Leadership Isn't About Comfort—It's About the Courage to Face What Matters Most
Leadership Isn't About Comfort—It's About the Courage to Face What Matters Most
Justin Steele
Social Impact Executive | Philanthropy Leader | Fractional Chief Impact Officer | Public Interest Technology Founder | Outdoor Equity Advocate | Ex Google, Ex Bain
March 3, 2025
I still remember the nervous tension backstage at Google's weekly all-hands meeting, known to Googlers as TGIF. It was early 2016. Beside me stood founders Larry Page and Sergey Brin, moments away from introducing my guest Bryan Stevenson, a tireless advocate for justice, to thousands of employees.
A colleague leaned in, voice uncertain: "Are you sure about this?"
Truthfully, I wasn't entirely sure. I had organized this TGIF, advocated persistently for Bryan to speak, and personally asked David Drummond—the Chief Legal Officer and highest-ranking Black executive at Google—to sponsor it. Less than two years into my tenure, still not firmly established, I knew my credibility and career at Google could rise or fall with the reception Bryan received. External speakers were rare at TGIF, and Bryan was one of the very first.
But that's precisely what leadership demands—stepping into uncertainty when your moral compass points toward discomfort rather than safety.
Where I Stand: A Necessary Preface
Before diving into my views on leadership, I want to be transparent about three core beliefs that underpin my perspective:
I believe there can be no true community unity as long as our human value is determined by traits we inherited, like ancestry, faith tradition, or race.
I believe companies should help build a more inclusive society and reduce harmful systems that treat some people as more valuable than others.
I believe real leadership requires humility about the limits imposed by human nature, particularly the reality that rapid disruption of any foundational identity—be it cultural, religious, or institutional—often triggers intense defensive reactions.
Many thoughtful people disagree with these positions, and that's okay. The tension between justice and unity, between challenging systems and preserving cohesion, is precisely what makes leadership so complex—and so necessary.
The Root of Leadership Is Risk
The etymology of 'leadership' reveals what we've forgotten: its Indo-European root leit means 'to go forth, die.' Our ancestors understood what we often prefer to ignore—that to lead means sacrificing something of ourselves. The comfortable leader is no leader at all.
In this context, our current leadership vacuum is no surprise. In an era of political polarization, shrinking social commitments, and rising authoritarianism, the scarcity of leaders willing to step boldly into uncertainty prevents the meaningful progress we desperately need.
Authority vs. Leadership: A Critical Distinction
Over time, successful organizations often favor authority over leadership, choosing the stability of preserving what works over challenging existing systems.
Authority keeps things running smoothly—fixing everyday problems and maintaining stability. Leadership, however, gets people to face challenges that need fresh thinking and uncomfortable changes. One preserves what is familiar; the other births what is necessary.
I experienced this firsthand at Google.org when we considered funding criminal justice reform efforts using data science to examine racial disparities in policing. Addressing systemic bias meant engaging with historical inequities embedded in American institutions—messy terrain that risked alienating stakeholders.
We chose leadership.
Google engineers volunteering with the Center for Policing Equity in 2017
The initiative we launched with the Center for Policing Equity not only identified patterns of bias but positioned Google as a pioneer in using technology to tackle complex social problems. This uncomfortable path allowed us to address systemic inequities, foster innovation, attract dedicated talent, and enhance our reputation.
What initially looked like choosing between doing good (purpose) and doing well (business benefit) revealed itself as a false dichotomy. The bolder path served both.
Discomfort Isn't Automatically Virtuous
However, discomfort itself isn't inherently productive. Human psychology underscores our deep need for belonging and group stability. Exercising leadership too abruptly can trigger defensive reactions and polarization, undermining the very progress being sought.
After all, we experience profound satisfaction from synchronized activities and group loyalty—vibing together at a concert, hugging a stranger after your star player hits the winning shot, worshiping together on a Sunday morning. Leadership must respect and harness this fundamental human desire for connection, rather than dismissing it as mere resistance.
That's why leaders must distinguish between systems worth challenging and those worth keeping or improving:
Unfair systems that value people differently based on characteristics they inherited deserve to be challenged, even when uncomfortable.
Structures based on skills, responsibility, and clear roles can help organizations function better.
Not all traditions imprison us; not all innovations set us free. Wisdom is knowing which chains to break, and which ties to protect.
Managing the Thermostat of Change
My graduate school professor Ron Heifetz taught me that leadership is creating just enough imbalance to drive change—pushing people outside their comfort zones but not overwhelming them. I see this as controlling a thermostat.
The tension must be neither too low (stifling progress) nor so high that people panic or rebel.
After the Charleston Church shooting in 2015, Google became more open to addressing difficult issues, creating an opportunity for bolder action. Such windows don't stay open forever. When society divides further, people's willingness to engage shrinks.
This puts corporate social responsibility leaders in a difficult position: push too far, and you might fracture your organization; never push, and you're not leading.
Leadership is the delicate art of disrupting comfort without sacrificing trust. This balancing act is among the most crucial leadership skills in corporate social responsibility. It's an art, not a science, and I've gotten it wrong as often as I've gotten it right.
The Moral Responsibility to Lead Uncomfortably
The moments before Bryan Stevenson took the stage at Google's TGIF meeting remain vivid in my memory. I awkwardly thanked Sergey for coming, and he gave me a puzzled look that seemed to say, "Who are you, and why are you thanking me for attending a meeting I created?"
I felt small, out of place—a sensation familiar to anyone exercising leadership beyond their formal authority.
Then Bryan took the stage and delivered one of the most powerful speeches I've witnessed, emphasizing the necessity of discomfort:
"We can't create more justice by just getting proximate, changing narratives, or being hopeful. We've got to do uncomfortable things. I've studied and looked for examples where injustice ended, oppression was overcome, or desperately needed change came—when people only did what's comfortable and convenient—and I can't find it. Injustice ends, oppression ceases, and bigotry changes only when we do uncomfortable, inconvenient things."
If discomfort is the price of justice, leadership is deciding that justice is worth that cost.
The times I've grown most as a leader—and had the most significant impact—occurred when I embraced discomfort rather than avoiding it.
Four Pathways Forward
Reflecting on leadership in this challenging moment, I see four paths forward:
Reclaim leadership beyond authority: Leadership mobilizes others around meaningful challenges. Start small, demonstrate incremental value, and build credibility as someone who responsibly challenges systems.
Manage healthy tension: Adjust the "organizational thermostat," creating enough discomfort to spark change without causing excessive resistance that halts progress.
Build connections across divides: Bring together diverse viewpoints, helping communities create their own solutions rather than forcing top-down changes.
Honor the need for belonging: Ensure people feel safe before initiating difficult change. Real transformation occurs when individuals feel they're valued members of something larger, not merely targets of change.
The Edge of Possibility
Ultimately, leadership isn't measured by comfort, authority, or ease. It's measured by the courage to stand firm in uncertainty, willing to risk discomfort for something greater than oneself.
Meaningful change has never traveled the path of least resistance. The road to justice has always been paved with discomfort. Leadership is the courage to walk toward the discomfort that guards the doorway to justice, knowing others might only follow once you've crossed the threshold.
#Leadership #Courage #EthicalLeadership #SocialImpact #DareToLead
As a Fractional Chief Impact Officer and strategic advisor through True Steele LLC, I partner with organizations ready to scale their success—but unsure of the path forward. Together, we'll clarify your vision, forge strategic partnerships, unlock new resources, and create practical pathways to transformative growth and systemic change. If you're ready to move from ambition to impact, let's connect.
