Questions to Ask an Entrepreneur
The general set, for a coffee, a networking conversation or a short mentoring call with someone who runs their own business. Twenty questions that cover the whole arc at a moderate depth and get past the elevator pitch to how the work actually goes and what they have learned the expensive way. If you want a bank to build your own selection from, the 100 questions to ask an entrepreneur list is the full reference.
The questions
Open any question for the note
How do you describe what you do when someone asks at a wedding?
Why ask it
It gets you the plain version rather than the pitch, and it is an easier opening than asking about the business model. How much they simplify also tells you who their customers are.
What does a Monday actually look like for you?
Why ask it
Founders are asked about vision constantly and about their calendar almost never. The answer is usually admin, quotes, chasing payment and one thing they meant to do last week.
What were you doing before this, and what did it teach you that still applies?
Why ask it
Previous jobs supply the skill the business is quietly built on, whether that is selling, a trade, a network or knowing how a specific industry buys. It also shows whether the leap was as sudden as it sounds.
Where does your work come from now: referrals, repeat customers, advertising, cold outreach?
Why ask it
This is the answer most worth having, and most businesses are more dependent on referrals than they realise. Ask what would happen if that one source went quiet for three months.
What kind of work do you turn down?
Why ask it
Refusals show what they have learned about which customers cost more than they pay. A founder who turns nothing down is usually still in the phase of taking anything, which is its own useful data point.
What is the bottleneck right now?
Why ask it
It is a present-tense question, so you get the real state of things rather than the version on the website. Common honest answers are their own time, one supplier, cash timing, or a hire they cannot afford yet.
What was the last thing you changed your mind about in the business?
Why ask it
It shows whether they are still adjusting to evidence, and the specific reversal is usually interesting: a price, a market, a product they loved, a person. A blank answer often means a business running on habit.
How do you decide something when you cannot get enough information?
Why ask it
Everyone running a business does this weekly. Look for a practical method, a small test, a reversible version, a deadline they set for themselves, rather than a statement about trusting instinct.
What is the most expensive lesson you have paid for?
Why ask it
Money makes the answer concrete: a bad hire, an unpaid invoice, a contract signed without reading, stock nobody wanted. Ask what they do differently now, since that is the transferable part.
How do you tell the difference between a bad idea and an early one?
Why ask it
It is the hardest judgment in the job and worth asking anyone who has made it a few times. The good answers involve a signal they wait for rather than a feeling.
How do you pay yourself, and how did you land on that number?
Why ask it
Many owners take too little for too long, and hearing how they set it is more instructive than any figure about revenue. Ask when they last changed it.
Who do you call when something goes badly wrong?
Why ask it
The answer tells you what support actually exists: an accountant, a former boss, a peer group, a spouse who has heard it all. If the answer is nobody, that is often the real story of the last year.
What do you do in a month when cash is tight?
Why ask it
Practical and rarely asked. Answers include chasing invoices, delaying their own pay, a line of credit, a difficult conversation with a supplier, and each one is a technique you may need.
What part of the business would fall over if you took a month off?
Why ask it
It locates everything that lives only in their head. Owners who can answer immediately have usually tried it and found out the hard way.
What do people misunderstand about running your own thing?
Why ask it
It gives them room to correct the version they hear at parties, and the answers tend to be about freedom being smaller than expected and admin being larger. Ask what they thought before they started.
How has this changed how you spend the time you are not working?
Why ask it
It gets to cost without asking about sacrifice, which invites a rehearsed answer. Notice whether they can describe an evening or a weekend that was genuinely theirs.
Who have you learned the most from, and what did they actually do?
Why ask it
The second half matters, because most mentoring that works is specific: someone made an introduction, reviewed a contract, sat in on a call. It also shows you what useful help looks like when you go looking for it.
How do you decide to stop something you have already put a lot into?
Why ask it
Knowing when to close a product, a shop or a partnership is a skill people only learn by doing it. Ask for the last thing they stopped and how long they waited too long.
What would you be doing if you had never started this?
Why ask it
A gentle question that gets at whether the choice still feels like the right one. The answer is often more wistful than the public story allows for.
Is there anything I could help you with?
Why ask it
Almost nobody asks this and it changes the character of the meeting. Small offers are the realistic ones: an introduction, a review, a customer name, sharing something they are hiring for.
Making a Short Conversation Count
Practical guidance for the conversation itself
Getting the meeting and keeping it useful
- Ask for something specific and small: twenty minutes on one topic, by phone, at a time that suits them. Open-ended requests to pick someone's brain are the ones that get ignored.
- Say why them. One line about what you read, bought or noticed does more than three paragraphs about yourself.
- Put your actual question in the request. It lets them answer usefully rather than arriving to a general conversation.
- Turn up with two questions, not twenty. Depth on two beats a survey of everything.
- Watch the clock and offer to stop on time. The person who ends the call at twenty minutes is the person who gets a second call.
- Do not use it as a pitch. If you want to sell them something, that is a different meeting and it should be asked for as one.
Follow-up questions that open an answer up
- What happened next. The consequence is nearly always more useful than the decision.
- How did you find that out. It gets you the method rather than the conclusion.
- What would you do with my constraints. It stops advice that assumes their contacts and their capital.
- Can you give me an example from this year. Recent examples are truer than career-defining ones.
- What did that cost. Time, money, a relationship, a customer. It gives scale to the story.
What not to expect from them
They cannot tell you whether your idea will work
Nobody can, and asking pushes them into either flattery or a discouraging guess. Ask what they would test first and how they would test it cheaply.
Introductions are earned, not requested at the first meeting
Their contacts are their reputation. Do the thing they suggested, tell them the outcome, and the introduction often follows without being asked for.
Free consulting has a limit
Reviewing your plan, sitting on your calls, or making your spreadsheet work is paid work. Ask what they charge if that is what you want.
Their answers describe their market and their moment
Costs, competition, platforms and rules change. Treat what they say as one data point and get a second conversation with someone in a different position.
Afterwards
- Send a short thank you the same day, naming the one thing you are going to act on.
- Do that thing, then report back within a month with what happened, including if it did not work. This is the entire difference between a contact and a relationship.
- Keep your notes in one place with the date. Advice from three founders reads differently side by side, and the contradictions are informative.
- Pass something back when you can: a customer, a candidate, an article about their sector, a genuine referral.
- Do not forward their private numbers or stories to anyone. Word travels in small industries faster than anything you would gain.