How Messing Up Makes Us Real Leaders

“I never lose. I either win or learn.”
– Nelson Mandela

Time and time again, in the early stages of a coaching or a leadership development relationship, I hear my clients speak of their “failures” with a tone of self-recrimination and regret as though they are forever doomed to drag the weight of a decision that did not go the way they want into all parts of their lives. Worse, somewhere they seem to have gotten the crazy idea that because they made a mistake that this somehow means they themselves are a mistake.


There’s actually dignity in falling down often: not only is it part of our human story to make mistakes, but it is also an essential part of our growth and the key ingredient to ultimate success.

Consider my dear friend (and a leader in his own right) whom I’ll call José. Even with being a sensitive, bright light full of good intentions, he, like so many of us, seems to be caught in a spiral of limiting results. We do something we are not proud of and because of that, we might make choices that further push our view of ourselves down and we label ourselves as lost causes so we end up making more unhelpful decisions. And the cycle continues.

Until, that is, we can begin to trust that maybe, just maybe, this messiness can serve a purpose. In fact, that’s the whole point of the messiness to begin with: to allow our discomfort with ourselves and our outcomes to show us how to get more comfortable and longer-lasting solutions. Seeing our mistakes (ours and those of others) as opportunities for learning and growth can cultivate self-compassion and boost self-esteem. This has a ripple effect of positivity – consider how challenging it is to show compassion towards others when we have a tough time giving it to ourselves.

Now reverse it – when we deepen our awareness and our willingness to practice self-compassion, we radiate this out to others as well.

The fact of the matter is that we all make mistakes. That’s part of being human.

But it’s how we handle them that defines our character. Do we beat ourselves up – and therefore miss the lesson contained within? Or do we breathe through those uncomfortable feelings, holding off on the self-shaming long enough to weed out the real learning here? The seeming failure can be opportunity in disguise – we actually improve our odds of future success by fully acknowledging and embracing it to both ourselves and others.

“The greatest mistake we make is living in constant fear that we will make one.”
-John C. Maxwell

To Hide – or Acknowledge – Our Errors?

It can be hard for us as humans to own up to making a mess of things. In fact, 67% of people actually hate admitting we’re wrong. Which is to say, in my book, that they’re afraid to acknowledge they’re not perfect.

By the way, have you ever been around someone who is so uptight because they’re trying to appear flawless? Not only is this super BORING, but it also creates anxiety in those around them. Who wants to be around Super Girl or Wonder Boy? We all have enough going on in our lives that when we interact with others, most of us are more attracted to those with self-awareness and integrity with whom we can just be ourselves. And this is next to impossible to be when we are filled with the anxiety of measuring up to someone else’s standards.

Any leader I have ever come across who tries to be perfect fails at the very art of leadership. Why? Because they are missing the point entirely: leadership is about inspiring people to grow and be more of who they are. How can we do this when we show every sign that we don’t think we need to grow (and learn) any more?

Team members don’t want to have to feel they’re walking on eggshells, fearful of making the slightest error. They want to feel supported on their journey towards becoming the best, most purposeful version of themselves. Blunders and learning are an integral part of that.

Odgers Berndtson Partner Silvia Eggenweiller casts some light on another version of mistakes.

“Our whole wealth of experience consists of the mistakes we have made.

We only become really good at something if we keep trying things out along the way, and sometimes fail ourselves.

Covering up mistakes, on the other hand, is usually much more expensive on balance than cultivating a good culture of mistakes.”

Berndtson labels failure a priceless opportunity.

And authentic leaders should see them that way as well.

Mistakes are Also How Innovation is Born

“A person who never made a mistake never tried anything new.”
– Albert Einstein

Tech companies, start-ups and smart consulting firms are leading the way in teaching all of us the value of failing…in fact, they very often have culture of “failing fast.” One innovative start-up I have recently worked with, for example, is creating something that has never been done before. At all. Given that no precedent has been set, how could they possibly have a successful end-product if they don’t allow mistakes to become a natural part of the creative process towards getting there?

The value in failing fast is that by making mistakes early on and learning from them off the bat, better, more impactful models can be built more quickly. In this way, errors have become a coveted part of their culture. Hearing more stories like this and broadcasting them can be impactful as well. Olga Rogacka writing in Success, lists common mistakes of leaders and cites individual case stories. Some of the common mistakes, among many others cited were:

  • Micromanaging
  • Correcting employee’s mistakes
  • Pushing too hard

In correcting employee’s mistakes, for example, one leader learned that instead of just fixing a mistake made by a team member, using it as a teaching moment gained far better results. Making it a coachable moment is not only far more effective than singling out or finger-pointing. It’s also way more compassionate for all.

Reading through other leaders’ experiences provides reassurance: they’ve made mistakes, too, and have used them to grow.

And that’s the attitude to take.

OK Leader – or Great Leader?

Writing in Inc., Lolly Daskal makes a defining statement:

“One of the ways you can tell a good leader from a great leader is how they handle their mistakes.”

Believing that a leader needs to set the right example, Daskal lists 4 basic ways we can define our leadership:

  1. Acknowledge where we ourselves went wrong, keeping the focus on our stuff.
  2. Learn the real lessons from mistakes and avoid repeating them.
  3. Share your learning with others so they can learn from your mistakes, too. That can cultivate an atmosphere of trust.
  4. Use your errors as a mechanism to move forward – not forgetting the error, but not allowing it to define who you are either. We are, after all, so much more than what we do.

Move beyond the stinking thinking that making a mistake is ‘bad,’ or ‘it’s my fault.’ Instead, embrace the lessons learned, move forward and, especially, give yourself grace.

“We all make them, the difference is what we do after we make the mistake, how we see the mistake – a learning experience or a failure.”
– Catherine Pulsifer

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