The short answer: the best questions to ask an entrepreneur are open-ended and specific: how they started, the hardest moment, a decision they’d make differently, how they found their first customers, and what they’d tell someone starting today. Pick 10 to 12 from the list below, ask follow-ups (“What happened next?” “How did you decide?”), and let the stories run. If you’re a former founder applying for a job, the second part of this guide covers the questions you’ll get, such as “Why are you leaving your business?” and “Will you be happy working for someone else?”, and how to answer them.
40 questions to ask an entrepreneur
Getting started
- How did you come up with the idea for your business?
- What were you doing before you started it?
- What made you decide to take the leap?
- How did you fund the business at the start?
- What did the first year look like, day to day?
Customers and growth
- How did you find your first customers?
- Who is your ideal customer, and how has that changed?
- What’s worked best for getting new customers?
- What have you tried that didn’t work?
- How do you know when a customer is happy?
Challenges and decisions
- What was the hardest moment in your business so far?
- Was there a time you almost gave up? What kept you going?
- What’s the biggest mistake you’ve made, and what did you learn?
- What’s a decision you’d make differently now?
- How do you make decisions when you don’t have all the information?
Money
- When did the business start to make a profit, if it has?
- How do you set your prices?
- What’s the biggest expense people don’t expect?
- How do you manage cash flow in slow months?
- Would you take investment again? Why or why not?
People and leadership
- How did you make your first hire?
- What do you look for when you hire?
- How would your team describe your leadership style?
- How do you handle conflict on your team?
- Who has helped you most along the way?
Daily life and balance
- What does a typical day look like for you now?
- How do you manage your time?
- How do you avoid burning out?
- What’s the part of the job you enjoy most, and least?
- How has running a business changed you?
Competition and the future
- Who are your competitors, and how do you stand out?
- How have changes in technology affected your business?
- Where do you see the business in five years?
- What would you do if the business failed tomorrow?
- What does success mean to you?
Advice
- What do you wish you’d known before you started?
- What skills matter most for an entrepreneur?
- What’s the best advice you’ve received?
- What would you tell someone starting a business today?
- Is there a book, person or resource you’d recommend?
How to run the interview
- Prepare, but don’t read the list. Choose 10 to 12 questions and keep the rest as backups.
- Research the business first so you don’t spend time on facts you could have looked up.
- Ask one question at a time, and follow up on the interesting parts.
- Ask for stories, not opinions: “Tell me about a time…” gets better answers than “Do you think…”.
- Ask permission to record and to quote them, especially for a published article or podcast.
- Send a thank-you afterward. See our thank-you email templates.
For former founders: job interview questions you’ll get
If you’ve run your own business and are now applying for a job, interviewers usually want to know why you’re making the move and whether you’ll be happy in a team with a manager. Common questions:
“Why are you leaving your business?”
Be honest and forward-looking. “The business reached a point where it could run without me, and I want to go deeper on product management at a larger scale than a five-person company allows.” If it failed, say so briefly and focus on what you learned. See our guide to reasons for leaving a job.
“Will you be comfortable working for someone else?”
Show that you understand the difference and want it: “Running a business taught me how much I value having a team to build with. I’m used to making calls quickly, but I’m also used to listening to customers and advisers who knew more than me. I’d bring the same attitude to working with a manager.”
“What did you learn from running a business?”
Pick two or three lessons relevant to the job, each with a specific example: selling to customers, managing cash, hiring, or making decisions without complete information.
“Will you leave to start another company?”
Be honest about your plans. If you’re committed to this path, say why: what you want to learn here and how long you see yourself staying. See where do you see yourself in five years.
“Tell me about a time you failed.”
Founders have plenty of material. Choose one with a clear lesson. See tell me about a time you failed.
