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Prepare or Just Wing It? (#127)

The Confident Leader

Most leaders have mastered the art of being able to wing it – think quickly and perform in the moment. However, when they do have the time to prepare they often stick to just winging it. This leaves them performing below their potential. 

One important key to success is confidence. An important key to confidence is preparation.
— Arthur Ashe (American Tennis Player)

This Week’s Edition

The game is won in practice. What areas of your leadership require greater preparation for you to perform you best?

Clarify Your Thinking

“Robin, one of my goals this year is to really improve my quarterly town hall meetings with my entire staff,” said Rick, the CEO of a business he founded about a decade ago.

“Great. What is your current approach? 

“I just wing it,” he said.  

“Well, is that approach working?” I asked.

“No. I feel like I fumble with my words. I don’t get to say everything that I want, and the days leading up to the event make me anxious.” 

“Have you thought about preparing in advance?” I asked.

“I have, but I don’t want to come across as overly rehearsed. Plus there is always new information coming in at the last minute that I want to include.”

Rick’s thinking that preparation will inhibit his performance is standing in the way of him actually preparing, but his lack of preparation is producing a subpar performance that is less than his full potential as a leader.

Old Thinking: I don’t have time to prepare. Plus if I did prepare I would come across too rehearsed. I’ll wing it and see what I get.

New Thinking: Maybe winging it for important leadership performances isn’t the way to go. If I prepare, maybe I can improve. My team deserves my best.

Thoughts Lead to Actions

For leaders, being able to handle uncertain situations in the moment is often a requirement of the job, and leaders need to be skilled at the art of “winging it” in those situations.

However, when your best is required, preparation is essential. It takes time, and you have to know how best to prepare for the situation: media training, keynote speaking, town hall meetings with your whole team, earnings calls, investor presentations, etc…

Think about these three things to take your leadership performance to the next level:

  1. Determine which type of leadership performance you want to improve.

  2. Identify the expert in that area, i.e., media training consultant, keynote speaker coach, online presentation guru, etc…

  3. Determine how you can access the expert’s expertise: read their book or hire them.

The pandemic put most leaders in a highly reactive mode. There wasn’t really any time to prepare, only time to respond to the daily onslaught of our evolving circumstances. Break the reactive cycle by choosing those areas of your leadership life where you can spend time preparing. 

Boost Your Performance

Dedicate yourself to being the best leader you can be. Your team deserves your best. Learn more in this week’s video about how a process to prepare will send your confidence soaring for your next leadership performance. Make 2023 your best leadership performance year ever.

What’s Your Opinion?

Which part of your leadership do you want to improve? 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.

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