In this episode of Little Wins, Karen Borchert sits down with Troy Hopkins, superintendent of North Stonington Public Schools in North Stonington, Connecticut. In a small district with just two buildings and 750 students, Troy leads with heart, humor, and a clear belief that culture, risk-taking, and visibility are the work.
Troy shares how being a student again—literally taking quizzes alongside kids—helps teachers feel at ease and gives him real insight to advocate for classrooms. He talks about modeling risk through memorable convocation themes (a mini-basketball, a robot, a hammer… and even a Flash costume) to give staff permission to try, iterate, and have fun. And he explains why stepping back to let others lead—like handing a tech plan to a teacher team—builds capacity, buy-in, and better results.
Whether you’re leading a rural district or a large system, you’ll find practical ideas for zapping, not sapping energy; creating teacher-led professional learning; and staying future-focused with AI, efficiency, and purposeful fun at the center.
💡 Little Wins in This Episode:
- Be a Student (Again): Sit with kids, take the quiz, feel the flow—then give feedback from a learner’s seat. Visibility that actually lowers anxiety and raises insight.
- Props with a Purpose: Mini basketballs (“take your shot”), a robot (demystify AI), a hammer (“Is there a better way?”)—memorable anchors that normalize risk-taking and iteration.
- Permission Culture: When leaders show up in costume or try something new, everyone gets permission to create, experiment, and find joy in the work.
- Let Others Lead: Shift from directing to developing—teacher-led tech planning produced a comprehensive, funded roadmap with real ownership.
- Celebrate Longevity & Belonging: From new-teacher lunches with mentors to a 47-year custodian’s standing ovation—rituals that say, “You matter here.”
Key Moments
02:10 Career Path to Superintendent
07:05 "Be a Learner" Classroom Quizzes
11:27 "Take Your Shot" Mini Basketball
13:20 Demystifying AI for Feedback
14:37 The Flash & Efficiency
15:28 "Is There a Better Way?" Hammer
24:28 Teacher-Led Tech Plan & Buy-In
37:34 Celebrating 47 Years of Service
39:21 Immerse Yourself in the Learning
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🧵 About the Podcast:
Little Wins is the podcast that digs into the small, deliberate actions school leaders are taking to build strong, human-centered cultures, one meaningful win at a time.
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What is Little Wins?
Little Wins is a podcast that shines a light on the small moments making a big impact in schools. Hosted by Karen Borchert, each episode features courageous conversations with principals, heads of school, and superintendents who are building trust, sparking belonging, and shaping culture—one hallway celebration, heartfelt gesture, or coffee-fueled conversation at a time.
Because in education, it’s the little things that often matter most—and they’re the reason people stay.