40 essential questions to ask your mentor

Perhaps you’re fortunate enough to have someone in your life whom you consider to be a mentor—someone whose advice you can rely on to guide you through the ins and outs of your life, career, or both. If you have someone like that in your contacts list, never forget to reach out to them for guidance when the need arises.

Remember, though, that mentors are only effective if they have pupils who are ready to learn, so come prepared with smart questions. Make sure they’re questions you can’t get relevant answers to from anyone else. To help you get started on your quest for guidance, here are forty major questions to ask your mentor. We’ve kept them career focused, but lots of these can be applied to more general topics about life that you may want advice for.

Questions for mentors about failure

When people say “you only fail if you don’t learn from a failure,” they’re taking a glass-half-full perspective. Because, let’s be honest: even if you learn something from it, a failure will still result in the success you wanted being out of reach. And that’s where a good mentor comes in.

With advice from a worldly mentor who’s been around the block and has fallen into the very traps you’re afraid of being ensnared by, you may be able to avoid certain catastrophes all together. Take another man’s failures as warning signs of what not to do, and you’ll save yourself a lot of time in the game of life.

1. What’s a big mistake you’ve made that you’d want others to avoid repeating?
2. What’s your strategy for overcoming failure?

3. What’s an essential lesson you learned as a result of failure?

4. When should I give up on a pursuit?
5. Do you believe in the sunk-cost fallacy?

6. How do you assess what feedback is legitimate?

7. How do you integrate feedback into your work and lifestyle?
8. How big of a risk is too big of a risk?

9. How do you determine which weaknesses can be overcome?

10. Can you tell a story of how you recovered from a massive blunder?

Questions for mentors about success

Identical to how mentors can educate you on mistakes you haven’t even considered making yet, your personal wisdom-dropping elder can also give you advice on how to attain success. Asking a mentor how to anticipate career-specific curveballs is a great way to prepare yourself for success before the competition even knows there’s a preparation phase underway.

11. What decision netted you the most success in your career?

12. Is there a particularly effective strategy for achieving success in this field?

13. Which people do I need to stick around to maximize chances of success in this field?

14. Where should I be networking?

15. Have you ever made a single change that led to tremendous success?

16. How can I be more strategic in pursuing my career goals?

17. What traits do I need to exhibit to stay ahead of the curve in this industry?

18. At how fast a clip can one reasonably expect to climb the ladder in this field?

19. What should success look like at this stage in my career?

20. What should I be focused on right now to smoothly transition into the next leg of my career?

Questions for mentors about introspection

Not a lot of people like to be honest with themselves about themselves, but if you’re a smart person who knows that a critical look in the mirror has immense value, then you should also consider letting a mentor act as a secondary mirror. There may very well be things about yourself that you subconsciously avoid addressing—things another pair of eyes might not shy away from calling out.

21. If you were me, what’s the single most important question you would ask you?
22. If you were me, what’s something you’d aim to change immediately?

23. How can I tell I’m not cherry-picking which feedback I accept about myself?

24. Is there a strategy to unlearning behaviors that are holding me back in this field?

25. Do I exhibit any warning signs that indicate this field won’t be right for me in the long run?

26. When is it time for me to contemplate changing career paths?

27. How do I ensure I’m prioritizing the right things?

28. Where do you feel I fall short?

29. How am I perceived by those around me?

30. What should I do right now to improve myself and my career prospects?

Questions for mentors about themselves

It should go without saying, but only ask these questions if you genuinely care about finding out the answers. There are some situations where a mentor’s personal backstory won’t be great for providing you with relevant insight, meaning you shouldn’t waste time with questions pertaining to nonessential trips down memory lane. Don’t ask out of some misplaced sense of obligation, since it won’t help you and it might rub your mentor the wrong way.

However, if learning more about your mentor and their lore will help you and you truly want to know the ins and outs of their life, then by all means, ask away. If your questions are genuine and thoughtful, they’ll sound that way, and might just earn you responses that’ll give you far more than you bargained for.

31. What’s the greatest obstacle you’ve overcome?

32. What’s an obstacle you couldn’t overcome?

33. What’s the most unexpected obstacle you’ve had to face?
34. What’s a good thing to be afraid of?

35. What’s been the most exciting point in your career?

36. Do you find any utility in holding onto regrets?

37. Where do you think you could’ve done better, had you known what you know now?

38. Which values got you to where you are today?
39. When did you know you’d “made it” and were where you wanted to be?

40. Has your definition of success changed over the years?