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The best questions to ask entrepreneurs that will help you grow

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.

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
  • How to make the most of your mentorship relationship

The importance of asking questions for great mentorship

Want to learn from the best? You better be ready to ask questions. Great mentorship starts with sharing information and getting insights. When you ask questions during your sessions, you’ll be able to make the most of your mentor’s expertise.

Some ways that asking questions for entrepreneurs can boost your mentorship relationship include:

  • Direct sessions towards your top concerns
  • Gain insights specific to your situation
  • Get industry know-how
  • Build rapport with your mentor

In particular, when you think of questions to ask successful entrepreneurs, you’ll be getting practical business advice to start or improve your own.

How to interview an entrepreneur

How you conduct and carry yourself when you’re speaking with your subject will go a long way to influencing the outcome of your interview.

If you’re interviewing an entrepreneur you particularly respect or consider of higher status (in the grand scheme of things), it’s important that you treat them as an equal, regardless of any pre-existing feelings you might hold. To come off as subordinate or timid will color their opinion of you immediately. This will likely diminish the quality of the conversation as a result.

Conversely, if you’re interviewing a new or younger entrepreneur - one that hasn’t [yet] reached the pantheon of the globally famous and mega-rich - you should likewise afford the same amount of respect and cordiality you would reserve for anyone else.

Regardless of who the subject is, it’s only right that you arrive at the interview properly prepared. You must have conducted sufficient background research to allow you to engage in a real conversation. A genuine back-and-forth will demonstrate to the interviewee that you are worthy and respectful of their time.

And, as the interviewer, it’s up to you to set the mood of the meeting, as well as the agenda. Know what you want to ask, know why you want to ask it, and arm yourself with sufficient knowledge to pick up on where the entrepreneur might take the conversation.

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.
  • Entrepreneurial questions focused on early failures and successes.
  • Informative questions about their business that provide some insights on operations.
  • Leadership questions about managing teams and harnessing people power.
  • Industry and job search questions for cracking the job hunt process and optimizing your profile.
  • Technology questions to boost your work using key tools and programs.
  • 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 online marketing techniques do you use?
  13. How should I decide where to set up my business?
  14. How did you push through your biggest business doubts?
  15. How did you handle fast growth and scale your business?
  16. What are the most common mistakes that new business owners make?
  17. How do you plan for the future of your business?
  18. How do you evaluate the past ups/downs of your business?
  19. What advice would you give to a new business owner?
  20. What’s non-negotiable when you start a business?
  21. How do you craft a great mission statement?
  22. How did you raise funding for your business?
  23. How has your business shifted over time?
  24. What KPIs do you use to measure your business success?
  25. What are you working on now?

Questions to ask successful entrepreneurs

Pick your mentor’s brain with questions for successful entrepreneurs. These questions get to the heart of the habits and mindsets of the scrappiest of entrepreneurs. You can ask questions for successful entrepreneurs that will give you a look into their daily lives and help you cultivate an entrepreneurial spirit.

  1. What are the three most important habits to be a successful entrepreneur?
  2. What is a typical day like for you?
  3. What’s your favorite aspect of being an entrepreneur?
  4. What are the biggest challenges to being an entrepreneur?
  5. How do you stay on top of industry trends?
  6. How do you handle the stress that comes with responsibility?
  7. How do you foster creative thinking?
  8. How do you know when you have a winning business idea?
  9. How do you decide when it’s time to move on from a business idea?
  10. What’s more important: innovation or integrity?
  11. How do you take care of your mental health?
  12. What’s your definition of success?
  13. When did you know it was time to become a full-time entrepreneur?
  14. How did you win over your first customers? First investors? First business partners?
  15. What’s your most satisfying entrepreneur moment so far?
  16. How should I invest my personal time to become a better entrepreneur?
  17. What’s the best strategy to target a new market?
  18. How do I know if my goals are too conservative or too ambitious?
  19. How did you learn to communicate about your business?
  20. Do you use social media to network?
  21. Who and what inspires your entrepreneurial ventures?
  22. Who do you look to for guidance and mentorship?
  23. How do you handle disagreements with your business partner?
  24. Have you ever felt unsure of a decision you made?
  25. What’s the most rewarding aspect of starting your own business?

Financial questions to ask an entrepreneur

Asking anybody about finances has the potential to drift into awkward territory. So when enquiring about finance-related topics with an entrepreneur, ensure that the questions remain legitimate informational queries and don’t cross the border into the realm of being inappropriate or even downright rude.

“So, how much are you worth?” for example, is a complete no-go.

Here are ten appropriate questions that you can go ahead and ask a financial entrepreneur instead:

  1. What were some of the biggest financial challenges you faced when starting your business?
  2. How did you fund your business in the early stages and what financing options would you recommend for a new entrepreneur?
  3. What financial metrics do you track to measure the success of your business?
  4. What are some common financial mistakes that you see entrepreneurs make and how can they be avoided?
  5. How do you manage your cash flow and ensure you have enough funds to cover expenses?
  6. What financial software or tools do you use to manage your finances and would you recommend them for a new entrepreneur?
  7. What advice would you give to a new entrepreneur who is struggling to manage their finances?
  8. How do you balance short-term and long-term financial goals for your business?
  9. What are some key financial ratios or indicators that you use to assess the health of your business?
  10. What are some strategies you have used to reduce costs and increase profitability in your business?

Podcast questions for entrepreneurs

If you’re carrying out an interview with an entrepreneur via a podcast, then you must account for the fact that this conversation is no longer for an audience of one, but an audience of many.

A podcast interview, as opposed to a one-on-one conversation for the purposes of mentorship, will often have different desirable outcomes for both the interviewee and the interviewer.

The podcast host will be looking to inform and entertain their listeners just as much, if not more, than they will be seeking to improve their own knowledge base. The interviewee might well be much more focused on raising awareness of their company, or promoting a new product, over teaching important business lessons to whoever is conducting the interview.

All of this should be determined prior to the interview taking place, either with a preliminary call or an e-mail/text exchange. This allows all participants to agree on an agenda and subjects to be covered. This way, all active participants can achieve their own respective goals and everything is in place for the recording to go smoothly.

Some pertinent questions to ask entrepreneurs on your podcast include:

  1. Can you give me a potted history as to your background and how you ended up where you are?
  2. What were some of the biggest challenges you faced when starting your business and how did you overcome them?
  3. How do you balance your personal life with the demands of running a business?
  4. What are some key lessons you’ve learned throughout your entrepreneurial journey?
  5. How would you describe your leadership style?
  6. Other than profits, how do you measure success? With what metrics do you benchmark your podcast?
  7. What advice would you give to someone who is thinking about starting their own business?
  8. How do you manage risk in your business and what strategies do you use to mitigate potential risks?
  9. What do you consider to be the most important factors and influences that will shape the future of your company and the industry at large?

Questions to ask a small business owner

When interviewing a small business owner it’s important that you pay them as much respect as you would if you were interviewing Elon Musk or Mark Zuckerberg.

Many contemporary industry titans started as small business owners, from Richard Branson to Howard Schulz (Starbucks) to Ralph Lauren.

You should always keep in mind that most small business owners care for their business as much as larger ones do and your conduct with them should show that you appreciate this fact.

Good questions for small business owners include:

  1. What inspired you to start this business?
  2. How did you come to recognize the gap in the market you could fill with a new business?
  3. What are the biggest challenges you’ve faced as a small business owner?
  4. How do you differentiate your business from others in the market?
  5. How do you measure success for your business?
  6. What do you believe sets your product or service apart from your competitors?
  7. How do you acquire new customers and retain existing ones?
  8. What are your plans for growth or expansion in the future?
  9. What do you think are the most important skills or qualities for a small business owner?
  10. What advice would you give to someone who is thinking of starting their own business?

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?

Leadership questions

Having great leadership skills is vital to entrepreneurial success. You should ask entrepreneurs questions about building their teams and managing them to get results. Company culture is a big factor in creating a sense of purpose and motivating teams to do great work. Ask about both managing issues, as well as promoting values on your teams.

  1. What are your daily habits for connecting with your team?
  2. How do you build trust with your employees?
  3. How do you keep your team motivated?
  4. How do you boost productivity without causing burnout?
  5. What do you look for in new team members?
  6. What techniques do you use to support employees who are under-performing?
  7. How do you encourage company culture?
  8. How important are technical skills on your team?
  9. How do you grow as a manager?
  10. How do you avoid micromanaging?
  11. How has remote work impacted your team for better or for worse?

Industry and job search questions

Landing your dream job starts with understanding the job search process. Lean on your mentor’s industry experience to get to know what hiring managers are looking for and how to stand out in the applicant pool. You might also ask an entrepreneur questions about interviews, cover letters, networking and more.

  1. What are industry managers looking for in new hires?
  2. How can I use networking to get a job interview?
  3. How do you network with others without pestering them?
  4. Are soft skills that important?
  5. How should I highlight my strengths on my resume?
  6. Is the cover letter that important?
  7. Should I attend industry conferences or workshops? Which ones?
  8. What are the most common interview mistakes?
  9. What types of interview questions should I prepare for?
  10. How can I boost my communication skills?
  11. How can I negotiate a higher salary or better job offer?

Technology questions

Knowing how to use technology can make a difference to your business. You should ask entrepreneurs questions about technologies, platforms, apps, etc. that further business goals and allow for innovative new projects.

  1. What are your three must-have technologies?
  2. How do you ask potential hires about the technology stack they are aware of?
  3. How do you incorporate technology into your daily business?
  4. How do you stay on top of new technologies and trends for your industry?
  5. What are best practices for incorporating new technology?
  6. How do you encourage technology with your teams?
  7. How do you find the right technologies for your business?
  8. What are the benefits to investing in technologies for your business?
  9. How do you track the effectiveness of technology at work?
  10. What are key considerations for remote work technologies?
  11. How do you ensure your technologies integrate well?
  12. How do you hire tech-savvy employees?


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?

Boost your mentorship relationship beyond questions

Questions are just the start of any great mentorship relationship. As you get to know your mentor and define your career goals, you can start turning questions into actions. If you asked questions about the job search process, try scheduling a mock interview for practice. Or if you’re interested in undertaking an entrepreneurial project, set up a due date to get initial feedback from your mentor.

While questions for entrepreneurs can help guide your mentorship sessions, you should also define key actions to improve your career potential. Be sure to ask your mentor about any next steps that he/she recommends 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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