image of a foam coffee cup with brown outer sleeveThe Leadership Caffeine series is over 200 installments strong and is dedicated to every aspiring or experienced leader and manager seeking ideas, insights or just a jolt of energy to keep pushing forward. Thanks for being along for the journey!

The true test of your leadership character isn’t measured by the absence of mistakes, but rather by the mistakes made in pursuit of growth and learning AND how you conduct yourself once you’ve made a mistake.

Show me a mistake-free leader, and I’ll show you someone hiding from the real issues confronting the business: people and strategy.


People are complicated. In spite of the myriad of assessment tools at our disposal, selection is still a judgment call with all of the inherent risks and biases of human decision-making. And the challenge of aligning skills and experiences with tasks while searching for that spark that stimulates people to work at their creative best is truly much more art than science.

You will make mistakes on people. Make them for the right reasons. Taking a chance on good people for the right reasons is worth the risk every day.

Remember, character always gets a positive vote. After a certain age, character is formed and nothing you can do will alter someone’s core character. You cannot change someone. Assess character carefully. Look for behavioral examples around values, and if the view is dissonant, it’s a non-starter.

Passion and desire are powerful reasons to take a chance on someone, even if others around you suggest this person isn’t right for a role. I like betting on the underdog if I’ve done my homework on the individual. Taking chances on people who show that extra spark is part of the essence of leadership. Much like character, you cannot teach passion, you can only help it emerge.

The greatest rewards I’ve enjoyed as a leader come from those people I selected against popular wisdom because I saw something. Of course, “something” is hard to codify and I’ve been wrong here as well. It doesn’t mean I will stop taking chances.


Much like the challenge of selecting and inspiring people to apply their talents, strategy is filled with ambiguity and uncertainty. Choosing what to do and importantly, what not to do is a core management task, yet human judgment in all its brilliance and all of its flaws is once again at the center of strategic decision-making.

Even in our data-driven world, selecting and then executing a strategy is like walking through a minefield on a fresh lava-flow blindfolded. There’s a high probability that somewhere between choice of path and the journey down that path, you will misstep with painful results. Assuming the essence of the strategy is sound, often, you can recover, adapt and proceed from execution missteps. These non-fatal errors are powerful learning experiences, teaching you and everyone around you how to spot gaps, fill in blind-spots and redouble efforts to get execution right.

While many view strategy as an event, with an outcome that is carved in granite and the granite set in concrete, in reality, it is effectively a testable hypothesis backed by a series of experiments. In a military metaphor, you engage in a series of skirmishes designed to test defenses and learn terrain, and then you push to conquer the ground. These skirmishes are the teaching experiences and your mistakes here are part of the process of figuring out how to get it right. The only mistake is not to decide to take action.

The best leaders I’ve worked around understand the need for the missteps. No one actively seeks them out, but they are an inevitable part of the pursuit of success.

The Bottom-Line for Now:

The least interesting professionals to me are those who cannot articulate a litany of mistakes on their way to their successes. The absence of mistakes…or, the unwillingness to admit prior mistakes is a character flaw and as mentioned above, there are no compromises when it comes to character. There’s no guarantee that some of your own mistakes won’t have painful consequences. Nonetheless, the mistakes made for the right reasons…in favor of great people and in pursuit of business success, are simply tickets to admission. Pay the price, take your lumps, learn and keep moving.

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An ideal book for anyone starting out in leadership: Practical Lessons in Leadership by Art Petty and Rich Petro.