(AUDIO) Building a Cathedral to Possibility: How Winchester and Jason Van Heukelum are Beyond the Four Walls of a Classroom
An Imperfect Leader: The Superintendents and Leadership Podcast
Release Date: 08/11/2026
(AUDIO) Jennifer Tickle Talks Values, Visas, and Ethical AI in Siena, Italy
An Imperfect Leader: The Superintendents and Leadership Podcast
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 , former Head of School at the International School of Siena, Italy (now the ), 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...
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(VIDEO) Jennifer Tickle: Values, Visas, and Ethical AI in Siena, Italy
An Imperfect Leader: The Superintendents and Leadership Podcast
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 , former Head of School at the International School of Siena, Italy (now the ), 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...
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(AUDIO) Beyond the Report Card: Reclaiming School Greatness with Vikas Pota
An Imperfect Leader: The Superintendents and Leadership Podcast
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 , founder of T4 Education and creator of the . 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...
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(VIDEO) Beyond the Report Card: Reclaiming School Greatness with Vikas Pota
An Imperfect Leader: The Superintendents and Leadership Podcast
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 , founder of T4 Education and creator of the . 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...
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Dr. Christina Kishimoto and the Radical Power of Relationship Capital
An Imperfect Leader: The Superintendents and Leadership Podcast
🚨 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 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...
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Back by Popular Demand: Casey Hallgarth and Why Relationships (Not Titles) Are the True Key to System Leadership
An Imperfect Leader: The Superintendents and Leadership Podcast
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...
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(AUDIO) Building a Cathedral to Possibility: How Winchester and Jason Van Heukelum are Beyond the Four Walls of a Classroom
An Imperfect Leader: The Superintendents and Leadership Podcast
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 , 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...
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(VIDEO) Curing the Testing Obsession: Winchester and Jason Van Heukelum are Reclaiming Joy and Agency in the Modern Classroom
An Imperfect Leader: The Superintendents and Leadership Podcast
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 , 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...
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(VIDEO) Leading with Curiosity with Max Silverman: The Power of Noticing and Wondering
An Imperfect Leader: The Superintendents and Leadership Podcast
We are heading back into the archives for a very special encore episode of An Imperfect Leader! When I first spoke with , the Executive Director of the , 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...
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(AUDIO) Leading with Curiosity with Max Silverman: The Power of Noticing and Wondering
An Imperfect Leader: The Superintendents and Leadership Podcast
We are heading back into the archives for a very special encore episode of An Imperfect Leader! When I first spoke with , the Executive Director of the , 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." ...
info_outlineAre 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 test scores post-COVID. He shares how he’s dusting off the rubrics for skills and dispositions to refocus on student agency and deeper learning.
- CTE Elevated: Why moving programs out of the basement and into state-of-the-art facilities changes the narrative for students and the community.
If you are looking for a path forward that balances accountability with the human need for creativity and curiosity, Jason’s story is your blueprint.
#EducationLeadership #CTE #StudentAgency #InnovationInEducation #Podcasserole #AnImperfectLeader #SchoolImprovement #ThePoliticsOfPossibility
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Follow Host Peter Stiepleman on:
LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/
Website: https://imperfectleader.com/
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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American education is at a crossroads, and the fight for justice cannot wait. Ezekiel Dixon-Roman and Sonya Douglass of Teachers College present The Politics of Possibility, a powerful series confronting the rollback of civil rights and student erasure. Featuring global voices, the series offers real strategies to honor every student's history. Watch Season 1 now.
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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.