20 Killer Questions to Ask an Entrepreneur to Learn About Their Journey

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.

Becoming an entrepreneur takes courage, passion, and a willingness to take risks. Entrepreneurs chart their own course work incredibly hard, and learn some tough lessons along the way.

As an aspiring entrepreneur myself, I’m fascinated by the journeys of other founders and business owners Hearing their stories provides inspiration, valuable insights, and practical advice

In this article, I’ll share 20 great questions to ask an entrepreneur to learn about their experience starting and running a business. Whether you’re just starting out or looking to grow your company, their answers will give you motivation, new ideas, and a dose of reality.

Why I Love Learning from Other Entrepreneurs

I started my first business 5 years ago while working a full-time job. It was thrilling to watch my side hustle take off, but also exhausting to run everything in my spare time.

My journey has been filled with accomplishments like quitting my day job and tripling my revenue. But it has also included missteps like issues with partners and nearly running out of cash.

Through it all, I’ve found it incredibly helpful to connect with fellow entrepreneurs who have been in my shoes. Their stories and advice have guided me in moments of uncertainty.

Here’s what I’ve gained most from learning from other founders:

Motivation to keep pushing. Hearing how other entrepreneurs overcame major obstacles reminds me that I can do the same. Their perseverance motivates me to work through tough times.
Ideas for improving my business. I always pick up useful tactics from other founders, whether it’s marketing strategies, productivity hacks, or ways to improve company culture.
Confidence to take the next step. When I’m unsure about expanding my business, talking to someone who has done it successfully makes me feel like I can handle it too.
Perspective on what really matters. Discussions with seasoned entrepreneurs remind me not to sweat the small stuff and keep focused on my bigger goals.
Inspiration to aim higher. Ambitious entrepreneurs inspire me to set bolder targets and really go after what I want. Their drive rubs off on me.

Connecting with founders who sincerely want to help others has made all the difference for my business. Now I strive to pay it forward by sharing my own experiences and knowledge.

20 Questions to Reveal an Entrepreneur’s Journey

If you want to dive into the entrepreneurial journey of someone you admire, here are 20 great questions to ask:

1. Why did you start this business?

Understanding an entrepreneur’s origin story and initial motivations provides helpful context for everything that followed. Were they passionate about solving a problem? Did they want to build something new? Ask them to share what drove them to take the entrepreneurial leap.

2. How did you come up with your business idea?

Fascinating ideas can arise from unexpected places. There’s a lot you can learn from understanding how an entrepreneur identified an opportunity or came up with an innovative concept.

3. What were the first steps you took to get started?

The beginning stages of entrepreneurship are scary and exciting. Ask about their first moves to turn their vision into reality. What gave them the confidence to dive in? What kept them motivated in those early days?

4. Did you start your business while working a day job?

Many founders start their companies as side hustles before making the leap to entrepreneurship full time. Ask how they managed that balancing act and knew when it was time to make the transition.

5. What has been your biggest challenge as an entrepreneur?

All business owners encounter major obstacles at some point. Find out what difficult lessons they’ve learned that made them a better entrepreneur.

6. Have you ever felt like giving up? What made you persist?

Even the most successful entrepreneurs experience dark moments filled with self-doubt. Asking this question shows how they made it through those low points and found the motivation to keep pushing forward.

7. What’s the best business decision you’ve made?

It’s instructive to learn about strategic choices that paid off well for another entrepreneur. This gives you ideas for decisions that could potentially work in your own business.

8. What’s the biggest mistake you’ve made?

Founders often learn more from mistakes than successes. Have them walk through a blunder that taught them key lessons about business or leadership.

9. Who has been your biggest mentor, and what have you learned from them?

Mentors provide invaluable guidance to entrepreneurs just starting out. Ask who played that role for them, and what lasting wisdom they gained from the relationship.

10. What daily habits or routines are most important for your success?

Successful entrepreneurs often have little tricks and practices that keep them grounded and effective. Try to uncover what works behind the scenes for someone you admire.

11. How do you stay motivated on a day-to-day basis?

The entrepreneurial journey has lots of ups and downs. Find out how they maintain high energy and passion in their work throughout all of it.

12. How do you handle stress and manage difficult emotions?

Running a business can be an emotional rollercoaster. Ask how they cope with anxiety, burnout, anger, or self-doubt when they arise.

13. How do you balance work and personal life?

Achieving work-life balance is tough for any business owner. Get tips on how they prioritize family time or self-care without sacrificing progress on their goals.

14. What leadership lessons have you learned over the years?

Skilled leadership is crucial for entrepreneurial success. Ask about principles and practices they’ve developed to become a better leader.

15. What are your best tips for building an outstanding team?

Great people make great companies. Probe for their best practices in recruiting, managing, and motivating top talent.

16. What advice do you have for starting entrepreneurs?

No one gives better advice than experienced entrepreneurs who have been in those shoes before. Ask them to distill their wisdom for someone just getting started.

17. What are the most important skills or traits for entrepreneurial success?

Take notes as they call out key attributes like persistence, flexibility, creativity, and risk-taking that have helped them achieve success.

18. What’s one thing you wish you had known when starting your entrepreneurial journey?

Every founder has lessons they learned over time that they wish they had known from day one. This question can uncover valuable perspectives.

19. What does the future look like for your business?

It’s inspiring to hear about the big visions successful entrepreneurs have for the future of their ventures. This can spark ideas about your own company’s potential.

20. How do you define success for yourself?

The most insightful entrepreneurs have a vision of success that goes beyond just money and fame. Find out how they measure a life well lived in business and beyond.

Gain Priceless Insights from Seasoned Founders

Having the chance to pick the brain of a successful entrepreneur is a truly invaluable experience. Their hard-won wisdom can fast track your success and help you avoid costly mistakes.

You’ll likely be amazed by their determination in the face of adversity. Their stories will inspire you to dream bigger and approach challenges with renewed passion.

The insights you gain will stick with you through every stage of your journey as an entrepreneur. Use their advice to outthink obstacles, plan smarter, and build something extraordinary.

Any time you get the chance to learn from someone further along, take it! Just by asking the right questions, you can uncover lessons that will fuel your entrepreneurial potential.

So seek out mentors and experienced founders who can be generous with their knowledge. Come armed with thoughtful questions that dig into their journey. Then soak up the wisdom that emerges from these fruitful conversations.

questions to ask an entrepreneur

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:

Can you give me a potted history as to your background and how you ended up where you are?
What were some of the biggest challenges you faced when starting your business and how did you overcome them?
How do you balance your personal life with the demands of running a business?
What are some key lessons you’ve learned throughout your entrepreneurial journey?
How would you describe your leadership style?
Other than profits, how do you measure success? With what metrics do you benchmark your podcast?
What advice would you give to someone who is thinking about starting their own business?
How do you manage risk in your business and what strategies do you use to mitigate potential risks?
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:

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

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.

Where did the idea for your business come from?
What did your initial business plan look like
How did you pick the name for your company?
How did you decide on the location for your business?
What makes your company stand out from all the other businesses in your niche?
How did you build your team?
How are you dealing with funding for your business?
How are you dealing with the negative publicity your company gets?
What problems are you trying to solve?
How do you plan on growing your business?
How do you effectively scale your business?

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.

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

10 Questions Every Entrepreneur Should Ask

What questions should you 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.

What questions should a business owner ask?

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.

Why should entrepreneurs ask the right questions?

What questions should you ask when starting a business?

In this list of questions, we will explore some key areas to consider when starting a business, including business planning, marketing, finance, and operations. By asking these questions, you can gain valuable insight and advice from an experienced entrepreneur. What inspired you to start your own business?