Leading with Heart: Dr. Darren Kennedy on the Human Side of School Leadership
An Imperfect Leader: The Superintendents and Leadership Podcast
Release Date: 11/11/2025
Be Bold or Go Home: Mike Miles on Rapid Systemic Transformation and the Houston Promise
An Imperfect Leader: The Superintendents and Leadership Podcast
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 important themes from the conversation, featuring word-for-word quotes from Superintendent Miles: 1. Rapid Transformation Through Organizational Coherence: Mike believes that significant school improvement...
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Reclaiming the Human Connection: Douglas Reeves on AI, Ethics, and Leadership
An Imperfect Leader: The Superintendents and Leadership Podcast
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, 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 administrators is the gift of time. By leveraging AI to handle administrative burdens leader can get out from behind their desks. 2. Moving from Cheating to Critical Editing: Rather than viewing AI solely as a cheating machine, the discussion shifts toward...
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In the Mess Together: Milena Garganigo on Systems Thinking and Supporting Teachers
An Imperfect Leader: The Superintendents and Leadership Podcast
How can we move from traditional schooling to truly empowered learning? In this episode of An Imperfect Leader, we sit down with , 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 unpacks a framework designed to personalize education through five key components: Path, Place, Pace, Voice, and Choice. A standout insight is her definition of Path. It isn’t just about the activities a student...
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Craig Randall: Maximizing Teaching and Learning Growth Through Trust-Based Observations
An Imperfect Leader: The Superintendents and Leadership Podcast
Are we observing for compliance or for growth? In this episode of An Imperfect Leader, , 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, stress, and anxiety, causing teachers to play it safe. Craig reminds us that "the way you get people to take risks is lower vulnerability. The way you lower vulnerability is by building trust." ...
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Closing the Trust Gap with Dr. Cory Scheer
An Imperfect Leader: The Superintendents and Leadership Podcast
This week, we're chatting about organizational trust with 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 that every leader needs to hear: The "Three-Legged Stool" of Trust: Trust isn't a vague soft skill. It’s a measurable structure. Cory breaks it down into three essential building blocks: competency, problem...
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Ahead of the Curve: Heather Naro on Personalizing Learning and Human-Centered Leading
An Imperfect Leader: The Superintendents and Leadership Podcast
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 international schools has grown from fewer than 1,000 to nearly 15,000. More importantly, the philosophy has shifted from "exclusive" environments to more inclusive systems. Human-Centric...
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The Pursuit of Better: Measuring Process Over Outcomes with Dan James
An Imperfect Leader: The Superintendents and Leadership Podcast
This week on An Imperfect Leader, I had the chance to sit down with , founder of 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 strong practitioners. But leading at scale requires a very different skill set. As Dan put it, the craft of being a great teacher is very different from the work of leading an entire school system. . Clarifying...
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When Kids Ran the Nation: Jennifer Light Offers Lessons in Democracy from Junior Republics
An Imperfect Leader: The Superintendents and Leadership Podcast
I am thrilled to share a very special crossover episode between our podcast, An Imperfect Leader, and from the ! Together, we sat down with , 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: Imagine a miniature city or nation run entirely by kids. Starting in 1895, Junior Republics gave children the power to act as senators, run businesses, and even debate major issues like women's suffrage (often reaching progressive...
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Haley Spira-Bauer Is Clear: Adaptability Is Not Optional
An Imperfect Leader: The Superintendents and Leadership Podcast
This week on An Imperfect Leader: The Superintendents and Leadership Podcast I’m joined by , COO and Chief Academic Officer at Fullmind and host of the . In a world where the education landscape is constantly shifting, Hayley makes a compelling case that adaptability isn’t optional, it’s essential. We explore how strong leaders connect the dots of data through storytelling - transforming numbers into a shared purpose and collective action. In a powerful “After Action Review,” Hayley shares a hiring mistake from early in her tenure and the lesson that reshaped her approach: skills can...
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Beyond the “Testing Obsession”: A Conversation with Dr. Jason Van Heukelum
An Imperfect Leader: The Superintendents and Leadership Podcast
I recently sat down with , Superintendent of Winchester Public Schools, to talk about what it really means to lead in a messy, high-pressure moment for public education. Jason embraces being an “imperfect” leader. In a field often paralyzed by the pressure for perfection, that mindset matters. Three takeaways that stayed with me: 🏛️ A Cathedral to Possibility: Winchester’s Emil and Grace Shahadah Innovation Center brings students together to explore a true buffet of options. It’s about social cohesion and shared opportunity, not silos. 🔄 Doubling Down on Agency: Amid...
info_outlineIn this episode, we are joined by Dr. Darren Kennedy, the High School Instructional Supervisor for Sumner County Schools (just outside Nashville, Tennessee). Dr. Kennedy, author of So You Think You Want to Be a Principal, 50 Voices from the Field, 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 collective aspiration: Darren emphasizes that values and beliefs must be established through an inclusive, collaborative process with the administrative team to form a unified coalition.
- The essential need for Human-Centered Leadership: Understand that leading an organization involves working with humans, and longevity in leadership requires mastery of the "human side of the work."
This episode is a must-listen for anyone responsible for student success and leader development.
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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:
Connect with APC Leadership Collaborative for support in navigating complex leadership situations: https://www.apccollab.com
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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.
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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.