is open to you.
What did you already know about the trade when you opened, and what did you have to learn on the job?
Why ask it
Splits the craft from the business. Plenty of good bakers, mechanics and designers open knowing the work and nothing about pricing, leases or payroll, so ask which gap cost them the most.
Who helped you most in the first year, and what did they actually do?
Why ask it
Push for the deed and not just the name: a guarantor on the lease, a partner doing the books at night, a former boss who sent work over. It corrects the version of the story where they did it alone and tells you what help to line up for yourself.
How did you end up in this location?
Why ask it
Price and luck decide this more often than strategy, and owners will usually admit it. Ask what the place costs them that they did not foresee: parking, the quiet side of the street, a landlord who is slow to fix things. If they work from home or a van, ask why they decided against premises.
When did you first believe it was going to work?
Why ask it
Owners tend to name a small, exact moment: a second order from the same customer, a month when the rent was covered by the tenth. If they say they are still not sure, take it as honesty and ask what would settle it.
How long was it before the business paid you a proper wage?
Why ask it
The gap between opening and taking a real salary is often years, and owners will usually give you the true number if you ask plainly. It is the most useful single figure for setting your own expectations.
What do you wish you had set up properly at the start?
Why ask it
Usually bookkeeping, written contracts, insurance, or separating personal and business finances. These are cheap to do at the beginning, expensive to retrofit, and unexciting enough that nobody warns you.
Money
How long did it take for the business to turn a profit?
Why ask it
Check what they mean by profit before you write the number down. Some businesses cover their costs within months only because the owner is not being paid, which is a different thing from making a living. If they are not there yet, ask what has to change for it to happen.
What sells the most here, and is that also what earns the most?
Why ask it
The best seller and the best earner are often different things: the coffee brings people in and the cakes carry the margin, or the repairs keep a shop open while the new bikes fill the window. If the owner has to stop and think, that tells you how closely the numbers are watched.
How do you set your prices, and when did you last raise them?
Why ask it
Two questions in one on purpose: the method is usually thought through and the date often is not. If prices have not moved in years while rent and supplies have, ask what gave way, and what they feared would happen if they put them up.
How do you pay yourself now?
Why ask it
Salary, drawings, or whatever is left at the end of the month tells you how settled the business is. If it is whatever is left, ask whether there are months when that is nothing. How an owner is paid and taxed depends on the country and on how the business is set up, so do not assume their arrangement would be yours.
What is your slowest month, and how do you get through it?
Why ask it
A slow season is hard to see from the customer's side of the counter, so ask how deep it goes as well as when it falls. What gets them through it, a credit line, savings, a second line of work, is the practical lesson. A business with no slow month is worth asking twice about.
Which cost has grown far bigger than you expected?
Why ask it
Answers here are concrete and you can use them: software subscriptions, insurance, card fees, stock that goes missing, delivery. That list is more use to a would-be owner than general advice about watching expenses.
Week to week, how do you know whether the business is healthy?
Why ask it
You learn which two or three numbers they actually watch, and whether cash is one of them. If the answer is that they can just feel it, ask what they felt the last time something was going wrong, and how late they noticed.
What mistake cost you the most money, and how long did it take to recover?
Why ask it
The recovery time is what makes this useful. A bad hire, a lease, a machine bought too early or a product line that never sold, with a real timeline attached, is worth more than any list of tips.
What is the best money you ever spent on the business?
Why ask it
The mirror of the costly mistake and usually just as specific: a van, a bookkeeper, a second till, a better sign. Ask how long they hesitated before spending it, because the delay is often what they regret.
Do you keep the books yourself, and at what point did you get help with them?
Why ask it
You are asking when the paperwork outgrew the owner. Most can name what forced it, a tax deadline, a lost invoice, a loan application, and that story is a better guide than a general rule. What has to be filed varies by country and by type of business, so ask how it works where they are.
Do friends and family expect a discount, and what do you tell them?
Why ask it
A light question with a real policy under it. A fixed answer, whether a set amount off or full price and a free coffee, usually comes from an argument that deciding case by case once started. It also shows how they keep the business apart from their private life.
What do you do when a mistake goes in your favour, such as a supplier undercharging you?
Why ask it
Too much change handed back, an invoice that left off a delivery, a refund paid twice. It is a small test and a real one, because nobody would ever find out. Notice whether the answer depends on who made the mistake, since a big supplier and a one-person firm often get different treatment.
When money is tight, who gets paid first: suppliers, staff or you?
Why ask it
Useful for a business ethics assignment because it has no clean answer: each of the three has a claim, and an owner has usually had to choose at least once. Which debts come first when a business cannot pay them all depends on the law where it is, so hear this as their priorities and not as a rule.
What is the most money you have walked away from on principle?
Why ask it
Putting a sum on it turns a claim about values into a story: a contract refused, a product taken off the shelf, a client they would not work for. An empty answer is no mark against them, because some trades rarely offer the temptation.
Customers
How do you market the business, and where do most of your customers come from now?
Why ask it
The two halves do not always match: an owner can pay for adverts and still get most of the work by word of mouth. Whatever the main source is, one referral partner, a single platform or passing trade, ask what they would do if it stopped, and compare it with how they found their first ten.
What part do social media and your website play in bringing in business?
Why ask it
The useful answer is one they can point to: a booking that came through a post, the share of orders placed online, a month they stopped posting and nothing changed. Plenty of owners keep an account going out of habit and will say so. Find out who does the posting and how long it takes them each week.
Why do customers choose you when somewhere cheaper exists?
Why ask it
A one-sentence answer means they know what they are selling: speed, trust, being nearest, being the one who picks up the phone. A long or defensive one may mean price is doing more of the work than they would like.
What do you want the business to be known for?
Why ask it
This is the mission statement question in plain words, and it gets a plainer answer: the best bread in town, turning up when promised, never talking down to a customer. Set it beside what they said about why customers choose them. When the two differ, ask which one the reviews mention.
What brings a customer back a second time?
Why ask it
The first sale can come from luck or an advert, while the second depends on what happened the first time. Ask whether they count repeat custom or simply recognise faces. Either can work, but only one of them will show a slow decline.
Who is your best kind of customer, and how did you work that out?
Why ask it
Best does not always mean biggest. Owners tend to describe the one who pays on time, comes back and sends friends, and the story of working it out often features a large customer who was more trouble than the money was worth. Ask whether they now go looking for that kind or just hope.
What marketing have you paid for that brought in nothing?
Why ask it
Most owners can name an advert, a directory listing or an agency that produced no customers, and they remember the bill. It may save you the same spend, though ask when it was, since what failed five years ago may behave differently now.
What do you do when a customer complains or leaves a bad review?
Why ask it
You want the procedure and not the philosophy: who replies, how quickly, whether they refund first and discuss it afterwards. Some owners still take every complaint personally after many years and will tell you so, which is worth hearing if you plan to trade under your own name.
Have you ever turned a customer away or stopped working with one?
Why ask it
A line many owners cross late and remember clearly. The reason, rudeness to staff, endless changes, work that never made money, shows where their limits are and how long it took to find them.
What do customers keep asking for that you have decided not to offer?
Why ask it
A deliberate no marks the edges of the business: no delivery, no custom orders, no Sundays. If they say yes to everything customers ask for, remember it when you ask what takes up their week.
What has changed about your customers in the last two years?
Why ask it
Grounded enough to avoid the usual talk about trends and gets at what they have noticed at the counter or in the inbox. Ask what they changed in response, because noticing without responding is common.
How is the business involved in the local community?
Why ask it
Sponsoring a youth team, giving a prize to the school raffle, lending the car park for a market. Some owners do it because they live there and some because it brings in custom, and most will tell you which. Doing none of it is not a failing, so ask instead how many requests reach them in a month.
Have you ever told a customer not to buy something from you?
Why ask it
A mechanic who says the repair is not worth doing, or a shop that sends someone to a rival for the right part, gives up a sale for the customer's sake. Owners who do it tend to say it comes back as trust, so ask for the time it did and the time it did not.
Where is the line for you between making the business look its best and misleading people?
Why ask it
Every business picks its best photographs and its kindest reviews, and nearly every owner has a point they will not go past: a made-up 'was' price, a 'handmade' or 'local' label that is only partly true. Ask for something they see other firms doing and refuse to copy.
Has a customer or supplier ever asked you to cut a corner, and what did you say?
Why ask it
Cash with no receipt, a date changed on a form, a job signed off before it is finished. The refusal is the part to collect: the words they used, and whether saying no lost them the work. They may leave out who asked, and you should let them.
Day to day
What does a typical day look like for you?
Why ask it
Ask them to walk you through yesterday, because nobody remembers an average day. You will hear how much of it was the trade itself and how much was messages, deliveries and fixing things. If they say no two days are alike, ask what the first hour always is.
What time does your working day start, and when does it really end?
Why ask it
'Really' invites the emails at eleven at night and the Sunday stock count. Compare the answer with the opening hours on the door, because the difference is the part of ownership a customer never sees.
What takes up most of your week that you did not expect?
Why ask it
The answers are usually admin, chasing payment, staffing and compliance rather than the craft they started for. This is the question that stops people romanticising ownership, which is a favour to anyone considering it.
Which tools or software could you not run the business without?
Why ask it
It may be a booking system, an accounting package, a group chat with the staff, or a paper diary that has worked for twenty years. Ask what they tried and dropped as well. Products and prices change, so take any recommendation as a place to start looking.
What was the first role you hired for, and did it work out?
Why ask it
First hires often go wrong, and the reason, the wrong role, no time to train, not enough money for the right person, is something you can plan around. Notice whether they hired to take work off their own plate or to grow. If they have never hired, ask what has stopped them.
What do you look for when you hire someone?
Why ask it
Small employers often put attitude or reliability ahead of experience, so ask how they test for it in an interview or a trial shift. If you are a student this is also free advice on getting a first job, and it is fair to say that is partly why you are asking.
How do you find good staff, and what makes them stay?
Why ask it
A small firm often cannot match a large employer on pay, so listen for what they offer in its place: flexible hours, training, real responsibility. If people leave quickly they will often say why, and it is worth asking what they changed after the last one went.
How would the people who work for you describe you as a boss?
Why ask it
Easier to answer than a question about leadership style, and harder to dress up. A specific habit, such as checking every invoice or never raising their voice, tells you more than a list of virtues. An owner with no staff can answer it for suppliers or regular customers.
What is the hardest conversation you have had with someone who works for you?
Why ask it
Letting someone go, refusing a pay rise, or telling a friend on the payroll that the work is not good enough. Do not press for names or details. What you are after is what they would now do sooner, and many owners offer that unprompted.
How do you decide what is fair to pay people when you could pay less?
Why ask it
Where there is a legal minimum, this is about everything above it. One owner ties pay to what the job brings in, another to what it costs to live nearby, a third to what the last person asked for. Find out whether the staff know how it is decided.
What would you want your staff to do if they saw you getting something wrong?
Why ask it
In a firm of five people there is no complaints department, so this asks whether anyone can disagree with the owner at all. Follow up by asking whether someone ever has. An owner who can describe the occasion, and say the person was right, has told you more than a policy would.
What do you still do yourself that you know you should have handed off by now?
Why ask it
Shows both where the business gets stuck and how they feel about letting go, and the answer tends to come fast: the invoicing, the ordering, the social media. If they say nothing needs handing off, ask who covers their work when they are ill.
What's the last thing you stopped doing on purpose?
Why ask it
Dropping a product line, a service, a market day or a difficult client takes more nerve than adding one. A vague answer may mean nothing has been reviewed in years, so ask which thing they would cut first if they had to.
Which rules, licences or inspections take more of your time than a customer would guess?
Why ask it
Most trades carry a layer of compliance that never appears in the founding story, from food hygiene to payroll filings. The rules differ by country, region and industry, so treat the answer as a list of things to look up for your own area and not as the list itself.
What do you do on a day when nobody comes in or the phone does not ring?
Why ask it
Quiet days are when the accounts, the deep clean and the calls to old customers either happen or do not. An owner with a ready list for them has usually lived through a long quiet spell. One who dreads them will often tell you that too.
Could you take two weeks off right now?
Why ask it
A quick test of whether someone owns a business or is self-employed inside one. A no, with an explanation of what would fall over, is more informative than any answer about work and life balance.
How do you balance the business with the rest of your life?
Why ask it
Look for a rule, not a feeling: no phone at dinner, shut on Mondays, someone at home who is allowed to say stop. An owner with no rule will often admit it with a laugh, and that is an answer as well. Keep the harder question about what the business has cost them for later in the conversation.
Risks
What is the biggest risk you have taken with the business, and did it pay off?
Why ask it
Signing a longer lease, hiring ahead of the work, dropping the customer who paid most of the bills. Ask what they stood to lose and how they decided, since the way of deciding carries over to your own choices even when the bet does not. A risk that failed is the better story, if they are willing to tell it.
What is the one thing about the business that worries you this year?
Why ask it
Putting a year on it keeps the answer concrete: a lease renewal, a new competitor two streets away, a key person hinting at leaving. If the answer comes quickly, ask what they are doing about it. If they say nothing worries them, leave it, because they may simply not want to tell you.
What is the one thing the business could not survive losing?
Why ask it
One client, one supplier, one member of staff, one platform account, or the owner's own two hands. Most small businesses lean hard on one of these. An owner who names theirs at once has thought about it, and a long pause is an answer too.
Which supplier, platform or landlord has the most power over you?
Why ask it
Dependency shows up in the terms: a rent review, a marketplace fee change, one distributor. This is where small businesses lose margin without doing anything wrong, and outsiders almost never see it.
Which competitor do you actually pay attention to, and why that one?
Why ask it
Naming a specific rival, and the specific reason, shows how they understand their own position. If they say there is no real competition, ask where a customer goes on the day they are shut. That is the competitor, whether it is another shop, a website or doing without.
If demand doubled next month, what would break first?
Why ask it
Forces an honest look at capacity rather than an optimistic one, and the answer is usually a person, a supplier or a piece of equipment. A quick, exact answer suggests they have been at that limit before, so ask when.
Have you ever come close to running out of cash?
Why ask it
Many owners have, and what they did about it is the part to listen for: a hard conversation with a supplier, a personal loan, a week spent chasing every unpaid invoice. A business can show a profit on paper and still run short of cash, so ask which it was.
How do you handle a customer who does not pay?
Why ask it
The first unpaid bill is often what produced the deposit, the written terms or the rule about payment before delivery. Ask how far they chase and when they give up, because the hours can cost more than the debt. What a business can do to recover money depends on where it is, so ask how it works there.
How do rising costs or a slow economy show up in your business?
Why ask it
Some trades feel it within the week and others a year later, and a few do better when people repair instead of replace. Ask what they noticed first: smaller orders, slower payment, customers asking for a cheaper option. Then ask what they changed, whether prices, hours or stock.
Has anything outside your control nearly closed you, and what did you change afterwards?
Why ask it
Roadworks outside the door, a flood, a supplier going under, a change in the rules. The second half matters more than the story: a cash reserve, a second supplier or a clause in the next lease is the lesson in a form you can use.
The long view
What is the most rewarding part of owning your own business?
Why ask it
Listen for what comes before money in the answer: a regular who has come in for years, an apprentice who now runs a job alone, not having to ask anyone's permission. Then compare it with the reason they gave for starting. If the two are different, ask when that changed.
What part of the work do you still enjoy the way you did at the start?
Why ask it
Many owners began because they liked the craft and now spend most of the week away from it. Whether they have kept a piece of it for themselves, a morning at the bench, one client they still look after, tells you how the business has treated them.
What are you proudest of?
Why ask it
Leave it open and do not add 'in the business', because the answer may be a person they trained or a bad year they survived, not a sale. It is a kind question to ask late on, after the ones about money and risk, and it often gives a school report its best quote.
How do you define success for the business?
Why ask it
For one owner it is a number, for another it is being home by six or keeping the same staff for ten years. Whichever it is, ask whether they have reached it. The definition also explains decisions that look odd from outside, such as turning down a second branch.
How has the business changed since you first opened?
Why ask it
A business that has been open a while has usually dropped products, moved its hours or found a different kind of customer. Which of those changes they chose and which were forced on them is the thing to find out. It also puts a date on their advice: what worked the year they opened may not be what works now.
What has owning the business cost you outside work?
Why ask it
Ask it gently, and only once the conversation is warm. Missed holidays, strain at home and friendships that lapsed are common answers. If the owner would rather not go there, drop it at once and move to something lighter.
When did you last think seriously about giving it up, and what kept you going?
Why ask it
'Last' assumes it has happened, which is usually right and makes it easier to admit. What kept them in is not always noble: a lease they could not exit, staff who depended on them, plain stubbornness. The plain reasons are the useful ones.
Who do you talk to when you face a decision you cannot make alone?
Why ask it
Running a business can be lonely, with no boss and often nobody else at the same level. A named person, an accountant, another owner down the road, someone at home, is a good sign. 'Nobody' is a common answer and worth hearing before you sign up for the same.
What is the hardest ethical decision you have had to make as an owner?
Why ask it
The word ethical can make an owner go formal, so if they stall, ask about a time the right thing and the profitable thing pointed in different directions. A fault found after the customer had paid, a friend on the payroll and a deal that needed a small lie are the usual shapes. For a class paper, write down how they reasoned as well as what they did.
Is there a rule you keep in the business that nobody requires of you?
Why ask it
A returns policy more generous than it has to be, never passing on a customer's details, closing on a day they could trade. A self-imposed rule shows what the owner thinks the business owes people, and there is often one incident behind it worth asking about.
How do you keep learning, both the trade and the running of a business?
Why ask it
Named sources are worth writing down, especially the free ones: a trade show, a supplier's rep, online videos, an evening course, other owners over a drink. If they say there is no time, ask what they would learn first with a spare week.
What do people misunderstand about owning a business like this?
Why ask it
Expect a frustration they have explained many times: what people assume they earn, how free their time is, how much of each sale they keep. Because they are correcting a stranger's guess and not defending a decision, the answer tends to be one of the frankest you will get.
Where do you want the business to be in five years?
Why ask it
Some owners have a plan with figures in it and many are thinking no further than the next lease renewal, which is an honest answer too. If five years is too far off, ask about next year. Follow it with the question about growing or staying the same size, since a five-year answer usually assumes one or the other.
Do you want to grow it, or keep it about this size?
Why ask it
There is no default answer, and a deliberate decision to stay small is a legitimate strategy rather than a lack of ambition. The reasoning tells you what they actually wanted from ownership.
What are you working on now that customers cannot see yet?
Why ask it
Gets you the real plan in place of the public one: a second site, a new supplier, a price rise, a website that has been half built for a year. If the answer is nothing, set it beside what they said about growing or staying the same size before you read anything into it.
Would you want someone in your family to take this over one day?
Why ask it
A yes, a firm no and 'I would not do that to them' all come up, and each says something about what the work has been like. It usually opens the wider plan, whether they mean to sell, hand it on or run it until they stop, without your having to ask about retirement.
What advice from other owners turned out to be wrong for your business?
Why ask it
Common wisdom about premises, discounts or hiring fits some trades and not others, and this asks where it failed for theirs. The reason it failed tells you how their business differs from the average one. If nothing comes to mind, ask which popular rule they have never followed.
What skills or qualities does someone need to run a business like yours?
Why ask it
Steer them towards the ones they did not have at the start, which keeps the answer away from a list of virtues. You may hear selling, reading a bank statement or saying no to a customer before you hear anything about the craft. Ask which of them can be learned in a job before going out alone.
Would you do it all again, and what would you do differently?
Why ask it
Loyalty to their own choices makes a yes to the first half likely, so the second half is where the information is. Push for one decision and not a general regret: the lease, the partner, the year they waited too long to raise prices. A no to the first half deserves time and no argument.
What advice would you give someone who wants to start their own business?
Why ask it
The classic closing question, and it earns its place once you make it specific. Say what kind of business you have in mind, or ask what they would tell a friend opening the same one tomorrow, and the answer gets blunter and more practical. If you hear only that it takes hard work, ask what that means in an ordinary week.
What should someone still at school or in a first job do now if they want their own business later?
Why ask it
Suits a student interview or a careers assignment, where the questions about money can feel too forward. The good answers are small and doable, such as working a season in the trade or learning to read a set of accounts. If you get 'follow your passion', ask what they were doing at your age.
Talking to Small Business Owners
Practical guidance for the conversation itself
Getting the Conversation at All
Be a customer first
Buy something, use the service, then ask. An owner is more likely to give time to someone who has already spent money with them than to a stranger asking to pick their brain.
Ask at the right hour
Most businesses have a quiet stretch, and it is not the same for a cafe, a builder and an accountant. Ask when theirs is and offer to come then. It can be the difference between twenty minutes and two.
Say how long you want and stick to it
Ask for twenty minutes and end at twenty minutes. An owner at work is interrupted all day, and being the person who respected the limit is how you get invited back for a longer conversation.
Bring a specific question, not a general one
Asking how to start a business gets a shrug. Asking how they priced their first job, or what their busiest month costs them in staffing, gets a detailed answer because it is a question they have actually solved.
Choosing Questions for the Conversation You Are Having
- Open with what made them start. Most owners have told that story before, so it is easy to answer and it settles both of you before the harder questions.
- For a school or college assignment, Starting out and The long view will carry a whole interview. If asking a stranger about money feels too forward, skip the cost and wage questions in the first group.
- For a business ethics class, the ethical questions to ask a business owner sit inside the groups they belong to: a mistake in their favour and who gets paid first under Money, misleading claims and cut corners under Customers, fair pay under Day to day. Keep the hardest ethical decision, in The long view, for when they have warmed up.
- For a coffee with an owner you admire, take one question from each group and let their longest answer decide where the rest of the time goes.
- If you are thinking of opening something similar, Money and Risks matter most. They land better after two or three easier questions.
- Five or six questions fill twenty minutes. Mark the ones you care about and leave the rest for another day.
Asking About Money Without Being Rude
- Ask about ranges and ratios rather than exact revenue: what percentage goes on rent, what a typical margin looks like, how long the slow season lasts.
- Ask what things cost rather than what they earn. Owners tend to talk freely about costs and guardedly about income.
- Frame it as what you should budget for, not what they make. It changes the question from curiosity to advice.
- Accept a deflection first time. If they skip a money question, move on and it will often come back later in the conversation.
- Never repeat their numbers to a competitor, a supplier or online. Small trades are small, and it gets back.
Where These Conversations Go Wrong
Asking for free consulting
There is a clear line between how did you learn this and please review my plan. The first is a conversation, the second is work, and asking for it unpaid is a quick way to wear out your welcome.
Talking to only successful owners
The most useful conversation is often with someone who closed a business, and many are willing to talk if approached respectfully. Interviewing only the survivors gives you a skewed picture of the odds.
Assuming their answers transfer
A business built ten years ago in a different town, with a lease signed before rents rose, may not be repeatable. Ask what has changed in their market since they started, and treat the answer as part of the advice.
Hiding that you plan to open a competitor
If you plan to open something similar nearby, say so before you ask anything, or do not ask. Small trades talk, the owner is likely to find out, and you will have used their answers under false pretences.
Afterwards
- 1Write down the numbers they gave you the same day, including how confident they sounded about each one.
- 2Send a short thank you that mentions one specific thing you are going to do differently.
- 3Leave an honest review or send a customer their way. It costs you little and it is the kind of thanks a small business can use.
- 4Have the same conversation with two or three more owners before you conclude anything, since single cases mislead.
- 5If you do start something, tell them how it went. An owner who gave you time will usually want to know what you did with it.