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Surprising Keys to Being a Successful Mentor

by | Freedom

No one is a successful mentor right out of the gate. Like anything else worth doing, being a successful mentor takes time, dedication, and sticktoitiveness. It also takes a little know-how, which is why it’s important to read up on all of the keys to being a successful mentor.

Some of the keys might surprise you. If you’ve never mentored anyone before (and even if you have), they might even go against your natural instincts as a leader. Regardless, these keys to success are tried and true methods for fostering and growing a deeply impactful mentor-mentee relationship.

Share Your Failures as Much as Your Successes

It’s always uncomfortable to talk about failure, and it’s especially counterintuitive when you’re a mentor. But, if you want to be the best mentor you can possibly be, you have to push past that awkwardness.

Think about all of the most influential people in your life. Were they perfect? Probably not by any stretch of the imagination. Even still, they were great mentors—not because they were flawless, but because they did amazing things in spite of their fallibility.

Letting your mentor in on your failures will help them to better see themselves in your successes.

Understand Where Your Mentee is Coming From

…And where they want to go.

One of the most important tasks that mentors take on is meeting their mentees where they are. If you can’t understand their perspective, then you won’t be able to help them shift it to see new possibilities.

To be the best mentor, you have to understand where your mentee is coming from—as well as where they see themselves heading over the next two to five years. You wouldn’t plan a road trip without knowing what Point A and Point B are, so then why would you enter into a mentorship situation without having a similar plan and understanding?

Listen to Learn

In order to get to that point of understanding, though, you need to listen. Unfortunately, most people listen to respond, instead of listening to learn.

As a mentor, you have to be willing and able to listen to your mentee and really hear them. Try as hard as you can not to filter their words through your own experience—and who knows? Maybe you’ll learn a thing or two from them about life.

Again, the most successful mentors are those that aren’t afraid to expose their failures, understand where their mentees are coming from, and listen to gain that understanding.


  1. Donita

    “If you can’t understand their perspective, then you won’t be able to help them shift it to see new possibilities.” This is so true and so easily overlooked. Thanks for the insight!

  2. Chris Music

    When you meet my mentor, you meet my future. I’m thankful for strong mentors in my life. #mentors

    • Ryan

      Love it!!!!

    • Deb

      Love this – and so true. I’d like to quote it… 🙂

  3. Bradley Below

    Aloha Jeff and Leslie. Im buckled up ready to LISTEN!!! To learn grow and apply. Thank you for believing in me. I appreciate your mentorship love and grace allowing us to overcome and become the best version of ourselves.

  4. Jim Wassermann

    Excellent description of mentorship

  5. Jarod Stancliff

    Thank you for the time and attention you put into bettering everyone who’s life you have touched! It shows in everything you do.

  6. Noelle Izumi

    You show us by example what it looks like to be an amazing mentor and friend. Thank you!

  7. Paul jay

    Just as one of your main mentors (John C. Maxwell) wrote – “Good Leaders Ask Great Questions” – your key point about genuinely listening to our mentees is a fresh reminder for all.

  8. Blake Barnes

    Phenomenal post, Leslie! I love the part about listening to understand the mentees perspective so you can help them shift it to see things in a new light. This very concept has allowed spurred my personal growth to new heights.

  9. Emily

    Sticktoitiveness! Just like you in adversity, Leslie. I aspire to build the strength you so clearly demonstrate.
    Thank you for sticking through so much.

  10. Paul Haber

    Every time I have the chance to get around you, I learn something new! Thanks for being there all these years.

  11. Stephanie

    This is so awesome what a great blog on being a successful mentor! Thanks for your insight Leslie!

  12. Josi

    Your strength and heart is an inspiration! Thank you for all you do to help lead and teach us to be better people and help make a difference in our future and generations to come!

  13. Ellen M.

    Sharing failures is so incredibly important! Normalizing the true experience of what it takes to be successful gives people a real understanding of what the journey looks like, and the perseverance it takes to succeed.

  14. Angela Beauregard

    This is a very encouraging and inspiring message. Thank you for your example! We are so grateful for you.

  15. Teresa Wassermann

    Such a great website! Thank you:)


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