When we talk about leadership, we often picture confidence and applause. For Caleb Dolan (North Carolina ’96), it began with humility and a lesson from home.

Growing up in rural Maine, he watched his father vote against extra funding for gifted programs, even though Caleb was in one. “Somebody’s got to think about what’s best for everybody,” his father said. Years later, that belief guided Caleb to Teach For America and into a classroom in Gaston, North Carolina, where he learned that true leadership starts with listening.

The Wake-Up Call

His assignment: teach remedial reading to students who had failed the state test. His reality: chaos. “I was legit terrible,” Caleb admits. “I didn’t know how to teach reading. I didn’t know how to create classroom culture.” Caleb quickly realized how much he had to learn. He remembers watching kids leave his class disengaged, then walk across the hall to another teacher’s class full of high-fives and energy. One student in particular, Tyrone Clemens, crumpled a paper and said, “‘What are you talking about?’ That was the kick in the butt,” he says. “I could have pitied myself, but the truth was, Tyrone was doing his homework in one class and not in mine. I was the problem.”

Caleb decided to switch things up. “I started watching successful teachers and copying them,” he says. The shift paid off. “Kids will at least honor that you’re trying.” By his second year, his students eagerly stayed for afterschool tutoring and improving fast. “That’s how we got to KIPP.”

Building KIPP Gaston College Preparatory

Wendy Kopp, Teach For America’s founder, later wrote about Caleb in One Day, All Children. When she visited his Gaston classroom in 1999, she saw the drive he and fellow teacher Tammi Sutton shared. After connecting them with KIPP co-founder Mike Feinberg, both were invited to start new schools. Caleb agreed—but only if they could do it in Gaston.

When The 74 Million profiled his early days, Caleb recalled going door to door in Gaston, trying to convince families to enroll in the new KIPP campus. He sat in living rooms, spoke in churches, and listened more than he talked. “I heard, ‘People like you haven’t necessarily done well by us in the past.’ We were asking families to believe in a vision that didn’t yet exist, but they trusted us. They recognized the difference between their current situation and what we saw as possible.”

That belief became KIPP Gaston College Prep, also known as The Pride, founded in 2001 on a peanut field. It started with 80 students and three blue, used school buses. Six years later, 61 percent of its first graduates earned college degrees, proving leadership rooted in listening can transform a community.

Raising the Bar

Caleb went on to help open another KIPP school. Today, the network has nearly 300 campuses. Even with this accomplishment, there’s room for improvement. “We’d fallen short for kids,” he admits. His focus now is reconnecting schools to a shared vision of excellence. “We’ve come together for the first time to do this work and benefit from each other’s expertise and do the right thing for kids.”

The goal is to consistently give families accessible and excellent education. “It shouldn’t be luck of the draw whether a parent signs their kid up for a good school,” Caleb says. “Whether you’re at KIPP Charlotte, KIPP Gaston, or KIPP Durham, you should see the same level of growth, of joy, and of postsecondary outcomes delivered.”

The Pahara Check

When Caleb joined the Pahara Fellowship for education leaders, he found himself among people with very different views. “One thing TFA really fosters is the idea that a lot of people are doing things that matter for kids,” he says. That openness was tested when a peer shared a view he disagreed with. “I was strident, almost judgy,” he states. But hearing colleagues express the same vision and passion for kids from a different perspective made him check himself. “That shook me out of my assumptions,” he says. “When I shut up for a minute, I realized where they were coming from.” That exchange reminded him growth requires discomfort. “Listen more, talk less,” he says. “And check that instinct to assume your clarity is everyone’s clarity.”

Grounded and Growing

Caleb jokes about his title now. “I remind myself that I’m a suit,” Humility continues to guide Caleb as KIPP’s Vice President of Regional and School Support. “Technically, my title sounds like I’m a Toyota dealer manager or something,” he jokes. “But what I actually do is far more human.”

In this role, Caleb finds ways to stay grounded and close to the realities of classroom life, like keeping in touch with his former students. “Being in contact with the kids I taught who are now in their twenties and thirties is incredibly grounding,” he says. “Postsecondary success isn’t a cure-all, but damn—those kids have healthier lives and more opportunity for their own kids.”

Even after three decades in education, Caleb humbly still calls himself a learner. “The science of reading stuff was mind-blowing to me,” he says. “People thought I was a great ELA teacher, but I did a lot wrong for a lot of years.” He’s learning from new research, from colleagues, and from former team members now running high-performing schools. “Eric and Carice Sanchez both started at TFA North Carolina and worked for me. Now they’re running Henderson Collegiate, which is doing five times better than we ever did. That’s exciting!”

Lessons for learning aren't confined to the walls of classrooms—they show up at home too. His eldest daughter, who is neurodivergent, continues to shape how he thinks about belonging. “It’s made me think a lot about what it feels like to navigate school when you’re pretty different,” he says. “How do we make sure every kid feels like they have a spot?” He doesn’t claim to have the answers. “There’s always more to learn,” Caleb says. “And that’s what keeps me grounded.”

A Legacy of Humility

That first paper ball on the classroom floor might have felt like failure, but it became the spark for everything that followed. Humility turned into action. Action turned into impact. And decades later, Caleb Dolan is still doing what he did then—learning from others, building alongside them, and finding purpose in the process proving humility isn’t weakness. It’s the blueprint for lasting change.