The Courage Your Team Is Waiting For You to Model
What’s the one courageous behaviour your company needs most right now?
I threw this question at a room full of leaders during my keynote on The Courage Advantage recently. I ran a live, anonymous poll—and within minutes, more than 200 leaders had weighed in. Here’s a sample of what they said:
- “Having the hard conversations.”
- “Acting with urgency.”
- “Failing fast—without fear.”
- “Letting go of outdated processes.”
- “Stopping work that isn’t delivering value.”
- “Admitting when something isn’t working.”
- “Making decisions without waiting for 17 approvals.”
Afterwards as I reviewed the data, five themes emerged.
- Truth-telling: Giving feedback that’s needed, not just safe
- Letting go: Of perfection, control, and “this is how we’ve always done it”
- Progress over polish: Moving forward even when the answer isn’t complete
- Trust over red tape: Trusting judgment on the ground over bureaucratic approval
- Smart risk-taking: Testing something new before feeling 100% ready
What have these all got in common? These behaviours fuel innovation, trust, agility, and growth. And they’re certainly not ‘comfortable’. Telling the truth? Risky. Letting go of control? Vulnerable. Acting without all the answers? Unsettling. Admitting something’s not working? Exposed.
In other words, courage doesn’t come wrapped in ease. It shows up in the tension, the stretch, the risk—and the decision to act anyway.
That’s why I believe we can’t talk about courageous cultures without talking about courageous leadership. Because systems don’t model values—people do.
What I Got Wrong About Courage
I used to believe courage was about getting comfortable being uncomfortable.
That was the premise behind my “Year of Fear”—365 days of deliberately doing things that scared me, from quitting my corporate job to start a company, to training for an Ironman with just 100 days’ notice. Even trying stand-up comedy.
And while it taught me a lot about pushing boundaries, my thinking around courage since then has shifted—on two big fronts.
First, I realised courage isn’t just about doing scary things. It’s about doing the right hard things—on purpose. Jumping out of a plane won’t help you give tough feedback to a colleague. Cold plunges don’t prepare you to call out a values breach in a team meeting.
Don’t get me wrong—I’ve jumped out of planes and still cold plunge regularly. But neither of those acts has put me in a better position to do the hard things I encounter on a week-to-week basis.
So do them, if you want to, but make sure you’re also building your courage where it really counts: in the small, uncomfortable moments that actually move the needle.
Like putting your hand up for a stretch opportunity. Or asking, “Why are we doing it this way?” or daring to suggest an alternative—especially when it goes against the grain.
Because that’s the kind of discomfort that grows your leadership edge and shapes culture.
Second, a conversation with Brené Brown earlier this year really reframed it for me.
She shared that she really dislikes the phrase “get comfortable being uncomfortable”—because some things are never going to feel comfortable, and nor should they.
Her example: If firing someone doesn’t gut you a little—if you’re not metaphorically curled up in the fetal position prior to having to do i—then you’re not the kind of leader she wants on her team.
She’s absolutely right. The hard conversations, the vulnerable calls, the decisions that impact people’s lives—those things don’t ever magically get easier. The goal isn’t to erase the discomfort. It’s to build tolerance for it.
“You can choose courage or you can choose comfort. You cannot have both.” – Brené Brown
I’ve had a number of these conversations with leaders who I consider to be brilliant at how they handle the hard stuff—who I watch deliver hard truths, delicate feedback and lean into the ‘wicked problems’ most run away from.
It’s easy to think they have somehow mastered the art of the ‘hard’ but they’re the first to stress to me that they don’t enjoy it or find it easy. They’ve just learned that discomfort isn’t the enemy of good leadership—it’s often the price of it.
How Rewarding Courageous Leadership Behaviours Shapes Culture
In today’s fast-changing world, courage isn’t optional. It’s the difference between organisations that evolve and those that get stuck.
But organisational courage doesn’t just hinge on individual bravery. It’s shaped by the systems and signals around us. The status quo gets reinforced by:
- What we reward (playing it safe over taking smart risks, agreement over dissent)
- What we recognise (the loudest voice, not the boldest idea)
- What gets walked past (behaviours that contradict our values)
- What we stay silent on (because it’s uncomfortable to challenge)
When these things go unchecked, they quietly teach people what not to do: Don’t question how things are done. Don’t speak up unless it’s safe. Don’t be the one who rocks the boat.
If we want more courage in our culture, we have to be deliberate about what we reward, recognise, and reinforce.
So, if you want more courage on your team, start by asking:
What behaviours am I rewarding, and what am I walking past?
Because if courage isn’t showing up on your team—it’s worth asking what might be standing in its place.
Are You Modelling the Courageous Leadership Behaviours Your Team Needs?
If someone in your team only observed your behaviour—not your values statement or strategy deck—what would they say is “acceptable” in your culture?
Would they say:
- It’s safe to speak up—even if the opinion is unpopular?
- It’s okay to challenge the status quo—or is it better to keep your head down?
- Mistakes are part of learning—or something to quietly avoid?
Here’s the challenge: Pick one courageous behaviour you want to see more of in your organisation. Then ask yourself honestly: Am I role modelling that behaviour consistently? Or am I unintentionally reinforcing the opposite?
Because the culture you build starts with the behaviour you walk past—and the courage you’re willing to show first.