John Rogers: The Future of Education Depends on Democracy
An Imperfect Leader: The Superintendents and Leadership Podcast
Release Date: 09/30/2025
The Tightrope of Leadership with Dr. Larry Cuban
An Imperfect Leader: The Superintendents and Leadership Podcast
Leadership isn’t about finding the perfect solution. It’s about learning from the daily grind of complexity. In this week’s episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I had the chance to speak with , former superintendent, Stanford professor, and author. A few insights that stayed with me, especially for leaders working in high-stakes environments: 1️⃣ Conflict isn’t a failure, it’s the work: Dr. Cuban shared that he couldn’t recall a single conflict-free day as a superintendent. Leadership is a constant balancing act (boards, unions,...
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Matt Pitman on the Shift from Being “Heard” to Being “Held” in School Leadership
An Imperfect Leader: The Superintendents and Leadership Podcast
What if the problem in our schools isn’t a lack of voice, but a lack of connection? In this episode, I had the opportunity to sit down with , author of , for a conversation that challenged many of the leadership norms we’ve inherited, especially the idea that effective leaders must remain stoic, distant, or emotionally neutral. Matt makes a compelling case that this model is no longer serving our schools. Instead, he invites leaders to rethink community, voice, and presence; and to move from making people feel heard to making them feel truly held. Here are three insights from our...
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Kaaren Andrews: If We Get Ninth Grade Right, Everything Changes
An Imperfect Leader: The Superintendents and Leadership Podcast
🎙️ New Episode Alert: If We Get Ninth Grade Right, Everything Changes In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast I get to talk with , National Director of the . This conversation zeroes in on why getting 9th grade right can dramatically improve graduation rates and disrupt long-standing inequities in our system. Here are three big ideas we dig into: 1️⃣ Ninth Grade: The Strongest Predictor of Graduation: Kaaren shares a powerful (and sobering) insight: students who are “on track” in ninth grade are three to four times more likely to...
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Mandy Traylor Says Don’t Move the Fences: Leading with Care and Community in Veribest ISD
An Imperfect Leader: The Superintendents and Leadership Podcast
I’m excited to share the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, featuring , Superintendent of Veribest ISD. Mandy offers a powerful look at what it means to lead with transparency, humility, and deep community trust. A few takeaways that stayed with me 👇 🤝 Shared Vision, Real Buy-In: Through a Texas Strategic Leadership pilot, Mandy brought together the board, staff, and local businesses to define what a Veribest graduate should be. The result? A vision everyone owns because they created it together. 🎓 Preparing Students for...
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Elena Aguilar on Why Presence Is a Leader’s Greatest Gift
An Imperfect Leader: The Superintendents and Leadership Podcast
Are you leading from a place of fixing… or from a place of presence? 🌱 In the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I had the honor of sitting down with Elena Aguilar, the visionary behind Transformational Coaching and author of eight bestselling books, including The Art of Coaching and Arise. 📚✨ Leadership can be a lonely journey. We’re often expected to have the answers, solve the problems, and move fast. But Elena reminds us that real transformation doesn’t come from quick fixes—it comes from going deeper and...
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Dr. Bryan Luizzi: When Leadership Doesn’t Go as Planned (Remastered)
An Imperfect Leader: The Superintendents and Leadership Podcast
The latest episode of An Imperfect Leader features , Superintendent of New Canaan Public Schools, and it’s a powerful reminder that leadership is less about having the answers and more about having the courage to step forward. From Connecticut classrooms to teaching and leading in Jordan, Bryan and I explore what it means to lead people in moments of uncertainty and change. 🎧 Three leadership themes to listen for: 1. Leading with “Yes” (and Courage, Not Recklessness): Bryan shares how a “lead with yes” mindset shaped his career and opened doors to unexpected...
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Richard Lemons on Why You Can’t Talk People Into Change and What Actually Works
An Imperfect Leader: The Superintendents and Leadership Podcast
This week, I had the privilege of sitting down with , Executive Director of Partners for Educational Leadership, for a conversation that every system-level leader should spend time with. Richard has spent decades helping leaders tackle the hardest work in education: changing systems without losing our humanity. Here are three themes leaders should listen for: 1. You Can’t Talk People Into New Mental Models: Richard reminds us that deeply entrenched beliefs about schooling aren’t shifted by better arguments or smarter PowerPoints. They change through radically different...
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Leading Without Flinching with Dr. Nyah Hamlett
An Imperfect Leader: The Superintendents and Leadership Podcast
🎙️ New Episode of An Imperfect Leader Some conversations stay with you long after the recording ends. My conversation with is one of those. Dr. Hamlett, former superintendent of Chapel Hill-Carrboro City Schools and now Chief Equity & Development Officer for Montgomery County Public Schools, offers a deeply honest reflection on leadership under pressure. Here are three themes leaders should listen for in this episode: 🔹 1. “Don’t Flinch” Leadership: Listen for how Nyah defines leadership as choosing courage over convenience, especially...
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Ben Thompson on Building Schools That Strengthen Communities
An Imperfect Leader: The Superintendents and Leadership Podcast
Facility planning and passing a facility bond can be among the most complex (and stressful!) challenges a superintendent faces. On this episode of An Imperfect Leader, I talk with , K-12 Director at and host of the . We explore how the spaces we design for learning can drive stronger student outcomes and strengthen community trust. Here are three takeaways I thought would be interesting for school leaders: Design Drives Outcomes: Ben reminds us there’s a direct link between the decisions we make about a space and the educational and social outcomes we want to achieve. ...
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Dr. Doug Bolton: Building Resilient Schools One Connection at a Time
An Imperfect Leader: The Superintendents and Leadership Podcast
In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast we had the pleasure of talking with clinical psychologist, author of , and director of school consultation for Formative Psychological Services. In Doug breaks down what it means to lead in a moment when educators are carrying unprecedented levels of stress and trauma, and how leaders can build schools that feel safe, connected, and resilient. 🔍 In This Episode, We Dig Into: • Connection as the foundation for everything: Doug explains why belonging isn’t a nice to have. It directly boosts...
info_outlineWhat does it really mean to lead for democracy in our schools today?
This week on An Imperfect Leader: The Superintendents and Leadership Podcast, I sit down with Dr. John Rogers of UCLA’s School of Education and Information Studies for a powerful conversation on one of the biggest drains on schools today: culturally divisive conflict.
Dr. Rogers makes a clear distinction between healthy political debate and the anti-democratic conflict fueled by violent rhetoric and misinformation. His research reveals both the financial and human toll:
💸 One midsize district spent $1M in staff time grappling with divisive conflicts.
🕰️ Another saw public records requests quadruple, eating up thousands of wasted hours.
💔 In high-conflict districts, 94% of superintendents said staff health (mental and physical) was negatively impacted.
So what can school leaders do when the attacks often come from outside their circle of influence?
Dr. Rogers points to three essential moves:
✨ Reclaim the Narrative: Reinforce the mission of public education as fostering a diverse, multiracial democracy.
🤝 Build Bridges: Create schools as “social centers” that bring communities together to solve problems.
🧩 Embrace Imperfect Leadership: Engage in shared inquiry and lean on the collective wisdom of your team and community.
🎙️ This is a must-listen episode for every superintendent, principal, and educational leader navigating today’s challenges.
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Follow Host Peter Stiepleman on:
LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/
Website: https://imperfectleader.com/
YouTube (video of conversation):
https://www.youtube.com/@animperfectleaderleadershi5144/featured
Instagram: https://www.instagram.com/animperfectleader/
Tiktok: https://www.tiktok.com/@animperfectleader
Follow Co-host Jamie Almanzán on:
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Superintendent Support Reimagined!
Zach Taylor and I are creating a reflective, virtual Community of Practice designed exclusively for Superintendents and Senior District Leaders. While calling it An Imperfect Leadership Community of Practice makes sense, I keep advocating for Talk Supt 🙂.
Want to learn more? Check out our video here 👇 or visit:
https://imperfectleader.com/imperfect-leadership-community-of-practice/
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An Imperfect Leader is sponsored by Yondr.
Schools around the world are seeing the damaging effects of phones on student engagement, social development, and mental health.
Yondr has developed a unique product and program to allow schools to become phone-free, from arrival to dismissal.
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Go to overyondr.com to learn more.
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An Imperfect Leader: Leadership in (After) Action is supported by ILAA, LLC, a firm dedicated to supporting aspiring, new, and established leaders. For more information, please find them at imperfectleader.com.
Music for An Imperfect Leader was written and arranged by Ian Varley.
Sam Falbo created our artwork, a wood-print inspired daruma doll butterfly.