Redefining School Leadership: A Conversation with Dr. Peter Dillon

An Imperfect Leader

INTRO: Welcome to today's episode of An Imperfect Leader, where we sit down with Dr. Peter Dillon, a superintendent in Western Massachusetts. Peter shares his experiences working in a rural region serving, at one time, two school districts and the lessons he learned along the way.

In this episode, he shares insights on leading multiple districts, the challenges and rewards of serving small communities, and the process of redesigning what it means to be a high school student in a post-COVID world. Don't miss this conversation about harvesting collective wisdom, overcoming budget crises, and fostering student voice and engagement. Dr. Peter Dillon shares his story and lessons learned, embodying the spirit of an imperfect leader.

BIO: Dr. Peter Dillon is the superintendent of schools for the Berkshire Hills Regional School District—serving the towns of Stockbridge, West Stockbridge and Great Barrington, Mass. At one point, he also served, simultaneously, as superintendent of the Shaker Mountain School Union, which serves Richmond, Hancock and New Ashford. Previously, Peter was executive director of policy in the Office of Portfolio Planning at the New York City Department of Education, where he helped to create and sustain more than 150 new schools. He was the principal of the Heritage School in East Harlem and he taught in New York and in the Republic of the Marshall Islands as a Peace Corps volunteer.

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Music for An Imperfect Leader was written and arranged by Ian Varley.

Sam Falbo created our artwork, a wood-print inspired daruma doll butterfly.

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My book, An Imperfect Leader: Leadership in (After) Action is available at Amazon.com or peterstiepleman.com.