Fragile Leadership: The Weight of Choosing Differently

On paper, it sounded simple, equity, opportunity, fairness. But in practice, it wasn’t simple at all.

The phone rang, and on the other end was a young Black attorney. His voice carried both hope and hesitation as he asked how he might become part of the network of attorneys that United Way used.

I had just stepped into the top leadership role. I was new, but I had already made my intentions clear: I wanted to break open the system, to move beyond the “legacy vendors” who were, more often than not, majority firms.

On paper, it sounded simple, equity, opportunity, fairness. But in practice, it wasn’t simple at all.

I remember wrestling with one of my earliest decisions. I was considering hiring a talented African-American man into a senior leadership role. At the time, it was uncustomary, almost unthinkable, for United Way, or any mainstream institution, to have two Black men in visible leadership.

I picked up the phone and called a member of our executive board, sharing my hesitation. Her response was simple: “You were right to call me.”

What she didn’t see was the storm inside me. I worried that if I made the wrong move, if he stumbled, people wouldn’t just second-guess him. They’d second-guess me. They’d second-guess the decision to put me in leadership in the first place.

That’s fragility. Not just of the system, but of leadership. My leadership.

Over time, I did begin opening doors, bringing in diverse vendors, service providers, and partners. But here’s the truth: our largest contracts still went to majority firms. They had longer track records. They carried institutional trust. And while I took calculated risks here and there, I could never shake the weight of uncertainty that came with choosing differently.

This isn’t just my story.

Talk to any Black leader, or any leader of color, who sits at the intersection of power and resources in a mainstream institution. The dilemma is the same: when you’ve fought so hard to get a seat at the table, do you risk it by inviting others who look like you, knowing that one stumble could make the whole table question whether you belong there at all?

Here’s the truth I’ve learned: most leaders hire and contract within their networks. It’s human nature. It’s how boards are built. It’s how teams are staffed.

The difference is this: for majority leaders, their networks come pre-trusted. For leaders of color, our networks come pre-questioned. The hurdle is higher. The risks feel heavier.

I felt this acutely when I transitioned into banking. I told a prominent Black community leader about my move to Midwest BankCentre and invited him to consider banking with us. His response was blunt: “Prove yourself.”

So I asked him, “Where do you bank now?”

He named a large, well-known bank.

“And did they have to prove themselves to you as it relates to community?” I asked.

He said no.

That’s the double standard. That’s the higher hurdle.

And yet, for those of us who do get the chance to lead, we can’t afford to ignore it. We have to name it. We have to resist the temptation to play it safe, to keep opportunities with the same familiar players. Because if we don’t use our platform to open doors, then when our time in leadership ends, we’ll be left with the haunting question: Did I do enough?

Leadership is fragile. But fragility isn’t failure, it’s the testing ground of courage. And the courage to choose differently? That’s what makes leadership transformative.

Key Takeaways for Leaders

Leadership fragility shows up when fear of being second-guessed holds us back from bold, equitable decisions.

Most leaders hire and contract within their networks, but not all networks carry the same level of institutional trust.

For leaders of color, the stakes are higher, and the risks heavier, but the responsibility to open doors is just as urgent.

Playing it safe may preserve your position, but it rarely expands opportunity for others.