50 Questions to Ask Your Mentor

Unlock valuable insights and accelerate your growth with 50 essential questions to ask your mentor. Empower your journey to success today!

The most valuable commodity on the planet is time. From janitors to CEOs...we all have the same 24 hours each day to work with. No amount of wealth can turn back the clock.

Mentors are generally selected for their experience and knowledge. They carved out a chunk of their time to help you. To get the most out of a mentoring session and to maximize every second, here are 50 questions you can ask a mentor to make the time meaningful and productive. 

You won't get through all 50 in one meeting. Pick 5-10 and try to get through those. Don't stress if you don't. Mentoring is organic and a Dialogue could spark off one questions which consumes the session.

Bring a notebook and pen. You might be surprised by the advice and life lessons you get in response to these questions:

  1. Can you share a particularly memorable experience you had in your career?

  2. What is one piece of advice you would give your younger self?

  3. What book, podcast, or resource has had the biggest impact on your professional life?

  4. Can you talk about a time when you had to make a major career pivot?

  5. How do you define and measure personal and professional success?

  6. What is one of your biggest pet peeves in the workplace and how do you handle it?

  7. Can you share a particularly creative solution you implemented in your work?

  8. What is your approach to work-life integration and finding balance?

  9. Can you talk about a time when you had to work outside of your comfort zone?

  10. How do you approach and manage workplace stress and anxiety?

  11. Can you share your journey to where you are now in your career?

  12. What was your biggest challenge in your career, and how did you overcome it?

  13. What skills or knowledge do you think are critical for success in your field?

  14. Can you walk me through a typical day in your role?

  15. How have you navigated challenges or obstacles in your career?

  16. What advice would you give to someone just starting in your field?

  17. How do you stay motivated and driven in your work?

  18. Can you share a specific project or accomplishment that you are most proud of?

  19. What key qualities do you think are important for a successful leader in your field?

  20. How do you stay current and up-to-date with industry trends and developments?

  21. Can you talk about a time when you had to make a difficult decision in your career?

  22. How do you manage your time and prioritize tasks effectively?

  23. Can you share any specific strategies you use to build and maintain professional relationships?

  24. What are the biggest challenges facing your industry right now?

  25. What is your personal philosophy or approach to work?

  26. How do you handle criticism and feedback in your work?

  27. Can you talk about a project that didn't go as planned and what you learned from it?

  28. Can you share any lessons learned from your biggest failure in your career?

  29. What role does collaboration play in your work and how do you foster it?

  30. Who do you look up to?

  31. What do you think is the key to success in your field?

  32. How have you adapted to changes in your industry or profession over the years?

  33. Can you talk about a time when you had to collaborate with a team with different backgrounds and perspectives?

  34. What is the biggest risk you have taken in your career and what did you learn from it?

  35. How do you approach problem-solving and decision-making in your work?

  36. Can you share any tips for effective communication in the workplace?

  37. What is the best way to manage stress in a high-pressure work environment?

  38. How do you prioritize and delegate tasks to a team effectively?

  39. What have been some of your biggest achievements and milestones in your career so far?

  40. Can you talk about a time when you had to lead and motivate a team through a difficult situation?

  41. What Technology do you use to maximize productivity?'

  42. How do you manage conflicts within a team or with colleagues?

  43. Can you talk about a time when you had to adapt to a new work environment or company culture?

  44. What are your goals for your career and how are you working towards them?

  45. How do you measure success in your work?

  46. Can you share any tips for successful time management and productivity?

  47. What is your approach to professional development and continuous learning?

  48. Are there subjects you steer clear of at work? Why?

  49. What was the most difficult change you went through in your career?

  50. What is the most valuable lesson you have learned in your career so far?

Mentor Resources can help any company or government agency to leverage technology to create tailored career development programs that are cost-effective. Our mentoring software - Wisdom Share is a cloud-based program that is simple and comes with guided workflows. Included are tools for administrators to attract, enroll, connect, and guide participants. We also provide analytics to ensure you can monitor your employee development program and easily see ROI metrics.

Reach out to us today for a Free Demonstration of our software.

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