Six Reasons Mentors Tell Failure Stories (and Why Mentees Listen!)

I’ve been mentoring a long time. I’ve lead mentoring groups for past seventeen years and did ‘issue of the day’ mentoring for a decade before that. When you’ve been at something that long, you pick up a few best practices along the way.

If you’ve been hanging around Radical Mentoring for long, you’ve probably heard me say the best mentors aren’t teachers, they’re facilitators. I believe a great mentor is one who can listen, ask good questions, bring others into the conversation, and tell a relevant story to make a point.

But what kind of stories are the most effective when mentoring? You might be sorry you asked because the answer is your failure stories. Over the years I’ve noticed how much more intensely young people listen to the stories of my failures than those of my successes.

So, why are mentees drawn to failure stories over victory laps?

  1. Authenticity – When I talk about winning “High Technology Entrepreneur of the Year,” I sound like everyone else. But when I tell them about being a 35-year-old MBA, making a naive decision about how to expand his company and burning through all his cash, that sounds different. They want to hear more . . . what I did wrong, what I learned, what I would do differently next time. They can’t get that kind of information anywhere else. And because they see me as real and authentic, they’ll listen and learn other stuff from me too.
  2. Approachability – If you feel like you’re around perfection, you’re going to be quiet. Walk softly. Project yourself to be as close to perfect as you can. But when a mentor demonstrates humility by sharing his failures, he’s more approachable. More accessible. And more helpful.
  3. Emotion – All decisions are made at an emotional level. I believe most meaningful learning happens when emotions are engaged. Hearing and feeling the pain, embarrassment, or remorse of a situation gone bad brings the mentee into the mentor’s circle. Hearing about a mentor’s passionate resolve to recover and learn from mistakes can galvanize a younger leader’s penchant to go for it, even if it fails.
  4. Value – Sometimes, it looks like good leaders find success effortlessly. It seems to come cheap. But the lessons learned from mistakes and failure are expensive. They take the skin off. Leave a mark. Young people know the value of lessons learned from painful experience. Wisdom comes from experience. Experience from mistakes. Mistakes are costly, thus valuable.
  5. Believability – We can spin the stories of our success to a level no one can believe. They don’t see how they could ever get to where we are or emulate what we’ve done. But when leaders share their failures, their successes become more believable. More doable for younger leaders. The cookies appear to be on the bottom shelf where they can be reached by mere mortals . . . like them.
  6. Challenging – When a young person sees a leader he looks up to share his failures and shortcomings, he may start to believe in himself. “If he can succeed after that, I know I can.” He sees his own potential. He sees the chance to stand on the shoulders of one who’s gone where he wants to go.

Mentors . . . open up! Loosen up! True strength is revealed through vulnerability, so tell your mentees where you’ve screwed up. Let them learn from your mistakes. They’ll make others, but maybe not the same ones.

Scripture: My flesh and my heart may fail, but God is the strength of my heart and my portion forever. (Psalm 73:26)

Mentor Tip: Don’t wait to tell your failure stories. You’ve got to include them when you tell your faith story. Remember your telling your whole story . . . and if you don’t include the rough parts, your guys won’t either and your mentoring season will suffer for it.

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