Mentorship: How to be an Excellent Mentee, 16 Example Questions

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You’ve identified someone who seems to be a great fit as a mentor: well respected, further ahead in a specific area (or many), and someone you want to emulate.  After hyping yourself up, you broach the topic, and they are humbled and excited to meet up and see where things go.  Heck yeah! 

Now what? 

It’s that moment as a kid when you realize reeling a fish in is fun until it’s flippin’ around at your feet.  Fired up, nervous, needing help, unsure of what to do next and pretty sure you made a mistake. 

Don’t freak out.  You didn’t make a mistake.  They want to meet with you.  You’re going to be prepared to make the most of meeting with them.  Promise.


Pursue Your Mentor: Timing

I asked Jon, one of my mentors, “what makes a great mentee?” and his response was simple: “A great mentee pursues the mentor.  With prepared questions, topics of interest and setting meeting times you show that you’re good soil.”  (Pictured is a pocketknife Jon gave me as a reminder of what I’m shooting for.  Good soil produces deep roots and good fruit)

Well, that doesn’t sound like magic.  I thought for sure being in a mentor/mentee relationship would have a bit more flash.  But it’s not about showmanship.  It’s about the simple, meaningful, purposeful, and lasting things.  A response that’s laced with wisdom and causes you to pause.  An accomplished person giving you something that’s priceless and non-renewable--time. 

If we take Jon’s advice, there are two major things we need to check off our lists as mentees.


Pursue the mentor through 1. Setting a date/time to meet 2. Crafting questions/topics.


Getting a date/time is simple enough but it does require you to offer early morning or evening to make it convenient for your mentor.  Pursue them by offering flexibility.  Send a message like “Thanks for agreeing to meet!  Please let me know what works best for your schedule, below are a few dates/times but I’ll gladly work around your availability.”  Don’t go crazy trying to cover every angle, offer different days of the week and various times.  Click send.

One of my mentors lives a few 100 miles from me so we meet at 6 am via FaceTime on Mondays once a month.  My other mentor, I’ve known for 25 years and we live in the same town, we meet for lunch on Tuesday’s once a month.  Rest easy, you’re not stuck with the day/time or cadence for the rest of your life.  I’ve had to move meetings several times and my mentors have too—these are real-life relationships.  And life is messy.


Pursue Your Mentor: Questions

Now you’ve got the date and time of your meeting, cadence still to be determined.  When you send the invite, you should include a set of questions in the body.  This communicates several things; you really do respect their time, this relationship isn’t one-sided, your posture is that of an eager student.  

My favorite thing that prepared questions to convey is that this will be a mutually beneficial relationship.  No need to keep saying over and over that you’re grateful/want to make the most their time/are humbled they’re willing to meet...etc. - thoughtful questions show them.  Your mentor will feel respected and most likely be impressed with how your questions challenged their thinking.  Iron sharpening iron. 


Below are 16 questions I’ve sent to my mentors over the years.  Let them get the juices flowing as you create your own list.


1. How did you approach “the talk” with your kids?

2. When were you at your leadership best?

2 a. What happened?

2 b. What led to that?

2 c. How do you maintain it?

2 d. What was the impact of your leadership best?

3. What question(s) should I be asking myself?

4. What are your routines?

5. Where have you failed in marriage/parenting?

6. What advice do you give your 20 yr old self?

7. Who do you know that I should know?

8. Where have you been, that I should go?

9. How do you define greatness?

10. Do you have a life verse? If so, what is it? 

11. What are your friends like?

12. How do you handle tithing/supporting missionaries?

13. Where have you seen leaders fail most often?

14. Who do you listen to?

15. How did you develop people around you in business?

16. What’s the best advice you’ve received?


A Few Final Thoughts

Some mentor relationships are for a season, some are for life.  Some mentors are swiss army knives, some are scalpels.  Have a very short list of things that will keep you from meeting with your mentor.  (Not being a morning person doesn’t count) Pay for their meal/coffee.  Lean in, take notes, do the stuff they suggest, ask more questions, communicate gratitude, be honest, and someday return the favor to an eager person who approaches you.

Want more?

Listen to episode #81, Tempered Resilience with Tod Bolsinger.

Watch the mullet and grizzly bear on the IOL YouTube channel.

Download a template to help get the IOL membership expensed.  (it’ll pop up)


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