Entrepreneurship questions for students and entrepreneurs

In this article, I will share with you a list of questions to ask entrepreneurs. These entrepreneurship questions are for students that want to start and want to learn from others.

This applies to both, even if you are an entrepreneur or you want to interview an entrepreneur you should read these questions.

If you are an entrepreneur this will help you to have a deeper knowledge about your business and strategies.

If you are a student or someone who wants to start a business, these questions will help you make an interview with an entrepreneur more effective.

Why You Should Interview an Entrepreneur

Learning from others can help you avoid making mistakes and develop strategies to grow your business during your journey as an entrepreneur or solopreneur.

The importance of asking questions to an entrepreneur is that you will gain insights that will help in your career path.

The life of an entrepreneur is full of challenges, in an interview with these people you can learn from other’s mistakes and start your career with more knowledge.

And for last, the best part of interviewing an entrepreneur is that you could gain a mentor that will be with you in your journey.

By having a mentor, you always gonna have someone to ask things about your business. A mentor can help you with almost all challenges because they already pass for them.

If you develop strong relationships with successful entrepreneurs, it will help build your network and you will have a lot of business opportunities.

You can have all these benefits starting with a great interview. Here I will share the things that you should ask entrepreneurs.

Best 60 Questions to Ask an Entrepreneur

First, I’ll share with you the top 10 questions I think every entrepreneur should answer about their personal life and business.

After that, I’ll give you some lists with questions on different topics that you can ask an entrepreneur.


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Questions Every Entrepreneur Must Answer

I have been doing research and I made this list with the top 10 questions that everyone should answer about business. 

To make these questions I mainly based on this article from the Harvard Business Review.

Let’s see these questions for entrepreneurs:

What are your company’s goals? Where Do You Want to Go?

Every entrepreneur should be explicit with the company’s goal. 

Entrepreneur’s personal goals and business goals are linked, both should go in the same direction.

Founders could have different expectations for a business, Is important having this clear to create a strong business.

If you are starting with a co-founder, is really important asking these questions to avoid future problems.

This is not a one-time thing, Both, companies and entrepreneurs should periodically ask themselves if the goals have changed or not.

What risk do you had/have to take in this business?

Entrepreneurs must be clear about the risks they are taking in a business.

By asking entrepreneurs this, you will learn how to assess risk and how to see explicitly what risks the business is exposed to.

How do you deal with fear and doubt?

All entrepreneurs have to deal with fear and doubt while they run their businesses.

Everyone could have an answer to this, they can give you a framework to deal with this and give you support in those difficult moments.

If you are an entrepreneur, you should ask yourself what to do in these moments.

How did you raise funding or financially prepare for your business?

There are many ways to finance a startup. The entrepreneur may have raised capital or bootstrapped the company.

By asking this you can see the points of view on the different forms of financing and apply it to your business.

What skills do you think every entrepreneur should have?

This is a generic question. But I think it’s important because every entrepreneur has a different answer. Thus, you may get different views on the skills you need to develop to grow your business.

By interviewing various entrepreneurs, you can derive value from this question. I do that in my newsletter.


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What do you look for when you are hiring?

Hiring people is one of the most difficult and stressful tasks an entrepreneur has to do.

With this question, you can have ideas about what to do in this hiring process.

Sometimes they can give you frames to do this efficiently.

What have been some of your biggest mistakes in running a business?

Learning from other mistakes helps you to don’t make it when you are running your own business.

Interviews with entrepreneurs are the best source of learning to create a business without making fool mistakes. Because of that, I started this newsletter.

How do you set your business apart from others in your industry?

Knowing how to identify the value proposition of a business is essential. With this question, you can understand how an experienced entrepreneur does it.

In addition, you can ask him to help you explicitly put the value proposition of your business

How do you measure the success of your business?

There are hundreds of ways to measure success in a business.

If you ask this question to different entrepreneurs from different industries, it will help you understand what each KPI (Key Performance Indicator) means and know how to apply it in your venture.

What advice would you give to students who want to become entrepreneurs?

You should always ask others for advice. There could be something that people want to share with you and you’re not asking.

By asking this question, you can get great advice from people with a lot of business experience.

If you are an entrepreneur, try to answer this too, sometimes we give advice but we don’t apply it. By doing this we can assess whether we are following our own advice or not.

Questions to ask you before starting as entrepreneur:

  • Can the strategy generate sufficient profits and growth?
  • What’s the source, if any, of our competitive edge? 
  • Is the market large enough?
  • Do diseconomies of scale make profitable growth impossible?
  • Are our offerings really better than our competitors’? 
  • If we are in a commodity business, are our costs lower than our competitors’?

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Personal questions for entrepreneurs:

  • What books do you recommend?
  • What inspired you to become an entrepreneur?
  • What are your strengths and weaknesses as an entrepreneur?
  • What is your definition of success?
  • What is your biggest fear as an entrepreneur?
  • What inspired you to become an entrepreneur?
  • What are your biggest goals for your business?
  • What is your favorite aspect of being an entrepreneur?

Financial questions for entrepreneurs:

  • Any advice about setting up a business in terms of accounting?
  • Should I get an LLC before starting a business?
  • How do you plan financially for your business’s future?
  • Have you ever taken out a business loan? Would you recommend it?
  • How do you finance your business?
  • What are your revenue streams?
  • What are your expenses?
  • How do you track your finances?

Business questions for entrepreneurs:

  • How did you come up with the idea for your business?
  • What is your business model?
  • What are your marketing strategies?
  • What are your challenges as a business owner?
  • What is your business model?
  • How do you market your business?
  • What advice would you give to other students who want to become entrepreneurs in your niche?

Technical questions for entrepreneurs:

  • What technologies do you use in your business?
  • How do you use technology to improve your business?
  • What are the challenges of using technology in your business?
  • What are the most important technologies for your industry?
  • How do you stay up-to-date on the latest technological trends?
  • What are your thoughts on the future of technology and entrepreneurship?
  • How do you think that AI affects your industry?

Legal questions for entrepreneurs:

  • What legal structures have you used for your business?
  • What are the legal requirements for your business?
  • How do you protect your intellectual property?
  • Any advice about setting up a business in terms of legal?

Other Questions about Entrepreneurship:

  • What are the best resources for entrepreneurs?
  • What resources for solopreneurs do you recommend?
  • Where do you see your business in five years? Ten?
  • Does your business look different now vs. when you first started? What has changed?
  • What routines do you follow each day?
  • How did you market your business when it was brand new?
  • What is the hardest part of being an entrepreneur?
  • What is your favorite part of being an entrepreneur?
  • What are your thoughts on failure?
  • What is your learning process like?

I hope this has been useful for you. Here you can read more:


Every week I share a list of resources for entrepreneurs and a new Interview with a solopreneur.

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