The Confidence Crisis Is Costing You

Education Is Freedom.  

Jim Keyes saw that on a student’s shirt while teaching at business school, and it later became the title of his book. The former 7-Eleven and Blockbuster CEO joined me on the Learn-It-All podcast™ to talk about what that idea means for today’s leaders.  

Education means freedom from fear. Freedom from being a victim to irrationality. Learning teaches the brain to bypass the human fight-or-flight response with knowledge and experience. In its wake, it gives a person confidence that they can use their knowledge not only to grow, but to navigate challenges.

We spend a lot of time in leadership conversations talking about confidence like it's a fixed trait: you either have it or you don’t.  We chalk up leadership criteria to some intangible quality that's hard to define.

But confidence is not a personality trait. It's a skill. And like every other skill, it can be developed. The question is whether your organization is actually doing the work to develop it.

We Are Setting Our Leaders Up to Fail

The data on this is sobering, and if you are a CHRO or L&D leader, it might be uncomfortable to read.

Wharton found that 59% of managers received no formal training before stepping into their role. The next domino to fall should be no surprise: 60% of those new managers fail within their first 24 months. And a 2024 global study by Harvard Business Publishing, surveying more than 1,100 L&D professionals across 15 countries, found that 70% say leaders must now master a wider range of behaviors than ever before to meet current and future business needs.

We are promoting people into the most interpersonally complex roles of their careers, handing them almost no preparation, and then wondering why they struggle.

Here is the part that frustrates me most. The people we promote into leadership are typically the best at what they did before. The top salesperson. The strongest engineer. The most productive individual contributor. Technical excellence is often what gets you the job. But technical excellence has almost nothing to do with what the job actually requires once you have it.  

Managing people, building trust, making decisions under pressure, inspiring a team through uncertainty: these are learned skills.  

When we skip that development, we are setting leaders and their teams up to fail.  

Your Leaders Are Already In The Cockpit. Did You Train Them For It?

You’re at cruising altitude and then you hit a rough patch of turbulence. Even in first-class, all you can do is hope that the pilot can handle it. They always do.

But how do they get there?

Jim is a licensed pilot. He flies jets, solo, at 45,000 feet above commercial airliners. And every year, he is required to spend three days in a simulator where instructors try to kill him.

Not literally. But close. Wind shear. Engine fires. Emergency decompression at a simulated 40,000 feet with ten seconds to get his mask on before losing consciousness. Every catastrophic scenario they can manufacture, they throw at him.

Why are they doing this?

"They are reprogramming my brain," he realized. "Training me to replace fear with knowledge."  

When something goes wrong in that cockpit, Jim doesn’t panic. He reaches for his checklist. He works the problem. He has bypassed his amygdala entirely and gone straight to his prefrontal cortex. Data over fight-or-flight.

That is neuroplasticity in practice. The brain, rewired through repeated experience, to respond to pressure with capability instead of collapse.

When your managers face their first difficult conversation, their first team crisis, their first moment of real pressure, are they more likely to operate from fight-or-flight, or are they more likely to rely on knowledge and experience?  

This is where most leadership development falls short.  

Real development works like that simulator. It creates pressure in a safe environment. It builds reps. It trains the brain to reach for knowledge when instinct would otherwise take over.  

Leadership training should be designed not just to teach, but to rewire, so that when the moment comes, your leaders are already ready for it.

Confident Leaders Want To Take The Swing

In 2007 Jim Keyes walked into one of the most impossible situations in American business history. Blockbuster. One billion dollars in debt. A third of it due within two years. Activist shareholders circling. The entire media industry in the middle of a seismic shift. And then 2008 hit, and Lehman Brothers collapsed, and the world changed overnight.

He was ready to walk away.

Then at a dinner at Bill Gates' house, he ran into Warren Buffett. Jim lamented that the situation at Blockbuster was impossible. Then Buffett asked him a life-changing question: "Would you rather be on the bench or at bat?"

For Jim the answer was clear. Re-engage.  

Even exceptional leaders hit walls. The difference between those who recover and those who don't is rarely about raw talent. It is about whether they have the knowledge, the preparation, and someone in their corner who believes in their capacity to learn their way through it.

AI Exposes Organizations That Stopped Investing in People

Here is what I keep coming back to when I talk to HR and L&D leaders right now. The conversation about AI in the workplace is almost always framed as a technology problem. Which tools to adopt. Which workflows to automate. Which roles might be affected.

But underneath all of that, AI is a confidence problem.

Here are the numbers:

According to McKinsey's Superagency in the Workplace report, 48% of employees rank training as the most important factor for AI adoption, yet nearly half report receiving minimal or no training at all. People are being handed the tools. They are not being prepared to use them. And without that preparation, adoption becomes anxiety.

We are on the cusp of the biggest technological transformation in human history, and the difference between organizations that thrive and organizations that fall behind will come down to how their people respond to change. And how people respond to change depends almost entirely on whether they have the confidence to engage with it rather than retreat from it.

You Can’t Hire Your Way Into Confidence

Confident leaders are not born. They are built. And they are built through deliberate, sustained investment in learning.

That means treating development as a core strategic function.  

In practice, it looks like this:  

Programs that create real pressure in safe environments.  

Managers who join their teams in training and model their learning.

Cultures where admitting you do not know something is treated as a strength rather than a liability.

Leaders at every level who understand that curiosity is a competitive advantage.

The 10-Minute Confidence Audit

Real leadership development takes time and practice. But the first step toward building that confidence can start much smaller. You just need ten minutes and something to write with.

Find a quiet spot. Open a notebook or a blank document. Answer these three questions as honestly as you can.

Where in your leadership role do you feel least confident right now?  

Hint: Don’t answer with what you think you should say. Answer with what keeps you up at night. The conversation you have been avoiding. The skill you know you are missing. The situation where you feel your fight-or-flight kick in before your judgment does.

What knowledge or experience, if you had it, would change that confidence level for the better?  

If you felt genuinely prepared for that moment you identified, what would you have learned, practiced, or experienced to get there? Name it specifically.

What is one thing you can do this week to close that gap?  

One thing. A conversation you could initiate. A skill you could start learning. A person whose perspective could help rewire how you see the challenge.

That is it. Three questions, one action, ten minutes.

The leaders I admire most are the ones who never stop asking these kinds of questions. And over time, that habit becomes the most durable form of confidence there is.

Stay curious. Keep learning.