32 Questions to Ask Successful People

Everyone has a different idea of what success looks like. Whether you plan to become a CEO, start your own business, or just want to be more successful in your current career, there are some best practices for achieving success. Learning from those who have already succeeded is a great way to shortcut your way to the top.

But what should you ask? It can be difficult to know where to start, especially if you’re new to the game. That’s why we’ve put together a list of questions to help you get started. These questions will help you figure out what it took for them to get to where they are today, and hopefully, give you the motivation to work towards your own definition of success.

32 Questions you should ask successful people:

  1. What is your definition of success?
  2. What did growing up look like for you?
  3. How did you decide what you wanted to do for a living?
  4. What are some of the biggest sacrifices you’ve made to achieve success?
  5. What was your first job?
  6. How do you deal with failures?
  7. What does a typical day look like for you?
  8. How do you stay motivated?
  9. How do you balance work and life?
  10. How have you dealt with adversity throughout your life and career?
  11. Who are some of the people who have helped you along the way?
  12. What role have mentors played in your life and career?
  13. How have you helped others succeed?
  14. What charities or organizations are close to your heart?
  15. In what ways do you give back to your community or industry?
  16. How hard were you willing to work for your success?
  17. What risks were you willing to take?
  18. Was there a specific moment or event that made you realize this is what you want to do with your life?
  19. How did you develop your skills/knowledge in this area?
  20. Was there a point where you almost gave up but didn’t – what kept you going?
  21. What would you have done differently if you could go back and do it again?
  22. How did you maintain your success after you achieved it?
  23. Did success change your life in unexpected ways? How so?
  24. Do your friends and family treat you differently now that you’re successful? In what ways?
  25. Do people sometimes try to take advantage of your success or position and how do you deal with it?
  26. What has been your biggest challenge at work? And how did you overcome it?
  27. What was the biggest thing you had to sacrifice for your career?
  28. What would you say is your work style? How do you approach work and get things done?
  29. How do you handle stress and pressure?
  30. How do you stay up-to-date in your industry/field?
  31. How do you build and maintain relationships with clients/customers/colleagues?
  32. What advice would you give to someone who is just starting their career or business?

Frequently Asked Questions

What is the key to success?

There is no single key to success, but rather a combination of factors that contribute to it. These include dedication, hard work, perseverance, and a willingness to take risks. But perhaps the most important element is having a clear and achievable goal. Without a concrete goal in mind, it can be difficult to stay focused and motivated.

That’s why aspiring entrepreneurs should take the time to define their goals and develop a plan to achieve them. With focus, determination, and a little luck, anyone can succeed in business.

Do successful people give up?

Most people think that successful people never give up, but that’s not always the case. Successful people know when to give up, and they aren’t afraid of failure.

They understand that failure is a necessary part of the journey to success. If you want to be successful, you must be willing to give up your old habits and embrace change.

You must be willing to fail, and you must be willing to keep trying until you achieve your goals. So don’t be afraid to give up your old habits. Be willing to embrace change, and be willing to fail. That’s the only way you’ll ever achieve success.


If you ask the right questions, you can learn from those who are already successful in their field. By asking them about their journey, their struggles, their motivation, and their advice, you can gain insights that will help you work toward your own definition of success. Remember that everyone’s path is different – so take what works for them and make it work for you!

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