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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Check latest episodes from An Imperfect Leader: The Superintendents and Leadership Podcast podcast
(VIDEO) Emily Sargent-Beasley on Navigating Transition & Complexity: How Effective Leaders Get Out of the Way
2026/10/20
What does it truly take to lead an educational community through complex transitions without falling into the trap of linear quick fixes? 🏫✨
In the latest episode of An Imperfect Leader, Emily Sargent-Beasley (President of the American College of Sofia) shares profound insights from her career in international education and her doctoral research at the University of San Diego.
Here are some leadership themes to listen for:
1️⃣ Navigating Transitions in Complex Systems: School transitions are deeply bounded by context, inherited conditions, and unseen relational dynamics. Rather than treating transition as a linear "A to B" technical formula, effective leaders recognize schools as complex network systems where quick fixes rarely yield simple outcomes.
2️⃣ Empowering Teacher Agency & Shared Leadership: Real instructional progress happens when leaders trust their educators to drive meaningful change. Leadership isn't about controlling every variable in a crisis. It's about setting up supportive conditions, stepping out of the way, and granting teachers the agency to execute.
3️⃣ Embracing Imperfection & Humility: True professional growth happens at points of tension and uncertainty. Moving away from over-packaged, rigid leadership models opens up space for vulnerability, curiosity, and continuous learning alongside your team.
🎧 Watch or listen to the full episode now to explore how to lead with intention, curiosity, and grace through organizational change!
-----
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
-------
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
-------
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.
(AUDIO) Emily Sargent-Beasley on Navigating Transition & Complexity: How Effective Leaders Get Out of the Way
2026/10/20
What does it truly take to lead an educational community through complex transitions without falling into the trap of linear quick fixes? 🏫✨
In the latest episode of An Imperfect Leader, Emily Sargent-Beasley (President of the American College of Sofia) shares profound insights from her career in international education and her doctoral research at the University of San Diego.
Here are some leadership themes to listen for:
1️⃣ Navigating Transitions in Complex Systems: School transitions are deeply bounded by context, inherited conditions, and unseen relational dynamics. Rather than treating transition as a linear "A to B" technical formula, effective leaders recognize schools as complex network systems where quick fixes rarely yield simple outcomes.
2️⃣ Empowering Teacher Agency & Shared Leadership: Real instructional progress happens when leaders trust their educators to drive meaningful change. Leadership isn't about controlling every variable in a crisis. It's about setting up supportive conditions, stepping out of the way, and granting teachers the agency to execute.
3️⃣ Embracing Imperfection & Humility: True professional growth happens at points of tension and uncertainty. Moving away from over-packaged, rigid leadership models opens up space for vulnerability, curiosity, and continuous learning alongside your team.
🎧 Listen to the full episode now to explore how to lead with intention, curiosity, and grace through organizational change!
-----
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
-------
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
-------
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.
You Might Enjoy: On Purpose with Jay Shetty
2026/10/20
Introducing EZRA FRECH: "I Was Put on This Earth to Change the Way We See Disability" from On Purpose with Jay Shetty.
Follow the show: On Purpose with Jay Shetty
Ezra Frech shares the mindset, discipline, and determination that have shaped his career and led him to win two Paralympic gold medals. From turning heartbreak in Tokyo into motivation to using visualization and meditation to perform under pressure, Ezra reveals how he prepares for the biggest moments of his career. He also opens up about competing on Dancing With the Stars, breaking down misconceptions about disability, and founding Angel City Sports to make adaptive sports more accessible to the next generation.
Instagram Teen Accounts: Built-in protections for teens.
Learn More. At https://chase.com/sapphirereserve
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
What We Discuss:
00:00 Introduction
01:20 "Pressure Doesn't Exist"
02:51 The Day Ezra Was Born
06:24 The 15-Hour Surgery At Age 3
11:15 The Kindergarten Letter
13:29 Learning To Handle The Stares
16:21 Overcoming Stigma And Bullying
23:18 Falling In Love With Sports
27:00 Changing Culture & Looking Ahead to LA 2028
31:09 Mentorship From Pau Gasol
33:56 A Message From Novak Djokovic
36:53 How Do You Define Confidence?
40:43 The Moment That Inspired His Paralympic Dream
44:35 Making Team USA At 14
48:41 How Running Blades Actually Work
52:09 Tokyo Heartbreak & "The Man In The Arena"
58:53 Visualizing Paris Gold Every Morning
01:04:50 Protecting His Good Leg
01:11:33 Winning Double Gold & The 20-Minute Rule
01:17:00 Meditation Under Pressure
01:20:34 A Lifelong Dream to Compete on Dancing With the Stars
01:24:14 Inside the Dancing With the Stars Family
01:27:19 Learning To Dance On A Blade
01:30:12 Pressure Is A Privilege
01:32:10 Making Adaptive Sports Mainstream
01:37:10 Ezra On Final 5
Episode Resources
Instagram | https://www.instagram.com/ezrafrech/
TikTok | https://www.tiktok.com/@ezrafrech
Facebook | https://www.facebook.com/teamezra05/
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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 [email protected].
(AUDIO) "You Are the Strategy": Transforming Chronic Absenteeism Through Relational Invitation with Shelley Berman
2026/10/13
When a student stops showing up to school, our default instinct as a system is often to drop the hammer: automated warning letters, threats of fines, or referrals to juvenile court. Here's the truth: those compliance letters don't build enthusiasm. They alienate families and often worsen the problem. In this latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, we sit down with veteran superintendent and former CASEL CEO Dr. Shelley Berman to tackle one of the most pressing challenges facing education today: chronic absenteeism.
Instead of treating attendance as an enforcement issue, Shelley challenges us to embrace an invitational, relationship-rich model grounded in belonging. As he reminds us: kids show up when the culture is positive and when they—and their families—feel genuinely known and valued.
💡 Key Takeaways & Practical Strategies from the Episode:
The Attendance Paradox: Many educators believe attendance is entirely a family issue outside their control, but research shows school culture and engagement actually have a massive influence. In fact, students with growing social-emotional competencies are half as likely to be chronically absent. You Are the Strategy: Quoting Superintendent Kevin Wilson of Winston-Dillard, before searching for external programs, school communities must look at how adults interact with kids and families every day. The 2x10 Strategy: Pioneered in places like Oregon's Umatilla School District (shout-out to Superintendent Heidi Sipe!), pairing an at-risk student with a staff member for just two minutes of conversation a day for 10 consecutive days about life, not attendance or schoolwork. The Relationship Audit: Bringing school staff together to map out which students have a champion on campus and proactively ensuring no child falls through the cracks without an adult connection. 📚 Two Free Reports You Need to Read: Shelley and his colleagues have documented how real school systems cut chronic absenteeism by double digits without adding extra staffing. We invite you to dive into both resources:
📄 From Compliance to Invitation: Lessons in Improving Attendance in 11 Oregon School Districts (highlighting the real-world trials, errors, and successes of 11 districts). 📄 Connection That Keeps Students Coming Back: Improving Student Attendance Through Relationships, Community, and Engagement (co-authored by Dr. Shelley Berman and CASEL Director of Research Risa Plate). 🎧 Tune in to the episode wherever you get your podcasts, and let us know: What is your school or district doing to move from compliance to true relational invitation?
-----
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
-------
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
-------
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.
(VIDEO) "You Are the Strategy": Transforming Chronic Absenteeism Through Relational Invitation with Shelley Berman
2026/10/13
When a student stops showing up to school, our default instinct as a system is often to drop the hammer: automated warning letters, threats of fines, or referrals to juvenile court. Here's the truth: those compliance letters don't build enthusiasm. They alienate families and often worsen the problem. In this latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, we sit down with veteran superintendent and former CASEL CEO Dr. Shelley Berman to tackle one of the most pressing challenges facing education today: chronic absenteeism.
Instead of treating attendance as an enforcement issue, Shelley challenges us to embrace an invitational, relationship-rich model grounded in belonging. As he reminds us: kids show up when the culture is positive and when they—and their families—feel genuinely known and valued.
💡 Key Takeaways & Practical Strategies from the Episode:
The Attendance Paradox: Many educators believe attendance is entirely a family issue outside their control, but research shows school culture and engagement actually have a massive influence. In fact, students with growing social-emotional competencies are half as likely to be chronically absent. You Are the Strategy: Quoting Superintendent Kevin Wilson of Winston-Dillard, before searching for external programs, school communities must look at how adults interact with kids and families every day. The 2x10 Strategy: Pioneered in places like Oregon's Umatilla School District (shout-out to Superintendent Heidi Sipe!), pairing an at-risk student with a staff member for just two minutes of conversation a day for 10 consecutive days about life, not attendance or schoolwork. The Relationship Audit: Bringing school staff together to map out which students have a champion on campus and proactively ensuring no child falls through the cracks without an adult connection. 📚 Two Free Reports You Need to Read: Shelley and his colleagues have documented how real school systems cut chronic absenteeism by double digits without adding extra staffing. We invite you to dive into both resources:
📄 From Compliance to Invitation: Lessons in Improving Attendance in 11 Oregon School Districts (highlighting the real-world trials, errors, and successes of 11 districts). 📄 Connection That Keeps Students Coming Back: Improving Student Attendance Through Relationships, Community, and Engagement (co-authored by Dr. Shelley Berman and CASEL Director of Research Risa Plate). 🎧 Tune in to the episode wherever you get your podcasts, and let us know: What is your school or district doing to move from compliance to true relational invitation?
-----
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
-------
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
-------
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.
(VIDEO) From Blackouts to Belonging: Chris Lynn and Leading the International School of Havana
2026/10/06
In the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, we sit down with Chris Lynn, Head of School at the International School of Havana.
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 Manifesto. Inspired by Kellett School in Hong Kong, the manifesto was developed over six months with input from the entire school community.
It rests on four foundational pillars:
🌿 Our Nature: We are diverse. 🎯 Our Choice: To make belonging intentional. 🤝 Our Action: The ordinary daily work of good community. 💙 Our Goal: A school where everyone feels accepted, included, and encouraged to be their true selves. This collective aspiration ties directly into their annual theme: #ShapedByUs.
⚡ 2. Imperfect Leadership in After Action (The Solar Project AAR) In the episode's After Action Review segment, Chris candidly deconstructs a high-stakes decision: attempting to implement a solar power, battery, and inverter system to secure energy resilience during Cuba's power and fuel crisis. Driven by urgency to protect learning, he pushed the technical plan forward quickly. However, new US banking restrictions, supply chain bottlenecks in Panama, and importation hurdles stalled progress.
His powerful takeaway? "I had a strategy. I didn't have enough collective aspiration to make it work".
In a moment of forward vulnerability, Chris admitted the oversight, made a mid-course correction, and leaned on the deep expertise of parents and local ambassadors to build a realistic, sustainable path forward.
-----
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
-------
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
-------
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.
(AUDIO) From Blackouts to Belonging: Chris Lynn and Leading the International School of Havana
2026/10/06
In the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, we sit down with Chris Lynn, Head of School at the International School of Havana.
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 Manifesto. Inspired by Kellett School in Hong Kong, the manifesto was developed over six months with input from the entire school community.
It rests on four foundational pillars:
🌿 Our Nature: We are diverse. 🎯 Our Choice: To make belonging intentional. 🤝 Our Action: The ordinary daily work of good community. 💙 Our Goal: A school where everyone feels accepted, included, and encouraged to be their true selves. This collective aspiration ties directly into their annual theme: #ShapedByUs.
⚡ 2. Imperfect Leadership in After Action (The Solar Project AAR) In the episode's After Action Review segment, Chris candidly deconstructs a high-stakes decision: attempting to implement a solar power, battery, and inverter system to secure energy resilience during Cuba's power and fuel crisis. Driven by urgency to protect learning, he pushed the technical plan forward quickly. However, new US banking restrictions, supply chain bottlenecks in Panama, and importation hurdles stalled progress.
His powerful takeaway? "I had a strategy. I didn't have enough collective aspiration to make it work".
In a moment of forward vulnerability, Chris admitted the oversight, made a mid-course correction, and leaned on the deep expertise of parents and local ambassadors to build a realistic, sustainable path forward.
-----
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
-------
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
-------
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.
(VIDEO) Courage, Systems, and Conviction: A Lesson in Vulnerability with Supt. Michael Hayden
2026/09/29
This week on An Imperfect Leader, we sit down with Superintendent Michael Hayden 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 instructional/literacy coaches across all content areas. Master Scheduling for Collaboration: Restructuring schedules to guarantee dedicated joint planning time for teachers. Community-Wide Connections: Expanding literacy beyond school walls by partnering with local pediatrician offices, hospital maternity wards, and regional bookstores to get books directly into hands and homes. 2. An Unfiltered After Action Review: Leadership Conviction & Vulnerability In our after action review, Michael reflects on one of the most gut-wrenching moments of his administrative career: canceling a football season during a playoff run for a state championship.
Prioritizing People Over Celebration: Despite intense backlash and public pressure, Michael stood firm in placing student well-being above athletic achievement. Confronting Adult Trauma: Michael openly shares how this crisis impacted him personally and a realization that school leaders must address adult mental health and trauma support so educators can show up fully for students. -----
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
-------
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
-------
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.
(AUDIO) Courage, Systems, and Conviction: A Lesson in Vulnerability with Supt. Michael Hayden with Supt. Michael Hayden
2026/09/29
This week on An Imperfect Leader, we sit down with Superintendent Michael Hayden 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 instructional/literacy coaches across all content areas. Master Scheduling for Collaboration: Restructuring schedules to guarantee dedicated joint planning time for teachers. Community-Wide Connections: Expanding literacy beyond school walls by partnering with local pediatrician offices, hospital maternity wards, and regional bookstores to get books directly into hands and homes. 2. An Unfiltered After Action Review: Leadership Conviction & Vulnerability In our after action review, Michael reflects on one of the most gut-wrenching moments of his administrative career: canceling a football season during a playoff run for a state championship.
Prioritizing People Over Celebration: Despite intense backlash and public pressure, Michael stood firm in placing student well-being above athletic achievement. Confronting Adult Trauma: Michael openly shares how this crisis impacted him personally and a realization that school leaders must address adult mental health and trauma support so educators can show up fully for students. -----
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
-------
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
-------
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.
(VIDEO) Process over Product: How Courageous Leaders Build Community Trust with Dr. Gustavo Balderas
2026/09/22
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 Dr. Gustavo Balderas, 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 Product: Moving Beyond the Vague Leaders often face high-stakes, emotional decisions like school consolidations or district boundary shifts. Dr. Balderas shared how slowing down, admitting when a process needs a pause or a mea culpa, and authentically engaging stakeholders changes everything. The ultimate goal isn't always total consensus; it's getting to a point where stakeholders can say, "I don't agree with you, but I understand why you made the decision."
2. Navigating "Leadership Compression" & Treating Leadership as a Relay Race With massive leadership transitions post-COVID, many educators are stepping directly from building principalships into the superintendency. Dr. Balderas refers to this as leadership compression (where time in the seat to learn political nuance and system navigation is condensed).
Check out the full episode to hear Dr. Balderas' inspiring origin story. From growing up in a migrant farmworker family to leading major school systems across the country.
-----
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
-------
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
-------
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.
(AUDIO) Process over Product: How Courageous Leaders Build Community Trust with Dr. Gustavo Balderas
2026/09/22
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 Dr. Gustavo Balderas, 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 Product: Moving Beyond the Vague Leaders often face high-stakes, emotional decisions like school consolidations or district boundary shifts. Dr. Balderas shared how slowing down, admitting when a process needs a pause or a mea culpa, and authentically engaging stakeholders changes everything. The ultimate goal isn't always total consensus; it's getting to a point where stakeholders can say, "I don't agree with you, but I understand why you made the decision."
2. Navigating "Leadership Compression" & Treating Leadership as a Relay Race With massive leadership transitions post-COVID, many educators are stepping directly from building principalships into the superintendency. Dr. Balderas refers to this as leadership compression (where time in the seat to learn political nuance and system navigation is condensed).
Check out the full episode to hear Dr. Balderas' inspiring origin story. From growing up in a migrant farmworker family to leading major school systems across the country.
-----
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
-------
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
-------
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.
(VIDEO) Chip Kimball and Three Leadership Lessons on Culture, Deep Thinking, and Knowing When to Hit Reset
2026/09/15
"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!
-----
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
-------
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
-------
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.
(AUDIO) Chip Kimball and Three Leadership Lessons on Culture, Deep Thinking, and Knowing When to Hit Reset
2026/09/15
"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!
-----
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
-------
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
-------
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.
(VIDEO) Jennifer Tickle: Values, Visas, and Ethical AI in Siena, Italy
2026/09/08
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 Jennifer Tickle, former Head of School at the International School of Siena, Italy (now the Head of School in Monza), 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 they wanted to be. This deep community alignment centered on three core anchors: Respect, Integrity, and Compassion.
2️⃣ The 9-Month Recruitment Reality Check (Systems Thinking) In an honest "After Action Review," Jen shares the reality of trying to recruit a highly qualified, non-European physics teacher without fully anticipating the bilateral visa challenges of her host country.
3️⃣ Reframing AI as a "Library Assistant" How do we teach critical thinking when answers are just a click away? In her Grade 7 music class, Jen teaches students to use AI ethically (not to write the work, but to act as a digital "library assistant" guiding them to the right book on the shelf).
True leadership isn't about being perfect. It's about having the humility to admit mistakes, learn alongside your community, and lead relationally.
🎧 Tune in to the full episode (And yes, you'll hear about Peter's newfound obsession with padel!).
#AnImperfectLeader #InternationalEducation #SchoolLeadership #AISH #Podcasserole #ValuesDrivenLeadership #RestorativePractices #SystemsThinking #GlobalRecruitment #EdTechIntegrity
-----
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
-------
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
-------
American education is at a crossroads, and the fight for justice cannot wait. Ezekiel Dixon-Roman and Sonya Douglass of Teachers College present The Politics of Possibility, a powerful series confronting the rollback of civil rights and student erasure. Featuring global voices, the series offers real strategies to honor every student's history. Watch Season 1 now.
------
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.
(AUDIO) Jennifer Tickle Talks Values, Visas, and Ethical AI in Siena, Italy
2026/09/08
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 Jennifer Tickle, former Head of School at the International School of Siena, Italy (now the Head of School in Monza), 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 they wanted to be. This deep community alignment centered on three core anchors: Respect, Integrity, and Compassion.
2️⃣ The 9-Month Recruitment Reality Check (Systems Thinking) In an honest "After Action Review," Jen shares the raw reality of trying to recruit a highly qualified, non-European physics teacher without fully anticipating the bilateral visa challenges of her host country.
3️⃣ Reframing AI as a "Library Assistant" How do we teach critical thinking when answers are just a click away? In her Grade 7 music class, Jen teaches students to use AI ethically (not to write the work, but to act as a digital "library assistant" guiding them to the right book on the shelf).
True leadership isn't about being perfect. It's about having the humility to admit mistakes, learn alongside your community, and lead relationally.
🎧 Tune in to the full episode (And yes, you'll hear about Peter's newfound obsession with padel!).
#AnImperfectLeader #InternationalEducation #SchoolLeadership #AISH #Podcasserole #ValuesDrivenLeadership #RestorativePractices #SystemsThinking #GlobalRecruitment #EdTechIntegrity
-----
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
-------
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
-------
American education is at a crossroads, and the fight for justice cannot wait. Ezekiel Dixon-Roman and Sonya Douglass of Teachers College present The Politics of Possibility, a powerful series confronting the rollback of civil rights and student erasure. Featuring global voices, the series offers real strategies to honor every student's history. Watch Season 1 now.
------
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.
Podcast reviews
Read An Imperfect Leader: The Superintendents and Leadership Podcast podcast reviews
5 out of 5
97 reviews
★★★★★
lahinda 2026/08/02
New Supt
I am in my first month as a superintendent. Your podcast has really helped me transition, giving me great insights and ideas
★★★★★
Khris T. 2025/10/24
Podcast Famous!
It was great to meet you in KC and thank you for the mention! Khris from GB
★★★★★
Muad'Dib-joker 2025/05/20
Good listen for educators
Easy fun listen. Great guests and discussion.
★★★★★
killgirl-c 2024/12/10
Thoughtful, engaging, tactical
Peter has access to inspiring guests, and presents the perfect mix of personal and professional in his storytelling and moderating that allows us to c...
★★★★★
Michele510 2024/07/17
Incentive to be better every day!
Peter and his podcast are an embodiment of true education and what it means to be a lifelong learner. Recognizing that we’re all imperfect, even many ...
★★★★★
Jc Nnz 2024/04/01
The HBR Leadership Podcast for Educational Leaders
Dr. Stiepleman’s expertise and humanity come through in his interview style. He puts guests at ease and bonds with them to provide excellent practical...
★★★★★
ListenerABCDE 2023/10/10
We need more leaders to be vulnerable!
Great concept and interviews - we need more like this!
★★★★★
bobtreeq 2023/09/15
Busy Leaders: If you listen to one podcast, this is the one
Peter’s exceptionally practical insights will be of great value to veteran senior leaders and aspiring leaders as well. His interviews are insightful...
★★★★★
Kit Standridge 2023/06/08
Learning so much
I had the pleasure of hearing Peter speak at a small event in Santa Fe and loved his way of being and what he had to say. I am gleaning so much wisdom...
★★★★★
J.A. Wright 2023/03/28
Invaluable Lessons in Leadership
Peter and his guests share invaluable lessons from their many insights earned over decades of public service. Their conversations remind us that stre...