Questions to Ask Business Owners
Questions for a conversation with someone who owns and runs their own business, the kind where they still know every customer and sign the cheques. They cover the first customers, the money, what actually takes up the week, and whether the owner could leave for a fortnight. Useful if you are thinking about starting something similar or want to understand how a small business really works.
The questions
Open any question for the note
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. Nearly every founding story leaves this out, and it is the part that determines whether the same path is available to you.
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 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.
Which part of what you sell actually makes the money?
Why ask it
Most owners discover their margin sits somewhere they did not plan: a service attached to a product, one client, repeat work rather than new. If they cannot answer, that itself tells you how closely the numbers are watched.
Where do your customers come from now?
Why ask it
Word of mouth, one referral partner, a single platform, or paid advertising, and each implies a different kind of fragility. Owners who name one dominant source are usually aware it is a risk and have not solved it.
What is your slowest month, and how do you get through it?
Why ask it
Seasonality is invisible from outside and brutal from inside, and the coping mechanism, a credit line, savings, a second revenue line, is the practical lesson. A business with no slow month is worth asking twice about.
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.
What was the first role you hired for, and did it work out?
Why ask it
First hires fail often, and hearing why, wrong role, no time to train, could not afford the right person, prevents you repeating it. Notice whether they hired to relieve their own bottleneck or to grow.
How do you pay yourself now?
Why ask it
Salary, drawings, or whatever is left at the end of the month tells you how stable and how well organised the business is. Owners who take what remains are often subsidising the business without accounting for it.
What would break the business if it disappeared tomorrow?
Why ask it
One client, one supplier, one member of staff, one platform account, or the owner's own presence. Every small business has a single point of failure, and the good operators can name theirs immediately.
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.
Have you ever come close to running out of cash?
Why ask it
Nearly everyone has, and what they did about it, invoice factoring, a hard conversation with a supplier, a personal loan, is the most transferable knowledge they have. Profitability and cash are different problems.
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, an unpaid invoice or a product line that never sold, with a real timeline attached, is worth more than any list of tips.
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.
What do people misunderstand about owning a business like this?
Why ask it
Owners have a standing frustration here, often about assumed income, assumed freedom or how much of the revenue they keep. It tends to be the most candid answer of the conversation.
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.
Could you take two weeks off right now?
Why ask it
The single best 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.
What is the eventual plan: sell it, hand it on, or run it until you stop?
Why ask it
Whether an owner has an exit in mind shapes everything from bookkeeping to whether the business can run without them. Many have never thought about it, which is worth knowing before you take advice on building one.
If a friend told you they were starting the same business tomorrow, what would you say?
Why ask it
Asking it as advice for someone else gets past the loyalty most owners feel to their own decisions. The answers are noticeably blunter than answers to whether they would do it again.
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. Owners give far more time to someone who has already spent money with them than to a stranger requesting a picking-your-brain call.
Ask at the right hour
Every business has dead time: mid-afternoon in hospitality, early morning in trades, the day after invoicing in professional services. Asking when they are quiet is 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. Owners are chronically interrupted, 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.
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 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 usually ends the relationship.
Talking to only successful owners
The most useful conversation is often with someone who closed a business, and they are usually willing to talk if approached respectfully. Only interviewing survivors gives you a badly 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.
Announcing you are starting a competitor
If you plan to open something similar nearby, say so early or do not ask. Owners find out, and being candid about your intentions is the only version of this that does not end badly.
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 a review or refer a customer to them. It is the cheapest way to repay the time and it is what they actually need.
- 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. Owners are unusually generous with people who close the loop.