An Imperfect Leader: The Superintendents and Leadership Podcast

What does it truly take to lead an educational community through complex transitions without falling into the trap of linear quick fixes? 🏫✨ In the latest episode of An Imperfect Leader, Emily Sargent-Beasley (President of the American College of Sofia) shares profound insights from her career in international education and her doctoral research at the University of San Diego. Here are some leadership themes to listen for: 1️⃣ Navigating Transitions in Complex Systems: School transitions are deeply bounded by context, inherited conditions, and unseen relational dynamics. Rather than treating transition as a linear "A to B" technical formula, effective leaders recognize schools as complex network systems where quick fixes rarely yield simple outcomes. 2️⃣ Empowering Teacher Agency & Shared Leadership: Real instructional progress happens when leaders trust their educators to drive meaningful change. Leadership isn't about controlling every variable in a crisis. It's about setting up supportive conditions,…

When a student stops showing up to school, our default instinct as a system is often to drop the hammer: automated warning letters, threats of fines, or referrals to juvenile court. Here's the truth: those compliance letters don't build enthusiasm. They alienate families and often worsen the problem. In this latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, we sit down with veteran superintendent and former CASEL CEO Dr. Shelley Berman to tackle one of the most pressing challenges facing education today: chronic absenteeism. Instead of treating attendance as an enforcement issue, Shelley challenges us to embrace an invitational, relationship-rich model grounded in belonging. As he reminds us: kids show up when the culture is positive and when they—and their families—feel genuinely known and valued. 💡 Key Takeaways & Practical Strategies from the Episode: The Attendance Paradox: Many educators believe attendance is entirely a family issue outside their control, but research…

In the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, we sit down with Chris Lynn, Head of School at the International School of Havana. Leading an international school in Cuba amidst daily grid uncertainties, fuel shortages, and complex operational challenges requires incredible resilience, empathy, and community-first leadership. Chris Lynn approaches each challenge with a human-centered approach. 🌟 1. The Belonging Manifesto To ensure that every student, staff member, and family feels safe, known, and valued, Chris spearheaded the co-creation of the school's Belonging Manifesto. Inspired by Kellett School in Hong Kong, the manifesto was developed over six months with input from the entire school community. It rests on four foundational pillars: 🌿 Our Nature: We are diverse. 🎯 Our Choice: To make belonging intentional. 🤝 Our Action: The ordinary daily work of good community. 💙 Our Goal: A school where everyone feels accepted, included, and encouraged to be their true…

This week on An Imperfect Leader, we sit down with Superintendent Michael Hayden of the Clyde-Savannah Central School District for a deeply moving conversation on leadership, literacy, and human-centered courage. Here are two key takeaways from this powerful conversation: 1. Thinking in Systems to Guarantee Middle School Literacy Michael shares how middle school serves as a crucial pivot point. Rather than leaving literacy to chance, Michael applied systems thinking across the district: Protecting Instructional Coaching: Even during state aid cutbacks, the district prioritized non-evaluative instructional/literacy coaches across all content areas. Master Scheduling for Collaboration: Restructuring schedules to guarantee dedicated joint planning time for teachers. Community-Wide Connections: Expanding literacy beyond school walls by partnering with local pediatrician offices, hospital maternity wards, and regional bookstores to get books directly into hands and homes. 2. An Unfiltered After Action Review:…

When we talk about leadership in education, it's easy to rely on broad phrases like "building relationships" or "equity" without defining what those actually look like in daily practice. In this week's episode of An Imperfect Leader, co-host Jamie Almanzan and I sat down with Dr. Gustavo Balderas, Superintendent of Puget Sound Educational Service District and former AASA and NABE National Superintendent of the Year. We explored what it takes to turn abstract ideas into concrete, actionable systems. Here are a couple of themes from our conversation that every leader can appreciate: 1. Process Is as Important as Product: Moving Beyond the Vague Leaders often face high-stakes, emotional decisions like school consolidations or district boundary shifts. Dr. Balderas shared how slowing down, admitting when a process needs a pause or a mea culpa, and authentically engaging stakeholders changes everything. The ultimate goal isn't always total consensus; it's getting to a point where stakeholders can say, "I don't…

"This was a fail, and I own it." This week, on An Imperfect Leader, Dr. Chip Kimball shows us what real leadership vulnerability looks like. His insights on international education and systems leadership brought up some themes every leader should reflect on: 1. The Power of the Reset Button: When Chip tried to streamline his team's global R&D process, the spark was missing. Instead of abandoning a noble goal, he had the vulnerability to admit the approach was a failure, hit pause, and launch "R&D 2.0". 2. Cultural Competence Over Standard Metrics Drawing from years leading major school systems in the U.S. and internationally, Chip noted that the greatest deficit facing American students often isn't math or science scores. It's cultural competence. When talking with university admissions officers, the consensus was clear: colleges aren't looking for kids who simply stack a dozen advanced courses. They are looking for a cross section of "smart and interesting" human beings. 3. Designing Ecosystems for Deep…

What happens when you ask an 11-year-old student, "Who do you want to be?" instead of "What do you want to be?" 🤔 In this episode of An Imperfect Leader, we sit down with Jennifer Tickle, former Head of School at the International School of Siena, Italy (now the Head of School in Monza), for a candid conversation about values, vulnerability, and the complex systems of international school leadership. Here are some themes from our discussion: 1️⃣ Define the "Who" Before the "What" Rather than relying on inherited values, Jen led a collaborative appreciative inquiry process with students, parents, and teachers to discover who they wanted to be. This deep community alignment centered on three core anchors: Respect, Integrity, and Compassion. 2️⃣ The 9-Month Recruitment Reality Check (Systems Thinking) In an honest "After Action Review," Jen shares the raw reality of trying to recruit a highly qualified, non-European physics teacher without fully anticipating the bilateral visa challenges of her host country.…

As we wrap up our summer encore series and gear up to launch Season 5 of An Imperfect Leader, we are closing out the sunny season with an absolute powerhouse of a conversation! ☀️🎙️ In our final summer encore episode, I sat down with Vikas Pota, founder of T4 Education and creator of the World's Best School Prizes. If you are a superintendent, head of school, or district leader, this episode is your ultimate reminder of why your school has every reason to be celebrated on a global stage. Here are three game-changing themes we deconstruct in this episode: 1️⃣ What Makes a School The Best in the World? Vikas shares that while exceptional leadership accounts for 90% of a school's success, the crucial remaining 10% comes down to a deep, embedded organizational culture. The world's top-performing schools excel because they commit to five research-backed, evidence-based strategies: community collaboration, environmental action, innovation, healthy living, and building the resilience to overcome adversity. 2️⃣ The…

🚨 How do you lead when the answer is "zero"? 🚨 In our latest encore episode of An Imperfect Leader, we sit down with the incredible Dr. Christina Kishimoto (Founder and CEO of Voice 4Equity and former superintendent in Hartford, Gilbert, and Hawaii) to talk about the radical power of relationship capital, the messy reality of school leadership, and what it truly means to lead with intention. During the conversation, Dr. Kishimoto shared a powerful story from the start of the 2020 pandemic. When her district needed $100 million for student devices to support online learning across seven islands, the state legislature unexpectedly funded her request at ZERO dollars. Instead of accepting defeat, she quickly pivoted. She called on her deep relationship capital by leveraging trusted partnerships in the private sector, nonprofits, the military, and Hawaiian Airlines to secure laptops, hotspots, and food for vulnerable families. Here are some of our favorite takeaways from this episode: 💡 Relationship Capital isn't…

This week on An Imperfect Leader, we're heading back into the archives to bring you a conversation that remains incredibly relevant today. My guest, Dr. Casey Hallgarth, Superintendent of Baker School District, shared timeless wisdom on leading with heart and integrity. Here is why this encore episode is a must-listen: 🤝 Relationships are the Foundation: Successful leadership isn't about the title. It's about authentic connections with staff, your board, and the community. 👂 The Power of Real Listening: To create a shared image of success, you have to convene groups and "really listen to what they're saying." 👣 Walking the Talk: Leading by example is the only way to foster true trust. Your actions must align with your words. 🧒 The Ultimate Filter: Casey uses one powerful question for every decision: "Will it help the kids?" It's a simple but vital reminder of why we do this work. Casey's roadmap for a thriving school environment is just as impactful now as it was then. #EducationLeadership #Podcasserole…

Are we preparing students for a four-year degree that only 20% will actually complete, or are we preparing them for life? In this special encore episode of An Imperfect Leader, we are revisiting a powerful conversation with Dr. Jason Van Heukelum, Superintendent of Winchester Public Schools in Virginia. This is an episode every school leader needs to hear, especially if you've ever felt that the current "testing regime" is sucking the joy out of your classrooms. Why should you care? Because Jason is doing something truly bold. He didn't just build a new CTE wing; he created the Emil and Grace Shahadah Innovation Center, which he calls a "cathedral to possibility". Key takeaways: Universal Career Exploration: In Winchester, career and technical education isn't "the track for those other kids." Every single student is required to participate. It's about breaking down social barriers and ensuring all students learn together. The "Elevate 2030" Vision: Jason gets vulnerable about the pressure to "double down" on…

We are heading back into the archives for a very special encore episode of An Imperfect Leader! When I first spoke with Max Silverman, the Executive Director of the University of Washington Center for Educational Leadership (CEL), our audience was much smaller. His insights on how we lead schools and support principals are more relevant today than ever. Max (now in an emeritus/advisor role at CEL) is one of those leaders who combines deep expertise with incredible humility. In this episode, we dive into: The Power of Simple Tools: Max shares a mantra that has stuck with me: "Simple tools lead to complex thinking, and complex tools lead to simple thinking." The Anatomy of Instruction: True leadership expertise can only be developed "in the presence of students." We talk about moving beyond spreadsheets to develop "habits of thinking"—noticing, wondering, and hypothesizing about what is actually causing learning. The After Action Review: Max gets vulnerable about a major decision to convert a comprehensive…

We are bringing back one of our most impactful conversations for an encore episode of An Imperfect Leader! Have you ever wondered why, in a profession where over 70% of teachers are women, only 28% of superintendents are? Or why so many leaders feel they have to be "perfect" just to survive? Dr. Rachel White joined us to dive into her groundbreaking work with The Superintendent Lab. She didn't just look at the numbers; she hand-collected data on nearly 13,000 leaders because a national database simply didn't exist. One of her most startling finds? One in five superintendents is named John, Matthew, or Michael. In this episode, we explore: Mirrors and Windows: How leadership serves as a "mirror" for students to see their potential and a "window" for the community to understand diverse lived experiences. The Hall of Mirrors: A candid look at how school boards sometimes hire based on fit, which can inadvertently reinforce the status quo. Leading with Curiosity: Moving away from hierarchy and toward a coaching…

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 should listen for: 1. "Don't Flinch" Leadership: Listen for how Nyah defines leadership as choosing courage over convenience, especially when decisions are uncomfortable or unpopular. 2. Student Voice as Shared Power (Not a Checkbox): Listen for how student voice can sharpen decisions, even when leaders don't ultimately go the students' way. 3. Imperfect Leadership, Vulnerability, and Accountability: Listen closely to Nyah's after-action reflection. It's a masterclass in humility, learning in real time, and leading as a human being, especially when systems and personal wellbeing collide. This episode is a reminder that…

📢 What an incredible conversation with Dr. Stephen Pruitt, President of the Southern Association of Colleges and Schools Commission on Colleges (SACSCOC). 🎧 In this encore episode, we dove deep into education, leadership, and driving real change. Here are the key takeaways: 🤝 Stakeholder vs. Shareholder: Dr. Pruitt made a powerful distinction: education needs fewer "stakeholders" and more "shareholders". What does that mean? Shareholders are people invested in a common vision who feel true ownership of the process. ✍️ Redefining Standards: Standards, he explained, are a contract between the State Department of Education and teachers. It's about shared agreement and collaboration, not top-down mandates. 🧠 Harvesting Wisdom: The development of the Next Generation Science Standards (NGSS) was a masterclass in inclusive design: 26 lead states, 40 writers, and countless public reviews to make sure every voice was heard. 🤔 Unintended Consequences: As Kentucky's Commissioner of Education, Dr. Pruitt created an…

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 district forced him to do "every job"—from HR and finance to literally walking through the mud to assess construction sites. We went deep on how that "boots on the ground" experience prepared him for state and national leadership, and why he believes the best leaders are simply "the best at getting better." Three takeaways you won't want to miss: Innovation = Newer AND Better: James challenges the educational platitude of being innovative. He notes, "We tend to get caught up in what's newer and forget to actually make sure it's better." If it's not improving outcomes for kids, it's just a "new shiny thing" contributing to…

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 school leader and board member needs to hear. Here are 3 themes from our talk to keep on your radar: The Money Matters Paradox: While most superintendents identify as instructional leaders, 54% reported that finance issues actually consume the bulk of their attention. In rural districts, that number jumps to nearly two-thirds. Curriculum and instruction? That ranked 10th on the list. As Anne put it, while instruction is the heart of the work, "it's money that matters" when it comes to daily time management. Shattering the 3-Year Tenure Myth: We've all heard that the average superintendent only lasts three years. It…

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 declining enrollment and how districts can reclaim their narrative in a competitive market. Here are themes from our talk that every educator and superintendent should hear: Accepting the End of the Monopoly: Brian argues that leaders must stop acting like they are the only game in town. He notes, "The monopoly's over with." To thrive, schools must treat families like customers and understand that competition from charters, private schools, and unschooling is the new reality. Leading with Emotion to Change the Narrative: While educators love data, Brian points out that data alone doesn't move people. To recruit…

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 cognitive justice and intelligent failure are essential. Here are 3 themes from our talk that will matter to leaders: Cognitive Justice is the True Moral Imperative: Equity isn't just about celebrating flags or hosting potlucks. Zaretta challenges us to look deeper. True justice means ensuring every student has the "cognitive resources" to accelerate their own learning. Embrace the "First Pancake": Learning requires a safe space for "intelligent failure." Zaretta uses a brilliant metaphor for new initiatives: when making pancakes, that first one is not quite right. As leaders, we have to use that information to "adjust the…

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 she deeply understands the unique, multiplex relationships that define rural education. Whether you lead a small rural district or a large urban system, Melissa's insights on leading through loss and building authentic credibility are universal. Here are 3 themes from our talk that you should pay attention to: The "Multi-Hat" Generalist: In rural districts, the organizational chart is flat. A superintendent might also be the principal, the HR director, and even the backup bus driver. This makes them high-level generalists with a real understanding of how every part of a school system actually works. The School as a…

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 every education leader should hear: Empowering Teacher Agency with Structured Systems: Heidi shares how her district uses a color-coded intervention system (Green, Orange, Red) that authorizes teachers to make immediate decisions for students without waiting for administrative approval. It's a masterclass in building shared leadership that prioritizes child needs over bureaucracy. Solving Chronic Absenteeism through Radical Partnerships: When healthcare access became a barrier to attendance, Umatilla didn't just track data, they partnered with a local physician to provide well-child checks and treatment for minor…

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 collective vision rather than a collection of individual classrooms. Whether you are a superintendent or a site leader, Jesse's insights on coherence are a game-changer. Here are some themes from his conversation that you won't want to miss: The Power of Looping and "Kid Talk": At Hillsdale, students stay with the same cohort of 112 students and four core teachers for two years. This "looping" allows for deeper relationships and more flexible interventions. They even have a weekly ritual called "Kid Talk," where teachers, counselors, and specialists sit down to discuss every single student's needs and successes. Leading…

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 director, we dove deep into why school boards often fail and, more importantly, how they can become effective. Here are some themes from our conversation: Student Outcomes vs. Adult Inputs: One of the biggest mistakes boards make is trying to "own" the strategic plan. AJ argues that the board's unique expertise is representing the vision and values of the community by defining student outcomes (the "what"). The superintendent then owns the "adult inputs" and the strategic plan (the "how") to get there. Authority is Collective, Not Individual: It's a common trap: an individual board member tries to go "rogue" to fix a…

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 as in their work with the Instructional Leadership Collective, they challenge the traditional top-down approach, moving beyond mere good intentions to create lasting impact through collective efficacy. Drawing on their latest book, Lead Collectively, they share how leaders can dismantle silos and build a culture where every student and adult feels seen and heard. Whether you are a principal, superintendent, or teacher leader, this episode offers a roadmap to move from shared belief to impactful action. It's so worth the listen! Three Themes to Listen For: Leadership as an Invitation to Belong: Using the unexpected…

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 does not have to be an incremental, multi-year process. He attributes the district's ability to move from 121 D and F-rated campuses to zero Fs in just two years to organizational coherence. 2. Preparing Students with Human Competitive Advantages: A major focus in Houston is cultivating human skills that AI cannot replicate, such as empathy, critical thinking, and team leadership. 3. Bold Leadership in a Fast-Moving…

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 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 teaching students to be better than AI. 3. Challenging the Bottom Feeder and Addressing Bias: Dr. Reeves describes AI as a bottom feeder because it scoops up from the Internet all the things that we have put in there for the last 50 years. Educators must teach students to think critically to identify societal errors and biases reflected in AI and then challenge it.…

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 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 does, but rather the various modalities they use to demonstrate knowledge. 2. Leadership Through "Side-by-Side" Presence: To break the mental model of the distant central office, Milena and her team utilize a backup system where central office administrators are physically present in buildings to support staff and students. She emphasizes being "in the mess" with teachers, serving as a co-researcher and…

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, 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." 🌟 Moving from a Deficit to a Strengths-Based Mindset: When we attach numerical ratings to pedagogy, we inadvertently start looking for what's wrong. Craig argues that "when I start to put a number on you, I start to look at what's wrong with you. It subconsciously develops a deficit mindset." 💬 The Power of Reflective Questions: The magic of a trust-based model happens in the follow-up conversation. Instead of telling, leaders…

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 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 solving, and care for others. As he says, "If you only have two of them, but one of them is less, it's gonna feel really wobbly and kind of wonky". Active Listening is Leadership: Want to strengthen the "care" pillar? Stop looking for perks and start listening. Cory notes that "active listening is the most effective way to strengthen trust for the care for others." Clarify Truth, Inspire Belief: Cory challenges every…

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 Leadership: Heather advocates for a people first leadership style, especially in international settings where staff often live and work in close proximity. By caring for the whole beings of her teachers (from airport pickups to shared Thanksgiving dinners), she fosters a collaborative culture where educators feel valued and empowered to go the extra mile. The Necessity of Intercultural Competence: Leading across borders requires a deep…

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 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 Your Ultimate Impact: Sustaining leadership over time requires something deeper than the job itself. Dan encourages leaders to stay grounded in their why behind the work. One question he asks leaders is simple but profound: What is your ultimate impact in this life? Measuring the Process, Not Just the Outcome: Growth rarely looks perfect. Dan talked about the importance of accepting "skinned knees" along the way.…

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: 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 conclusions long before adults did). This "radical student agency" reminds us that when we trust young people with real-world responsibility, they are capable of extraordinary things. 🏃‍♂️ The MIT Project on Embodied Education: We also took a deep dive into how movement and physical activity can be integrated into academic instruction to enhance learning, creativity, and executive function. Dr.…

This week on An Imperfect Leader: The Superintendents and Leadership Podcast I'm joined by Hayley Spira-Bauer, COO and Chief Academic Officer at Fullmind and host of the Learning Can't Wait Podcast. 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 be developed, but values and mission alignment are foundational. If you believe leadership is about learning in public, growing through missteps, and staying anchored to purpose, this episode is for you. Listen wherever you get your podcasts. ------- Follow Host Peter Stiepleman on: LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/ Website: https://imperfectleader.com/…

I recently sat down with Dr. Jason Van Heukelum, 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 post-pandemic test score panic, Jason felt the pressure to retreat to compliance. Instead, he's recommitting to student agency and project-based learning through the district's Elevate 2030 plan. 🏃‍♂️ Run Toward a Vision: Jason's advice to aspiring leaders: don't run away from what you dislike. Instead, run toward something you believe in. Lead toward possibility. Toward humanity. If you haven't seen it, the documentary…

🚨 Are schools preparing students for a world that no longer exists? I recently had the privilege of sitting down with Ted Dintersmith, the force behind Most Likely to Succeed and Multiple Choice, and author of What School Could Be (with a new book on math coming soon!). Our conversation centered on one big idea: the status quo isn't enough anymore. 🤖 AI changes the game: If we're training students to do what computers now do best, we're aiming at the past. We need to shift from compliance and percentile rankings to creativity, empathy, purpose, and real problem-solving. 🛠️ Career-connected learning is for everyone: Innovation Centers across the country are giving graduates (college-bound or not) hands-on experiences in fields from cybersecurity to advanced trades, so they graduate with multiple pathways, not just one. 🌟 The change is already happening: Not through mandates, but in "bright spots" where students tackle authentic community challenges. If you care about reimagining school, I hope you'll listen.…

In the latest episode of An Imperfect Leader, I sat down with Patrick Green, author of Classroom Management in the Digital Age, to explore how schools can move beyond compliance and toward deeper focus, connection, and self-management in the digital age. Here are three ideas that really stood out during our conversation: 1️⃣ From compliance to self-management: We often say we want creativity and collaboration, yet we still design systems around compliance. Patrick challenges that mismatch. The real goal isn't control. It's helping students develop self-management. 2️⃣ Leading with curiosity, not "tech panic": How we approach students about technology matters. Patrick shared a moment when his initial reaction to students gaming caused them to scatter. They sensed fear, not curiosity. His takeaway was powerful: validate the student before questioning the behavior. 3️⃣ The underrated skill of being alone with your thoughts: In a world of constant consumption, students are losing opportunities for quiet…

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 Dr. Larry Cuban, 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, families, and communities all pulling at once). 2️⃣ Be a "good enough" leader: Burnout often comes from chasing an ideal that doesn't exist. Dr. Cuban argues for being good enough (not mediocre), but well-matched to your context. 3️⃣ Excellence can't be mandated: Lasting improvement doesn't come from top-down pressure. It comes from tapping into the wisdom of people doing the work every day. For school leaders, that often means…

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 Dr. Matt Pitman, author of The Connection Conundrum, 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 conversation that every leader should wrestle with: 🎧 3 Leadership Reflections Worth Your Time 1. From "Heard" to "Held": Surveys and listening sessions are easy. Accountability is harder. Matt argues that voice only becomes authentic when leaders publicly explain how stakeholder input shaped a final decision. When people can see their fingerprints on the outcome, trust grows. 2. Lead as a…

🎙️ 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 Kaaren Andrews, National Director of the Center for High School Success. 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 graduate 🎓. 2️⃣ Going Upstream: From Remediation to Prevention: Using Archbishop Desmond Tutu's river metaphor, Kaaren challenges us to stop pulling students out downstream and ask why they're falling in upstream 🌊. Instead of relying on credit recovery after failure, her work centers on proactive ninth-grade success teams where students are truly seen and known. 3️⃣ Human-Centered Leadership:…

I'm excited to share the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, featuring Mandy Traylor, 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 Life: From Adulting 101 to Lady Falcon Self-Defense, Veribest ISD is equipping students with real-world skills that extend far beyond the classroom. 💛 Relational, Human-Centered Leadership: Mandy defines an imperfect leader as someone confident enough to lead—and humble enough to admit mistakes. Her guiding wisdom: "Work hard and be nice to people" and "Don't move fences until you know why they were built." 🌱 Building culture is…

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 tending to the roots. 🌳 Here are four powerful takeaways from our conversation: 🔹 Prioritize Internal Healing: Your internal state shapes everything around you. As Elena shared, "What you can do of greatest benefit to the world is attend to your own healing." 🔹 Focus on Your Sphere of Control: When external pressures feel overwhelming, resilience is built by going deeper into what you can influence. 🎯 🔹 Presence Is the Greatest Gift: So many leaders…

The latest episode of An Imperfect Leader features Dr. Bryan Luizzi, 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 opportunities. 2. Balancing Stewardship and Innovation: Great leaders honor what works while still pushing forward. Bryan tells the story of New Canaan's transformation of a 1970s planetarium into The Dome, an immersive learning space where students create, not just consume. 3.Why Imperfection Matters: Perfection freezes leaders. Excellence invites learning. Bryan reflects on a major leadership misstep after returning from Finland and the…

This week, I had the privilege of sitting down with Dr. Richard Lemons, 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 experiences that disrupt assumptions and invite reflection. 2. Student Voice Cuts Through Ideology: When adults stop debating and truly listen to students, clarity emerges. Student voice has the power to quiet political noise and re-anchor leaders in purpose and moral urgency. 3. Imperfect Leadership Is the Only Way Forward: Richard reframes leadership growth as living in a space of being consciously imperfect (aware of what…

🎙️ New Episode of An Imperfect Leader Some conversations stay with you long after the recording ends. My conversation with Dr. Nyah Hamlett 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 when decisions are uncomfortable or unpopular. 🔹 2. Student Voice as Shared Power (Not a Checkbox): Listen for how student voice can sharpen decisions, even when leaders don't ultimately go the students' way. 🔹 3. Imperfect Leadership, Vulnerability, and Accountability: Listen closely to Nyah's after-action reflection. It's a masterclass in humility, learning in real time, and leading as a human being, especially when systems and personal wellbeing collide.…

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 Ben Thompson, K-12 Director at McMillan Pazdan Smith Architecture and host of the Idea Exchange: The Future of K-12 Education podcast. 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. Collaboration Comes First: High-quality school design depends on meaningful engagement with the people who will use the space every day. That includes curriculum leads, maintenance teams, guidance counselors, and students. ives. Process Protects the Future: In his "Imperfect Leadership in After Action" review, Ben shares how skipping engagement or…

In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast we had the pleasure of talking with Dr. Doug Bolton, clinical psychologist, author of Untethered, and director of school consultation for Formative Psychological Services. In Untethered: Creating Connected Families, Schools, and Communities to Raise a Resilient Generation, 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 student achievement, improves mental health, reduces behavior issues, and increases attendance. And it starts with leaders creating that sense of belonging for staff first. • Why punishment doesn't work — and what does: Misbehavior is often stress behavior. Instead of tightening rules, Doug urges leaders to double down…

This week we're sitting down with someone who has walked the walk for nearly four decades: Terrie Morgan, 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 shaped everything from sibling placement to trauma-informed decisions under the McKinney-Vento Act. Spot the Systemic Ripples. Missing staff input on a PreK–8 center created community "angst." Terrie talks candidly about what she learned, and how leaders can avoid preventable unintended consequences. Communication is a System. Terrie starts with the Board and "boots on the road" (teachers, principals, staff) at the same time.…

I'm excited to share my conversation with Dr. Richard Ramos, 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 Innovation Labs and how Dr. Ramos reframed summer school into an "Everyone Can Create" experience rooted in curiosity and strengths. Embracing Imperfection: A candid story about a costly mistake, a supportive superintendent, and the leadership lesson Dr. Ramos now carries with him: communicate, include others, and don't lead in isolation. If you're passionate about student-centered learning and the human side of…

In 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…

How do we prepare students to become empathic individuals and global citizens in an increasingly complex world? Dr. Paul Freeman, 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 individuals, and global citizens. 💡 Highlights from the conversation: Making Thinking Visible: Moving from compliance to engagement. The Necessity of Discomfort: Encouraging deep, sometimes uncomfortable, conversations that build critical thinking. Commitment to Diversity, Equity, and Inclusion: Continuing to build a diverse, inclusive community through professional learning and material audits. Deliberate Practice:…