Six Reasons Mentors Tell “Failure” Stories: Guest Post by Regi Campbell


Today’s blog is a Guest Post from Regi Campbell. Regi is an entrepreneur, CEO, investor and an author. But his passion is mentoring and enlisting older, wiser mentors to focus on intentional relationships with younger men. I know you will enjoy Regi’s words as much as I do!

Six Reasons Mentors Tell “Failure” Stories

I’m a leader. Not bragging. Didn’t really set out to be. But through fifteen startup companies, five CEO jobs, a couple of church starts and a few other ministry launches, I’ve been cast as a leader. Years ago (thirteen to be exact), I bought into the idea that more time with fewer people yielded greater impact. I got that principle from Tim Elmore, a man I love and deeply respect. I began mentoring eight young leaders each year, spending three hours each month pouring what I’ve learned, i.e. ‘what’s in my cup’… into theirs.

I sometimes do this by telling stories. And I’ve noticed how much more intensely young people listen to the stories of my failures than those of my successes.

Why are mentees drawn to failure stories over victory laps?

1. Authentic –  When I talk about winning “High Technology Entrepreneur of the Year”, I sound like everyone else. But when I tell them about having an MBA at 35 years-old, but making a naive decision about how to expand my company and burning through all my cash, that sounds different. They want to hear more…what I did wrong, what I learned, what I would do different 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. Approachable – 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. Emotional – All decisions are made at an emotional level. I believe the 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. Valuable – Sometimes, it looks like good leaders find success effortlessly. It seems to come cheap. But the lessons learned through mistakes and failure are expensive. They take the skin off. Leave a mark. Young people know the value of lessons learned from painful experiences. Wisdom comes from experience. Experience come from mistakes. Mistakes are costly, thus valuable. 

5. Believable – 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, 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.

If you’re a mentor, open up. Loosen up. True strength is revealed in vulnerability, so tell your mentees where you’ve screwed up. Let them learn from your mistakes. They’ll make others, but at least they won’t make the same one’s you made.

If you’re a young leader, press your mentor. Give him a “C’mon man!” Make him take you to the biggest mistakes he’s made and share what he’s learned. Don’t let him off the hook. Force him to get real with you. You’ll both be better for it. 

Regi’s track for mentoring men in small groups can be found at You can also follow Regi on twitter @radicalmentor.   


Six Reasons Mentors Tell "Failure" Stories: Guest Post by Regi Campbell