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How I Failed as a Mentor…

I have mentored, to one extent or another, numerous professionals from earnest young go-getters looking to conquer the world to worried and displaced middle-aged workers looking for safe harbor. Mentoring isn’t easy; it’s an emotionally charged rollercoaster. To do it right, you can’t give your mentee the answers; rather you must gently guide them, as they learn and process the lessons.

From the outside looking in, I seem to be an unparalleled success, and I have many young people who have asked me to teach them the magic formula for success. For my part, I can never quite see myself as a success. There was a time when I wanted to be a supervisor, and once I was, I immediately wanted to be a manager, a director, a vice president and a CEO.

Success eludes the malcontent.

Similarly, I wanted to be a published author (not self-published, which to me is to being published as owning a home is to being a monarch), but once I was, I wanted to have 50 articles in print before I was 50, and so on. I fear that success will forever elude my grasp not because I can’t reach it, but because having done so, it is no longer success. Therefore, it is always with rue that I address those who ask me the secret to my success, but I have yet to turn down a request to mentor anyone.

Related: Why Entrepreneurs Need Mentors and How to Find Them

Recently, I failed miserably mentoring a young professional. It’s said that youth is wasted on the young, and I think a lot of the bashing millennials get is jealousy from those grown old who are seeing the best years behind them, while looking down the loaded barrels of living in an old folks home and learning to love BINGO. Yet, I take full responsibility for the failure of mentoring this young gentleman.

Failure surrounds us all.

My first mistake was not recognizing him for what he really was. It’s an immense ego stroke to have someone say, “I want to be you. Will you teach me?” So, blinded by my own narcissism, I set out to teach the young man what he needed to know. But it was soon obvious that he didn’t really want to learn how to achieve what I have achieved, rather, he wanted a magic potion that would turn him into me. He thought he knew what it meant to “pay your dues” but he constantly asked questions like, “Can they make me do that?!” When told they can, do and will, he would sulk and say “Well, I’m not putting up with that.”

I had mentored (very successfully for the record) a different young man with similar ambitions. But with him I made it clear: The point of paying your dues is to learn everything you can about business and management; what to do, and what not to do. Unfortunately, I was never able to convince the second young man that patience is a virtue. The difference between these two was striking. The first was always complaining about how someone had victimized him, stolen his ideas or wronged him, in some way.

The second was full of excitement, even when he was working with bosses with the brains of a seagull. He used his time to make important contacts and to build a network. The first used his time to lip off to supervisors and drift from job to job. When the first mentee festooned his Facebook page with pro-Trump rhetoric, I sagely warned him against politicizing his brand. He went off on me with such vehemence that not only did I drop him, but so too did many others.

Related: How Complaining Rewires Your Brain for Negativity

The mentee mental space will out.

So what did I learn from all this? Well for starters you can lead a horse to water but you can’t make it think. I could provide the best advice (I effectively advised both the same way), but if the mentee doesn’t want to listen and learn, it is all for naught.

Secondly, I learned that if the person you are mentoring sees you as the sole source of learning you will fail. Hero worship is not conducive with true learning; it’s not a mentorship, it’s the beginning of a cult. You can’t be the source of truth for someone you are mentoring; for mentoring to work the mentee must push back and question the advice. Not in a confrontational and dysfunctional way, but in a way that challenges your beliefs and forces you to rethink your most cherished pearls of wisdom.

Related: Great Leaders Get Their Wisdom Through Reciprocity, Risk, and Respect

Finally, I learned that the mentor cannot want success that is beyond the dreams or reach of the mentee. If the mentee is always going to be the guy in the workplace complaining about how unfair the new HR policy is or how big a jerk the CEO is, or…well you get the picture, the mentee has already established barriers he or she will never overcome with or without your help.


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