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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At the end of every interview we have for teacher candidates, we say, “What questions do you have for us?” And they always ask, “What kind of support can I expect?” And we always say, “Don't worry, we'll give you a mentor.”

But it's not real mentorship. I mean, it's support with the difficult kid, or the field trip form, or the grade card. But it isn't coaching. 

That's where partners like EdConnective step in. Because they provide real coaching, observations and feedback with practice. EdConnective ensures that every student thrives by facilitating exceptional educator growth. If you're looking for support for your people, for your leaders, for science of reading efforts, for recruitment and retention initiatives, check out EdConnective.com.

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Imperfect Leaders! Are you facing challenges filling open Speech-Language Pathologist positions within your district? Empat Speech understands the critical need for qualified professionals in your schools. The recognize that communication lies at the heart of academic success. Don't let open positions hinder your students' progress. Partner with Empat Speech today and ensure every child in your district has access ot the speech therapy they deserve.

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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.