25 Questions to Ask an Entrepreneur

My blog analytics tell me that a lot of people find this site using the search term “questions to ask an entrepreneur.”

So why not give the public what they want?

If you're interviewing an entrepreneur, for school or business, here are 25 key questions (plus a few supplementals) that you might profitably ask:


How did you get started in this business? Did you found the company?
Is this your first business? (If not, ask what the others were, and what happened to them.)
Were you exposed to entrepreneurship as a child (say, from family members or friends)?
How did you finance your business? What have been your most effective sources of financing over the years?

What are the revenues of the business? (They may or may not answer this.)
How many employees do you have? Full- or part-time? (This gives you some idea of the company size in case they didn't answer the revenue question.)
What is an average workday like for you?
Who are your customers? What are your most significant products or services?
How has your market changed in the past few years? How has your business changed to keep pace?

How have sales grown in the last few years? (gives you an idea of how successful the business is.)
Is the business profitable? What kind of profit margin does it have? Is that pre-tax or after-tax?
What are the most crucial things you have done to grow your business?
What plans do you have now to expand your business further?
What systems have you used to automate your business to give you more time for business planning and development?

What outsiders have been most important to your business success? (e.g., bankers, accountants, investors, customers, suppliers, mentors, etc.)
Do you have a business plan? A marketing plan? When was it last updated? (gives you some idea of how sophisticated their planning process is)
How do you market your products or services?
What has been your most effective marketing tactic or technique?
What’s the worst business advice you’ve ever received?

What three pieces of advice would you offer entrepreneurs starting out today? (asking for three is a lot, but it forces your subject to dig deeper than just saying , “Just do it,” or “Hire good people.”)
How long do you plan to keep operating this business? Do you have an “exit” strategy for getting out of the company?
If you were to start another business, what might it be? 
Do you believe business has any obligation to make the world a better place?
How does your business “give back” to the community or to society? 

(c) Rick Spence, Canadian Entrepreneur 2014

Note to students: Don't try to ask all these questions in one interview. Pick and choose. 

And never be afraid to follow up on the best answers by saying, "That's really interesting, Tell me more." Or ask for more info by saying, "Can you give me an example of that?"

Note to teachers: For permission to reprint this list at no charge, please e-mail me at rick (at) rickspence.ca