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

Why Should You Ask Entrepreneurs Questions?

Gain Real-World Insights

Books and courses provide theory, but speaking with real entrepreneurs gives you practical advice and firsthand experiences that can help shape your own path.

Learn from Mistakes

Many entrepreneurs share the lessons they wish they knew earlier—which can save you from making the same mistakes.

Understand the Mindset

Success in entrepreneurship often comes down to resilience, adaptability, and problem-solving. Asking questions helps you learn how successful founders think and make decisions.

👉 Example: Instead of just asking, "How did you start?", dig deeper with, "What challenges did you face in your first year, and how did you overcome them?"

Key Questions to Ask Entrepreneurs

1. How Did You Come Up With Your Business Idea?

Understanding how successful entrepreneurs identify opportunities can help you develop your own business idea.

Follow-up Questions:

1. What problem were you trying to solve?
2. Did you validate your idea before launching? If so, how?
3. How did your initial idea evolve over time?

2. What Was Your Biggest Challenge in the First Year?

Most businesses struggle in the beginning. Learning about early-stage obstacles can prepare you for what’s ahead.

Follow-up Questions:

1. How did you handle financial challenges in the beginning?
2. What mistakes did you make early on?
3. How did you stay motivated through tough times?

3. How Did You Fund Your Business?

Many aspiring entrepreneurs worry about raising capital. Learning how others financed their business can provide practical funding strategies.

Follow-up Questions:

1. Did you bootstrap or seek investors? Why?
2. How did you manage cash flow in the early stages?
3. What financial advice would you give to new entrepreneurs?

4. How Did You Find Your First Customers?

Sales and marketing are critical for any startup. Understanding how an entrepreneur found their first paying customers can provide valuable marketing insights.

Follow-up Questions:

1. What marketing strategies worked best for you?
2. How did you build trust with early customers?
3. If you had to start again, what would you do differently?

5. What Strategies Helped You Scale Your Business?

Once a business starts growing, the challenges change. Learning about scaling strategies can help you prepare for future expansion.

Follow-up Questions:

1. How did you hire your first employees?
2. What systems and processes helped you scale?
3. How did you maintain quality while growing?

6. How Do You Handle Competition?

No business exists without competition. Learning how entrepreneurs differentiate themselves can help you build a stronger brand.

Follow-up Questions:

1. How did you position your business against competitors?
2. What mistakes do new entrepreneurs make when dealing with competition?
3. Have you ever had to pivot due to competition?

7. What Advice Would You Give to New Entrepreneurs?

This open-ended question often reveals some of the most valuable insights from experienced business owners.

Follow-up Questions:

1. If you could go back, what would you do differently?
2. What’s the most important skill an entrepreneur should develop?
3. What books, podcasts, or mentors influenced you the most?

8. What Marketing Strategies Worked Best for You?

Marketing is one of the biggest challenges for new entrepreneurs. Learning what worked for others can help you develop smarter strategies.

Follow-up Questions:

1. Which marketing channels have brought you the best ROI?
2. How did you build brand awareness early on?
3. What marketing mistakes did you make in the beginning?

9. What Was Your First Major Business Failure, and What Did You Learn?

Failure is a huge part of entrepreneurship. Learning how business owners recovered from setbacks can prepare you to bounce back from your own challenges.

Follow-up Questions:

1. How did you adjust your strategy after failing?
2. What mindset shifts helped you overcome that failure?
3. If you had to do it again, what would you do differently?

10. What Are the Most Important Traits of a Successful Entrepreneur?

Success isn’t just about having a good idea—it’s about the mindset, habits, and discipline behind it.

Follow-up Questions:

1. What personal habits contributed most to your success?
2. How do you stay disciplined and focused?
3. Do you think entrepreneurship is something people are born with, or can it be learned?

11. How Do You Manage Risk in Your Business?

Entrepreneurs constantly take risks, but the best ones know how to calculate and manage them effectively.

Follow-up Questions:

1. How do you decide which risks are worth taking?
2. What’s the biggest risk you ever took in your business?
3. How do you balance risk-taking with financial security?

12. What’s Your Process for Making Big Decisions?

Great entrepreneurs make smart, high-impact decisions—often under pressure. Learning their decision-making frameworks can help you make better choices in your own business.

Follow-up Questions:

1. Do you rely on data, intuition, or a mix of both?
2. Have you ever made a decision you regretted? How did you handle it?
3. What’s the hardest decision you’ve ever had to make in your business?

13. How Do You Stay Motivated When Things Get Tough?

Every entrepreneur faces burnout, doubt, and tough times. Understanding their motivation strategies can help you build mental resilience.

Follow-up Questions:

1. Have you ever thought about quitting? What kept you going?
2. How do you handle stress and setbacks?
3. What daily habits help you stay focused and motivated?

14. How Do You Balance Work and Personal Life?

Entrepreneurs are known for working long hours, but burnout is real. Learning how they manage their time can help you create a sustainable work-life balance.

Follow-up Questions:

1. How do you separate business from personal life?
2. Have you ever felt burned out? How did you recover?
3. Do you believe work-life balance is possible for entrepreneurs?

15. How Do You Build a Strong Team?

A business is only as good as the people behind it. Knowing how entrepreneurs hire, train, and manage teams can give you insights into leadership.

Follow-up Questions:

1. What qualities do you look for when hiring?
2. How do you create a positive company culture?
3. What’s the biggest lesson you’ve learned about leadership?

16. How Did You Decide on Your Pricing Strategy?

Pricing can make or break a business. Understanding how entrepreneurs set profitable yet competitive prices can help you avoid underpricing or overpricing your products.

Follow-up Questions:

1. How did you determine the value of your product/service?
2. Did you experiment with different pricing models?
3. How did your pricing evolve as your business grew?

17. What’s the Most Underrated Skill an Entrepreneur Should Have?

Most people focus on leadership, creativity, and resilience, but some skills are overlooked. This question can reveal hidden strengths that successful entrepreneurs rely on.

Follow-up Questions:

1. What skill has unexpectedly helped you in business?
2. Is there a skill you developed later that you wish you had earlier?
3. How can aspiring entrepreneurs develop this skill?

18. How Do You Deal With Self-Doubt?

Even successful entrepreneurs struggle with imposter syndrome and doubt. Learning how they manage it can help you build mental toughness.

Follow-up Questions:

1. Have you ever felt like giving up? How did you push through?
2. What habits or mindset shifts help you stay confident?
3. Do you think self-doubt ever fully goes away?

19. How Do You Know When to Pivot?

Many startups fail because they resist change, while others pivot too soon. Learning how entrepreneurs identify the right time for a shift can be a game-changer.

Follow-up Questions:

1. What signs told you it was time to pivot?
2. How do you test a new direction before fully committing?
3. What’s the biggest lesson you learned from pivoting?

20. How Do You Stay Ahead of Industry Trends?

Successful entrepreneurs anticipate changes rather than react to them. Learning their methods can help you build a future-proof business.

Follow-up Questions:

1. What sources do you use to stay informed?
2. How do you decide which trends are worth following?
3. Have you ever been ahead of a trend that later became huge?

21. What Was the Best Investment You Made in Your Business?

Not all investments are financial. This question helps uncover the most impactful decisions an entrepreneur made—whether hiring a mentor, upgrading technology, or taking a big risk.

Follow-up Questions:

1. Was this an obvious investment, or did it feel risky?
2. How long did it take for you to see the return on this investment?
3. If you could only invest in one thing today, what would it be?

22. How Do You Keep Customers Coming Back?

Customer retention is often more valuable than customer acquisition. Learning how entrepreneurs build loyalty and repeat business is crucial for long-term success.

Follow-up Questions:

1. What strategies have worked best for customer retention?
2. How do you create strong relationships with customers?
3. Have you ever lost customers? What did you learn from it?

23. How Do You Handle Hiring the Right People?

Hiring is one of the hardest and most critical aspects of running a business. Learning how entrepreneurs attract and keep the best talent is essential.

Follow-up Questions:

1. What qualities do you look for when hiring?
2. Have you ever made a bad hire? How did you handle it?
3. What’s the best hiring advice you’ve ever received?

24. What’s the Biggest Sacrifice You’ve Made for Your Business?

Entrepreneurship often comes with personal sacrifices—time, relationships, financial security. This question reveals the real cost of success.

Follow-up Questions:

1. Do you regret any sacrifices you made?
2. How did you balance personal life with business growth?
3. What would you do differently if you could go back?

25. How Do You Handle Criticism and Negative Feedback?

No entrepreneur is immune to criticism from customers, investors, or competitors. Learning how they process and act on feedback is key.

Follow-up Questions:

1. Have you ever received harsh criticism that helped you improve?
2. How do you filter useful feedback from noise?
3. How do you respond to online or public criticism?

26. What’s the Hardest Business Decision You’ve Ever Had to Make?

Entrepreneurs often face tough choices that shape their businesses. Learning about these moments can provide deep insights into problem-solving under pressure.

Follow-up Questions:

1. What made this decision so difficult?
2. How did you weigh the risks vs. rewards?
3. Looking back, would you make the same decision again?