An Imperfect Leader: The Superintendents and Leadership Podcast

Peter Stiepleman

Welcome to An Imperfect Leader: The Superintendents and Leadership Podcast, a series of conversations with leaders who look back at decisions they made and consider: * What happened? * What got overlooked? * What did they learn about relationships or what new relationships were formed? * What frustrated them? * What could they have done differently? * And in the end, what was something good that came out of their experience – because it is through one's mistakes where the greatest learning takes place. I'm Peter Stiepleman. I'm your host AND I'm an imperfect leader. I spent more than 20 years teaching and leading, first in the Oakland Public Schools in Oakland, CA and then in the Midwest – Missouri, to be exact – where I was a teacher, a principal, an assistant superintendent and the superintendent of the 4th largest school district in a state of more than 500 districts. I am constantly striving to learn from my experiences and from the experiences of other leaders. The aim of this podcast is to lift the learning and lift the imperfect leaders up. That way, when you hear the term imperfect, you'll see strength, strength from the candor needed to recognize imperfection as a real advantage.

  1. 6d ago ·  Video

    (VIDEO) Zaretta Hammond on Reclaiming Cognitive Justice and the Power of the "First Pancake"

    Are we settling for "belonging" in our schools while leaving student brainpower underdeveloped? I recently had a deep, transformative conversation with Zaretta Hammond, author of Rebuilding Students' Learning Power. 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 look deeper. True justice means ensuring every student has the "cognitive resources" to accelerate their own learning. Embrace the "First Pancake": Learning requires a safe space for "intelligent failure." Zaretta uses a brilliant metaphor for new initiatives: when making pancakes, that first one is not quite right. As leaders, we have to use that information to "adjust the batter" rather than abandoning the work when it gets messy. The Discipline of Assessing Current Reality: Don't assume your systems (like PLCs) are functioning just because people nod their heads. Zaretta shared a powerful lesson on "due diligence" after realizing a school she was coaching called every meeting a PLC, but lacked true team continuity.  If you're ready to stop "plugging and playing" strategies and start building real teacher capacity, this episode is a must-listen. #CognitiveJustice #ZarettaHammond #InstructionalEquity #AnImperfectLeader #ScienceOfLearning #EducationLeadership #SuptChat #EdChat #Podcasserole ------- 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 -------  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 -------  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.    ------    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. ------ 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 ------ 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.

    1h 1m

  2. 6d ago

    Zaretta Hammond on Reclaiming Cognitive Justice and the Power of the "First Pancake"

    Are we settling for "belonging" in our schools while leaving student brainpower underdeveloped? I recently had a deep, transformative conversation with Zaretta Hammond, author of Rebuilding Students' Learning Power. 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 look deeper. True justice means ensuring every student has the "cognitive resources" to accelerate their own learning. Embrace the "First Pancake": Learning requires a safe space for "intelligent failure." Zaretta uses a brilliant metaphor for new initiatives: when making pancakes, that first one is not quite right. As leaders, we have to use that information to "adjust the batter" rather than abandoning the work when it gets messy. The Discipline of Assessing Current Reality: Don't assume your systems (like PLCs) are functioning just because people nod their heads. Zaretta shared a powerful lesson on "due diligence" after realizing a school she was coaching called every meeting a PLC, but lacked true team continuity.  If you're ready to stop "plugging and playing" strategies and start building real teacher capacity, this episode is a must-listen. #CognitiveJustice #ZarettaHammond #InstructionalEquity #AnImperfectLeader #ScienceOfLearning #EducationLeadership #SuptChat #EdChat #Podcasserole ------- 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 -------  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 -------  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.    ------    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. ------ 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 ------ 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.

    1h 1m
  3. You Might Also Like: On Purpose with Jay Shetty

    6d ago ·  Bonus

    You Might Also Like: On Purpose with Jay Shetty

    Introducing Stop Waiting to “Figure It Out!” (Do THIS In The Next 48 Hours to FINALLY Take the First Step in Finding Your Purpose) from On Purpose with Jay Shetty. Follow the show: On Purpose with Jay Shetty Jay taps into the question so many people quietly carry: “Is this really what I’m meant to do?” With honesty and clarity, he challenges the myths we’ve been taught about purpose, that it’s a single calling, that passion comes first, or that clarity arrives before action. Instead, Jay reframes purpose as something you build through curiosity, experimentation, and small, consistent steps. He reminds us that most people aren’t lost, they’re avoiding what they already know because of what it might cost. Jay offers a practical framework for finding direction. He points to the things that come naturally, what deeply moves or frustrates you, the challenges you’ve lived through, and even who you envy as signals worth paying attention to. These aren’t random, they’re clues guiding you toward the work that’s truly aligned with you. The message is simple but powerful: stop waiting for certainty, start moving, and trust that clarity comes through action. In this episode you'll find: How to Find Your Purpose How to Turn Passion Into Purpose How to Start Before You’re Ready How to Overcome Fear of Failure How to Build Confidence Through Action How to Become More Yourself The quiet ideas you keep returning to, the things that light something up inside you, the dreams you keep pushing aside, they matter for a reason. Start where you are, with what you have, and trust that clarity often comes after action, not before it. With Love and Gratitude, Jay Shetty JAY’S DAILY WISDOM DELIVERED STRAIGHT TO YOUR INBOX Join 900,000+ readers discovering how small daily shifts create big life change with my free newsletter. Subscribe here: https://news.jayshetty.me/subscribe  Check out our Apple subscription to unlock bonus content of On Purpose! https://lnk.to/JayShettyPodcast  00:00 Intro 01:21 The Biggest Lie About “Following Your Passion” 02:20 The Myth of Having One True Calling 03:25 Why You Won’t Feel Certain When You Find It 04:06 Your Purpose Doesn’t Have to Be Your Job 05:36 4 Real Places to Look for Your Purpose 11:02 4 Hidden Obstacles That Keep You Stuck 14:50 Stop Trying to “Find” Your Purpose — Start Testing It 16:25 The 1% Rule That Changes Your Direction 17:44 Stop Talking About It, Start Doing the Work  18:43 Your Environment Shapes Your Future 19:39 Discomfort Means You’re on the Right Path 20:27 The One Action to Take in the Next 48 Hours 22:26 The 3 Paths That Lead You to Purpose See omnystudio.com/listener for privacy information. DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to team@podroll.fm.

  4. Jun 2 ·  Video

    (VIDEO) Dr. Melissa Sadorf and Why Rural Schools are the Soul of Their Communities

    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 Dr. Melissa Sadorf, Executive Director of the National Rural Education Association and author of The Resilient Rural Leader. 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. Here are 3 themes from our talk that you should pay attention to: The "Multi-Hat" Generalist: In rural districts, the organizational chart is flat. A superintendent might also be the principal, the HR director, and even the backup bus driver. This makes them high-level generalists with a real understanding of how every part of a school system actually works. The School as a Community Anchor: A rural school is often the largest employer and the primary gathering space in a town. Melissa reminds us that school closures aren't just administrative decision. They are the potential "erasure of a community's identity."  Vulnerability as the Currency of Credibility: Melissa argues that imperfection isn't a liability; it's a strength. Being transparent about mistakes and uncertainty is what builds the deepest trust with your staff and board. As Melissa beautifully put it: "Resilience isn't because there's an absence of loss. It's really... what you build in the presence of loss." Listen to the full episode of An Imperfect Leader here! #RuralEducation #LeadershipResilience #AnImperfectLeader #SchoolBoard #SuptChat #EdChat #NREA #RuralSchools ------- 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 -------  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 -------  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.    ------    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. ------ 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 ------ 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.

    59 min

  5. Jun 2

    Dr. Melissa Sadorf and Why Rural Schools are the Soul of Their Communities

    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 Dr. Melissa Sadorf, Executive Director of the National Rural Education Association and author of The Resilient Rural Leader. 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. Here are 3 themes from our talk that you should pay attention to: The "Multi-Hat" Generalist: In rural districts, the organizational chart is flat. A superintendent might also be the principal, the HR director, and even the backup bus driver. This makes them high-level generalists with a real understanding of how every part of a school system actually works. The School as a Community Anchor: A rural school is often the largest employer and the primary gathering space in a town. Melissa reminds us that school closures aren't just administrative decision. They are the potential "erasure of a community's identity."  Vulnerability as the Currency of Credibility: Melissa argues that imperfection isn't a liability; it's a strength. Being transparent about mistakes and uncertainty is what builds the deepest trust with your staff and board. As Melissa beautifully put it: "Resilience isn't because there's an absence of loss. It's really... what you build in the presence of loss." Listen to the full episode of An Imperfect Leader here! #RuralEducation #LeadershipResilience #AnImperfectLeader #SchoolBoard #SuptChat #EdChat #NREA #RuralSchools ------- 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 -------  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 -------  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.    ------    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. ------ 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 ------ 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.

    1 hr

  6. May 26 ·  Video

    (VIDEO) Heidi Sipe: Leading with Clarity and Compassion

    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 Heidi Sipe, 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 immediate decisions for students without waiting for administrative approval. It's a masterclass in building shared leadership that prioritizes child needs over bureaucracy. Solving Chronic Absenteeism through Radical Partnerships: When healthcare access became a barrier to attendance, Umatilla didn't just track data, they partnered with a local physician to provide well-child checks and treatment for minor illnesses directly through the school. It's a powerful example of looking outside the system to solve internal challenges. Leading with Transparency During a Crisis: Heidi reflects on her Grim Reaper nickname earned during the recession when she had to cut $1.9 million from a $13 million budget. She discusses the painful but right decision to deliver news of potential layoffs in person, looking every impacted staff member in the eye rather than sending a letter. Heidi's story is a reminder that while the work is impossibly difficult, leading with a human heart and a clear system makes all the difference. #SchoolLeadership #RuralEducation #SystemsThinking #AnImperfectLeader #TeacherAgency #SuperintendentLife #EducationInnovation #NREA #Podcasserole ------- 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 -------  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 -------  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.    ------    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. ------ 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 ------ 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.

    56 min

  7. May 26

    Heidi Sipe: Leading with Clarity and Compassion

    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 Heidi Sipe, 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 immediate decisions for students without waiting for administrative approval. It's a masterclass in building shared leadership that prioritizes child needs over bureaucracy. Solving Chronic Absenteeism through Radical Partnerships: When healthcare access became a barrier to attendance, Umatilla didn't just track data, they partnered with a local physician to provide well-child checks and treatment for minor illnesses directly through the school. It's a powerful example of looking outside the system to solve internal challenges. Leading with Transparency During a Crisis: Heidi reflects on her Grim Reaper nickname earned during the recession when she had to cut $1.9 million from a $13 million budget. She discusses the painful but right decision to deliver news of potential layoffs in person, looking every impacted staff member in the eye rather than sending a letter. Heidi's story is a reminder that while the work is impossibly difficult, leading with a human heart and a clear system makes all the difference. #SchoolLeadership #RuralEducation #SystemsThinking #AnImperfectLeader #TeacherAgency #SuperintendentLife #EducationInnovation #NREA #Podcasserole ------- 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 -------  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 -------  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.    ------    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. ------ 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 ------ 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.

    56 min

  8. May 19

    Moving from Command-and-Control to Shared Stewardship: Jesse Boise and 25 Years of Coherence at Hillsdale High

    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 #Imperfect Leader ------- 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 -------  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 -------  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.    ------    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. ------ 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 ------ 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.

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About

Welcome to An Imperfect Leader: The Superintendents and Leadership Podcast, a series of conversations with leaders who look back at decisions they made and consider: * What happened? * What got overlooked? * What did they learn about relationships or what new relationships were formed? * What frustrated them? * What could they have done differently? * And in the end, what was something good that came out of their experience – because it is through one's mistakes where the greatest learning takes place. I'm Peter Stiepleman. I'm your host AND I'm an imperfect leader. I spent more than 20 years teaching and leading, first in the Oakland Public Schools in Oakland, CA and then in the Midwest – Missouri, to be exact – where I was a teacher, a principal, an assistant superintendent and the superintendent of the 4th largest school district in a state of more than 500 districts. I am constantly striving to learn from my experiences and from the experiences of other leaders. The aim of this podcast is to lift the learning and lift the imperfect leaders up. That way, when you hear the term imperfect, you'll see strength, strength from the candor needed to recognize imperfection as a real advantage.

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