Human Side Up: Kenny Williams on falling down, getting up, and leading on

Kenny Williams, CLARA fo-founder and former Chicago White Sox Executive Vice President, knows what it takes to win on and off the field. As the longest-serving Black head of operations in major American sports history, he’s built championship teams, battled bias, and stayed focused on what—and who—gets overlooked. In this conversation, Williams reflects on the early lessons that shaped his leadership style, the value of failure, and why building inclusive teams requires more than good intentions.

Leading yourself first

Williams didn’t always see himself as a leader. In school, he refused to speak in front of the class. “I told all of my teachers, I’m not doing it. And I sat in my chair, terrified.” That fear stayed with him into adulthood, even when he was offered the White Sox GM role—he turned it down the first time it came up. “I didn’t want a public role. I just wanted to do my job.”

But what Williams lacked in comfort, he made up for in clarity. “I’ve been around a lot of smart people. I’ve made it a point to hire people that I thought were smarter than me. And, oftentimes I found myself maybe not the smartest person in the room, but the most logical and the most structured.” Over time, he learned to lean into those strengths and trust that others would fill in the rest.

The value of falling down

In the early years, Williams didn’t think much about the importance of failure. That changed after winning the World Series. “I started to focus on some people that fell on their ass, got up. And still, continue to grind and push forward.”

“A lot of people take a setback as a negative in their life, and they’re so busy looking down at the floor in their feet. The whole woe is me that they haven’t looked up to see that opportunity pass right by them.”

Williams now sees discomfort as necessary: “you’re not going to achieve anything great in life if you don’t put yourself into an uncomfortable situation and get through it, push through it and come out on the other side.”

Creating teams that push back

Williams has built some of the most tightly knit teams in sports, but that didn’t happen by avoiding conflict. It happened by welcoming it. “I recognized early on that if you didn’t have substantial confidence in you, that I could shut you down, shut down a room. So I had to have people around me that were not afraid.”

When he interviewed Ozzie Guillén for the White Sox manager job, they argued. “The first question I asked him during the interview was: I said, let me tell you something. ‘Why should I hire you?’ And he went off: ‘You know me, you know what I bring to the table. Why would you bring me up here if you weren’t going to hear me out?’”

By the end of the meeting, Guillén had the job.

Williams also made a point to include interns in high-stakes conversations. “I would allow the interns in, where trade discussions, very sensitive or contract discussions, very sensitive information. I’d allow the interns in and would ultimately ask them a question in the room because you don’t know who’s holding back valuable information or a valuable opinion.”

Why inclusion makes you better

When Williams hears people question the value of DEI, he doesn’t hold back. “I am so out of patience with people. I don’t get it. I’ve not gotten a clear explanation on why some people feel the way they do about this subject.”

In a recent conversation, a successful executive implied that DEI initiatives lead to unqualified hires. Williams responded: “There was an implication that all DEI efforts are resulting in people who aren’t qualified for positions... Productivity in organizations, in schools that subscribe to the ideas behind diversity, equity, inclusion, belonging, see 30% productivity gains! Whereas those that don’t, don’t see those types of gains.”

For Williams, also it’s personal. “Let’s take, for instance, the person that didn’t go to college. But started their own business and for whatever reason, they’re now back in the marketplace... So where do they get credit for that? Where do you account for that in the traditional resume? The answer is you really don’t.”

That belief helped drive the creation of CLARA—not to replace human judgment, but to expand it. “We’re not here to automate away decisions. We’re here to make sure every candidate gets seen.”

Legacy isn’t measured in trophies

It wasn’t a championship or an award that validated Williams’ leadership. It was his father’s funeral. “I turned around and a large part of the people that I worked with in the front office had flown out there for the day, just for that. They didn’t stay. They just came to support me and flew home.”

“And that’s when I knew: ‘oh, I must have done something right.’” A reminder that leadership isn’t about having the loudest voice, it’s about listening, learning, and lifting others up.

To hear more from Kenny Williams on what real leadership looks like, listen to this episode of Human Side Up here.