The best questions to ask an entrepreneur are open-ended ones about how she started, how she runs and markets her business, what challenged her, and where she intends to take the company next. Ask them one at a time, and follow up on any detail that surprises you, since a follow-up can turn a general answer into a specific one. These groups work for anyone who plans to interview a founder, whether you are a student, a journalist, or a host. If interviewing a woman whose work you admire makes you nervous, a list sorted by subject gives you something steady to come back to.
How to Ask Entrepreneur Interview Questions That Open a Conversation
Before you interview an entrepreneur, read her website, her social media accounts, and any earlier interviews. Introduction to Reporting and Writing, a free online textbook published by Northwestern University, calls background research the first and most important step. The same chapter advises opening with a question that builds on that research, which shows her from the start that you did the reading.
Poynter’s Roy Peter Clark advises reporters to ask open-ended questions that cannot be answered with a yes or no, and to ask one question at a time. He also tells them to be patient and not break a silence with a new question, and the Northwestern chapter notes that a source sometimes needs more time to think.
Closed questions still have a place. Writer Chip Scanlan, in advice shared by IJNet, says they are useful when you need a direct answer, so save them for factual details such as the year she opened. He also cautions against double- and triple-barreled questions, which allow a source to sidestep the harder part.
The Northwestern chapter suggests asking more “what” questions than “why” questions, because “what” can prompt less defensiveness and sometimes more depth. It adds that the most important follow-up question might be “Can you tell me more about that?”, so keep that line ready for every group below.
Questions to Ask an Entrepreneur about How She Got Started
- What were you doing professionally before you launched this business?
- What problem did you notice that motivated you to solve it?
- How did you choose your first product or service?
- When did it begin to feel like a legitimate business to you?
Begin here, because she knows these answers best, and an origin story gives both of you a comfortable opening before the more detailed questions. For examples of how successful entrepreneurs have told their stories in public, see our profiles of 11 famous women entrepreneurs, including Madam C.J. Walker and Whitney Wolfe Herd.
Questions about Running a Business Day to Day
- What does a typical week look like for you at this stage of the business?
- Which responsibilities have you delegated, and which do you still handle personally?
- What routines make running a business manageable for you?
- What surprised you most about running a small business?
Day-to-day questions to ask a business owner move the conversation from her story to the work itself, so your audience gets a realistic picture of the role. If her first answer stays general, ask her to describe one recent day in detail, because a single specific morning is easier for listeners to imagine than a summary of long hours.
Questions about Her Product or Service and Her Customers
- Who is your ideal customer, and how did you find your first one?
- What do customers tell you they value most about your product or service?
- How has your offering evolved since your first sale?
Customer questions keep the conversation concrete, since she can answer them with examples from real sales and customer feedback. They also show how closely she listens to the people she serves, and that matters to anyone deciding whether to buy from her or work with her.
Questions about How She Markets Her Business
- How do you market your business today, and how has that changed since you began?
- What role does social media play in how customers find you?
- Which marketing effort produced less than you expected, and what did you learn from it?
- Where do most new customers first discover your company?
Marketing answers show the methods behind a result, and other founders can adapt those methods for their own companies. Ask her to compare one channel that performs well with one that disappointed her, because a single comparison is easier to remember than a long list of platforms.
Questions about Funding and Money, If She Chooses to Share
- How did you finance the business during its first year?
- Did you choose to raise funding, and what factors influenced that decision?
- What has contributed most to the company’s growth?
- What does growth mean to you, apart from revenue?
Money is a personal subject, so ask before the interview whether she is comfortable discussing it, and respect her answer either way. Phrase the funding question so that either answer sounds ordinary, since a founder who grew from savings or revenue has as useful a story as one who took outside investment. The Northwestern chapter also suggests saving the most uncomfortable question for last, so if revenue figures feel sensitive, place them near the end.
Questions about Her Biggest Challenges and What She Learned
- What were the biggest challenges in the early stages, and how did you handle them?
- What is one decision that did not work, and what did you adjust afterward?
- Which setbacks turned out to be opportunities to learn?
- Was there a moment when you considered closing the business?
A hard year is personal, even for a founder who has told her story many times, so follow her lead on how much to disclose. Allow a pause after she answers, because the Northwestern textbook observes that sources often add detail when it falls to them to fill a silence. Framing these as “what” questions, as in “What did you change?”, follows the same chapter’s advice and keeps the focus on her decisions.
Questions about Leadership and Personal Growth
- How would your team describe your leadership style?
- What did you have to learn when you hired your first employee?
- Who do you consult when you face a difficult decision?
- Where have you seen the most personal growth since you started?
- What do you think makes a good entrepreneur?
Ask for one concrete example with each answer, so your audience can picture the situation she describes. The question about what makes a good entrepreneur can also bring out the qualities she looks for in the people she hires, which listeners who manage teams can apply themselves.
Questions about the Long Term and Her Advice
- Where would you like the company to be in five years?
- What would you like your company to represent in the long term?
- Which successful entrepreneurs have influenced your approach to work?
- What advice would you offer a woman starting a business this year?
- What should I have asked you that I did not?
Save these interview questions for women entrepreneurs for the end, once she is comfortable and her earlier answers have given you material for follow-ups. The final question comes from the Northwestern textbook, which recommends closing with a question about what you did not ask and another about who else you should contact.
How to Prepare If You Are the Founder Being Interviewed
Answering these questions yourself is a different experience from asking them, especially the first time. The groups above are the questions to prepare for, so write a short, true answer to one question in each group, with a single example, and decide ahead of time what you will share about money and funding. To prepare for that first interview, read our guide to media training for founders.
A Pink Fins Media interview would put questions like these to you about the company you built, and you would receive short clips to share on your own channels. If you would like to be the one answering, or you know a woman who should be, use the Nominate a Woman button at the top of this page.
Frequently Asked Questions
What Are Good Questions to Ask an Entrepreneur?
Good questions explore how she started, how she runs and markets her business, and what she learned from her biggest challenges. Research her website, social media accounts, and recent interviews first, so your questions build on what she has already said. Keep them open-ended, and save yes-or-no questions for factual details such as dates.
What Questions Should I Ask an Entrepreneur in an Interview?
Begin with the early stages of her business, then move to her daily operations, customers, and marketing. Ask about money and funding only if she has agreed to discuss them, and close with her advice and a question about anything you missed.
How Many Questions Should I Prepare for an Entrepreneur Interview?
Prepare more questions than you expect to use, organized by subject, so you can skip ahead when one answer covers several topics. Leave time for follow-ups such as “Can you tell me more about that?”, because a follow-up can draw out details your list did not anticipate.
Should I Ask an Entrepreneur about Money in an Interview?
Ask her before the interview whether she is comfortable discussing money, and respect her answer either way. If she agrees, phrase the funding question so that any answer sounds ordinary, and place revenue figures near the end.
How Should I End an Interview with an Entrepreneur?
The Northwestern textbook recommends closing with a question about what you did not ask and another about who else you should contact. Save both for the last few minutes, after the rest of your list.
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