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The Paradox of Uncertainty (#162)


The Confident Leader


Daniil Medeved, the third ranked men’s tennis player, confessed to doubting his ability to beat his next opponent, Alcaraz, in the U.S. Open semi-finals last weekend. Did his confession put him at a disadvantage with Alcaraz?

“If a man will begin with certainties, he shall end in doubts; but if he will be content to begin with doubts, he shall end with certainties.”

— Francis Bacon (English philosopher and statesman) 

This Week’s Edition

Each of us experiences uncertainty about our leadership at some point. What we do in the face of that uncertainty is what creates the stories we talk about for years to come. 

Clarify Your Thinking

By staying content with being uncertain, Medvedev, played Alcaraz, and ended up beating him. It was an unexpected upset that proved Francis Bacon’s theory:

If [someone] will be content to begin with doubts, [t]he[y] shall end with certainties.

Few of us like uncertainty let alone allow ourselves to be content with it. We prefer to play in the claustrophobic box of certainty.

The problem… leadership doesn’t work that way. If you are leading from the front, you are on the frontlines of things we’ve never seen before. Uncertainty is the standard. 

Old Thinking: I’ve got to be certain that I can prevail or I want try. Otherwise, I think it is too risky. 

New Thinking: I’m not certain about my prospects. Should I even try? I think I’ve got to stay in the game and run the risk of losing. It’s possible I may find data that will resolve some of my uncertainty. 

Thoughts Lead to Actions

In my line of work as an Executive Coach, I talk with leaders who deal with uncertainty on a daily basis. Whether its a pressing issue or a challenging situation, those leaders are tentative, hesitant and perhaps even questioning their own judgement. 

To question yourself or to doubt your leadership is part of the territory. From my vantage point, it is a good thing. It means the leader is wrestling, thinking and engaging the difficulty.

The next time you are questioning your leadership, ask yourself these questions:

1. What’s the big question I’m wrestling with?

“Do I have the skills and ability to beat Alcaraz?”

2. If I move forward can I gain useful information?

“If I play him, I’ll know his game better and test my skills.”

3. What do I need to do to be content with uncertainty?

“I’m a good tennis player. I want to see how well I can compete against the best.”

While Medvedev ended up winning the match that is not really the point. The point is, he embraced his uncertainties in pursuit of certainty. He was going to get that certainty one way or another – win or lose. At that point, at least he would know.

Boost Your Performance

The character, Harold Abrahams, in Chariots of Fire is a runner who’s has always won his races. After his first loss, he says, “if I can’t win, I won’t run.” In this week’s video, find out how his girlfriend responded… leadership wisdom for the ages. 

What’s Your Opinion?

How do you arrive at being content with uncertainty? Share it with me at

If you are going to be a leader, you might as well be a good one. Don’t let doubt count you out. Have a confident week!

Robin Pou, Chief Advisor and Strategist

We live to make bad leadership extinct so forward this newsletter to others who strive to be confident leaders. 


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What is “The Confident Leader”?

During the Covid-19 Pandemic, I began a video series called “Panic or Plan?” It was designed to equip leaders to navigate the doubt they experienced and to rise in the confidence they needed to lead during turbulent times. It took off. I then started this newsletter to equip leaders in the same fashion each week for the doubt that crashes across the bow of their leaderSHIP.