1
0 Comments

Are these really the best questions to ask an entrepreneur?

Hello!

I'm the founder of https://milestones.so/, a platform of smart tools that grows your business by applying the experience of successful founders to your own projects.

I'm finalising the list of questions for Season 2 of the case studies, and wanted to check with you all if there are any questions you'd love to ask founders and entrepreneurs that I might have missed here.

What would be most helpful for you, that I can ask everyone I interview? Or any I should remove from this list.

Here's the current shortlist:

  1. What’s your most successful marketing channel, and what made it so effective?

  2. What’s the most surprising insight you’ve gained from your audience’s feedback?

  3. How did you get your first 10 customers, subscribers, or patrons?

  4. What’s the most effective way you’ve increased your revenue without increasing your workload?

  5. What’s your approach to pricing your products, services, or memberships?

  6. What’s your most successful product, service, or content offering,, and why?

  7. What’s the smallest change you made that had the biggest financial impact?

  8. What are your five most essential tools and why?

  9. What’s a recurring process or system that saves you time or money?

  10. What unique tactic or strategy in your business are you most proud of?

  11. What book do you recommend the most to people and why?

  12. What was an unexpected mistake on your business journey, and what did it teach you?

  13. What’s a common misconception people have about running your type of business, and what’s the reality?

  14. What’s your best advice for attracting and keeping your most loyal customers, fans, or followers?

  15. What was your first big win, and how did it shape your business?

  16. How do you manage your day/week?

  17. What’s a skill you’ve learned that had the biggest ROI for your business?

  18. How do you approach planning and achieving long-term goals?

  19. If you started over today, what’s the first thing you’d do to grow faster?

  20. What motivates you to keep going during challenging times, and how do you stay inspired?

on January 5, 2025