170 Questions to Ask Successful People

Have you ever wondered what sets successful people apart? What habits, mindsets, and experiences have propelled them to the top of their fields? If you’re looking to learn from the best and accelerate your own journey to success, asking the right questions is key.

In this article, I’ve compiled a comprehensive list of questions designed to uncover the secrets behind the achievements of accomplished individuals.

From their paths to success and the challenges they’ve overcome to their daily routines and the advice they’d give to aspiring success stories, these questions will provide you with valuable insights and actionable strategies.

So, are you ready to dive deep into the minds of those who have reached the pinnacles of their professions?

Path to Success

  1. What first step did you take on your path to success?
  2. Can you share a pivotal moment that steered you towards your current path?
  3. How did you identify the career or industry you wanted to succeed in?
  4. What were your initial goals, and how have they evolved?
  5. Who were your role models or inspirations in your journey?
  6. What was the biggest risk you took that paid off?
  7. How have your definitions of success changed over time?
  8. Did you have a clear vision of your success, or did it develop over time?
  9. How important has setting clear goals been in your success?
  10. What do you wish you had known when you first started?
  11. How do you measure success in your profession?
  12. Can you share a breakthrough moment in your career?
  13. What’s the most important decision that contributed to your success?
  14. How do you prioritize opportunities that come your way?
  15. How did you build your support network?
  16. What sacrifices have you made to achieve your level of success?
  17. How do you balance ambition with practicality?
  18. How do you handle doubt from yourself or others?
  19. What habits did you form early on that helped you on your path?
  20. Can you discuss a time when you had to pivot or drastically change your strategy?

Challenges and Overcoming Them

  1. What was the most challenging period in your career, and how did you overcome it?
  2. Can you share an instance where you faced significant opposition or criticism?
  3. How do you approach risk and failure?
  4. Have you ever doubted your path, and how did you find clarity?
  5. What strategies do you use to overcome mental blocks or lack of motivation?
  6. How do you handle stress and pressure, especially in critical moments?
  7. Can you describe a failure that eventually led to success?
  8. How do you recover and bounce back after a setback?
  9. What lessons have you learned from your biggest failures?
  10. How have your challenges shaped your leadership or work style?
  11. What advice do you have for dealing with rejection?
  12. How do you maintain resilience in the face of continuous challenges?
  13. What’s the toughest decision you’ve had to make, and how did you arrive at it?
  14. In hindsight, is there a challenge you wish you had handled differently?
  15. How do you discern when to keep pushing through a challenge or when to pivot?
  16. How do you prepare for potential challenges in your projects or endeavors?
  17. Can you share a time when you had to make a significant sacrifice for your career?
  18. How do you ensure your team stays motivated and focused during tough times?
  19. What role do mentors or advisors play in overcoming obstacles?
  20. How do you manage the balance between your work and responding to challenges?
  21. How important is feedback in overcoming obstacles, and how do you seek it?
  22. Can you share an experience where overcoming a challenge led to unexpected opportunities?
  23. How do you adapt to challenges in your industry?
  24. What techniques have you found effective for decision-making in difficult situations?
  25. When facing a new challenge, what steps do you take to tackle it efficiently?

Advice for Aspiring Success Stories

  1. What’s the single most important piece of advice you’d give to someone starting in your field?
  2. How important is having a mentor, and how would you recommend finding one?
  3. What common mistakes do beginners make, and how can they be avoided?
  4. Can you share any resources (books, podcasts, etc.) that significantly impacted your journey?
  5. How do you continue to grow and develop professionally?
  6. What traits do you believe are most important for success in your industry?
  7. How can someone stand out in a competitive field?
  8. What’s the best way to network and build professional relationships?
  9. How important is it to take risks, and can you share how risk-taking has benefitted you?
  10. What habits should someone develop early in their career?
  11. Can you share any strategies for time management and productivity?
  12. How do you keep up with industry trends and stay ahead of the curve?
  13. What’s your approach to goal setting and tracking progress?
  14. How can someone effectively communicate their value and work?
  15. What’s the importance of personal branding, and how can one develop it?
  16. How do you recommend dealing with imposter syndrome?
  17. Can you share how to effectively balance learning new skills while deepening existing ones?
  18. What role has failure played in your journey, and what can others learn from it?
  19. How can one make the most out of feedback, even if it’s negative?
  20. What’s your advice for maintaining motivation during challenging times?
  21. How important is work-life balance, and how can it be achieved?
  22. Can you share strategies for making critical career decisions?
  23. What’s the key to building and maintaining professional relationships?
  24. How can someone recover and learn from career setbacks or failures?
  25. What advice do you have for someone feeling stagnant or unsure of their next step?

Mentorship and Networking

  1. How did you find your first mentor, and how did they impact your career?
  2. Can you share how to approach someone you admire for mentorship?
  3. What qualities do you look for in a mentor or networking partner?
  4. How important has networking been for your career?
  5. What strategies have you used to maintain and nurture professional relationships?
  6. Can you share tips for effective networking without feeling transactional?
  7. How do you balance the give and take in mentoring and networking relationships?
  8. What’s your advice for someone who feels uncomfortable or anxious about networking?
  9. How has mentorship changed or evolved as you’ve progressed in your career?
  10. Can you share an experience where networking led to a significant opportunity?
  11. How do you recommend utilizing social media for networking and building connections?
  12. What are common networking mistakes, and how can they be avoided?
  13. How do you keep in touch with contacts without being overbearing?
  14. Can you discuss the benefits of having a diverse network?
  15. How do you measure the success of your networking efforts?
  16. What role do professional organizations or clubs play in networking?
  17. How do you approach networking at large conferences or events?
  18. Can you share a story where a casual connection turned into a crucial network link?
  19. How do you ensure authenticity in your professional relationships?
  20. What advice do you have for mentoring others?
  21. How do you select whom to invest time in for mentoring?
  22. What impact has mentoring others had on your own success?
  23. How do you handle situations where a mentorship doesn’t work out?
  24. What are your thoughts on reverse mentoring (learning from those younger/in lower positions)?
  25. How can someone best prepare to be a productive and receptive mentee?

Daily Habits and Productivity

  1. Can you describe your morning routine and how it prepares you for a successful day?
  2. How do you prioritize tasks and manage your time effectively?
  3. What productivity tools or apps do you find indispensable?
  4. How do you minimize distractions and stay focused during the workday?
  5. Can you share a habit that has significantly increased your productivity?
  6. How do you structure your day to maximize efficiency and output?
  7. What routines help you wind down and prepare for the next day?
  8. How do you manage work-related stress to maintain productivity?
  9. Can you discuss the importance of breaks and how you incorporate them into your day?
  10. How do you handle days when you’re feeling less motivated?
  11. What’s your strategy for tackling big, daunting tasks?
  12. How do you decide what tasks to delegate and to whom?
  13. Can you share an example of a productivity hack that works for you?
  14. How do you manage emails and communication to avoid getting overwhelmed?
  15. What role does physical exercise play in your daily routine?
  16. How do you balance urgent tasks with important but not urgent tasks?
  17. Can you share how you recover from a productivity slump?
  18. What advice do you have for improving focus and concentration?
  19. How important is a dedicated workspace, and how do you optimize yours?
  20. Can you discuss the role of goal setting in daily productivity?
  21. How do you ensure you’re consistently making progress on longer-term goals?
  22. How do you deal with interruptions or unexpected demands on your time?
  23. How do you keep track of your accomplishments and reflect on your productivity?
  24. What’s been the biggest change you’ve made to improve your productivity?
  25. Can you share how you balance work and personal tasks throughout the day?

Personal Growth and Learning

  1. How do you approach setting personal development goals?
  2. What skills are you currently focusing on developing, and why?
  3. Can you share a learning experience that significantly impacted your career?
  4. How do you stay motivated to continuously learn and grow?
  5. How do you incorporate learning into your busy schedule?
  6. What habits have you adopted to foster continuous learning?
  7. Can you share how you recover from a setback in your personal growth journey?
  8. What resources do you recommend for someone committed to personal development?
  9. How do you measure progress in your personal growth?
  10. Can you discuss when you had to unlearn something to move forward?
  11. How do you balance developing soft skills vs. hard skills?
  12. What’s your approach to taking on new challenges as learning opportunities?
  13. How important is it to step outside your comfort zone for personal growth?
  14. What advice do you have for someone struggling to see growth or progress?
  15. How do you stay curious and open to new ideas?
  16. Can you share a personal development goal you’ve set and achieved and how you did it?
  17. Can you share a habit or practice that has facilitated significant personal growth?
  18. How do you deal with the fear of failure when trying to learn new things?
  19. What role does self-reflection play in your personal growth?
  20. How do you prioritize which skills or areas to focus on for growth?

Work-Life Balance

  1. How do you define work-life balance, and how has your definition evolved?
  2. Can you share strategies you use to balance work and personal life?
  3. What challenges have you faced in achieving work-life balance, and how have you addressed them?
  4. How do you manage boundaries between work and personal time?
  5. What role does technology play in your work-life balance?
  6. Can you discuss the importance of downtime and how you ensure you get enough?
  7. How do you handle periods of high workload without sacrificing your well-being?
  8. Can you share a time when your work-life balance was off and how you corrected it?
  9. How do you prioritize your health and well-being amidst a busy schedule?
  10. What advice do you have for someone struggling with work-life balance?
  11. How important is flexibility in achieving work-life balance?
  12. Can you share how hobbies or outside interests contribute to your overall success?
  13. How do you ensure your relationships don’t suffer due to work commitments?
  14. What measures do you take to avoid burnout?
  15. How do you handle work while dealing with personal issues or emergencies?
  16. Can you discuss the role of delegating in maintaining a healthy work-life balance?
  17. How do you stay productive at work to ensure your personal time is truly yours?
  18. How do you communicate your work-life balance needs with your employer or team?
  19. What role do planning and organization play in achieving balance?
  20. Can you share an example of a work-life balance goal you set and achieved?
  21. How do you reassess and adjust your approach to work-life balance over time?
  22. What’s the biggest misconception about work-life balance you’ve encountered?
  23. How do you balance professional ambitions with personal happiness?
  24. Can you discuss how setting expectations with colleagues and family helps maintain balance?
  25. What’s your top tip for someone just starting to navigate work-life balance?

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.

Final Thoughts

Remember, success is a unique journey for everyone, and what works for one person may not work for another. Use these questions as a starting point to have meaningful conversations, but don’t be afraid to adapt and personalize them to fit your own goals and circumstances.

With curiosity, dedication, and a willingness to learn, you can unlock the secrets of success and pave your own path to extraordinary achievement.

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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.