What Are Good Questions to Ask a Business Owner
Twenty questions for a conversation with an owner of a small or mid sized business, whether you are considering starting one, taking a job there, or writing about them. Each notes what the answer tends to expose and where owners tend to be vague.
The questions
Open any question for the note
What does a normal Tuesday actually look like for you?
Why ask it
Cuts through the version of the job that appears in interviews and gets you the hours, the interruptions and the admin. If the answer is that no two days are alike, ask them to walk through yesterday instead.
How long was it before the business paid you a wage you could live on?
Why ask it
One of the few numbers most owners will give honestly, and it is the single most useful figure for anyone considering the same path. An answer of we are not there yet, delivered casually, is the answer to pay closest attention to.
Where do your customers actually come from right now?
Why ask it
The word actually matters, because the marketing story and the real source often diverge. Owners who cannot answer this are usually running on referrals they have never tried to measure, which is a fragile position.
How much of your revenue comes from your largest customer?
Why ask it
A blunt question about concentration risk, and a figure above roughly a third changes how you should read everything else they say. Anyone who has thought seriously about the business will know the number without checking.
What did you get wrong in the first year that you would warn someone about?
Why ask it
Ask for the warning rather than the lesson, since warnings come out specific: a lease, a partner, a first hire, an unpaid invoice. Answers about working too hard are a deflection, so ask what it cost them in money or time.
What part of this job did you not know you were signing up for?
Why ask it
Usually surfaces the unglamorous work that fills an owner's week: collections, insurance, staffing rotas, licensing. This is the question that most often changes a listener's mind about wanting to do it.
What do you still do yourself that you know you should have handed off by now?
Why ask it
Reveals both their bottleneck and their relationship with control, and almost every owner has an immediate answer. If they say nothing needs handing off, ask who covers their work when they are ill.
Who was your first hire, and did it work out?
Why ask it
The first hire is remembered in detail because it is where an owner learns whether they can manage anyone. Notice whether they describe what they learned about hiring or only what the person did wrong.
How do you set your prices, and when did you last raise them?
Why ask it
Two questions in one on purpose: the method may be considered, while the date usually is not. Owners who have not raised prices in years are often quietly absorbing cost increases, which explains a lot about their margins.
What does your slow season look like, and how do you get through it?
Why ask it
Nearly every business has one, and how they cover payroll through it tells you how much cushion actually exists. If they claim no seasonality, ask which month was worst last year.
What cost surprised you with how big it grew?
Why ask it
Answers here are concrete and transferable: software subscriptions, insurance, payment processing, shrinkage, freight. This is more useful to a would be owner than any general advice about watching expenses.
What advice from other owners turned out to be wrong for your business?
Why ask it
Tests whether they can distinguish their situation from received wisdom, which is the skill that separates operators from readers of business books. A blank here often means they have not made many decisions against the grain.
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. Watch for a dismissive answer, since owners who claim no real competition are often losing customers without knowing where they went.
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.
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. Owners with a clear answer have usually been close to that limit already.
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, that is worth knowing before you take a job or invest anything.
What's the last thing you stopped doing on purpose?
Why ask it
Deliberate subtraction is rarer than addition and shows a willingness to cut something that was not working. Vague answers here often mean the business has accumulated products, services or clients nobody has reviewed in years.
Was there ever a point where you nearly closed or sold, and what changed?
Why ask it
A serious question, so ask it late and accept a short answer. Owners who have been through it usually name a specific month and a specific decision, and that story tells you more about them than any success will.
What would have to be true for you to take a month off?
Why ask it
A practical test of whether they have built a business or a job with their name on it. The list of conditions is effectively their succession plan, whether or not they call it that.
If you started again tomorrow, what would you do differently, and what would you keep exactly the same?
Why ask it
The second half is the part that earns its place, since almost anyone can list regrets and few can name what they got right on purpose. Whatever they would keep is the thing they believe the business actually runs on.
Getting a Straight Answer
Practical guidance for the conversation itself
Before and During
Say Why You're Asking
An owner answers a curious student differently from a prospective competitor. Open with your reason and what you plan to do with the answers, and you will get numbers rather than platitudes.
Ask for Ratios, Not Their Income
How much do you make ends the conversation. Share of revenue from the top customer, months of payroll in reserve and roughly how long to a living wage all get answered because none of them expose a personal figure.
Anchor Everything to a Real Period
Last Tuesday, last January, the past two years. Time bound questions produce specifics, while questions in the abstract produce the speech they give at networking events.
Take the Warning Seriously
When an owner names the thing that nearly sank them, stay there for two or three follow ups. That story usually contains more usable information than the rest of the conversation combined.
Send Something Back
A short note about what you did with their advice, a customer referral, or an introduction is what makes a second conversation possible. Owners are asked for their time constantly and remember the few people who closed the loop.
Adjust for the Kind of Business
- Restaurants, retail and other premises based businesses: 9, 10 and 11 matter most, since rent, staffing and waste drive the outcome.
- Service firms and agencies: 4 and 7 are the important pair, because the owner is often still the product.
- Online and product businesses: press hard on 3, where acquisition cost and dependence on one platform hide, and on 11, where processing fees, freight and returns show up.
- Family businesses: 8, 18 and 19 need care, as the answers involve relatives who may be in the room.
- Businesses under five years old: 2, 5 and 15 tell you the most about whether it is working.
- Long established businesses: 14, 17 and 20 surface whether anything has been reconsidered in the past decade.
Common Pitfalls
Don't Ask for the Secret
What's the key to your success invites a slogan. Ask about a specific decision, a specific month or a specific number and you get something you can use.
Don't Fish for Confidential Material
Supplier terms, staff pay, client names and margins are usually off limits for good reason. Ask how they think about the category rather than for the figures.
Don't Pitch Halfway Through
If you asked for advice and then start selling, the conversation is over and so is the relationship. If you want to sell them something, ask for that meeting separately.
Don't Treat One Owner as Data
Every owner generalizes from their own experience, which was shaped by their market and their timing. Ask three owners the same questions before you draw a conclusion.
Ready Made Sequences
Twenty Minutes With a Stranger
- 1Open with: "What does a normal Tuesday actually look like for you?"
- 2Move to: "What part of this job did you not know you were signing up for?"
- 3Then ask: "What did you get wrong in the first year that you would warn someone about?"
- 4Close with: "If you started again tomorrow, what would you do differently, and what would you keep exactly the same?"
If You Are Thinking of Starting One
- 1Start with: "How long was it before the business paid you a wage you could live on?"
- 2Follow with: "What cost surprised you with how big it grew?"
- 3Then: "Where do your customers actually come from right now?"
- 4End on: "What would have to be true for you to take a month off?"
If You Are Considering Working There
- 1Begin with: "Who was your first hire, and did it work out?"
- 2Ask: "What do you still do yourself that you know you should have handed off by now?"
- 3Then: "If demand doubled next month, what would break first?"
- 4Finish with: "Week to week, how do you know whether the business is healthy?"