BEFORE THE Webb School closed its 153rd year, which saw the largest enrollment in school history and the most diverse student body with students from five continents, 22 countries, and 12 states, plans were already underway to exceed expectations in the next school year.
During 2022-2023, Webb continued an intentional focus on the school’s firm foundations of honor and character, along with the pursuit of the three A’s — academics, arts, and athletics. At the same time, a path for the future in the form of a strategic plan emerged to equip the school and Webb students for what Head of School Ken Cheeseman said are “the greatest challenges and opportunities they will face in the future.”
“The Webb School is in a strong position to continue to be both relevant and sustainable long into the future,” said Cheeseman, completing his third year as head of school. “Webb has powerful programs and performances in the three A’s — academics, arts, and athletics — under the direction of a dynamic leadership team, faculty and staff, and board of trustees, along with strong support from our parent associations, alumni, donors, and friends.”
In comments to the Webb community, Cheeseman related key ideas from a recent conference he attended in England with heads of schools from all over the U.S., the U.K., and for-profit and not-for-profit leaders from both sides of the Atlantic.

“In our discussions, we grappled with the observation that there has been a tectonic shift in how much of our world operates. It was insightful to hear so many perspectives.”
Cheeseman explained that most of the conversations centered on several central questions:
- Amid these tectonic shifts in how our world operates, what will the future demand of our students and us?
- For what ends are we preparing our students?
- What processes, assessments, and student showcases should we use to equip students to be their very best, competing most favorably in a changing world while being agents of goodness?
Continuing to think about these questions, Cheeseman noted the significant advantages students gain from a Webb personalized education with small class sizes, small advisories, and small grade levels, where every student is known and valued.

“Our size allows for the formation and growth of deep, healthy relationships between outstanding faculty and staff and our students in which they are both nurtured and challenged to know their passions and gifts and develop them with character above all else.”
Cheeseman also pointed to other aspects of the “Webb Difference,” emphasizing honor, character, and personalized education. Included are the Emerging Voices Program, which stresses writing across the curriculum and public speaking; a global education to prepare students to live and work in a globally connected world; and the Wilderness Instruction and Leadership Development (WILD) program to provide extensive training in outdoor skills, leadership, and confidence.
“Being one of the most diverse schools in Tennessee, with a powerful honor code and college-preparatory standards, we are a microcosm of the world our graduates will inherit. I am confident that Webb graduates will be equipped to thrive and lead in every corner of the globe.” GN