April 7, 2022

25 Questions to Supercharge Your Mentoring Meetings

25 Questions to Supercharge Your Mentoring Meetings

You’ve had solid conversations with your mentor. And you’re making steady progress towards your professional development goals. Congratulations! Now is the perfect time to bolster your mentoring meetings with even richer conversation.

At legacy Talent Development, we’ve been championing successful mentors and mentees for nearly 20 years. Most pairs attribute part of their success to asking the right questions. But with so many questions and limited time, it can be a challenge to choose the most impactful. That's why we curated a slate of 25 thoughtful leadership questions for you to use as a launching point. Add your unique twist with words and phrases that fit your style. You may be surprised how asking these questions elevates the discussion and supercharges your mentoring relationship!

1.    How do you define success at work?

2.    What thought leaders do you look to for inspiration?

3.    Who are the industry-specific leaders you admire or have provided helpful information?

4.    What books, podcasts or videos do recommend on leadership?

5.    Do you even get impostor syndrome? How did you learn to get over it?

6.    How do you keep your team motivated?

7.    How do you handle conflict among team members?

8.    How do you delegate tasks to your team?

9.    How do you grow high performers on your team when you can’t promote them?

10. What are your favorite tips for having great 1:1 meetings with team members?

11. How do you continue to grow and develop as a leader?

12. Which leadership skills were the most difficult to develop?

13. What’s the most important leadership lesson you’ve learned?

14. What was the biggest risk you took in your career and how did it impact you?

15. What is your biggest leadership weakness?

16. What was your proudest moment as a leader?

17. What are your current goals as a leader?

18. Was there ever a role you were hired for but didn’t feel 100% qualified to do?

19. What do you wish you had known before taking your first management role?

20. What habits have you adopted to be a more effective leader? Which do you avoid?

21. Is there anything you wish you’d have done differently in your career? 

22. What unexpected obstacles have come up in your career?

23. What do you wish you knew 10 years ago?

24. What are the most important lessons you’ve learned within our organization?

25. If you were me, what questions would you be asking you?