Questions to Ask an Entrepreneur About Starting a Business
Questions to ask an entrepreneur about starting a business are for the half hour you get with a founder who has already done what you are thinking of doing. The 59 questions follow the story in order: getting started, the first customers, the early money, the setup and the help, and how it all looks from where they stand now. The last group turns the table, with questions to ask someone starting a business right now, such as a friend or relative in their first months.
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The questions
Each question, and why to ask it
Getting started
What problem did you notice first, and how did you know other people had it too?
Why ask it
An idea usually starts as an irritation in a job or a request from one person. Press on the second half, because it shows whether they checked with anyone before spending money or simply got lucky.
What did the first version of this look like, and what did it cost to make?
Why ask it
Ask them to describe it plainly: a spreadsheet, a borrowed van, one product on a folding table. If it was rougher and cheaper than the business you can see today, that resets your sense of how much you need before you can begin.
How did you test whether anyone would pay before you built it properly?
Why ask it
You are listening for something a buyer had to commit to: a pre-order, a paid pilot, a market stall, a page with a price on it. If there was no test at all, ask what they would run now, since that is the version you can copy this month.
Did you start it on the side, and how long did you run both?
Why ask it
The overlap is where the evenings and weekends went, and its length tells you how slowly the first income arrived. Ask what their employer knew, and read your own contract before copying the arrangement, because rules on side work differ from one employer to the next.
When did you leave your job, and what was the trigger?
Why ask it
A real trigger, such as a signed contract, a set number of months of expenses saved or a redundancy, is more useful than advice about following your gut. Ask whether they would wait for the same thing again.
How long was it from deciding to do this to taking the first payment?
Why ask it
The gap is usually longer than the story suggests and is filled with things nobody mentions: a registration, a supplier, a website, a first quote that went nowhere. Asked as a length of time, it gives you something to put in your own calendar.
What did you have to learn before you could open, and how did you learn it?
Why ask it
Every trade has its own answer, from quoting a job and reading a contract to basic bookkeeping or a formal qualification. How they learned it matters as much: a course, a patient friend, or an expensive first mistake with a real customer.
Did you write a plan, and which part of it turned out to matter?
Why ask it
Some founders had a long document written for a bank and some had a page of sums on the back of an invoice. Whichever it was, the part they still looked at six months later, perhaps the list of costs or the names of the first people to call, is the part to write for yourself.
What did your first week of actually doing it look like?
Why ask it
Ask for it day by day. An honest account is often less about the product than about phone calls, a bank appointment, chasing a supplier and wondering what to do at ten in the morning with no boss, and it makes your own first week easier to picture.
First customers
How did you get your first ten paying customers, one by one?
Why ask it
One by one is the important part, because it forces specifics rather than a channel strategy that only existed later. If most of the ten were people they already knew, that is worth knowing before you budget for advertising.
Who was the first stranger to buy, and how did they find you?
Why ask it
Friends and former colleagues buy out of goodwill, so the first sale to someone with no reason to be kind is where the business really begins. How that person found them points to the channel worth trying before any other.
What did you say when a customer asked how long you had been doing this?
Why ask it
Every new business is asked for a track record it does not have. Some founders leaned on a previous job, some offered a trial, and some simply admitted this was their third client. Borrow the wording you could say with a straight face.
What did you get wrong about who your customer was?
Why ask it
The buyer a founder pictures at the start and the one who ends up paying can be different people, and the correction may have come from a sale nobody expected. Find out how they noticed, because that method is something you can repeat.
Who else was already doing this, and why did customers choose you over them?
Why ask it
The rival may be another firm, the customer doing the job themselves, or nobody bothering at all. What buyers said when they switched is more reliable than the founder's own theory of why, so ask for their words.
How did you set your first price, and what happened when you raised it?
Why ask it
A first price is often a guess or a copy of a competitor's, so the story of the first increase tells you how much room there was. Ask how many customers actually left.
What did early customers complain about most?
Why ask it
Complaints in the first months are free research, and founders tend to remember them word for word. Ask which ones they fixed and which they decided to live with, because the second list shows what the business chose not to be.
What did you promise a customer early on that nearly broke you?
Why ask it
It is easy to overcommit when you need the sale, and the story usually turns on a deadline, a custom job or a price. What they say now when the same request comes in is a line you can borrow.
Which early customer do you wish you had turned down?
Why ask it
There is usually one: the buyer who wanted a discount, changed the brief every week or paid three months late. Write down the warning signs they describe, since you are likely to meet the same person in your own first year.
What marketing did you try at the beginning that did nothing?
Why ask it
Knowing what failed in their trade, whether flyers, paid ads, a launch event or months of daily posts, can save you the same spend. Check when they tried it, because what works changes quickly.
What number were you watching to know it was working?
Why ask it
A founder who can name one, such as repeat orders, weekly bookings or referrals, has told you what to count in your own first months. If they watched nothing, what they wish they had counted is just as useful.
Early money
How much money went in at the start, and where did it come from?
Why ask it
Each source carries its own pressure, whether savings, a credit card, family, a small loan, a grant or an investor. Knowing which it was explains much of the advice you hear for the rest of the conversation, since someone spending their own savings and someone repaying a bank see risk differently.
What were you living on in the first year?
Why ask it
This one is about their household, not the business: savings, a partner's salary, contract work, a room at a parent's house. Whatever covered the rent while revenue was thin is the thing you would need your own version of.
Which cost turned out much bigger than you had budgeted for?
Why ask it
The surprises are the lines missing from a first budget: insurance, card fees, packaging, software subscriptions, returns, a deposit on premises. Add theirs to yours and then look up the real figure for where you live.
What did you spend money on early that you would not spend again?
Why ask it
Expect a short, specific list, perhaps an office, a logo, a custom-built system or stock bought in bulk before anyone had ordered. Each item is a lesson they paid for and you get for the price of a coffee.
How long did you wait between doing the work and being paid for it?
Why ask it
A business can be busy and still run out of cash if customers pay in sixty days and suppliers want paying in seven. Ask what they changed: deposits, shorter terms, payment on delivery. That is easier to set up before the first invoice than after the tenth.
Did you borrow or take outside money, and what did it cost you beyond the interest?
Why ask it
A loan can come with a personal guarantee, an investor with a say in decisions, family money with awkward dinners. Listen for the strings more than the amount. Terms vary by lender and country, so treat this as their experience and get your own advice before signing anything.
When did the business first cover its own costs for a full month?
Why ask it
This comes earlier than the founder's wage and is the first proof the thing can stand up. Ask what changed in that month, a bigger order, a cut cost or a higher price, since one of those is usually doing most of the work.
How long was it before the business paid you a wage you could live on?
Why ask it
Public versions of a founding story tend to skip this figure, which is why it is worth asking for in private. It sets your expectations better than any revenue number, and it tells you how long your own savings or second income would have to last.
How much of a cushion would you want in the bank if you were starting today?
Why ask it
Asked in months of living costs, this gets a clearer answer than asking for a sum. Their figure reflects their rent, their family and their trade, so the useful part is the reasoning behind it.
Setup and help
What legal or tax setup do you wish you had sorted out on day one?
Why ask it
You may hear about a separate bank account from the start, the choice of business structure, a written agreement with a co-founder, or a bookkeeper hired before the first tax deadline. What is required depends on the country, the state and the type of business, so take their list to an accountant or lawyer where you are.
Which licences, permits or insurance did you need before the first sale?
Why ask it
Founders often learn about these from an inspector or a customer's contract and not in advance. The list is specific to their trade and location, so use it as a set of things to look up with your own local authority and insurer.
Did you start alone or with a partner, and what did you put in writing?
Why ask it
Who owns what, who puts in what and what happens if one of you leaves are easy to agree while everyone is still friendly. If nothing was written down, ask how that went the first time they disagreed about money.
Who was the first professional you paid, and was it worth it?
Why ask it
Whether it was an accountant, a solicitor, a designer or a web developer, the choice shows which job they could not safely do themselves. Find out what the fee bought them, in hours saved or in mistakes avoided.
What did you keep doing yourself for too long?
Why ask it
Most owners start out doing the books, the support, the deliveries and the website themselves. The task they held on to longest is where their attention was trapped, so ask what finally made them hand it over.
Who was your first hire, and would you hire that role first again?
Why ask it
Listen for what the hire took off their plate, because that is the work they had misjudged as easy or could no longer fit in. If they would choose a different role now, the reason is a shortcut for your own first hire.
Who did you have to ask for help, and how did you ask?
Why ask it
Wording a request for a loan, an introduction or a favour is a skill, and someone who has built a business has had plenty of practice. Get the actual sentence they used, not just the name of the person.
Who did you talk to when you could not tell anyone how it was really going?
Why ask it
Staff, customers and family all need to hear that things are fine, which leaves a founder very few people to be honest with. Another owner, a former boss, a paid adviser: whoever it was, find your own equivalent before you need them.
Which tool or habit did you set up early that you still use?
Why ask it
Anything that has survived years of growth is worth copying on day one: a spreadsheet of every enquiry, an invoicing app, a folder of receipts, a Friday hour for the accounts. Expect it to be plainer than you would guess.
Looking back
Which month were you closest to stopping?
Why ask it
Asking for a month rather than a feeling gets you a real story instead of a resilience speech. What they did that month, borrowed, cut, sold something, asked for help, is the practical part.
What nearly ended the business that you never saw coming?
Why ask it
The risks that sit in nobody's plan are things like a landlord selling up, a supplier folding, a platform changing its rules or an illness. Hearing a real one makes it easier to ask what your own business would depend on.
What did it cost you outside of money?
Why ask it
Give them room on this one, since the honest answer may be time with children, a relationship, sleep, health or friendships that went quiet. It is rarely volunteered, and it belongs in your decision as much as the money does.
Knowing what you know now, would you start it again?
Why ask it
A quick yes tells you little, so wait for what comes after it: the conditions, the thing they would refuse to repeat, the year they would skip. A founder who has to think before answering has told you something as well.
What did you have at the start that I might not have?
Why ask it
Asked with plain curiosity, this brings out the head start: a partner's income, a client list from an old job, a spare room, a skill others would have had to pay for. It shows how much of their route is open to you and which parts you would have to replace.
What advice did you take that turned out to be wrong for your situation?
Why ask it
It teaches you to filter advice instead of obeying it, including what they are telling you across the table. Listen for the popular rules, such as raise money early, hire fast or pick a narrow niche, and for what about their situation made one of them a bad fit.
What has changed since you started that would make it harder or easier today?
Why ask it
They are describing a market as it was when they began: what advertising cost then, what the rent was, who the competitors were. Their answer tells you which parts of the story to discount and which still hold.
If you had to start again with half the money, what would you do in the first three months?
Why ask it
The constraint is what makes this worth asking, because it strips away advantages they may not realise they had. Listen for whether the answer starts with selling something or with building something.
If my idea were yours, what would you test first?
Why ask it
This works better than asking whether the idea is good, which makes them a judge and tends to get a polite yes. A test has a cost and a date, so you leave with something to do on Monday.
What do you think I am picturing wrong about the first year?
Why ask it
It invites them to puncture the tidy version of the story, the one told at dinners and on panels. Be ready for an answer about admin, loneliness and the sheer number of small decisions, not about the product.
Who else should I talk to who started more recently than you?
Why ask it
Someone two years in remembers prices, paperwork and platforms as they are now, which a founder of fifteen years may not. An introduction from them also gets a reply where a cold message might be ignored.
Someone starting now
What are you selling, and who is the first person you expect to buy it?
Why ask it
For a friend or relative who is launching right now, this is a kind question as well as a useful one. A name or a clear type of buyer means the idea has met the real world, and a vague answer is a prompt to go and find one, not a reason to doubt them.
What made you decide to do this now?
Why ask it
There is usually an event behind the timing: a redundancy, a birthday, a client who offered work, a child starting school. Knowing it tells you how much pressure they are under, which shapes what kind of help is welcome.
What has to happen before you can take your first payment?
Why ask it
This turns a big plan into a short list: a registration, a price, a way to be paid, one finished thing to sell. People in their first weeks often find that saying the list aloud shows it is shorter than it felt.
How long can you keep going before it needs to pay you?
Why ask it
Ask gently, and only if you know them well enough to talk about money. A person with an answer in months is planning, and one who has not thought about it may thank you later for raising it.
What have you heard from the people you hope will buy?
Why ask it
Encouragement from friends is pleasant and tells them little. What a possible customer said, in that customer's own words, is the thing worth repeating back, and asking for it nudges them to have those conversations if they have not yet.
How are you fitting this around everything else you have on?
Why ask it
A business that starts in evenings and weekends takes its hours from sleep and family, so this is a question about them as much as about a schedule. It lets a new founder say they are stretched without having to say the business is struggling.
What part of this are you dreading?
Why ask it
It might be selling, the accounts, telling a parent or the first cold call. Saying it aloud is a relief, and it is often the one place a friend can actually do something, even if that is only sitting beside them while they send the first invoice.
What would you like from me: an opinion, an introduction, or just a first customer?
Why ask it
People starting a business are handed a great deal of advice they did not ask for. Offering a choice lets them say what would help, and it stops you delivering a critique when they wanted a cheer.
Where should I send people who might want this?
Why ask it
A link, a phone number or one sentence you can repeat is what turns goodwill into a referral. If they have nothing to give you yet, putting that together is a small, real job you could do with them this week.
How will you know in six months whether it is working?
Why ask it
Meant as help with picking a marker, not as a challenge: a number of customers, a month that covers costs, a set amount saved. Then ask again in six months, because being remembered is its own kind of support.
Getting Real Answers From a Founder
Practical guidance for the conversation itself
Ask about their business, not business in general
Anchor every question to a transaction
Asking how they find customers produces a lecture. Asking about the third sale they ever made produces a story with a name, a price and a reason. Keep pulling the conversation back to single events.
Ask for numbers with a range attached
People who will not name their revenue will often tell you how many months it took to break even, roughly what they started with, or what a typical order is worth. A range is enough to plan against.
Follow up with what happened next
Most first answers stop at the decision. The consequence, whether the customer stayed, whether the hire worked out, is where the lesson actually is.
Ask when the opposite advice would be right
It is a gentle way to test whether a strong opinion is a rule or a preference, and it gets them to name the conditions their advice depends on.
Correct for the fact that they made it
- Before you meet, list what you would be starting with: savings, free hours a week, contacts, skills. Hold it against their starting point as they talk, so you notice the gaps while you can still ask about them.
- Ask about the competitor who did roughly the same thing and did not survive. It is the fastest way past the story that success was inevitable.
- Take patterns from several founders rather than a plan from one. A single account is a case study, not evidence.
- Write the year next to every figure they give you. A rent, a wage or an advertising cost from their first year needs checking at today's prices before it goes in your budget.
- Notice how much of their explanation is luck being retold as strategy. Most people do this without meaning to.
Respecting the meeting you asked for
- Ask for a specific slot, thirty minutes, and end at thirty minutes even if they are enjoying it. That is what gets you a second conversation.
- Send one short paragraph in advance saying where you are and the two things you most want to ask. It keeps the opening minutes for their story instead of yours.
- Do not bring a pitch or ask them to sign a confidentiality agreement. You came for their experience, not to sell them anything.
- Describe your own idea in two sentences, and only when they ask. Every minute you spend explaining is a minute of their experience you do not hear.
- Take notes, and write down their exact words and figures rather than your interpretation.
- Follow up within a month saying what you actually did with the advice. It is rare, it is remembered, and it is the whole basis of asking again.
What to do with the answers
- Turn the advice into one testable next step this week: ten conversations with buyers, one paid pilot, a price on the table.
- Write down which of their claims you can check, then check them: what things cost, what a licence requires, how long an approval takes.
- Verify anything legal, tax or regulatory with someone qualified in your own jurisdiction. Founders are describing what happened to them, not what applies to you.
- Keep a note of the advice you decided not to take, with the reason. It is worth rereading in a year.
When the person is still starting
- The last group is for a friend, relative or classmate who is in their first months, and the job is different: you are there to help them think, not to collect lessons.
- Ask two or three and stop. A new founder is questioned by their bank, their family and themselves already, and a fourth round over dinner feels like an audit.
- Leave out your own verdict on the idea unless they ask for it. A question about their first buyer does more good than an opinion on whether buyers exist.
- If you offer something, make it small and definite: one introduction, an hour checking the price list, being the first paying customer at full price.
- Go back to the same questions a few months later. What has changed in the answers is the most honest progress report they will get.