Interviewing

15 Questions To Ask an Entrepreneur If You Want To Become One

October 5, 2021

Established entrepreneurs often have insights, experience and advice they can share to help new entrepreneurs on their personal journeys. Interviewing effective entrepreneurs can help you learn more about the steps they took to get where they are.

If you are interested in becoming an entrepreneur, learning what questions to ask those in the field can help you increase your takeaways from the interview. In this article, we define what an entrepreneur is and provide 15 questions you can ask an entrepreneur that can help you discover what the career entails and to confirm your interest in entrepreneurial endeavors.

What is an entrepreneur?

An entrepreneur is an individual who creates, launches and starts a new business, usually in response to an unfulfilled market need. While exact definitions can differ, typically entrepreneurs are innovative self-starters who create full-time, profitable and sustainable enterprises.

Entrepreneurship can sometimes require large upfront investments and an initial financial risk. Because of this, it can be helpful for entrepreneurs to possess traits like perseverance, tenacity and ingenuity that can facilitate their journeys.

Related: The 9 Different Types of Entrepreneurship

15 Questions to ask an entrepreneur

If you have the opportunity to interview an entrepreneur, here are some questions you can ask that can help you develop your own entrepreneurial strategies and ideas:

1. What inspired you to develop your idea?

Entrepreneurs are individuals who successfully transformed an idea from theory into reality. Executing an idea can require confidence, commitment and determination. Learning what motivated an entrepreneur to take action toward implementing their idea can help you evaluate your own ideas, motivators and challenges.

2. How have your priorities changed from when you first started?

Often, as entrepreneurs explore ways to develop their business, they have one goal in mind: success. In the early stages of an entrepreneur's career, they may have perceived success differently than they do now. Drawing on your interviewee's career experience and personal growth can help you evaluate your own priorities.

For example, they may say their priority now is creating happy, productive teams and a healthy work culture. In the beginning, their priorities may have been more centered on growth. They might reveal certain considerations you can incorporate to find earlier success.

Related: 20 Factors To Consider When Starting a Business

3. Knowing what you know now, is there anything you would have done differently when you were first starting out?

Learning what an entrepreneur would have done differently can help you make smarter choices up front. Try to find ways you can incorporate their answer into your early strategy and use them to guide some of your own decisions. They might provide valuable lessons that can help you grow your business and mitigate risks. Maybe they reveal areas where they spent too much time and energy that didn't generate a positive return, or they could share actions they would have taken sooner.

4. How did you decide where to establish your company?

Where you offer your products and services can have a large impact on your success. Listen for their top considerations when deciding where to market their offerings. They may reveal decision-making factors that influenced their success or explain location aspects they wish they'd known sooner. Whether they market their products remotely or in a physical store, you can learn a lot from their criteria and use it to influence your own deciding factors.

5. What challenges did you have to overcome at the beginning of your journey?

In entrepreneurship, some challenges can be inevitable. However, learning what to expect can help you prepare for challenges before they arise. Not all challenges are negative, learning from early obstacles can help you grow your business, refocus your efforts and teach you important recovery skills. Their answer to this question can also reveal a lot about how much they overcame to achieve their success. Stories like these can serve as inspirational reminders to persevere even when things don't go the way you expect.

6. What is unique about your business?

A key quality of many entrepreneurs is their innovation, or ability to offer something interesting and new. Their ingenuity can help them rise above the competition and find success in their own, unique way. Learning what unique strategies an entrepreneur employs can help you understand what differentiates successful new businesses from their competitors.

7. What advice would you give to someone who is trying to become an entrepreneur?

Established entrepreneurs likely have experience they can share that may help you on your journey. Asking general questions like this can encourage your interviewee to consider factors you might not think to ask them about. Try to use their response as guidance for creating actionable steps you can apply to achieve your goals.

Related: 25 Job Ideas For Future Entrepreneurs

8. How did you first select your employees?

As companies grow and teams expand, many entrepreneurs find they need help. Deciding who to bring with you in the first part of your journey can have a large impact on the direction your business goes. Especially as a new business with a small team, individual's contributions can shape your company. By asking what early steps an entrepreneur took to develop his team, you can determine important hiring and partnership considerations.

9. How did you raise funding?

Often, one of the biggest obstacles to starting a new business venture is funding. Finding interested investors and sponsors can take time, patience and persistence. You can learn a lot from experienced fundraisers. Try to find out where they started looking for investors, how they persuaded others to accept their vision and what strategies they took to get started with limited funds. They may provide valuable advice like presentation tips, outreach strategies and budgeting processes.

10. What strategies did you first use to market your business?

For a business to grow, it's often important for them to connect with and expand their audience. Marketing can be an investment, and using your money wisely can help you raise awareness of a product or service without spending all your resources early on. Incorporating established marketing practices that led others to success can help you focus your efforts and develop marketing plans that accomplish as much as possible.

Related: Getting Started in Marketing: A Beginner's Guide

11. How did you establish your culture?

Many entrepreneurs have a goal to do things differently. Translating your personal values, vision and expectations into a functioning business can take time, effort and experience. While ingenuity and vision are important qualities for entrepreneurs, learning how to communicate and share your goals with others can be an important skill as well. Try to gain insight from their answer that you could use to spread your ideas and keep the core values within your business stable.

12. How do you define success?

Learning an entrepreneur's opinions on success can help you shape your own definition. The answer may surprise you. Popular definitions of success might revolve around profit and growth, but their definition could be a thriving team, satisfied customers or achieving work-life balance. While revenue and profits are certainly driving factors of success, there may be other takeaways you can focus on as you begin your own journey.

Related: 32 Tips For Becoming a Successful Entrepreneur

13. What have you enjoyed most about starting your own company?

Just as established entrepreneurs can tell you want to be wary of, they can also inform some positive events associated with beginning a new venture. While it's important to prepare for obstacles and consider common setbacks, finding joy in the process can help motivate and inspire you to keep going. Their answer might reveal why the journey was worth it for them, and it can inspire you in your efforts as well.

13. What are the qualities of a good entrepreneur?

By asking this question, you can determine which skills or practices are important for entrepreneurial success. They might recommend technical skills or business development traits that can help you navigate the business side of your journey. But they might also give insight into soft skills like communication, networking and problem solving that you can develop to improve your journey. There may already be certain qualities or personality traits you feel represent you. Identifying with successful traits can show early on how much success you can find as an entrepreneur.

Related: Entrepreneurial Skills: Definition and Examples

14. How long did it take you to find success?

Entrepreneurship can be a long and involved process. Many new ventures experience initial setbacks and unexpected deviations from their original goal. Entrepreneurs that can adapt and remain flexible often find new opportunities that allow them to grow into something unique and effective. Referring to their answer later on in your own journey can help you remember successful businesses don't always have linear trajectories.

15. What are you working on now?

This question can also reveal a lot about the entrepreneurial process. Some entrepreneurs constantly set new goals for themselves. The goals they have now can illustrate that entrepreneurship can be an unending process. It can also prepare you for some things you may have to look forward to later in your own career.

Jobs for entrepreneurs

If you're seeking a business-related job involving entrepreneurship, there are multiple options to consider. Here's a list of 10 jobs that involve being an entrepreneur:

1. Social media manager

2. Business development manager

3. Sales representative

4. Research and development specialist

5. Development associate

6. Business reporter

7. Recruiter

8. Business technology specialist

9. Systems analyst

10. Financial advisor


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