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

Connect with Troy Hopkins

LinkedIn: https://www.linkedin.com/in/troy-hopkins-5560a068
Website: https://www.northstonington.k12.ct.us/

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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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