DOWNLOAD: 42 Questions

The most powerful source of inspiration is questions. Questions for yourself, and questions for your clients. Questions help us to more readily explore and discover information that we may have never found otherwise.

I created these questions for my group and one-on-one coaching programs. Use these questions to generate new ideas, identify your purpose, and produce better outcomes.

Entrepreneurial Goals & Results

  1. If you imagine that it’s December 31st of this year, what do you want your lifestyle and business to look like?
  2. What does a day-in-the-life of [your name] look like?
  3. What would your day look like, if your business and lifestyle were producing the results you desire?
  4. What changes are you making to make that happen?
  5. If you could change ONE thing immediately in your business what might that be?
  6. What are your biggest challenges with the entrepreneurial lifestyle right now?
  7. What are your biggest challenges in attracting more of your ideal clients right now?
  8. What steps are you taking to overcome those challenges?
  9. What are you doing to ensure you turn your learning into action?
  10. What entrepreneurial habits or strategies have you developed to stay focused and productive in your day-to-day?
  11. What is your definition of success and have you reached it?
  12. What’s the number one thing you need to do now to reach it?
  13. Have you taken the time to break your goals down into tasks, and schedule those tasks?

Entrepreneurial Reflection

  1. What is the #1 thing you are best at, of all your gifts & skills?
  2. What do you consider to be your greatest achievement?
  3. What’s the single most important reason for your success?
  4. Why do you do what you do?
  5. How did you come to be an entrepreneur?
  6. In the beginning, what motivated you to become an entrepreneur?
  7. What’s an example of work that you do?
  8. What’s your least favorite part about being an entrepreneur?
  9. What would you be doing right now if you weren’t here doing this business?
  10. What’s your most memorable experience as an entrepreneur?
  11. What’s the strangest thing you have ever done as an entrepreneur?
  12. Looking back, what’s one thing you would do differently?


Lifestyle Questions

  1. How does being an entrepreneur affect your relationships with your friends and family?
  2. If you could never work again, would you and why, and what would you do instead?
  3. If you could be anything other than an entrepreneur, what would it be and why?
  4. How is running a business different than what you thought it would be?

Entrepreneurial Growth

  1. What’s your favourite entrepreneurial book?
  2. What do you do on a daily basis to grow as an entrepreneur?
  3. Who’s your favourite influencer that you follow for advice and guidance? (entrepreneurial or from your niche)
  4. What’s one thing you wish you understood about owning and running a business before you started?


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