"That's really the eye-opener, right? You are no longer the know-it-all, you are the one that has to find a space where I'm trusting my team in a way that I haven't had to before."
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Charles is 54 years old, and, as a leader, he feels like he’s starting over.
Four months into leading a global initiative managing hundreds of millions in philanthropic funding, he’s confronting an uncomfortable truth: his staff know more than he does. Many of them are quite a bit younger. And rather than working against that reality, he’s embraced it and found it oddly liberating.
“I’m at the bottom of a ladder again, or the bottom of a mountain again, and I’m gonna have to learn a bunch, and I’ve got to be really humble about that. My staff are much younger, many of them are much younger than I am and know much more than I do.”
The foundation grew explosively in the last two years, from roughly 30-40 staff to over 200. But the organization manages over $2 billion in assets—making it simultaneously a mid-sized organization (headcount-wise) and a large one (resource-wise). The growth brought relief to overloaded teams, a sense of pride, and genuine international diversity. Charles’s team is now the most culturally diverse in the organization, spanning multiple continents.
But with that growth came a reckoning. Some long-tenured staff have struggled to adapt. Charles describes a core group who’d been through thick and thin together suddenly experiencing a dissipation of their tight-knit space—a loss of control that, for some, still hasn’t resolved.
“My sense is that there are a few people in that core group who struggled with that, and still, to this day, continue to struggle with that.”
Charles’s own leadership transformation predates his current role. He describes his earlier style with unflinching honesty: “inspirational didacticism.” He could rally people around a mission, but he was hard on them—focused on the destination without much patience for how people might struggle to get there.
That changed through an unexpected teacher: parenting. Navigating a difficult period with one of his children, Charles learned something counterintuitive about how people change.
“Agreeing with him what was important, and then leaving him to make the decision, and creating the space for him to make an unthreatened decision for himself—very quickly resulted in him making the right decision.”
Once the threat of finger-wagging dissipated, his son could find his own way forward. Charles realized this wasn’t just about teenagers. It’s fundamental to how humans operate: remove the threat, create a trusted environment, agree on what matters, then step back.
Now, leading a globally dispersed team navigating political complexity, he’s applying that lesson daily. The work itself is intellectually, politically, and emotionally complex. And the foundation’s primary funder’s culture adds another layer of pressure.
“It is not a patient, forgiving environment. These are people who make a lot of money every day. The pressure of that is immense.”
Charles’s team members have lonely jobs. His director for one region runs all funding across three countries in Latin America—one person. When Charles considers what support he’d offer his leaders if he had unlimited resources, he answers immediately: coaching and space.
“They all need coaching support. They need help to be able to talk through—because they all have lonely jobs.”
“When you’re dealing with complexity, you need brain space, you need time, you need space. You have to grapple with things. If your world is too vertical, you’ve got too many things on the vertical and on the horizontal—that’s when I think things get broken. People get broken.”
Charles’s advice for leaders navigating growth is deceptively simple: don’t let it happen to you.
“Sit down and try to think ahead of what the shape of it is most likely going to look like, and predict. It’s actually not that difficult to do. You can predict certain aspects of growth and the impact of growth on you, the organization, and you can prepare people.”
The foundation, Charles observes, still behaves like a 30-person organization—systems, structures, and ways of working designed for a small team, now stretched across 200 globally distributed employees. The adjustment hasn’t fully happened.
The hardest part, Charles argues, is getting senior leaders to relinquish control. It’s easy to delegate tasks; it’s extraordinarily difficult to devolve the power of decision-making.
“It’s very hard to devolve the power of decision making and positional power is a very addictive, and it becomes part of our way of seeing ourselves. Right? It becomes our personality.”
Charles compares organizational growth to adolescence—tracking the changes the way parents mark their children’s height on a door frame. Organizations don’t do that, he says, and the growing pains from around 8 to 200-300 people are brutal.
“I think when we grow, the most painful bit is that interim bit. I think it’s probably from eight to 200 or 300. That’s probably the space where it’s like the Incredible Hulk bursting out of his clothes. All the growing pains happen there, the really tough ones.”
For Charles, the journey has required holding two things simultaneously: the accumulated wisdom of a 30-year career and the humility of a beginner. His meditation practice helps.
“How do you both have ignorance and leadership at the same time? How do you hold both those things in your hand?”
It turns out that simply holding the question, accepting the paradox, is a powerful way to lead.