An Imperfect Leader: The Superintendents and Leadership Podcast

Some conversations stay with you long after the recording ends. My conversation with  Dr. Nyah Hamlett  is one of those.  In this encore episode, 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 shoul...

What happens when you trade a massive suburban district for a rural community with only 1,200 students? According to my latest guest, it might just be the best career move you'll ever make. I recently sat down with Dr. James F. Lane , former acting Assistant Secretary of the US Department of Education and author of Leading with Laser Focus . James shared how cutting his teeth in a small rural dist...

What happens when you trade a massive suburban district for a rural community with only 1,200 students? According to my latest guest, it might just be the best career move you'll ever make. I recently sat down with Dr. James F. Lane , former acting Assistant Secretary of the US Department of Education and author of Leading with Laser Focus . James shared how cutting his teeth in a small rural dist...

If you feel like your "number one love"—instructional leadership—is constantly being pushed to the background by budget spreadsheets, you aren't alone. I recently had a fantastic conversation with Dr. Anne LoBue   (Columbia University's Teachers College) and Dr. Christopher Tienken (Seton Hall University) about the 2025 American Superintendent Study . We did some serious "myth-busting" that every...

If you feel like your "number one love"—instructional leadership—is constantly being pushed to the background by budget spreadsheets, you aren't alone. I recently had a fantastic conversation with Dr. Anne LoBue   (Columbia University's Teachers College) and Dr. Christopher Tienken (Seton Hall University) about the 2025 American Superintendent Study . We did some serious "myth-busting" that every...

Is the era of the public school monopoly officially dead? According to my guest, Brian Stephens , the answer is a resounding yes. And if school leaders don't adapt, they risk becoming "dinosaurs." Brian is a combat veteran, attorney, and the leader of CAISSA K-12, a firm that has helped return over 30,000 students to traditional public schools. In our conversation, we tackled the hard truth about...

Is the era of the public school monopoly officially dead? According to my guest,  Brian Stephens , the answer is a resounding yes. And if school leaders don't adapt, they risk becoming "dinosaurs." Brian is a combat veteran, attorney, and the leader of CAISSA K-12, a firm that has helped return over 30,000 students to traditional public schools. In our conversation, we tackled the hard truth about...

Are we settling for "belonging" in our schools while leaving student brainpower underdeveloped? I recently had a deep, transformative conversation with  Zaretta Hammond , author of  Rebuilding Students' Learning Power . We moved past the surface-level "equity talk" to discuss what it really takes to move a student from a dependent learner to a cognitively independent one. Zaretta's insights on cog...

Are we settling for "belonging" in our schools while leaving student brainpower underdeveloped? I recently had a deep, transformative conversation with Zaretta Hammond , author of Rebuilding Students' Learning Power . We moved past the surface-level "equity talk" to discuss what it really takes to move a student from a dependent learner to a cognitively independent one. Zaretta's insights on cogni...

What does it actually mean to be a resilient leader? Is it just about weathering the storm, or is it about what you build while the storm is still raging? I recently had a conversation with Dr. Melissa Sadorf , Executive Director of the National Rural Education Association and author of The Resilient Rural Leader . Melissa has spent over 30 years as a teacher, principal, and superintendent, and sh...

What does it actually mean to be a "resilient" leader? Is it just about weathering the storm, or is it about what you build while the storm is still raging? I recently had a conversation with Dr. Melissa Sadorf , Executive Director of the National Rural Education Association and author of The Resilient Rural Leader . Melissa has spent over 30 years as a teacher, principal, and superintendent, and...

What does it mean to be a nationally recognized rural leader while navigating the messy, imperfect realities of the superintendency? In the latest episode of An Imperfect Leader, I sit down with  Heidi Sipe , Superintendent of Umatilla School District, to discuss how she has led her district for 19 years through innovation and intense challenge. Here are a few topics from our conversation that eve...

What does it mean to be a nationally recognized rural leader while navigating the messy, imperfect realities of the superintendency? In the latest episode of An Imperfect Leader, I sit down with Heidi Sipe , Superintendent of Umatilla School District, to discuss how she has led her district for 19 years through innovation and intense challenge. Here are a few topics from our conversation that ever...

How do you keep a school transformation alive for 25 years when most initiatives fizzle out after three? Jamie Almanzán recently sat down with Jesse Boise , Assistant Principal at Hillsdale High School, to talk about the staying power of Small Learning Communities (SLCs) and what it truly means to lead with humility. Hillsdale is a "living artifact" of what happens when a school commits to a colle...

How do you keep a school transformation alive for 25 years when most initiatives fizzle out after three? Jamie Almanzán recently sat down with Jesse Boise , Assistant Principal at Hillsdale High School, to talk about the staying power of Small Learning Communities (SLCs) and what it truly means to lead with humility. Hillsdale is a "living artifact" of what happens when a school commits to a colle...

Is your school board focused on the right things, or is it caught in a "dumpster fire" of adult drama? I recently had an terrific conversation with AJ Crabill , author of Great on Their Behalf , about how to move from dysfunctional governance to a system that actually serves children. AJ has seen it all. From serving as a parent leader to becoming a state agency leader and a national governance di...

Are you leading in isolation? Education leadership can often feel like a lonely journey - navigating everything from systemic challenges to the day-to-day realities of school life. In this episode of An Imperfect Leader, we sit down with veteran educators and co-authors Peter DeWitt and Michael Nelson to discuss their transformative framework for collective leadership. In our conversation as well...

In the latest episode of An Imperfect Leader, we sit down with Mike Miles, Superintendent of Houston ISD, to discuss his career in driving high-performance cultures and rethinking how schools prepare students for the future. This conversation provides a deep look into what he describes as the largest and fastest transformation of a large urban district in the history of Texas. Here are three impor...

How can artificial intelligence actually make us  more human? In the latest episode of An Imperfect Leader, we sit down with Dr. Douglas Reeves to discuss his timely new book, Education and the Ethics of AI: Enduring Values in a Changing World . Here are three essential themes from our conversation: 1. Reclaiming Time for the Human Side of Leadership: Dr. Reeves argues that AI's greatest gift to a...

How can we move from traditional schooling to truly empowered learning? In this episode of An Imperfect Leader , we sit down with Dr. Milena Garganigo , Assistant Superintendent for the Clayton School District, to discuss breaking traditional leadership models and centering student agency. Here are three key themes from their conversation: 1. The Five Pillars of Empowered Learning: Dr. Garganigo u...

Are we observing for compliance or for growth? In this episode of An Imperfect Leader,  Craig Randall , author of Trust-Based Observations , describes how we can transform school culture by reimagining the way we support our teachers.  Here are three big takeaways from our conversation: 🛡️ Lowering Vulnerability to Encourage Risk-Taking: Traditional, high-stakes observations often lead to trauma,...

This week, we're chatting about organizational trust with  Dr. Cory Scheer, founder of TrustCentric Consulting and author of Closing the Trust Gap . If you think your team trusts you, you might want to check the data. Research shows that leaders typically have a "31% on average, higher perception of how trust is doing versus frontline employees." Here are three big themes from our conversation tha...

I am thrilled to share my latest conversation with Dr. Heather Naro, Head of School at Schutz American School in Alexandria, Egypt. Heather brings over three decades of experience in international education to a discussion centered on inclusion, culture, and the pursuit of better. Here are three key themes from our conversation: The Radical Shift Toward Inclusion : Since 1992, the number of intern...

This week on  An Imperfect Leader , I had the chance to sit down with Dan James , founder of Story 19 Consulting and a former U.S. Paralympic coach, for a thoughtful conversation about leadership and what he calls the "pursuit of better." Here are a few ideas from our conversation that stayed with me: From Subject Matter Expert to Leader of Scale: Many of us move into leadership because we were st...

I am thrilled to share a very special crossover episode between our podcast, An Imperfect Leader , and  Mason Pashia from the Getting Smart Podcast ! Together, we sat down with Dr. Jennifer Light , a professor at MIT, to explore the the history of Junior Republics and the cutting-edge work of Embodied Education. Here are two key takeaways from our conversation: 🏙️ The Legacy of Junior Republics: I...