(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
Release Date: 08/11/2026
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 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.