The best questions to ask entrepreneurs that will help you grow

March 10, 2021

Need questions to ask successful entrepreneurs that will help with your business, career, and personal growth? Don’t worry, here at MentorCruise, we’ve got your back.

The best questions to ask entrepreneurs that will help you grow

Asking questions is an important part of growing as a person and as a business. In the business world, there is a common misconception that asking questions is a sign of weakness and that you’re not smart enough. That is not true. Studies have shown that asking well-thought-out questions is a sign of intelligence. It’s also one of the traits successful people have in common.

Asking the right questions to entrepreneurs can lead you to the business or career of your dreams. It also offers you an opportunity to learn from other people’s mistakes so you don’t repeat them. It’s also the quickest way to learn what works and what doesn’t.

You’ll learn:

  • How to ask the right questions
  • The best questions to ask entrepreneurs and founders

7 tips for forming great questions to ask entrepreneurs and founders

1. Know why you are asking the questions.

When you ask questions with clear intent, you won’t get distracted during your conversation or interview. Knowing why you are asking certain questions will help you stay focused, and you’ll be able to gather valuable facts or opinions that you actually care about. It will also help you avoid asking unnecessary questions just to fill the time.

2. Be a good listener.

Try to listen to the person you are talking to and understand what they are saying. Being a good listener will help you ask questions the other person will enjoy answering.

3. Use the right wording.

When asking questions, try to use a neutral tone and avoid asking potentially leading questions. Try to keep your questions open-ended to get the best possible answers. Open-ended questions can sometimes provide you answers you didn’t expect.

4. Build a hierarchy of questions.

It’s important that you structure your questions. General questions should be followed by more specific ones, ask only one question at a time and use something from the answer as a lead to the next question.

5. Ask these kinds of questions:

If you want your questions to be dynamic, think about these specific categories and ensure that you don’t ask too much of one type of question:

  • Personal questions about their take on entrepreneurship.
  • Business-oriented questions about the nitty-gritty behind building a business.
  • Informative questions about their business that provide some insights on operations.
  • Stories about specific events that happened to them.
  • Accountability questions about how they keep themselves and their business growing.

6. Avoid Yes/No questions

These are questions that don’t move the needle forward and may even provide awkward periods of silence as the entrepreneur or founder tries to think of what to say next. The best questions to ask successful entrepreneurs are ones that will allow them to provide a wealth of valuable information.

7. Be clear and specific. Avoid vague questions.

Many entrepreneurs are pressed for time and energy. Asking vague questions that don’t have a clear purpose in mind can be more frustrating than helpful. Remember here, you want to find value from their wisdom and build a foundational relationship with them. Asking generic questions won’t cut it.

Therefore, this goes to say to take these sample questions with a grain of salt. Make sure they fit within the context and the wheelhouse of the entrepreneur.

List of questions for entrepreneurs, founders and business owners

Here are the best questions that you can ask an entrepreneur. Don’t forget to put your own twist on them to make them your own and in line with your purpose.

Ice breakers

These are great first questions to warm-up and get at ease with one another. They help with creating a friendlier and more comfortable atmosphere that will encourage the other person to share information with you.

  1. What kind of a person are you?
  2. Try to describe yourself in 3 words only.
  3. What are your strengths and your weaknesses?
  4. Top 3 websites or blogs you can’t imagine your day without. Why those three?
  5. Your top 3 mobile apps that help you stay organized and on top of your game.

Personal questions

Asking entrepreneurs personal questions can offer you a great insight into how they see entrepreneurship and what tools and tactics are they using to achieve the entrepreneurial mindset. You can also ask questions about dealing with failure staying focused when times are difficult, etc.

  1. What books do you recommend for every entrepreneur to read?
  2. What motivates you to keep going?
  3. How do you manage the stress?
  4. How are you taking care of your mental health?
  5. How do you prevent burnout?
  6. What does your typical workday look like?
  7. How do you manage your work-life balance?
  8. What are your values and ideals?
  9. How do you deal with self-doubt and doubt from others?
  10. When did you know you wanted to be an entrepreneur?
  11. What do you enjoy most about entrepreneurship? What do you find the hardest about it?

Business-oriented questions

Feel free to ask questions about their business. After all, business-oriented questions to ask entrepreneurs are very important as building ventures is what they do for a living. You can also ask about tips for scaling a business and how they network as an entrepreneur.

  1. How did you start your business?
  2. What are some mistakes you wish you could have avoided?
  3. What advice would you give to starting entrepreneurs?
  4. How can I come up with a great name for my company?
  5. How do you come up with business ideas?
  6. How can I protect my idea so others don’t steal it?
  7. What are the biggest mistakes first-time entrepreneurs can make?
  8. What kind of entity should I set up if I’m only starting my business journey?
  9. What are you most excited about at work right now?
  10. What are your tips for building a great team?
  11. How do you market your business?
  12. What can I do to support your work?

Informative questions

These questions will provide you with some general information about their company. You can ask about the company’s name, headquarters, vision, mission, goals, and the future of the company. You can also ask more detailed and in-depth questions regarding how they are running their business.

  1. Where did the idea for your business come from?
  2. What did your initial business plan look like
  3. How did you pick the name for your company?
  4. How did you decide on the location for your business?
  5. What makes your company stand out from all the other businesses in your niche?
  6. How did you build your team?
  7. How are you dealing with funding for your business?
  8. How are you dealing with the negative publicity your company gets?
  9. What problems are you trying to solve?
  10. How do you plan on growing your business?
  11. How do you effectively scale your business?


People love to talk about themselves and things that happened to them and entrepreneurs are no different. Don’t hesitate and ask about memorable events that happened to them. You can even ask some more in-depth personal questions. Those in-depth questions will provide you with even more valuable answers. Don’t be afraid to ask questions that require a bit of critical thinking.

  1. To what do you owe your success?
  2. What was your biggest failure and how did you pick up from it?
  3. Are you happy and what would you change?
  4. Do you ever get impostor syndrome and how do you deal with it?
  5. What are some hard choices you had to make to get where you are?
  6. Is there something you would’ve done differently?
  7. Who is the one entrepreneur that is your biggest example and inspiration?
  8. What was the toughest moment in your business journey? How did you go past it and move forward?
  9. Is there any popular entrepreneurial advice that you agree/disagree with? Why?
  10. What was your biggest ‘A-ha’ moment so far?
  11. Is there something that is simply non-negotiable for you?

Join MentorCruise to find the right mentor for your professional needs.

In this guide, you learned how to ask the right questions and what questions to ask an entrepreneur to keep you motivated and inspired. Entrepreneurs love sharing their knowledge and experience so don’t let the fear of rejection stop you from asking questions.

The road to establishing a successful business can be rocky and tricky to navigate and sometimes we all need help to overcome obstacles. If you feel stuck on your business journey, a business mentor might be the answer you’re looking for. Learn how to choose the right mentor for yourself and your business. Having a good relationship with your mentor can help you grow professionally and personally.

Let MentorCruise help you be the best entrepreneur you can be. Get mentoring from a trained, experienced expert & be on the career track you want to be. Apply today!

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