Leading Through Uncertainty with Tom Woelper, Cheshire Academy

Tom Woelper, Head of School at Cheshire Academy, shares how he approaches leadership as a balance of vision, accountability, and community energy—drawing on the three meanings of a conductor to guide a 230‑year‑old institution. He reflects on navigating financial pressures, fostering belonging in a diverse boarding‑day community, and shaping personalized pathways that help students thrive…