130 Questions to Ask Successful People

Ever wonder what’s going on inside the heads of successful people? What’s their secret sauce?

Asking the right questions might just unlock their wisdom. Whether you’re curious about their habits, decisions, or how they overcome challenges, these questions are keys to unraveling the mysteries of success. 

So, get ready to dive in and explore the secrets behind their success! Who knows, the answers might just spark the next big idea in you!

Questions To Ask About Understanding Success

  1. How do you define success, personally and professionally?
  2. How have your definitions of success changed over time?
  3. What’s a moment that made you feel incredibly proud of your achievements?
  4. What advice would you give to people who want to follow a similar path to yours?
  5. What is the most fulfilling aspect of your success?
  6. How do you handle the pressure and expectations that come with success?
  7. Looking back at your journey, is there anything you would do differently?
  8. What’s next for you, and what are your goals for the future?
  9. What impact do you want to have on the world through your success?
  10. How do you measure your success beyond financial metrics?
  11. What role does personal satisfaction play in your definition of success?
  12. What are some non-materialistic successes that you are proud of?
  13. What skills do you think are most important for achieving success?
  14. How do you maintain a sense of purpose in your journey to success?
  15. How do you balance societal expectations of success with your own?

Questions To Ask About Career And Professional Growth

  1. What was your biggest challenge, and how did you overcome it?
  2. Can you share a mistake you made and what you learned from it?
  3. How do you continue to learn and grow professionally?
  4. How do you handle criticism and use it to improve?
  5. How do you set goals and follow through with them?
  6. How do you approach learning something new?
  7. What’s the biggest risk you’ve taken in your career, and did it pay off?
  8. Can you share a time when you had to make a really tough call in your career?
  9. How important is networking in your profession, and how do you do it?
  10. How do you ensure your personal biases do not affect your work decisions?
  11. What’s something about your career path that surprised you?
  12. Can you share a story of an unexpected encounter that turned into a fruitful relationship or partnership?
  13. Can you share a significant sacrifice you made to achieve your success?
  14. How do you maintain strong relationships in your professional network?
  15. How do you keep your skills and knowledge relevant to changing trends?
  16. Can you share a time when a failure led to an unexpected success?
  17. How do you set boundaries in your professional life?
  18. How vital have branding and personal branding been in your journey?
  19. What’s one common mistake you often see people make in your industry?

Questions To Ask About Personal Habits And Mindset

  1. What is one habit you believe contributes to your success?
  2. How do you deal with self-doubt if it ever comes up for you?
  3. How do you stay motivated during tough times?
  4. How do you deal with failure or setbacks?
  5. How do you celebrate your achievements?
  6. What’s one thing you do regularly to keep your brain sharp?
  7. What role does curiosity play in your work?
  8. How do you stay grounded when you achieve big wins?
  9. How do you manage your time effectively?
  10. How do you keep your ego in check amidst your success?
  11. How important is passion for what you do in your career?
  12. How do you manage distractions while working?
  13. How do you maintain a positive mindset?
  14. What are some strategies you use to stay focused on your goals?
  15. How do you integrate your work values with your personal values?
  16. What role does empathy play in your professional life?
  17. Can you tell us about a time you were out of your comfort zone and what you learned from it?
  18. Who are some of the people you admire and learn from, and why?
  19. Can you share a piece of advice you received that you cherish?
  20. What’s a book that has significantly influenced your journey?
  21. How do you maintain your motivation on days when everything seems to go wrong?
  22. Can you name a person who has had a strong impact on you? What did they teach you?
  23. How do you push through your worst fears?
  24. How do you cultivate resilience in the face of adversity?
  25. How do you react when your ideas are challenged, and how do you convince others to see your point of view?

Questions To Ask About Leadership and Team Management

  1. What do you consider to be the most crucial quality of a leader?
  2. How do you foster innovation in your team or organization?
  3. How do you decide what to delegate and what to handle yourself?
  4. How do you handle conflicts or disagreements at work?
  5. Can you tell us about a time when you had to rely on your team to solve a problem?
  6. How do you approach mentorship as a mentor and a mentee?
  7. How do you ensure your team stays motivated and committed?
  8. How do you nurture new talent within your team or organization?
  9. How do you handle underperformers in your team?
  10. Can you share an example of a tough feedback you had to give? How did you handle it?
  11. How do you ensure your team shares and works towards your vision?
  12. Can you share a time when your leadership skills were put to the test?

Questions To Ask About Decision-Making And Problem-Solving

  1. How do you handle unexpected changes or new challenges in your work?
  2. How do you decide which projects or tasks are worth your time?
  3. Can you share an instance where you decided based purely on your gut instinct?
  4. Can you share a time when you had to decide with incomplete information?
  5. How do you approach risks in your profession?
  6. How do you handle situations where you must work with people you don’t necessarily get along with?
  7. Can you share a time when you had to make a decision that wasn’t popular but was right?
  8. What is your approach toward customer satisfaction and retention?
  9. How do you evaluate opportunities that come your way?
  10. How do you approach conflicts between your personal values and professional demands?

Questions To Ask About Industry Insight and Future Trends

  1. What’s one thing about your industry you wish would change?
  2. Can you name a trend in your industry that you think is particularly promising for the future?
  3. What’s a trend in your industry that you’re skeptical about?
  4. What’s the most unusual but effective strategy you’ve used in your work?
  5. What’s a common misunderstanding people have about your line of work?
  6. Can you share a marketing strategy that has been very effective for you?
  7. What’s the biggest thing you’re struggling with in your work right now?
  8. How do you strategize the future growth of your business or career?
  9. Can you share some unspoken rules in your field of work that others might not be aware of?

Questions To Ask About Social Responsibility And Ethics

  1. How do you ensure your business practices are ethical?
  2. Can you share how your business contributes to societal or environmental welfare?
  3. What role do you think businesses should play in addressing societal issues?
  4. How do you handle situations when there’s a conflict of interest?
  5. How do you ensure your decisions align with your ethical standards?
  6. How do you balance profit and ethics in your business?
  7. How do you promote diversity and inclusion within your organization?
  8. Can you share an instance where you saw a positive societal impact due to your business?
  9. How do you ensure the sustainability of your operations?
  10. How do you handle dilemmas that put your business interests against societal or environmental interests?
  11. In your view, what is the biggest ethical challenge facing your industry today?

Questions To Ask About Financial Perspective

  1. How do you make financial decisions, especially when investing in your business or career?
  2. What is your approach toward financial independence and retirement planning?
  3. How do you manage wealth and ensure its growth for the future?
  4. Can you share a significant financial mistake you made in your journey and how did you recover from it?
  5. What are some financial indicators you closely watch in your business or career?
  6. What’s your philosophy when it comes to saving versus investing?
  7. How do you approach diversification in your investments?
  8. Can you share a piece of financial advice that has significantly helped you in your journey?
  9. What’s your take on debt?
  10. How do you ensure financial transparency in your business?

Questions To Ask About Health and Work-Life Balance

  1. How do you balance your work life with your personal life?
  2. How do you ensure you’re taking care of your physical and mental health?
  3. How do you handle the stress that comes with your work?
  4. What is one aspect of your work-life balance that you think could be improved?
  5. How important is a healthy lifestyle to your professional success?
  6. How do you unplug and detach from work during your free time?
  7. How do you maintain your mental health while dealing with the pressures of success?
  8. How do you approach work-life balance, and has your perspective changed over time?
  9. How do you handle the pressure of high expectations?
  10. What are some ways you manage work-related stress and avoid burnout?

Questions To Ask About Innovation And Creativity

  1. How do you foster a culture of innovation and creativity?
  2. How do you find inspiration for new ideas?
  3. Can you share an innovative idea that you had that was initially rejected but you proved its worth eventually?
  4. How do you handle the fear of the unknown when exploring new ideas?
  5. How important is continuous learning in fostering creativity and innovation?
  6. How do you integrate emerging technologies into your creative process?
  7. How do you maintain a balance between creativity and practicality in your projects?
  8. Can you share an instance where a creative risk led to unexpected rewards?
  9. How do you respond to failure in creative pursuits?

Frequently Asked Questions

Can I modify these questions? 

Yes, you can definitely modify these questions or even use them as a basis to formulate your own. The goal is to ignite meaningful and insightful conversations that can help you learn from the experiences of successful people.

Are there any ethical considerations to keep in mind while asking these questions?

Yes, ethics are essential in any conversation, especially when discussing personal experiences and insights. Here are some ethical considerations to bear in mind:

Confidentiality: Respect and maintain the privacy of shared information.
Consent: Obtain permission before asking personal or sensitive questions.
Respect: Always treat the person you’re talking to with kindness.
– Truthfulness: Be clear about your intentions if using the information for specific purposes.

How should I approach someone to ask these questions?

Approaching someone with respect and genuine curiosity is key. Ensure that your request for their time is polite, express the purpose of your questions, and show appreciation for their insights. People are generally more willing to share their experiences when they feel respected and valued.

What if someone doesn’t want to answer a specific question?

It’s crucial to respect an individual’s boundaries if they don’t want to answer a specific question. Here’s how you can handle such situations:

Express understanding: If someone isn’t comfortable with a question, acknowledge their feelings and move on. You could say, “I understand this might be a sensitive topic; let’s move to the next question.”

Stay respectful: Don’t push or try to convince them to answer. Respecting their privacy and maintaining a positive atmosphere during the conversation is essential.

Redirect: Have other questions ready to divert the conversation to a different topic. This can keep the conversation flowing without any awkwardness.

What if I get answers that I didn’t expect or contradict my beliefs?

In conversations with successful individuals, you’re likely to encounter viewpoints different from yours. 

Rather than viewing this as a challenge, consider it an opportunity for growth. With an open mind, you can leverage these unexpected responses to broaden your understanding and perspective.

Confronting beliefs contrary to ours can be challenging, but it’s a crucial part of personal and professional development. These instances offer a chance to reevaluate your own views and deepen your comprehension of success. 

Embrace this process as part of your continuous learning journey, turning every answer, expected or not, into a valuable insight.


Everyone’s journey to success is unique, filled with valuable lessons, challenging moments, and unexpected turns. These questions can help you delve into the minds of successful people and uncover their strategies. 

But the most important thing is to take these insights and use them to shape your own path. So, go out there, ask away, and blaze your trail to success! 

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Robby Salveron

Robby is a multimedia editor at UpJourney with a journalism and communications background.

When she's not working, Robby transforms into an introverted art lover who indulges in her love for sports, learning new things, and sipping her favorite soda. She also enjoys unwinding with feel-good movies, books, and video games. She's also a proud pet parent to her beloved dog, Dustin.