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 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
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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.
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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: http://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.

