Good Questions to Ask an Entrepreneur
Insightful questions to learn about the entrepreneurial journey, decision-making, resilience, and lessons from building a business.
1What inspired you to start your business, and what problem were you trying to solve?
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What inspired you to start your business, and what problem were you trying to solve?
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Why this works
Reveals the origin story and the core motivation behind the venture.
2What was the hardest part of getting started, and how did you overcome it?
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What was the hardest part of getting started, and how did you overcome it?
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Why this works
Surfaces early challenges and the resilience required to push through.
3What does a typical day or week look like for you now?
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What does a typical day or week look like for you now?
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Why this works
Provides realistic context on how entrepreneurs actually spend their time.
4How did you fund your business initially—savings, investors, loans, or bootstrapping?
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How did you fund your business initially—savings, investors, loans, or bootstrapping?
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Why this works
Clarifies the financial path and trade-offs of different funding models.
5What's the biggest mistake you've made, and what did you learn from it?
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What's the biggest mistake you've made, and what did you learn from it?
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Why this works
Invites reflection on failure and how it shaped better decision-making.
6How do you decide what to prioritize when everything feels urgent?
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How do you decide what to prioritize when everything feels urgent?
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Why this works
Reveals frameworks for decision-making and how entrepreneurs manage overwhelm.
7What skills or knowledge do you wish you'd had when you started?
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What skills or knowledge do you wish you'd had when you started?
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Why this works
Identifies gaps that would have accelerated success and what to learn early.
8How do you handle stress, burnout, and the emotional rollercoaster of entrepreneurship?
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How do you handle stress, burnout, and the emotional rollercoaster of entrepreneurship?
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Why this works
Addresses the mental health side and how sustainable practices are built.
9What role does failure play in your business, and how do you recover from setbacks?
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What role does failure play in your business, and how do you recover from setbacks?
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Why this works
Explores mindset and whether failure is seen as feedback or catastrophe.
10How did you find your first customers, and what worked best for early traction?
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How did you find your first customers, and what worked best for early traction?
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Why this works
Provides tactical insight into customer acquisition and validation.
11What's one thing you do differently now compared to when you started?
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What's one thing you do differently now compared to when you started?
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Why this works
Shows evolution and what experience teaches about running a business.
12How do you balance growth ambitions with maintaining quality or culture?
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How do you balance growth ambitions with maintaining quality or culture?
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Why this works
Reveals trade-offs and how entrepreneurs navigate scaling challenges.
13What advice would you give to someone considering starting their own business?
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What advice would you give to someone considering starting their own business?
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Why this works
Invites distilled wisdom and practical guidance for aspiring entrepreneurs.
14How do you measure success—revenue, impact, freedom, or something else?
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How do you measure success—revenue, impact, freedom, or something else?
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Why this works
Clarifies values and what success actually means beyond external metrics.
15What role do mentors, advisors, or your network play in your success?
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What role do mentors, advisors, or your network play in your success?
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Why this works
Assesses the importance of community and who helped along the way.
16How do you know when to pivot versus when to persist?
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How do you know when to pivot versus when to persist?
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Why this works
Explores the tension between grit and adaptability.
17What's the best investment you've made in your business—time, money, or otherwise?
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What's the best investment you've made in your business—time, money, or otherwise?
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Why this works
Reveals what drives ROI and what entrepreneurs value most.
18How has entrepreneurship changed you as a person?
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How has entrepreneurship changed you as a person?
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Why this works
Invites reflection on personal growth and the transformative nature of the journey.
19What keeps you motivated when things get tough?
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What keeps you motivated when things get tough?
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Why this works
Shows what sustains entrepreneurs through hard seasons.
20If you could start over, would you do anything differently?
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If you could start over, would you do anything differently?
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Why this works
Reveals regrets, lessons, and what hindsight teaches.
Learning from Entrepreneurs
Expert tips and techniques for getting the most out of these questions.