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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

Release Date: 06/16/2026

The Monopoly is Over: Brian Stephens and Why Public Schools Must Compete or Risk Becoming Dinosaurs show art 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 show art (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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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 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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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 universal....

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An Imperfect Leader: The Superintendents and Leadership Podcast

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 , 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...

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An Imperfect Leader: The Superintendents and Leadership Podcast

How do you keep a school transformation alive for 25 years when most initiatives fizzle out after three? Jamie Almanzán recently sat down with , Assistant Principal at Hillsdale High School, to talk about the staying power of 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: ...

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An Imperfect Leader: The Superintendents and Leadership Podcast

How do you keep a school transformation alive for 25 years when most initiatives fizzle out after three? Jamie Almanzán recently sat down with , Assistant Principal at Hillsdale High School, to talk about the staying power of 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: ...

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More Episodes

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:

  1. 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.

  2. Leading with Emotion to Change the Narrative: While educators love data, Brian points out that data alone doesn't move people. To recruit families back, you have to win their hearts first. He explains, "We're not led with facts and data. We're led with emotion, and we use facts to support those decisions." Successful districts find their stories and use them to build an emotional connection with the community.

  3. The Difference Between Being "Nice" and Being "Kind": In a powerful leadership lesson, Brian deconstructs a mistake he made early in his career: going along to get along. He realized that true support means telling the truth, even when it’s uncomfortable. He advocates for clear-is-kind leadership: giving authentic feedback that actually helps a district improve rather than just making people feel good.

Public schools are doing incredible work, but as Brian reminds us, "they didn't understand how great they were." It's time to stop being the best-kept secret and start advocating for the programs we offer every day.

#PublicEducation #SchoolLeadership #EnrollmentMarketing #AnImperfectLeader #EducationReform #SuptChat #EdChat #ReclaimTheNarrative #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 3 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. 

Homepagewww.waterscenterst.org

Thinking Tools Studiohttps://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.