All Episodes  172: Will Steel | Authentic Leadership Is a Lie
172: Will Steel | Authentic Leadership Is a Lie

172: Will Steel | Authentic Leadership Is a Lie

Will Steel is a leadership coach, former Royal Air Force pilot, international best-selling author, and host of the Free to Lead podcast. In this episode of The Prestigious Initiative, Will challenges one of the most common myths in modern leadership: that people should simply “be authentic.” Drawing from decades of coaching executives, athletes, and entrepreneurs across 26 countries, Will explains why most leaders operate from unconscious patterns rooted in approval-seeking, fear, and outdated identity. He breaks down how these hidden dynamics quietly sabotage performance, decision-making, and fulfillment. Together, Chris and Will explore what authentic leadership actually means, how to dismantle ego-driven behavior, and how leaders can reclaim clarity, agency, and inner authority. This is a deep, practical conversation about leading without masks, excuses, or external validation.

The Prestigious Initiative The Prestigious Initiative
Apr 15, 2026
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The Mask You Forgot You're Wearing

You know the feeling. You're in a meeting, talking to a colleague, or maybe just ordering coffee. And a voice in your head pipes up: What do they think of me? Do I sound smart enough? Am I coming across the right way?
You're not being fake. You're just... adjusting. Slightly. Shaping yourself to fit the moment.
Here's the problem: most of us do this so automatically, we don't even notice anymore. We've been pretending for so long that we've forgotten we're wearing a mask.
My guest today, Will Steel, has spent over two decades helping leaders peel that mask off. A former Royal Air Force pilot, international best-selling author, and host of the Free to Lead podcast, Will brings a unique perspective to the table. He doesn't buy the popular "just be authentic" advice. In fact, he thinks most people aren't authentic at all.
"People are pretending, and they're pretending that they're not pretending. And it's kind of unconscious."
Today, we're diving into what real leadership looks like—how to drop the ego, stop seeking approval, and actually show up as yourself.

The Day Will Learned to Be Himself

Will's journey to understanding authenticity started in one of the most structured environments imaginable: the Royal Air Force.
"When I went in, I had a certain picture of what an officer and leadership looked like."
He got advice from those who'd gone before him: keep your head down, stay out of trouble, don't be mouthy. Just get through officer training so you can start flying.
So Will did exactly that. He stayed quiet. He didn't speak up. He was a ghost.
After 16 weeks, his flight commander called him in.
"She said, 'You're like a ghost. I can't recommend you for graduation. An officer has to speak up, man, and take command.'"
She gave him two choices: leave the Air Force or do the course again.
Will was devastated. His friends were about to graduate, and he was going back to the beginning. But in that moment of defeat, something shifted.
"I thought, you know, I've been trying to be what I thought I'm supposed to be like, and it isn't working. So screw it. I'm just going to be myself."
He stopped performing. He stopped pretending. He just showed up as Will.
Eighteen weeks later, he graduated with the leadership trophy.
That's the paradox. Trying to be what you think a leader should be makes you less effective. Being yourself—the real you—is what people actually follow.

The Pretending-Not-Pretending Problem

But here's where it gets complicated. As Will pointed out, "being yourself" isn't as simple as it sounds.
"Once you get more deeper and more philosophical, you go, well, which self? Who are you?"
This is the ancient question, and it's at the heart of Will's work. Most of us have built an identity over decades—layers of coping mechanisms, protective strategies, and stories we decided about ourselves when we were too young to know better.
"In an early moment in life, something happens. And when this thing happens, you make decisions about yourself, about others, and about life. That then starts to shape, you know, 'I'm not good enough.'"
Will shared his own story. His dad once told a family story about how they couldn't afford a third baby, were hoping for a girl, and then Will "popped out." Everyone laughed. Will didn't.
"For me, how I heard that was they didn't want me. And they really didn't want me. They wanted a girl. I just had this declaration: I'm the best."
That declaration drove his entire life. Trophies, ribbons, becoming a pilot—none of it ever fixed the feeling underneath. Because the feeling wasn't about the accomplishments. It was about a story he'd made up as a child.
"Whatever you accomplish, it never fixes that thing inside of you where you feel what you felt when that thing happened when you were little."
This is why so many high performers feel empty despite external success. They're trying to solve an internal problem with external solutions. And it never works.

The Observer and the Reactor

So how do you actually do the work? How do you start seeing the difference between the real you and the automated programs running underneath?
Will introduced the concept of becoming the observer.
"If you can actually be that observer, you're going to start to get an experience of who you really are."
He gave a simple, powerful example. Walking his dog in London, he saw a woman and had an automatic thought: God, she's fat.
"That was the thought that was automatic. And I go, wait, that's not me. That's not how I'm committed to being. I'm not having that. Let that go."
Years ago, he might have gone into a whole internal dialogue about that person. Now, he catches it, recognizes it's not who he wants to be, and lets it drift away.
"If you can't catch it, you've got to catch that stuff. That's like, that's disgusting. That's not me. That's not what I'm committed to."
This is the gap between reaction and response. Between being a puppet to your automatic programming and being a conscious chooser.
I connected this to something I've experienced in martial arts.
"When you are in the ring sparring with somebody, when they stop moving, they're thinking. And as soon as they start moving again, then they're going to act. When they stop moving, that's when you start to move."
The same is true in conversation. When someone's eyes drift up, they're in their head. A good leader notices. A great leader pauses and waits for them to come back.

Performance Driven by Ego vs. Clarity

One of the most powerful distinctions Will made was between performance driven by ego and performance driven by clarity.
When you're reacting from ego—feeling threatened, needing to look good, defending yourself—you're just a puppet. Someone pulls a string, and you dance.
"If you're functioning from a reaction right now, like a threat or you feel like somebody's out to undermine you or they're out to make you look stupid, you're now in a reaction. There's not going to be as powerful as being able to go, wow, oh, just got a reaction. Okay. And this is what we're doing."
The alternative is clarity. Seeing the situation as it is, not through the filter of your old wounds. Being present enough to actually listen.
Will shared a practice that sounds terrifying but is incredibly powerful.
"Every time you drift off when somebody is talking to you, see if you can say, 'I'm so sorry. I drifted off then. Can you say what you said again? I really wasn't listening for the last 10 seconds.'"
Most people are terrified to do this. They think they'll look stupid. But the opposite is true.
"They don't. They just literally go, oh, okay. And then they go back 10 seconds into the conversation. People are great."
Meanwhile, the person who pretends they were listening has now lost the thread entirely. They're not present. They can't help. They can't lead.

The Green Beret and the Mortar Attack

Near the end of our conversation, Will shared a story that stopped me cold.
He was leading a program with a Green Beret sergeant who'd spent 11 years back-to-back in combat. This guy had lost so many people. During an exercise about fear, he came to Will and said, "I can't feel anything, man. I have no feelings. I'm like dead inside."
They spent the meal break digging into what happened. The soldier recalled one specific moment. He heard someone call in a mortar attack—on their own position. He stood up, took two paces, and then the mortars dropped. Six of his guys died. Many more were injured. He was okay.
And he'd spent years believing it was his fault. That he should have said something. That he killed them.
Will asked him a simple question.
"Let's say you had said something immediately, and everybody could take two paces. Do you think it would have made a difference?"
The soldier thought about it. "No. I mean, we all still got blown up."
"Exactly. So did you kill them, or did those mortars kill them?"
In that moment, the story broke. The soldier realized he'd been carrying a weight that was never his to carry.
"He came in the next day and it was like smiling. He goes, 'I just got, I can be happy.'"
This is the power of doing the work. Not analyzing for years. Just seeing the difference between what happened and the story you made up about it.

Freedom Through Awareness

Will's parting message stayed with me long after we finished recording.
"Freedom doesn't come from becoming more impressive. It comes from becoming more aware."
You can accumulate titles, money, and accomplishments. You can have everyone around you calling you successful. And you can still feel empty.
Because the external never fixes the internal.
The only way out is through. The work of seeing yourself—your patterns, your reactions, your old stories—and realizing they're not really you. They're just programs you picked up along the way.
And once you see them, you have a choice.
That's real leadership. That's freedom.
You can find Will Steel and his book Free to Lead through his website and on LinkedIn. And if this episode challenged you, share it with someone who's serious about growth.
Until next time, stay intentional. Stay disciplined. And keep leading from the inside out.
The Prestigious Initiative
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