Connecticut Boarding School Leader Joins NAIS “Member Voices” to Discuss Navigating a 230-Year-Old Institution Through Uncertainty
Cheshire Academy Head of School Tom Woelper P’26 was invited to share his leadership philosophy on Member Voices, the official podcast of the National Association of Independent Schools (NAIS), in an episode released June 1, 2026.
The 43-minute conversation — part of NAIS’s ongoing series spotlighting independent school leaders from across the country — explores how Woelper approaches the realities facing today’s boarding and day school heads: financial pressures, evolving student needs, and the challenge of honoring a 230-year-old institution’s legacy while keeping it firmly oriented toward the future.
Woelper framed his leadership philosophy around three distinct meanings of the word “conductor” in a metaphor that captures the balance of vision, accountability, and community energy he brings to Cheshire Academy each day. He also spoke candidly about fostering a genuine sense of belonging in a diverse New England boarding and day school community, and about the school’s commitment to creating personalized pathways that help every student thrive, both academically and personally.
“Returning to time with students is what keeps me inspired,” Woelper noted during the episode, reflecting on a truth that sits at the center of Cheshire Academy’s mission: that the work at this Connecticut independent school is always about the young people on campus.
The episode also touched on Cheshire Academy’s international identity and the enduring impact of students who travel from across the globe to learn alongside their peers. The Academy’s International Baccalaureate® Diploma Programme and Global Citizenship Distinction were explored as frameworks for developing purposeful global leaders.
The NAIS Member Voices podcast is produced for independent school leaders, educators, and families who want a deeper look at the conversations shaping private school education. Woelper’s appearance marks the latest in a growing record of Cheshire Academy faculty and staff bringing their expertise to national and international platforms.
In April, MIT Technology Review featured Cheshire Academy as a case study in responsible AI adoption, spotlighting Librarian and Technology Coordinator George Aiello and IB Coordinator and French Teacher Miriam Przybyla-Baum for their leadership in helping students navigate generative AI with critical thinking and purpose. The following month, Science Teacher Stephen Murray was selected as one of four educators worldwide to present at the Middle States Association’s inaugural AI Demo Day, where he shared how AI-assisted feedback on student lab reports produced a 64% increase in scores. And English Teacher Jaimeson Lynch offered a neuroscience-backed examination of homework’s role in student learning that drew wide attention from educators across the private and independent school community.
Together, these moments reflect what Woelper described in the podcast as one of Cheshire Academy’s defining strengths: a faculty and leadership team at this Connecticut boarding school that contributes to the national and global conversation.
Listen to the Episode
Hear more of what Woelper had to say about "Leading Through Uncertainty" on Apple Podcasts.
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