What If AI Were Your Business Partner? A Conversation with Matt Leta
An Imperfect Leader: The Superintendents and Leadership Podcast
Release Date: 10/07/2025
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...
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Communication is a System: Lessons from Terrie Morgan
An Imperfect Leader: The Superintendents and Leadership Podcast
This week we’re sitting down with someone who has walked the walk for nearly four decades: , 2024 Kentucky Superintendent of the Year and a truly humble, student-centered leader from Hardin County Schools. Terrie brings warmth, honesty, and hard-earned wisdom from 36 years of service - and she doesn’t hold back. If you care about leading with heart and systems-level clarity, this is an episode you’ll want to save and share. 🌟 Here are some standout lessons you’ll hear: Put Students First - Every Time. Terrie’s guiding question: Can I defend this as best for kids? It...
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Dr. Richard Ramos: Let Students Lead the Way
An Imperfect Leader: The Superintendents and Leadership Podcast
I’m excited to share my conversation with , Superintendent of the Miami Unified School District in Miami, Arizona. Dr. Ramos brings such heart to his work - lifting student voice, building true community partnerships, and embracing the beautiful messiness of leadership. Here are the three big themes from our conversation: Student Agency & Community Collaboration: How a simple idea (a Business Partner Café) became a student-led space where young people host, present, and guide conversations with local business partners. Innovation & Project-Based Learning: A look inside Miami’s...
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Leading with Heart: Dr. Darren Kennedy on the Human Side of School Leadership
An Imperfect Leader: The Superintendents and Leadership Podcast
In this episode, we are joined by , the High School Instructional Supervisor for Sumner County Schools (just outside Nashville, Tennessee). Dr. Kennedy, author of , shares powerful insights on creating transformational change in school culture and academics. Leaders, here are three things you will learn from this episode: The power of focusing on Tier One Instruction over Intervention: Darren recounts his experience as a principal of a turnaround middle school where an initial heavy reliance on supplemental intervention programs resulted in only marginal progress. Why values must be a...
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Paul Freeman on Courage, Conversation, and Confident Leadership
An Imperfect Leader: The Superintendents and Leadership Podcast
How do we prepare students to become empathic individuals and global citizens in an increasingly complex world? Dr. , Superintendent of Guilford Public Schools and Connecticut’s Superintendent of the Year, joins An Imperfect Leader: The Superintendents and Leadership Podcast to discuss leading transformational change through confident vulnerability. Dr. Freeman shares how Guilford’s Portrait of a Graduate (POG) model guides instruction across all grade levels: developing students as adaptable learners, responsible collaborators, critical thinkers, effective communicators, empathic...
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From Reflection to Renewal: Dr. John Anzalone and the North Star of Student-Centered Leadership
An Imperfect Leader: The Superintendents and Leadership Podcast
In this week’s episode, we sit down with , Superintendent of the Camas School District (WA). Dr. Anzalone shares his powerful reflections on leadership and what it truly means to lead with humility. Here are 3 lessons on imperfect leadership and courageous strategy we learned from John: 🌟 1. Establish a Clear North Star: Every financial decision should point back to one thing: students. 💬 2. Lead with Courage and Vulnerability 🤝 3. Rebuild Trust from Within: 🎙️ Key Takeaway: Healthy systems are built on healthy relationships. Reflection, trust, and...
info_outlineWhat If AI Were Your Business Partner? How can school leaders use AI as a thought partner and collaborator?
The conversation around AI isn’t about the future anymore, it’s about now. This week’s episode is a thought-provoking one. I sit down with Matt Leta, founder and CEO of FutureWorks, a serial entrepreneur, and a forward-thinking voice on AI in leadership and education.
Matt doesn’t just talk about AI. He lives it. In this conversation, he shares how he launched a company with AI as his business partner, what he learned from the experience, and how those lessons connect to leadership, resilience, and systems thinking.
Here are three big takeaways from our conversation:
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AI as a Thought Partner and Collaborator: Imagine treating AI not as a tool, but as a colleague. Matt shares how FutureWorks was built on this idea.
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Resilience and Learning Through Failure: Matt opens up about nearly losing everything (an “eight-figure collapse”) that he now calls his real MBA. His story is a powerful reminder that leadership requires both courage and reflection, especially in times of crisis.
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Human Comfort and Change Management: Even the best technology fails if people aren’t ready for it. We explore how to help teams move from curiosity to confidence.
This episode will stretch your thinking about what it means to lead—and learn—in the age of AI.
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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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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.
Learn why 1 Million Students use Yondr every day.
MINIMIZE DISTRACTIONS. MAXIMIZE LEARNING POTENTIAL.
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.