Killer Questions to Ask Potential Mentors Part 2

 If you had 30 minutes with one of your role models, what three questions would you have asked them to make the conversation interesting for both parties, and for them to want to become your mentor?

The Muppies community shared their responses below, compiled by Muppies member Javad Mushtaq. We’ll share these questions weekly so come back next week for the final set. If you’re interested in Part 1, take a look here


Journey / Leadership style / General:

  • What do you most enjoy about your work?
  • “Gut” decisions vs. “Analytical” decisions and the balance between the two
  • What’s your technique to influencing a leader/people to change
  • What do you believe you do differently than others in your position/sector?
  • How have you overcome your obstacles?
  • If everyone in this world could have one characteristic, what would you choose?
  • Look into their background and figure out when they made difficult decisions. Key inflection points where they “bet it all”, and how they made the decision. Even better if the decision went against them.
  • Ask them what the opportunities are they see from their perch today – there are almost certainly opportunities they have visibility on that are too small for them to pursue given their current responsibilities, but could have vast potential.
  • What keeps you up at night? (This gives you a sense of their current biggest personal challenge and stimulates a more intimate, personal conversation that can lead to a mentor-mentee type of relationship. It’s a high-risk question though because it can be taken the wrong way.)


The young version of them:

  • If you were to give advice to the younger version of you, what would it be?
  • What would the you today tell the you of 20 years ago when it came to advice as you were about to pursue this path?
  • What is the one thing you did too early as you pursued this path?
  • What is the best career or leadership advice you’ve received? How has it shaped your decisions and enable you to reach where you are today?