Winning is a Strong Drive for Leaders, But Be Clear on What Winning Means

In my interview with Khari Brown, CEO of Capital Partners of Education, he shared a smart insight about a challenge for all leaders: channeling the drive to win in ways that are always productive, and knowing when to let something go.

Q. Were you in leadership roles early on?

A. I gravitated to sports pretty early. My parents were more into the arts and music, but as soon as I found basketball, that was where my attention went. Those were foundational experiences that guide the way I think and act and lead.

If we’re keeping score, I want to be on the winning side, not the losing side. But team sports made a big impact on me in helping to see how teams come together – the role of the coach, the best player, the role players.

“If we’re keeping score, I want to be on the winning side, not the losing side.”

Sports were my first leadership opportunities. I was a quiet kid and I didn’t ever see myself as a leader. But my coaches were mentors to me, and asked me to do things in a leadership capacity that I didn’t know I was capable of doing.

They said, “You’re already a leader of the team, and we want you to be a little bit more vocal, and we want you to step forward in these situations.” So I took on the role of being a captain at Tufts University.

Q. How have your parents influenced you?

A. My mom worked for 40 years for Children’s Hospital in Boston. My dad probably worked 20 years in the last job that he had before he retired. They never missed a day, and were always very hard working.

My mom is probably the most empathetic person I know, and instilled that deep value of always trying to consider what other people might be thinking and feeling, and how can we help that person feel better? Where she and I differ is we would watch sports together, she would always feel sorry for the other team, and I would always want my team to destroy the other team.

Q. What do you see as your biggest leadership lessons?

A. When I started, I really felt underprepared, and so I worked incredibly hard to try to learn everything, because I did not have the formal training to run an organization from top to bottom. It was a lot of trial by fire. I did that for seven years, and gradually grew as a leader. The lesson there was not to be afraid to fail and innovate.

Another big lesson happened in a meeting with a major donor who had had enormous success in business. He had come to the United States with nothing. He wanted to do things in a big way.

“The lesson there was not to be afraid to fail and innovate.”

He said to me, “I think your program is great. I want to help it grow. We’re going to make this thing big. How many students do you have today?” And I said, “About 100.” And I was thinking within the realm of the model that we had, because it just wasn’t really a scalable thing, particularly in a city like D.C., which is relatively small.

He said, “How many students can you help?” I said, “We could probably grow to about 150.” He said, “What are you talking about? How many kids are there in D.C. public schools?” I said, “55,000 or so.” He said, “Why is that not your answer?”

It hit me over the head. How could I begin to remake the program so that we could attract support from people who are really looking to solve this problem or trying to do it in a bigger way? I couldn’t do it with the organization I had, and it took a while to change the model so that we could grow it further.

Q. In terms of how you’ve evolved as a leader, how are you handling situations differently today than you would have in the past?

A. Early on, I described my competitiveness as an asset, but sometimes that led me to dig in my heels and take things personally. I learned that I have to be bigger than that. I’m representing a lot of people, and I can swallow a little bit of pride to know that I am right, and that I don’t need to win everything. Because sometimes when you win, you lose. What does winning really look like? It’s not about scoring points in a debate or getting the last word.

Q. Do students apply to be part of your program?

A. We recruit them. We look for students who wouldn’t otherwise be found. Our target is kids who are middle-performing academically, and don’t have a lot of adults in their lives who are able to really support and guide their college and career aspirations. Unfortunately, this is a population that’s really under-resourced, and so we have to go and get them. They’re not knocking down our door.

Q. What is your playbook for the mentors to help these kids?

A. Sometimes it’s not advice. Sometimes it’s just encouragement. It’s, “Hang in there. You can do it. I believe in you.” The best mentors are able to say, “Look, you can do more than you know. And I believe in you. But you’ve got to do this in order to get to where you want to go, and I’m going to help you there.”

If you develop trust, and there’s a rapport there, that can be really impactful. You have to develop that level of trust first, but sometimes you can call someone out when they’re underperforming and say, “Hey, you told me this, but your report card says this. You can do better than this.”

Our students often deal with really difficult things in their personal lives, and it’s about helping them navigate through trauma. Just being the support, and providing consistency, is really important. Sometimes you show up, you show up, you show up, and then there’s a breakthrough. You didn’t do anything different between the 25th time and the 26th time. It’s just that the 26th time is when things really open up, and you’re able to break through.

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