There’s a moment that happens in almost every workshop I facilitate.

It usually comes on the first morning, when I ask participants to take a few minutes and think about a time they showed up with courage at work. Not the big dramatic version, not the moment they gave a speech or handled a crisis. Just a real, everyday moment when they chose to be honest even though it was uncomfortable. When they stayed in a difficult conversation instead of finding a reason to leave it.

I give them time. And then I ask them to share.

What I’ve consistently noticed across groups, industries, and levels of leadership is the silence that follows.

It isn’t that people don’t have stories. It’s that they’re searching for something that fits the definition. Something they feel confident calling courageous. And most of them come up empty, or they minimize what they do have: “I’m not sure this counts, but…”

That pause tells me something important.

I don’t think most leaders struggle with vulnerability because they’re unwilling. I think they’ve never been shown what it actually looks like in practice. They’ve been told to be authentic, to lead with empathy, to create psychological safety, and then handed almost nothing concrete to work with. So they default to armor. Not because they want to, but because armor is what they know.

What gets built in that gap isn’t indifference. It’s distance. Leaders who genuinely care about their teams but have learned to keep things professional, to stay composed, to solve instead of sit with discomfort. And over time, the people around them learn to do the same. They start reading the room, editing themselves, bringing only the parts of the conversation they think are welcome.

Teams begin adapting around what isn’t being said. That’s not a dysfunction; it’s a very rational response to an environment where vulnerability hasn’t been modeled as safe.

And no amount of a culture initiative changes that. What changes it is someone being willing to go first. To be, as Brené Brown puts it, the person in the arena.

That’s the work I do. And it’s why I’m so committed to the Dare to Lead™ workshops: we don’t just talk about courage. – We teach it.

We give leaders the language, the practices, and the lived experience of what it actually feels like to show up differently. To stay in the room when everything in them wants to armor up and walk out.

In August, Jamie Nau and I are co-facilitating a four-day Dare to Lead™ training in the Bay Area, August 27–30. Twenty hours of courage-building work, grounded in Brené Brown’s research, designed for leaders who are ready to move from knowing this work to actually practicing it.

If you’ve been sitting with that question, what would it look like to lead with more honesty, more presence, and more courage? This is the room for that.

I’d love for you to be in it.

You can learn more and register at ownyourleadership.org.