Favorite Questions to Ask Entrepreneurs

Last week I was at a dinner sitting next to a successful entrepreneur that had built his business to hundreds of employees over the course of 10+ years. Once we finished with the standard chit chat, I asked my favorite question for late stage entrepreneurs:

When did you know you were going to be successful?

Often, it takes two, three, or even four plus years before it feels like you’ve made it. Of course, it isn’t a switch that turns on overnight. Rather, it’s the confluence of hiring momentum, sales progress, market adoption, and scalable infrastructure.

After asking this question, it got me thinking about other fun questions for entrepreneurs. Here are my favorites:

  1. What was the inspiration for your startup?
  2. What was the biggest inflection point in your startup?
  3. How long have you known you wanted to be an entrepreneur?
  4. How did you meet your co-founder?
  5. When did you know the time was right to go full-time?
  6. What was your original idea and how did it change with market feedback?
  7. How did you find your first customers?
  8. How did you find your first investors?
  9. What are your biggest learnings so far?
  10. What were your biggest challenges?
  11. What would you have done differently?
  12. Who was your most important mentor?
  13. What keeps you busy now?

Try these questions out the next time you talk to an entrepreneur and see where the conversation goes. Learning from entrepreneurs is one of my favorite things, and these questions set the stage.

Try these questions and let me know some of your favorite questions to add to the list.

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