My flesh and my heart may fail, but God is the strength of my heart and my portion foreverPsalm 73:26

 This is a practical topic for every mentor (and mentee).  When I met with the very first man I agreed to mentor years ago, I told him a couple of things up front.  One of them was that it is a lot easier to learn from the mistakes of others, and that I had made 100’s of them.  I had a lot to tell him.

When people approach me about mentoring, I usually tell them that one of the key ingredients to being a successful mentor is to put your pride in your back pocket and take a large dose of humility daily. Just like a vitamin, humility goes a long way to forge a relationship with the next generation.

Mentoring is not about just sharing your successes in life. By most standards, the typical mentor has had some level of success in his or her career. But all  have learned from their mistakes and most have been helped along the way.

The best mentors are willing to share their failures as illustrations of what can go wrong. I was asked to speak to an MBA class at the UNC Kenan-Flagler Business School years ago.  The class was about commercial real estate, and I asked the professor, Tony Ciochetti, what he wanted me to talk about.

His answer surprised me.  He wanted me to talk about real estate deals that went bad, and the reasons that they went bad. It was intended to provide context to his students that not all projects or developments are successful.

From my own experience, I came up with 10 projects where things went wrong, or were based on assumptions which turned out to be incorrect, leading to some very difficult workouts.

The session with the MBA students went well. They learned that you can plan for a lot of things, but you can’t plan for everything that might happen during a project that might take 2 years to complete.

One is prudent to consider tax consequences, but but having all of the rules altered in the middle of the project by a change of law can result in drastic changes to the outcome. That actually happened in 1986.

Shifting back to mentoring, I have commented many times that every relationship has at least four levels of communication. These levels are separate and usually are done sequentially. The levels are:

  • Fact – sharing a fact such as “today is Wednesday”.
  • Opinion – sharing your opinion about a topic such as “Wednesday is the worst day of the week”.
  • Feeling – sharing your feelings such as “I hate Wednesdays”.
  • Transparency – Sharing that “I have difficulty with Wednesdays because it reminds me of my father’s recent death”.

As noted, rarely does one get to the transparency level. Women reach feeling much faster than men, and most men get stuck at communicating at the opinion level. Think about your conversations with your friends, and I think you will realize how accurate this is.

Most conversations are not done at an authentic and transparent level at the beginning  Part of that, I think, is that we fear being vulnerable and admit our insecurities and mistakes. Also, men are brought up in a culture where the mantra is to “never let them see you sweat.”

Why is this important? Well, one of the highest values of the next generation is that they crave authenticity. They want to interact with people who are real with them and willing to share their lives – both the good and the bad.  That, of course, requires mentors to develop an ability to be transparent.

Regi Campbell writes a weekly blog for Radical Mentoring. I’ve attended one of his annual workshops in the Georgia mountains, and admire what he has accomplished, although he admits it took over 10 years to gain a foothold with his process.

In a recent blog, he observed that the intensity of young people increases when your stories are about failure you have experienced.  They don’t take well to what he calls “victory laps” which often looks like self-promotion than being authentic. I agree.

Regi ascribes the power of “failure stories” to the following (I have added one at the end):

  • Authenticity – Your failures taught you lessons of what you did wrong and what you learned, as well as what you would do differently the next time. Mentees can’t get that information from any other source. They see you as real and authentic, and become more willing to listen to other stuff.
  • Approachability – You drop your guard by telling them that you aren’t perfect yet you managed to succeed despite your own shortcomings. It is an expression of humility which goes a long way to being more accessible.
  • Emotion – Regi suggests that all decisions are made at an emotional level. Most meaningful learning is the result of engaging ones’ emotions, including emotions of pain, embarrassment or remorse when things go badly.
  • Value – Mistakes are costly, thus valuable because it leads to wisdom gained from a painful experience. There’s value in that.
  • Believability – Most mentees won’t connect with your success stories – they can’t relate to your achievements, but they can relate to your shortcomings. They can see that their success can be accomplished despite setbacks and failure along the way.
  • Challenging – Young people look up to a leader who shares his failures and shortcomings. It may be the start of helping them believe in themselves and realize their own potential. They also see “the chance to stand on the shoulders of one who’s gone where he wants to go.”
  • Transparency – Sharing personal failures gets the level of communication past Fact, Opinion and Feeling in a hurry. If you are willing to show humility and transparency, your mentee will develop trust and be transparent in return.

The challenge is pretty straightforward.  Mentors need to be willing to express humility and vulnerability to their mentees.  They want to know that you messed up, and that you learned from your mistakes.  They will make their own mistakes, but possibly not the same ones you did. In addition, you will develop an ability to communicate at a deeper level.

Secondly, every failure I have experienced is part of my faith journey. With few exceptions, I have found scriptural verses or biblical stories that I have found which have shown me how God has used my failure to grow me to be the person He wanted me to be.  I am always quick to share the spiritual side of my journey to my mentees.

MENTOR TAKEAWAY:   Don’t hesitate to share failure stories. It’s actually part of your faith story.  No one ever succeeded without setbacks along the way. If you don’t share your rough spots, your mentee won’t either, and your mentoring will suffer.

WORSHIP: Listen to Amy Grant sing “Better than a Hallelujah” which reminds us that God is with us through our successes and failures. One line is “Beautiful the Mess We Are”:  Better Than A Hallelujah – Amy Grant – Vevo

 COMMENT:  I would be delighted at comments on this or any other post. You can comment by clicking on the icon at the top of the page, or emailing me at  SUBSCRIBE:  You can receive an email notice of each post by clicking on the icon at the top right corner of the site (  and entering your email address.











3 thoughts on “Failure

  1. Thank you sir for these insights, sometime ago, l believed that being silent about my failures will earn me the respect of those l mentored, until one day, due to ill health l missed a session with my mentees, another leader decided to discuss my failures. I didn’t know until several weeks after, but surprisingly, my mentees didn’t show it, they seemed to honour me more, knowing I had failed, but God had raised back up gloriously. From that experience God delivered me from Shame and feelings of fear that my past would hinder my role as a mentor.

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