Moving from Command-and-Control to Shared Stewardship: Jesse Boise and 25 Years of Coherence at Hillsdale High
An Imperfect Leader: The Superintendents and Leadership Podcast
Release Date: 05/19/2026
(VIDEO) Leading Without Flinching with Dr. Nyah Hamlett
An Imperfect Leader: The Superintendents and Leadership Podcast
Some conversations stay with you long after the recording ends. My conversation with 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...
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(VIDEO) Laser Focus: James Lane and Cutting Through Initiative Fatigue to Save the Learning Moment
An Imperfect Leader: The Superintendents and Leadership Podcast
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 , former acting Assistant Secretary of the US Department of Education and author of . 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...
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Laser Focus: James Lane and Cutting Through Initiative Fatigue to Save the Learning Moment
An Imperfect Leader: The Superintendents and Leadership Podcast
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 , former acting Assistant Secretary of the US Department of Education and author of . 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...
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Beyond the Three-Year Myth: The Truth About the Superintendency
An Imperfect Leader: The Superintendents and Leadership Podcast
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 (Columbia University's Teachers College) and (Seton Hall University) about the . 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...
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(VIDEO) Beyond the Three-Year Myth: Anne LoBue and Chris Tienken Share the Truth About the Superintendency
An Imperfect Leader: The Superintendents and Leadership Podcast
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 (Columbia University's Teachers College) and (Seton Hall University) about the . 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...
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The Monopoly is Over: Brian Stephens and Why Public Schools Must Compete or Risk Becoming Dinosaurs
An Imperfect Leader: The Superintendents and Leadership Podcast
Is the era of the public school monopoly officially dead? According to my guest, , 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:...
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(VIDEO) The Monopoly is Over: Brian Stephens and Why Public Schools Must Compete or Risk Becoming Dinosaurs
An Imperfect Leader: The Superintendents and Leadership Podcast
Is the era of the public school monopoly officially dead? According to my guest, , 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...
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(VIDEO) Zaretta Hammond on Reclaiming Cognitive Justice and the Power of the "First Pancake"
An Imperfect Leader: The Superintendents and Leadership Podcast
Are we settling for "belonging" in our schools while leaving student brainpower underdeveloped? I recently had a deep, transformative conversation with , author of . 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....
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Zaretta Hammond on Reclaiming Cognitive Justice and the Power of the "First Pancake"
An Imperfect Leader: The Superintendents and Leadership Podcast
Are we settling for "belonging" in our schools while leaving student brainpower underdeveloped? I recently had a deep, transformative conversation with , author of . 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...
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Dr. Melissa Sadorf and Why Rural Schools are the Soul of Their Communities
An Imperfect Leader: The Superintendents and Leadership Podcast
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 , Executive Director of the National Rural Education Association and author of . 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...
info_outlineHow 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 by a Constitution: Hillsdale isn't run by command and control. Instead, they are guided by a formal Constitution that codifies shared decision-making. As Jesse notes, this means leaders must be "stewards" of the school’s values rather than individual actors. It’s about being "greater than the sum of [your] parts".
- The Strength of the Imperfect Leader: Jesse shared a powerful story about a time he fell short by letting his own biases drive a committee meeting. He and Jamie discussed how humble leadership (admitting mistakes publicly and acting as a tool for staff support) is actually the strongest form of leadership.
If you’re looking for a roadmap on how to align your school’s structures with your deepest values, this episode is a must-listen.
Listen to the full episode of An Imperfect Leader: The Superintendents and Leadership Podcast here!
#EducationLeadership #SmallLearningCommunities #AnImperfectLeader #SchoolCulture #TeacherRetention #EdChat #SuptChat #Podcasserole #Imperfect Leader
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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://youtu.be/VkKiXpczSEAhttps://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 IXL. Boost learning with a platform proven to deliver results. IXL gives educators a complete K–12 curriculum and personalized learning plans that adapt to every student.
Trusted by over 1 million teachers and 96 of the top 100 school districts, IXL helps schools outperform on state tests, and helps teachers focus on what matters most.
IXL: Powerful data. Personalized learning. Real progress.
Discover what IXL can do for your school at IXL.com/imperfect
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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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The Mosaic Project, one of our favorite organizations, has over 25 years of experience empowering students to celebrate differences, communicate assertively, and resolve conflicts peacefully at their outdoor school. Their innovative SEL curriculum is now available to An Imperfect Leader listeners at a 10% discount through their new documentary film-based Mosaic Classroom Project!
The Project’s ready-to-use lesson plans include film, original music, “gametivities”, and real conversations. We’re proud to partner with The Mosaic Project in helping educators build inclusive, peaceful learning communities! Just mention An Imperfect Leader during the onboarding process to receive the 10% discount.
Learn more about The Mosaic Classroom Project.
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Think differently. Think in systems. Reach out to The Waters Center for Systems Thinking to learn more about how systems thinking capacity building can strengthen your team and organization.
Homepage: www.waterscenterst.org
Thinking Tools Studio: https://thinkingtoolsstudio.waterscenterst.org
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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.