Leading With Curiosity and Humanity: Faculty Spotlight on Head of Upper School Colleen Kyle

For Kyle, now head of Upper School at Rivers, that binary never quite held up. “I admire Haidt’s ideas, but this one always seemed like a false contrast,” Kyle reflects. “Schools like Rivers know that Excellence with Humanity is not only possible, but the best possible way to develop young scholars, and everything I’ve learned about this school since has only confirmed this to be true.” 

Kyle joined the Rivers community for the 2026–27 school year, bringing a wealth of experience from renowned independent schools—Deerfield Academy, The School for Ethics and Global Leadership (SEGL), Lakeside School, and Roland Park Country School (RPCS). “I’ve seen lots of great models of leadership and teaching,” says Kyle. “From RPCS, I learned how much fun and affirming school spirit can be; from Lakeside, I learned that you can only have rigor and excellence if you also prioritize equity and a global perspective; and from SEGL, I learned that it’s possible to tackle really difficult issues if you provide students with models and methods that allow them to come to their own perspectives.” 

Kyle has a deep passion for literature, which stems from her education at Oak Knoll School in New Jersey, where her teachers Margaret Crocco and Harriet Marcus were particularly influential. Years later, Mrs. Marcus visited Kyle’s Lakeside School class on grandparents’ day. “I taught them a poem that she had taught me, T.S. Eliot’s ‘The Hollow Men,’” Kyle recalls. “It was magical to hear her voice as my students wrestled with that bleak poem; I’ll never forget it.” 

No matter what position she holds in a school, staying active in the classroom and as an advisor is essential for Kyle. This semester, she designed and teaches a senior English elective, Leading Well: Profiles in Ethical Leadership. 

“My syllabus starts with Dwight Eisenhower’s quote: ‘The supreme quality of leadership is integrity’—and interrogates it,” Kyle explains. “Is this really true? Can’t someone be a powerful leader without being good? The course allows students to reach their own conclusions about what leading well means.” 

So far this semester, students have studied general concepts of leadership and ethics and have examined profiles of Gloria Steinem, Dolly Parton, John McCain, Lorne Michaels, and Ernest Shackleton. 

Head of School Ryan S. Dahlem recently visited the class as a guest speaker, connecting Ernest Shackleton’s survival saga to leadership by sharing his own personal experience on an expedition to climb Mount Vinson (16,050 ft.), Antarctica’s highest peak.

Dahlem shared that on the ice in Antarctica, the team roped together to support anyone who stumbled during the ascent. The expedition leader modeled Shackleton’s morale-building approach by participating directly in physical work, Dahlem said—shoveling snow alongside the team and calling out “hots are ready” before meals froze almost instantaneously. When a storm trapped the team at high camp with fuel running low to melt ice for life-essential water, the expedition leader waited out the weather rather than attempting a dangerous descent. The storm passed two days later, illustrating a key rule, per Dahlem: “The summit is halfway.” Getting back safely is the goal. 

Asked by a student whether hardship builds or reveals character, Dahlem noted the importance of both preparedness and a positive attitude: “If you can persist, it builds the perspective that ‘I can do hard things.’” 

Next, Kyle’s class will tackle Shakespeare’s Henry V and Stacey Abrams’ autobiography, Lead from the Outside. 

Overall, Kyle says she’s been energized by natural campus connections at Rivers this fall. “There are authentic bonds between colleagues that foster such fruitful collaboration in service to our students,” she says. “There’s a strong culture of trust that is so important and inspiring. It allows all of us to stretch ourselves and take risks together.” Nurturing these qualities is a core priority for Kyle, who also hopes her students develop relentless curiosity and sound judgment. Referencing a line by writer Daniel Pink, she adds, “The future belongs to humans who master questioning.”