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  • Writer's pictureMark Olivito

A Leadership Challenge: Stay Humble. Hustle Hard

Updated: Jul 3, 2022

Have you ever met a great leader that doesn’t exude confidence? Probably not.

But sometimes, like all great strengths, confidence can be over-played and it can creep into…

  • Confidence’s twin evil brother: Arrogance

  • Confidence’s twin evil cousin: Cockiness

I would venture to guess that Confidence, Arrogance, Cockiness are adjectives that are somewhat common among C-suite leaders in the eyes of those that matter most: The people they are supposed to lead. Ask anyone that has gone through a formal self assessment where peers weigh into various leadership characteristics and they can tell you how humbling the process can be.

Which brings me to another great graphic a friend shared with me recently.

If you believe that TRUST is critical to sound relationships, than what better characteristic could describe a leader than…


Not the typical word you hear when your thinking about titans of industry right?

But it IS possible to be humble, and also a driver with a healthy dose of confidence.

The great Tom Peters has 2 great concepts that inject a dose of humility in every leader

  • WDYT: Ask What do you think? Then shut up and listen.

  • MBWA: Management by wandering around. Get out of the ivory tower.

If both aren’t done daily, it will never become part of the leader’s DNA.

I’ll take this concept one step further.

How many mistakes does a leader make in a given month? I’m not talking about simple “errors.” I’m talking about real mistakes, that if we had the chance to go back in time and un-wind a decision or series of events, a better outcome would have resulted. If you are in the business of growth and pushing the envelope, then there should be a handful by definition.

Team “Contact” Drill:
  • Pull your management team into a lessons learned session of the mistake.

  • Take responsibility, OWN it. Explain what the person in the mirror could have personally done differently to create a better outcome.

  • Ask the team for their feedback, agreement, disagreement, other perspectives.

  • Ask the team for their thoughts, ideas, concerns on the road ahead.

  • Make some commitments

  • Follow-through

There’s no magic formula. But it’s a fact that leaders don’t do enough listening. That’s unfortunate, and it creates an environment that does not get the most of their teams talent.

There’s a thing about listening: It’s a skill. It takes practice.

Leadership is a CONTACT SPORT. However, sometimes the “contact” is not outward, it needs to be directed to yourself, with the people you lead. Thick skin optional, open mind mandatory.

The great Jim Collins has written extensively about this trait and he describes it as “Level 5 Leadership” in Good to Great. Here’s a great HBR primer on the topic:

Level 5 Leadership: The Triumph of Humility and Fierce Resolve

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