135 Questions to Ask Successful People

Are you eager to unlock the secrets of success? Learning from those who’ve paved their way to triumph can illuminate the path ahead and transform your journey.

The thought-provoking questions in this list are designed to delve deep into the lives of successful individuals. Discover the milestones they’ve reached, the philosophies that guide them, and the daily rituals that prop them up.

Whether you’re seeking mentorship, personal growth, or a better work-life balance, these inquiries are your gateway to unrivaled insight and inspiration. Let’s get started!

Success Milestones

  1. What was the first major achievement in your career, and how did you reach it?
  2. Can you share a pivotal moment in your journey that significantly pushed you closer to your goals?
  3. Which milestone are you most proud of, and why?
  4. How do you measure success, and has this definition changed for you over time?
  5. Was there a particular success that was most rewarding on a personal level?
  6. After achieving your initial goals, how did you decide what to pursue next?
  7. How did you celebrate your first big success?
  8. Can you identify one milestone that signified you had “made it” in your industry?
  9. What accomplishment are you currently working towards?
  10. How do you set and prioritize your goals and milestones?
  11. Did you ever achieve a milestone you thought was unattainable?
  12. Which of your success milestones came with the hardest sacrifices?
  13. How have your milestones affected your personal and professional relationships?
  14. At what point in your career did you start setting bigger or more public milestones?
  15. Looking back, is there a milestone that you would now approach differently?

Personal Background

  1. What’s your origin story, and how has it shaped your path to success?
  2. Was there someone in your early life who inspired your ambitions?
  3. Can you point to any particular experiences in your childhood or education that directed you toward your current career?
  4. How has your upbringing influenced your work ethic and drive?
  5. In terms of background, what do you believe differentiates you from others who might have had similar goals?
  6. How did you decide on the field or industry you wanted to succeed in?
  7. Did your background provide any unique challenges or advantages in your journey to success?
  8. What role has your cultural heritage played in your personal and professional development?
  9. Was there an early mentor or experience that steered you toward success?
  10. How did your aspirations evolve as you gained more life experience?
  11. Did any particular failings in your background set the stage for future successes?
  12. How important do you think background shapes one’s potential for success?
  13. Can you share a story from your past that may surprise people, given where you are now?
  14. To what extent have your family’s expectations influenced your career choices?
  15. Looking back, would you have taken a different path, given your personal background?

Daily Habits and Self-Improvement

  1. What daily habits do you believe significantly contribute to your success?
  2. Is there a morning routine you follow rigorously?
  3. How do you structure your day to maximize productivity?
  4. What self-improvement practices do you recommend for sustained success?
  5. Can you name a habit you changed that positively impacted your professional life?
  6. How do you ensure you’re consistently growing and learning?
  7. Do you have any habits focused on maintaining health and wellness, given your busy schedule?
  8. Is there a particular book or resource you’ve found invaluable for personal development?
  9. How do you stay focused and maintain your enthusiasm day to day?
  10. What’s one small daily habit that makes a big difference in your life?
  11. Do you use any tools or apps to track your habits and productivity?
  12. How important is discipline versus flexibility in your daily habits?
  13. What role does reflection or meditation play in your daily routine?
  14. How do you deal with distractions and stay on track with your daily goals?
  15. Can you share a habit you’re currently trying to develop or break?

Challenges and Overcoming Obstacles

  1. What was the biggest obstacle you faced on your path to success, and how did you overcome it?
  2. Can you share a time when you failed and how you responded to that failure?
  3. How do you handle moments of doubt and uncertainty?
  4. What strategies do you use to cope with stress and pressure?
  5. Is there an instance where an obstacle turned out to be a blessing in disguise?
  6. How do you prepare for potential challenges you might face in your work?
  7. Have you ever experienced burnout, and how did you recover from it?
  8. What advice would you give to someone facing a seemingly insurmountable challenge?
  9. How has overcoming obstacles changed the way you approach new projects or goals?
  10. In hindsight, what’s one challenge you wish you had handled differently?
  11. How do you stay resilient when things don’t go as planned?
  12. Can you describe a risk you took that did not pan out and what you learned from it?
  13. What’s the most important lesson you’ve learned from a failure or setback?
  14. How do you maintain the motivation to push through tough times?
  15. At what point do you decide to pivot rather than push through a challenge?

Career and Professional Development

  1. What’s the most valuable piece of career advice you’ve ever received?
  2. How do you stay current and competitive in your industry?
  3. Can you share a crucial career decision that was a turning point for your success?
  4. How do you approach networking and building professional relationships?
  5. What skills do you believe are essential for success in today’s work environment?
  6. What is the process you undertake when evaluating new opportunities?
  7. How do you balance continuing education with your professional responsibilities?
  8. Can you discuss a moment when a professional risk you took paid off?
  9. What role has professional development played in achieving your successes?
  10. How do you identify and cultivate talent within your team or organization?
  11. What’s your approach to giving and receiving feedback?
  12. How do you tackle the challenge of remaining innovative in your work?
  13. Can you share an experience of a professional failure and what it taught you?
  14. How important is a work mentor, and have you ever had one?
  15. How do you deal with competition within your field?

Personal Philosophy and Values

  1. What are the core values that guide your decisions in both life and work?
  2. How do you ensure that your actions align with your personal philosophy?
  3. Can you share how your values have influenced a major life decision?
  4. How do your personal beliefs impact your leadership style?
  5. What role do ethics play in the way you conduct business?
  6. How have your values evolved with your success?
  7. In what ways do your values set you apart from competitors?
  8. Have you ever had to make a difficult decision that tested your values?
  9. What is a critical aspect of your personal philosophy that you would never compromise on?
  10. How do you balance personal convictions with professional obligations?
  11. Is there an instance where upholding your values led to a loss or sacrifice?
  12. How do you handle situations where your values seem at odds with others?
  13. What’s the most profound piece of wisdom you’ve ever received that aligns with your philosophy?
  14. What impact do you hope your values will have on the world around you?
  15. Can you share an example of a time when staying true to your values resulted in a positive outcome?

Mentorship and Influences

  1. Who has been the most significant mentor in your life, and what was the most important thing they taught you?
  2. How do you find and choose individuals to mentor or take advice from?
  3. Have you ever had a protégé, and how has that experience affected you?
  4. How have the influences in your life shaped your approach to success?
  5. What’s the most impactful piece of advice you’ve given as a mentor?
  6. Can you share a story where mentorship helped you navigate a difficult period in your career?
  7. What qualities do you look for when seeking out new mentors or advisors?
  8. How do you integrate the insights from your mentors into your own strategies for success?
  9. In your view, what’s the biggest benefit of having or being a mentor?
  10. How has your role as a mentor changed as you’ve become more successful?
  11. Can you describe a lesson learned from a mentor you later applied to a critical situation in your career?
  12. What’s the most unexpected source of influence or mentorship you’ve encountered?
  13. How do you pay it forward when it comes to sharing the knowledge you’ve gained with others?
  14. How do you maintain relationships with your mentors and mentees over time?
  15. What part does mentorship play in building a legacy?

Work-Life Balance and Personal Passions

  1. How do you balance your professional aspirations and your personal life?
  2. What hobbies or activities do you credit with enhancing your effectiveness in your work?
  3. Has your idea of work-life balance changed as you’ve become more successful?
  4. How do you prioritize your time, especially when work demands conflict with personal interests?
  5. What strategies have you implemented to avoid burnout?
  6. Can you share how your personal passions have positively impacted your professional life?
  7. How do you disconnect from work and genuinely relax?
  8. Have you had to make compromises in your personal life for the sake of your career, and were they worth it?
  9. What’s one activity you always make time for, no matter how busy you are?
  10. How important is it for you to cultivate a life outside of your professional endeavors?
  11. How do you juggle family commitments with a demanding career?
  12. What role does travel or exposure to different cultures play in your work-life balance?
  13. Have your personal relationships influenced your career path or decisions?
  14. Do you integrate any of your personal passions into your professional world?
  15. How do you measure personal success versus professional success?

Future and Legacy

  1. What goals do you still strive to achieve, and why are they important to you?
  2. What sort of legacy do you hope to leave behind?
  3. How do you envision the future of your industry, and how do you plan to shape it?
  4. What projects are you excited about tackling in the upcoming years?
  5. How do you prepare to transfer your knowledge and experience to the next generation?
  6. What changes do you hope to influence your community or the world?
  7. How do you want to be remembered by your peers and the public?
  8. What’s the biggest impact you hope your work will have in the future?
  9. How do you ensure your work remains relevant and valued in a changing world?
  10. Do you involve yourself in philanthropic endeavors, and how do these align with your vision for the future?
  11. What message would you like to pass on to aspiring entrepreneurs or leaders?
  12. How do you plan on maintaining personal growth as your career evolves?
  13. What innovation or change in your field do you wish to spearhead or witness?
  14. How do you think future generations will build upon the foundation you’ve set in your work?
  15. What steps are you taking to ensure your contributions are sustained after you retire?

Frequently Asked Questions

How do I approach a successful person to ask them questions?

Be respectful and considerate of their time. A concise, well-thought-out message or email explaining your intent and the specific insights you hope to gain can be a great way to request a moment of their time. 

Remember to be flexible with scheduling and express genuine appreciation for any time they can provide.

What should I avoid asking successful people?

Avoid questions that pry into personal matters not directly related to their success or those that could come off as invasive or disrespectful. Focus instead on their journey, experiences, and advice rather than personal details that are not publicly shared.

How can I apply the answers to my own life?

Reflect on the core lessons and themes that emerge from their responses. Look for patterns, habits, or philosophies aligning with your goals and consider how to integrate these learnings into your daily life and long-term planning.

Final Thoughts

Embarking on the quest for success can often be daunting, but armed with the wisdom gleaned from those who have already reached their peaks, the journey feels less solitary.

These questions serve not just to satisfy curiosity but to inspire action and foster growth in our own lives. So, go ahead—ask away, learn relentlessly, and let the answers you uncover steer you toward your own version of success.

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Robby is a multimedia editor at Enlightio 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.