Ice-Breaking QuestionsHere are questions to ask when you meet an entrepreneur for the first time.

1. How did you come to be an entrepreneur?2. Why do you do what you do?3. What would you be doing right now if you weren’t here?

Get to Know Them QuestionsThese questions will help you get to know them so they’ll warm up to you.

6. In the beginning, what motivated you to become an entrepreneur?7. Tell me about your first entrepreneurial experience as a kid.8. How have your entrepreneurial motivations changed since you first started?9. What do you consider to be your greatest achievement?10.Describe to me the most exciting minute of your entrepreneurial journey.11.What does a day-in-the-life of (their name, better remember it) consist of?12.What’s the single most important reason for your success?13.What was the tipping point for your business? (Privet)14.What do you enjoy most about what you do?15.What’s your least favorite part about being an entrepreneur?16.What’s the biggest thing you struggle with as an entrepreneur?17.What’s the strangest thing you’ve ever done as an entrepreneur?18.How does being an entrepreneur affect your relationships with your friends and family?

(Balance)19. If you could be anything other than an entrepreneur, what would it be and why?20.Looking back, what’s one thing you would do differently?

Critical Thinking QuestionsOnly entrepreneurs know to ask these types of questions.

25.How is running a successful business different than what you thought it would be?26.What do you do on a daily basis to grow as an entrepreneur?27.What entrepreneurial hacks have you developed to stay focused and productive in your

day-to-day?28.What things about entrepreneurship do you struggle to understand?29.What popular entrepreneurial advice do you disagree with?30.How would you like people to remember you and your company?

Seeking Wisdom QuestionsThis is where you start asking probing questions to get their best advice.

33.Looking back, what’s one thing you wish you understood about entrepreneurship before you ever got started?

34. If you could offer a first-time entrepreneur only one piece of advice, what would it be?35.What systems have you set up in your business to help it grow?36.Besides money, what are your favorite ways to compensate people?37.What creative things do you do to develop a likeable company culture?38.Walk me through the ideal path you’d like someone to take to go from normal consumer

to loyal customer?

39.Why volunteering and giving back is important for an entrepreneur

Creative Entrepreneurial QuestionsHere are a couple creative entrepreneurial questions that are fun to ask.

40.What’s your favorite metaphor for describing entrepreneurship?41. If you had to battle a giant, what weapon would you use? It’s a metaphor.42.How do you think being an entrepreneur has turned you into a better person?43.How do you think being an entrepreneur has hindered you from becoming a better

person?

If You Dare QuestionsAsk these questions at your own risk.

46.Do you think you’re good at what you do?  (mastery of skill) converting your skills to talent

47.What makes you uncomfortable? (people that take away my energy)