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30 Questions to Ask Entrepreneurs (So You Can Become One)

Learn from the professionals - we've compiled a list of questions to ask successful entrepreneurs that can help you become one yourself.

By Hannah Donor • Aug 7, 2022

The beginning stages of entrepreneurship can feel overwhelming. It’s hard to know exactly what you don’t know about starting a business. Although internet research can be immensely helpful, it cannot speak to personal experience. By connecting with a successful entrepreneur, you can benefit from their wisdom and gain knowledge that may not be commonly available online, preparing you to start your own business in a completely different way.

Why You Should Interview an Entrepreneur

When starting a small business, it’s important to remember that you’re not alone. Running a business as a solo act is isolating by nature, so forming a network of support from the start can bolster your confidence and help you strategize for more effective growth and sustainable success.

Whether you’ve been in business for a while and are looking for advice on scaling (growing), or are brand new to entrepreneurship and need to know what things to do before starting a business, interviewing someone with real entrepreneurial experience will go a long way in preparing you to enter the field.

Best Interview Questions to Ask an Entrepreneur

1. Why did you decide to start your own business?

Every business owner has a “why” – the reason they chose the unconventional route of entrepreneurship as opposed to a corporate career. Understanding their reason for choosing the business owner path can help you to understand what motivated their success and discover your own reason (or reasons).

2. What advice would you give to someone just starting their own business?

This is the most obvious question you should ask, but also one of the most important! Every business owner has gone through the trying and risky experience of being a new business owner, and every one of them will have direct experience with what worked and what didn’t. You’re meeting with this entrepreneur to get their advice, so don’t be afraid to ask for it!

3. How do you deal with fear and doubt?

Even someone as prolific as Maya Angelou experienced the phenomenon known as imposter’s syndrome, once confessing, “I have written 11 books, but each time I think, ‘Uh-oh, they’re going to find out now.’ I’ve run a game on everybody, and they’re going to find me out.” By asking your interviewee how they deal with self-doubt as an entrepreneur, you’ll gain strategies for conquering fears that will inevitably come up throughout your own venture into business ownership.

4. What routines do you follow each day?

Success is in the details, and most accomplished people follow strict routines and daily habits to keep their busy days running smoothly. This can be as simple as setting an alarm and always getting up when it goes off, eating the same breakfast each morning, or even having multiples of the same outfit so they don’t have to think about what to wear each day.

5. Where do you see your business in five years? Ten?

No entrepreneur is ever done growing their business – it’s an ongoing journey with ever-changing goals and aspirations. Asking the entrepreneur you’re interviewing what their vision for the future is will inspire you to dream big and never stop pursuing success. It will also give you an idea of future milestones you can pursue in your own business.

6. How does your business look different now vs. when you first started?

Similar to asking for advice on just starting out, ask your interviewee to reflect on how their business has grown and shifted over the years. Are they where they expected to be? Did they pivot a completely different direction than originally planned? How does where they are now compare to where they expected to be at this time in their business?

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

Small businesses require a special twist that makes them different. This may be a unique spin on their product or service, or it may come down to well-crafted branding. Find out how your fellow entrepreneur has distinguished themself from the competition and brainstorm how you can do the same.

8. How did you market your business when it was brand new?

Without the reputation or booming revenue of a larger business, you’ll need to develop strategies for marketing your business and building a loyal audience from scratch. Every business owner has to tackle this at the start, so you’ll definitely want to find out how the person you’re interviewing did this. How did they leverage networking or advertising or social media to start connecting with potential investors or customers?

9. What is the hardest part of being an entrepreneur?

Running your own business won’t always be easy. Like any job, no one loves it all the time. Starting your own business is going to be difficult. It’s going to take a lot of time and determination to make it a success, but knowing what hurdles you may encounter will make it easier to overcome them.

10. What is your favorite part of being an entrepreneur?

Follow up preparing for the worst by hoping for the best! Find out what your interviewee truly loves about the entrepreneurial path. Why are they glad they chose to start their own business? What makes it fun or exciting? These joys are what you will cling to when times get tough.

11. What qualities do you think every entrepreneur should possess?

Ask them what makes a good entrepreneur, but don’t be downhearted if you don’t possess those qualities! Everyone is different and thus approaches entrepreneurship differently, so you may just not fit the mold they would expect. Nevertheless, this is an important question to ask. It can affirm the qualities you do possess and give you ideas of how you can form new habits and cultivate the qualities of a successful entrepreneur.

12. How have you grown personally from becoming an entrepreneur?

Entrepreneurship is extremely personal. Your business is completely your own, so it’s impossible to separate it from yourself as you might be able to with a standard employment situation. As such, starting a business will inevitably result in growth and change in you personally. By asking for stories of personal growth from a successful entrepreneur, you can get the inside scoop on how you should seek to grow personally.

13. What have been some of your biggest learning experiences in running a business?

Failures are opportunities to learn and do better next time, and no business is without their fair share of mistakes and failures. Although you will likely find your own mistakes to make, you can avoid some of them by asking an entrepreneur what failures they’ve learned from over the years.

14. What do you look for when outsourcing or hiring?

When your business outgrows what you can accomplish as a solopreneur, you’ll need to consider hiring employees or outsourcing work to contractors and freelancers. Ask an entrepreneur who has done this before what qualities they look for in potential hires to prepare you for when it’s time to find the right person to further your business’s success.

15. What will you never compromise on with your business?

Whether it be your personal values or your business ethics, you will face situations as a business owner that may require compromise. Decide what your non-negotiables are so you will not compromise yourself or your business from the get-go. Learning what other entrepreneurs won’t compromise on can help you figure out what matters most to you.

Fun Questions to Ask an Entrepreneur:

  1. Who is your biggest role model?
  2. How do you define success?
  3. What makes a good leader?
  4. At what point did you look at your business and consider it a success?
  5. What would you change about your business journey if you could go back?

Financial Questions to Ask an Entrepreneur

  1. How did you raise funding or financially prepare for your business?
  2. Any advice about setting up a business in terms of legal/accounting?
  3. Should I get an LLC before starting a business?
  4. How do you plan financially for your business’s future?
  5. Have you ever taken out a business loan? Would you recommend it?

Bad Questions to Ask an Entrepreneur

  1. What do you think of my business?
  2. Do you think my business will fail?
  3. May I pick your brain on something?
  4. Mind if I copy your idea?
  5. How can I make money as fast as possible with my business?

How to Find an Entrepreneur to Interview

Finding a local business owner to interview is the ideal scenario so you can connect in person and form an ongoing relationship. Talk to your local small business development center to inquire about any business owners they would recommend in your area. They’ll also have a lot of resources for helping you get started and to make sure your business is legally above board.

Once you connect with an entrepreneur who has enough experience under their belt to mentor and support your business journey, set up a time to meet, and print a copy of these entrepreneur interview questions to take with you.

Written by
Hannah Donor

Hannah Donor is a freelance copywriter and social media strategist with 5+ years of experience helping small businesses authentically curate the written word to reach and inspire their target market. Learn more at hannahleedonor.com.

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