57 Interview Questions to Ask Business Owners

Business owners have a lot of responsibilities to carry. From dealing with clients and customers to making sure the product or service is up to par, to managing a team, there’s a lot a business owner has to do. Often we see business owners as untouchable figures who have it all together, but in reality, they are just like us! They too have worries, stress, and doubts. 

Asking questions can help you to get to know business owners. These questions cover a range of topics, from the beginnings of starting a business to the challenges of growing the business and everything in between. By the end of the interview, you should have a good sense of what it’s like to be a business owner and whether it’s the right path for you. 

48 Interview questions for business owners that will help you gain the insight you need:

  1. When did you realize that you wanted to be a business owner?
  2. Why did you choose the industry you are in? 
  3. What form of business do you have, sole proprietorship, partnership, or corporation?
  4. How did you come up with the idea for your business? 
  5. What was the most difficult thing about starting your business?
  6. What are your long-term goals for your business? 
  7. What are the core values of your business? 
  8. Does your business have a stated mission statement, the reason for its existence?
  9. What do you see as the greatest opportunities for your business in the future? 
  10. What makes your company stand out from your competitors? 
  11. How does your pricing strategy compare to that of your competitors?
  12. How do you attract and retain customers? 
  13. How do you market your products or services? 
  14. What role does technology play in your business?
  15. How do you handle shipping and logistics?
  16. What are the most important aspects of a good relationship with a supplier?
  17. How do you handle customer complaints and feedback?
  18. How do you manage risk and protect the business against potential threats?
  19. What succession planning do you have in place for the long-term future of the business?
  20. Are there any charitable causes or community initiatives that your business supports?
  21. Do you have expansion plans for the future, and if so, what markets or products do you have in mind? 
  22. What day-to-day tasks do you delegate to others? And what do you like to keep for yourself? 
  23. Describe your customer base. Who are they and what do they need from your product or service? 
  24. How did you come up with your business model? And how has it evolved since you started? 
  25. How do you manage employee performance and what methods do you use to track progress?
  26. What are the biggest challenges your employees face, and how do you help them overcome them?
  27. What benefits do you offer your employees, and how do these benefits help attract and retain top talent?
  28. What sales strategies do you think have been most effective?
  29. What role do failure play in your life and your business? 
  30. How has your business changed since you started it? 
  31. Who are some of your role models or mentors in the industry? 
  32. What would you say is your superpower as a business owner? Or what quality do you think is essential to the success of a business owner? 
  33. What values or guiding principles guide you in running your business? 
  34. How do you effectively market or sell your product/service? Do you have any tips for those who struggle in this area? 
  35. Do you have any advice for aspiring business owners who are still in the ideation phase but have not yet taken the plunge? 
  36. How much capital did you need to get started and where did that money originally come from (e.g. personal savings, grants, loans, etc.)?
  37. How do you measure success – is it purely financial, or are there other indicators you consider?
  38. What are some of the biggest challenges facing businesses today, and how have they specifically impacted your industry?
  39. Are there any current trends or start-ups in your industry that excite or concern you?
  40. What would be your ideal partner or customer?
  41. What are the things about running a business that people don’t often think about or consider? (e.g., long hours, emotional labor)?
  42. What are the most common misconceptions about business owners? 
  43. Can you see yourself continuing to run this particular business for many years to come, or do you plan to “cash out” at some point and move on?
  44. Looking back at everything, what would be one piece of advice you wish someone had given to you when first starting as a business owner?
  45. Do you have any regrets since becoming a business owner? If so, what are they? 
  46. Do you think there is such a thing as too much hard work when it comes to running your own business? Or is there no such thing as too much hard work when it comes to something you are passionate about? 
  47. Is there anything else that we didn’t touch on that you think is important for people to know about what it means to own your own business/be an entrepreneur?
  48. Do you have any upcoming projects or goals that we can help promote?

9 Questions to ask about the life of business owners:

  1. What does your daily work routine like?
  2. How do you balance work and personal life as a business owner? 
  3. How many hours do you work on average per week? 
  4. How do you deal with stress and anxiety?
  5. How do you manage your time and prioritize your tasks? 
  6. Are there any funny or memorable moments during your journey as a business owner so far that have stuck out in your mind? Or what has been one of the biggest challenges during your journey so far?
  7. What has been your proudest moment as a business owner? 
  8. How do you get along with people who have different personalities, backgrounds, or views in the world of business?
  9. If you had the chance to start your career over again, what would you do differently?

Frequently Asked Questions

Are business owners entrepreneurs?

Business owners can be considered entrepreneurs if they meet the definition of that term. This includes taking financial risks to start or grow their business. Many business owners work hard to create a product or service that fills a need in the marketplace, and they are often rewarded with profits and success. However, there is no guarantee of success in owning a business, and many entrepreneurs experience failures along the way.

What are business pains?

Business pains are the frustrations and problems that businesses experience. These can include difficulties with sales, marketing, customer service, or other aspects of the business. Business pains can be a major obstacle to success and can impact a company’s bottom line. Addressing and resolving these issues is critical for any business.

What do business owners struggle with?

One of the most common struggles is finding new customers. This can be difficult, especially if the business is in a competitive industry. Another problem is managing finances. Balancing the books and making sure the business is profitable can be difficult, especially for new businesses. Finally, business owners often struggle with maintaining employee morale. This can be difficult when times are tough and employees are feeling pressure.


Running a business is hard work, but it can also be incredibly rewarding. If you’re thinking about starting your own business, interviewing existing entrepreneurs is a great way to learn more about what it entails and the challenges you can expect to face along the way. Use this list of questions as a starting point for further research and reflection as you consider whether building a business is right for you.

How useful was this post?

Click on a star to rate it!

As you found this post useful...

Share it on social media!

We are sorry that this post was not useful for you!

Let us improve this post!

Tell us how we can improve this post?