Failure Coaching for Leaders

This post is adapted from my upcoming book: Pitfalls of Fear Driven Leaders and how to Overcome


The “It’s OK to Fail” club has more and more members. Its adherents are industry leaders, sports figures, executive and life coaches, therapists and people with success stories because, truth be told, they almost all had to fail before their first quantifiable success. Beyond that, business and organizational development specialists know the vital importance of freedom from fear of failing in innovation and the formation of authentic, productive work environments.

The wonderfully titled John Maxwell book, Failing Forward has as its subtitle: How to make the most of your mistakes. Vlogger Chantelle Adams, in her video series “The Courage Revolution”,  has an episode entitled, “How to Fail Like a Pro”.

So failure is finally coming out of the closet and getting the honor it’s due!

To coach yourself or others in how to make the most of failure, here are some tips

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Just Jump! Why I Force Myself to Jump off the High Dive Board


Several years ago I realized that fear of conflict with certain individuals was holding me back from being the person I wanted to be. It was like fearing a shadow when the shadow appears 10 times larger than the actual object it represents.

So I did two things: First, I finally killed the tiger that had been dogging my dreams for years. I literally beat my dream tiger over the head with the butt of a rifle (because, of course, in dreams the bullets come out in slow motion) while yelling, “Die you stupid beast! Die! Die! Die!” When I woke up I exclaimed (to no one in particular) “I Killed the tiger!”

That was a landmark moment for my psyche. I started to wonder: what else can I conquer?

So the second thing I did – and continue to this day, was to force myself every time I swim at a local pool to jump off the high board at least once. I mean the 12 to 15 foot one that causes me to get vertigo when my fear of heights sets in.

What is it about that practice? It’s the act of continuing to climb and to walk without hesitation right over the edge of one of my creepiest fears. It means, yea I’m scared as heck but I’ll do it anyway. Hey, I survived it again.

There is something about this activity that has slowly rewired my brain to keep walking even when I’m quaking inside. Keep walking through to that difficult conversation that must be had. Keep walking through to that financial venture that may succeed or may bust. Keep walking through the many nay-sayers until I get to my one needed “Yay-sayer”.

Leadership and courage go hand in hand. That doesn’t mean you don’t gave to go through a process nor does it suggest you will eliminate fear. It does mean that you meet that fear with forward momentum.

T.D. Jakes said, “You cannot conquer what you will not confront”. This goes from conquering a fear of heights or of public speaking to being the first Chinese immigrant in your family to succeed in a multi-cultural environment to breaking barriers no one in your age group has ever broken through.

Do I still get scared up on that high board? You bet! I started doing this challenge late in life so the fear is hard-wired within me.

But fear no longer stops me. That is the victory.

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