33 Questions To Ask an Entrepreneur

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Bailey Maybray
Bailey Maybray


You can learn a lot by talking to entrepreneurs. They can teach you how to deal with failure. They can advise you on managing employees. They can even offer tips on how to revolutionize industries, raise millions of dollars, and create groundbreaking products.

Questions To Ask an Entrepreneur: A woman stands on a ladder over a crowd of people.

But before meeting with an entrepreneur, you need to come prepared with questions. To get you started, consider using some of the following — which cover mentorship, finances, business, and more.

Business Questions To Ask an Entrepreneur

1. How will I know if I need to move on from my business?

Entrepreneurs learn to recognize when they need to move on from an idea or business, as 90% of startups fail. You can gain insights on how to identify signs of a failing idea, and what to do when failure seems inevitable.

2. What’s the right structure for my business?

A business can take on different structures, depending on their ownership, industry, and more. Do your research, then find entrepreneurs in your industry who can weigh in.

3. When should I make my first hire?

Delegating important tasks to an employee is a big step. An experienced entrepreneur can tell you why they brought on their first employee, including their financial situation and what the new job entailed.

4. How do you find the right suppliers?

If you sell a physical product, a supplier can make or break your business. Cheap material, for example, could undermine the integrity of your product. Ask for advice to identify the good suppliers from the bad.

5. What numbers should I look at to measure my success?

How to measure success looks different for every business. It might involve total revenue, net profit, or even market share. If you feel lost regarding which numbers to prioritize as an entrepreneur, ask a veteran one what they use.

6. When will I know if I need to raise funding?

Almost 7 in 10 entrepreneurs use their own money to get started. But as your business grows, so does your need for capital. Asking an entrepreneur with knowledge of fundraising can put you on the right path to raising cash when you need it.

Questions To Ask an Entrepreneur Mentor

7. How should I define success as an entrepreneur?

Entrepreneurs launch businesses for different reasons. Some want to become their own boss. Others want to make millions of dollars. A good mentor can provide advice on how you should define success for yourself.

8. What’s the best piece of advice you’ve received?

By asking your mentor questions, you can get invaluable insight on entrepreneurship. Learn the advice that guides successful founders. What tips do they remember to this day?

9. How can I best support you?

Treat your mentorship as a two-way relationship. Your mentor offers their experience and advice to you. But they may expect to learn something from you, too. So, ask them what you can do in return.

10. What mistakes should I avoid?

Try as you may, it’s hard to account for every situation and every risk. Ask your mentors what common business pitfalls you should avoid.

11. How can I reach my goals?

Sometimes, it’s easy to get lost in the big picture. Asking your mentor what you should do in the short term and long term to achieve your goals can help you find concrete steps to your dream.

12. What can I do to better my business?

Give your mentor a rundown of your venture and ask them what you can do better. They might advise you to improve your messaging or reduce spending in a certain area, and give you an objective opinion on your business plan.

13. Where do you get your information (such as news) from?

Entrepreneurs need to keep a pulse on the world, including business trends, news, and more. So, when interviewing one, ask them where they get their information from. They might recommend new websites, blogs, podcasts, shows, newsletters, and more.

Questions To Ask Young Entrepreneurs

14. How do you reward yourself when you succeed?

Entrepreneurship is a marathon, so ask founders how they keep themselves motivated. They might take the day off after hitting a major milestone, or enjoy a night out with friends.

15. How did you decide between becoming an entrepreneur and working for someone else?

Taking the leap into entrepreneurship takes commitment. Ask entrepreneurs how they landed on that decision, and what factors they considered.

16. What inspired you to become an entrepreneur?

Some might have founded their business during the pandemic, while others may have launched a venture in their college dorms. Asking young entrepreneurs for what inspired them can offer you insights into whether entrepreneurship works for you.

17. Where do you see yourself in five years?

When you ask a young entrepreneur where they see themselves, you can gain insights into their motivations and future goals. This, in turn, can inspire you to dream big.

18. What would you tell other young aspiring entrepreneurs?

Young founders can offer invaluable insights into their most recent hurdles, lessons, and victories. Ask them what they would tell other people in their boat. You might get a better understanding of the world of entrepreneurship today.

19. What’s the biggest challenge you face as a young entrepreneur?

Age can be a double-edged sword for entrepreneurs. On one hand, it affords them time to make mistakes. On the flip side, it makes them face challenges unique to their age — such as investors regarding them as naive or family encouraging them to get a regular job. Learn what their biggest challenges are, and how they overcome them.

Financial Questions To Ask an Entrepreneur

20. How do you choose ideas to invest in?

Founders can be bombarded with ideas. Ask them how they choose which ones to invest in. What criteria do they look at? What does their process look like?

21. What should I look for when finding someone to help with my finances?

Most business owners will hire someone to handle their finances and operations. But this decision requires careful planning and research.

Finance entrepreneur Chase Spenst offers the following advice: “Find someone who can bookkeep and build reports that keep you in the loop. Ideally, this person has run businesses before. Look for someone who’s naturally curious.”

22. What should I prioritize to set my business up for financial success?

Businesses often have limited budgets but a plethora of needs. Learn how to prioritize. This might be investing in developing your product first, for example, or hiring an accountant.

23. How do I raise money?

Raising money might mean finding investors, crowdfunding, and more. Consider how much ownership you want to retain, how much money you need, and how fast you need to raise it. An experienced entrepreneur can help you navigate the process.

24. How much money should I save for myself?

Many entrepreneurs invest all profit back into their business. But, eventually, you need to give yourself a salary and enjoy the fruit of your labor. Ask an entrepreneur to figure out the balance.

25. Where should I invest money earned through my business?

Once you have some money on hand, it may be difficult to choose how to allocate it to different departments. Get some advice on optimizing your cash, like building out operations or increasing marketing efforts.

26. How much capital did you raise to start your business?

By asking this question, you get insights into the amount of money you can expect to spend at the start. Using this information, you can then budget and plan accordingly — especially if they have information specific to your planned industry.

Fun Questions To Ask an Entrepreneur

27. Tell me about a time you said “I’m done with this” and wanted to walk away.

Entrepreneurs get burned out — fast. Whether a co-founder jumps ship before launch or a marketing campaign flounders, entrepreneurs often find themselves wanting to give up. Learn what helps keep founders going to combat feelings of defeat you might feel in the future.

28. Do you ever feel dumb or stupid?

Even the most confident person makes obvious mistakes. This question prompts the interviewee to divulge not-so-grand moments, which can be learning moments for you.

29. What does your morning routine look like?

Highly productive people are more likely to maintain a regular morning routine — including entrepreneurs. You might have one you follow, but asking this question will inspire you to try new activities.

30. How do you balance your personal life with your career?

A business owner doesn’t keep 9 to 5 hours — it can be helpful to learn how entrepreneurship impacts your social life. Get insights on how founders find work-life balance, even during the crazy times.

31. What’s your biggest achievement in life?

From launching a successful product to changing an industry, thriving entrepreneurs likely have a plethora of achievements. But what matters most to them varies. Asking this question can tune you into different ways to view success in business.

32. Would you change anything about your career?

As an entrepreneur, you will make an innumerable amount of mistakes. By asking a more experienced professional what they would change in their careers, you can learn potential pitfalls to avoid.

33. What makes a bad entrepreneur?

Let’s face it: Not everyone can be a successful entrepreneur. This question tunes you into traits to avoid as you strive to become a founder. You could take their advice, identify negative characteristics in you, and then try to mitigate them with better habits.

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