(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
Release Date: 09/15/2026
(VIDEO) From Blackouts to Belonging: Chris Lynn and Leading the International School of Havana
An Imperfect Leader: The Superintendents and Leadership Podcast
In the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, we sit down with , Head of School at the Leading an international school in Cuba amidst daily grid uncertainties, fuel shortages, and complex operational challenges requires incredible resilience, empathy, and community-first leadership. Chris Lynn approaches each challenge with a human-centered approach. 🌟 1. The Belonging Manifesto To ensure that every student, staff member, and family feels safe, known, and valued, Chris spearheaded the co-creation of the school’s...
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(AUDIO) From Blackouts to Belonging: Chris Lynn and Leading the International School of Havana
An Imperfect Leader: The Superintendents and Leadership Podcast
In the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, we sit down with , Head of School at the Leading an international school in Cuba amidst daily grid uncertainties, fuel shortages, and complex operational challenges requires incredible resilience, empathy, and community-first leadership. Chris Lynn approaches each challenge with a human-centered approach. 🌟 1. The Belonging Manifesto To ensure that every student, staff member, and family feels safe, known, and valued, Chris spearheaded the co-creation of the school’s Belonging...
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(AUDIO) Courage, Systems, and Conviction: A Lesson in Vulnerability with Supt. Michael Hayden with Supt. Michael Hayden
An Imperfect Leader: The Superintendents and Leadership Podcast
This week on An Imperfect Leader, we sit down with Superintendent of the Clyde-Savannah Central School District for a deeply moving conversation on leadership, literacy, and human-centered courage. Here are two key takeaways from this powerful conversation: 1. Thinking in Systems to Guarantee Middle School Literacy Michael shares how middle school serves as a crucial pivot point. Rather than leaving literacy to chance, Michael applied systems thinking across the district: Protecting Instructional Coaching: Even during state aid cutbacks, the district prioritized non-evaluative...
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(VIDEO) Courage, Systems, and Conviction: A Lesson in Vulnerability with Supt. Michael Hayden
An Imperfect Leader: The Superintendents and Leadership Podcast
This week on An Imperfect Leader, we sit down with Superintendent of the Clyde-Savannah Central School District for a deeply moving conversation on leadership, literacy, and human-centered courage. Here are two key takeaways from this powerful conversation: 1. Thinking in Systems to Guarantee Middle School Literacy Michael shares how middle school serves as a crucial pivot point. Rather than leaving literacy to chance, Michael applied systems thinking across the district: Protecting Instructional Coaching: Even during state aid cutbacks, the district prioritized non-evaluative...
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(VIDEO) Process over Product: How Courageous Leaders Build Community Trust with Dr. Gustavo Balderas
An Imperfect Leader: The Superintendents and Leadership Podcast
When we talk about leadership in education, it’s easy to rely on broad phrases like "building relationships" or "equity" without defining what those actually look like in daily practice. In this week's episode of An Imperfect Leader, co-host Jamie Almanzan and I sat down with , Superintendent of Puget Sound Educational Service District and former AASA and NABE National Superintendent of the Year. We explored what it takes to turn abstract ideas into concrete, actionable systems. Here are a couple of themes from our conversation that every leader can appreciate: 1. Process Is as...
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(AUDIO) Process over Product: How Courageous Leaders Build Community Trust with Dr. Gustavo Balderas
An Imperfect Leader: The Superintendents and Leadership Podcast
When we talk about leadership in education, it’s easy to rely on broad phrases like "building relationships" or "equity" without defining what those actually look like in daily practice. In this week's episode of An Imperfect Leader, co-host Jamie Almanzan and I sat down with , Superintendent of Puget Sound Educational Service District and former AASA and NABE National Superintendent of the Year. We explored what it takes to turn abstract ideas into concrete, actionable systems. Here are a couple of themes from our conversation that every leader can appreciate: 1. Process Is as Important as...
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(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...
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.