The Compassionate Leader's Companion Series #1: The Leadership Trait You Can’t Fake Or Skip: Why Courage Comes First

By Laurel Donnellan, Sarah Feely, and Darryl Brown (Originally published at Forbes.com)

In a world that rewards speed, scale, and certainty, the most transformative leaders share one foundational quality that doesn't show up on any balance sheet.

I've been in leadership development long enough to know that most organizations don't have a courage problem — they have a naming problem. We dress it up in strategy decks and OKRs, we talk about innovation and disruption, but we rarely say the quiet part out loud: real transformation requires the willingness to be uncomfortable, be wrong, and sometimes be alone in your conviction. That willingness has a name. It's courage, and it has to come first.

That's why courage is the first of the 12 principles in the Donnellan Leadership Method, and it's why I recently sat down with two of my favorite humans — Sarah Feely, Chief Learning Officer at Compassionate Leaders Circle, and Darryl Brown, Board of Trustee at Fordham University, Faculty at Compassionate Leaders Circle and a veteran media executive — to explore what courage actually looks like across a lifetime of leadership.

We didn’t arrive at courage as Principle One by theory alone. Years ago, I was conducting quantitative interviews for what would eventually become this framework. I sat down with a remarkable casting director and acting coach who fought her way into show business through sheer force of will — eventually landing casting roles in major motion pictures despite not having a background or connections in the business. We had a long, rich interview about how she navigated her career. Three days later, she called me back. She said she'd forgotten to tell me something essential: Courage has to come first.

That was it. That was the moment. We put courage first because of her. And it has been a recurring theme in every Forbes post interview, leadership change model, and project we have completed since. 

Courage Is the Ticket on the Transformation Train

Feely, who brings both the precision of a trained facilitator and the instincts of a natural leader to her work, put it simply when we spoke: "Courage is the ticket on the train. You can do a lot of work and a lot of thinking, but if you don't access courage, not a lot of really transformative stuff can actually happen."

She's right. And in my years of working with leaders across industries, I've watched brilliant, well-resourced, well-intentioned people stall at exactly this threshold. Not because they lack strategy. Not because they lack talent. But because they haven't yet made the internal decision to be courageous — to promote what I call responsible risk.

Responsible risk is what separates the visionary leader from the reckless one. It's the space between being completely risk-averse and putting your people in unnecessary danger. It's going to the rally knowing there are risks, but going anyway — with training, with support, and with clarity about what you're walking into. In our conversation, Brown reminded us that Martin Luther King understood this. He didn't send people into the streets unprepared. He gave them tools, community, and strategy. That's what real leadership looks like.

Alignment: The Inner Architecture of Courage

One of the most powerful moments in our conversation came from Brown, who has spent decades in media executive roles and brings a deep spiritual intelligence to his understanding of leadership.

Brown described what his 95-year-old Jesuit spiritual advisor calls the alignment between head, heart, and hands: "What's going on in your head needs to be in sync with your heart before your hands go out and do. And when that happens, there is a flow." He continued, "When you have the courage to go out and stand by what that alignment is pushing you to do — therein lies freedom."

This is the thing most leadership programs miss. They train the head. They occasionally touch the heart. But courage lives in the integration of the two — and it acts through the hands. Muhammad Ali, whom Brown spoke about with visible emotion, didn't just believe the Vietnam War was wrong. He said so publicly, at age 25, at the peak of his boxing career, at enormous personal and professional cost. He was stripped of his heavyweight title. He risked imprisonment. He did it anyway, because his head, his heart, and his convictions were in alignment.

For the leaders I work with, I often find that the biggest barrier isn't uncertainty about what to do. It's the gap between knowing and doing. Courage is what closes that gap.

The False Self Is Costing You More Than You Think

Brown introduced a concept during our conversation that I want every leader to sit with: the true self versus the false self.

"The false self is driven by ego," he said. "It's the one that says I can't step out, I can't take a chance. And the true self is the authentic self. When you're in alignment — head, heart, and hands — you don't have to be in the middle of the herd anymore. That's the freedom I feel."

The false self is expensive. It's the leader who doesn't give honest feedback because they're protecting their likability. It's the executive who scales back a bold idea because the board might push back. It's the manager who can't let their team fail — and therefore can't let them grow.

Compassionate leadership asks for something harder: not just for you to be brave, but for you to help others be brave. As I've put it, the shift from visionary individual to true leader is from "I'm the creative, I'm the decision-maker" to "how do I empower others to find their courage, their creativity, their voice?" That's the real work, and it doesn't happen without courage as the foundation.

Hope Is Not a Strategy — Until You Make It One

We also spent real time on hope, which is inextricably linked to courage for me. Feely shared data from the World Happiness Report showing that the two societal factors most correlated with positive emotions were people's sense of freedom and their sense of being surrounded by generosity. Not GDP. Not status. Freedom and generosity.

When I think about what keeps me going — what makes me believe, despite everything, that leaders can choose a different and better way — it comes back to action. Jane Fonda, whom I had the privilege of hearing speak recently at 80 years old, said it plainly: “Hope comes from action.” Sometimes we need to act our way into good thinking.

Brown’s invitation for the road: "Spend time alone and reflect on the good you can do — and then have the courage to go out and do it. Look at it through abundance, not scarcity."

That is, the entire foundation of compassionate leadership. Courage isn’t a personality trait you’re born with or a competency you check off a list. It’s a daily practice. It’s giving constructive feedback to a superior when you would rather skip it; it’s standing up for your political values and going out to protest when it's more comfortable to stay home; it’s allowing others to grow and make mistakes when you would rather do things yourself, in the way you like doing them.

Put courage first. Everything else follows. You can listen to our conversation about courage, led by Feely, here.