(VIDEO) Chip Kimball and Three Leadership Lessons on Culture, Deep Thinking, and Knowing When to Hit Reset
An Imperfect Leader: The Superintendents and Leadership Podcast
"This was a fail, and I own it." This week, on An Imperfect Leader, shows us what real leadership vulnerability looks like. His insights on international education and systems leadership brought up some themes every leader should reflect on: 1. The Power of the Reset Button: When Chip tried to streamline his team’s global R&D process, the spark was missing. Instead of abandoning a noble goal, he had the vulnerability to admit the approach was a failure, hit pause, and launch "R&D 2.0". 2. Cultural Competence Over Standard Metrics Drawing from years leading major school...
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(AUDIO) Chip Kimball and Three Leadership Lessons on Culture, Deep Thinking, and Knowing When to Hit Reset
An Imperfect Leader: The Superintendents and Leadership Podcast
"This was a fail, and I own it." This week, on An Imperfect Leader, shows us what real leadership vulnerability looks like. His insights on international education and systems leadership brought up some themes every leader should reflect on: 1. The Power of the Reset Button: When Chip tried to streamline his team’s global R&D process, the spark was missing. Instead of abandoning a noble goal, he had the vulnerability to admit the approach was a failure, hit pause, and launch "R&D 2.0". 2. Cultural Competence Over Standard Metrics Drawing from years leading major school...
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(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...
info_outline"This was a fail, and I own it." This week, on An Imperfect Leader, Dr. Chip Kimball shows us what real leadership vulnerability looks like. His insights on international education and systems leadership brought up some themes every leader should reflect on:
1. The Power of the Reset Button: When Chip tried to streamline his team’s global R&D process, the spark was missing. Instead of abandoning a noble goal, he had the vulnerability to admit the approach was a failure, hit pause, and launch "R&D 2.0".
2. Cultural Competence Over Standard Metrics Drawing from years leading major school systems in the U.S. and internationally, Chip noted that the greatest deficit facing American students often isn't math or science scores. It's cultural competence. When talking with university admissions officers, the consensus was clear: colleges aren't looking for kids who simply stack a dozen advanced courses. They are looking for a cross section of "smart and interesting" human beings.
3. Designing Ecosystems for Deep Thinking In an era dominated by AI and social media algorithms, schools must intentionally protect human connection.
Leading systemically isn't about avoiding mistakes, it's about creating an ecosystem where teams can safely experiment, reflect, and grow.
Give a listen!
What’s a time you had to pause a flawed process and hit reset on a noble goal? I'd love to hear your thoughts!
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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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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.