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An Imperfect Leader

An Imperfect Leader

Written by: Peter Stiepleman
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 An Imperfect Leader: Leadership in (After) Action is a series of conversations with leaders who look back at decisions they made and ask themselves: What happened? What got overlooked? What did you learn about relationships or what new relationships were formed? What frustrated you? What could you have done differently? And in the end, what was something good that came out of the experience – because it is through our mistakes where our greatest learning takes place. I'm Dr. 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 with 19,000 children and 3,000 employees. 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.© 2025 Relationships Social Sciences
Episodes
  • Elena Aguilar on Why Presence Is a Leader's Greatest Gift

    Elena Aguilar on Why Presence Is a Leader's Greatest Gift
    Jan 6 2026
    Are you leading from a place of fixing… or from a place of presence? 🌱 In the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I had the honor of sitting down with Elena Aguilar, the visionary behind Transformational Coaching and author of eight bestselling books, including The Art of Coaching and Arise. 📚✨ Leadership can be a lonely journey. We're often expected to have the answers, solve the problems, and move fast. But Elena reminds us that real transformation doesn't come from quick fixes—it comes from going deeper and tending to the roots. 🌳 Here are four powerful takeaways from our conversation: 🔹 Prioritize Internal Healing: Your internal state shapes everything around you. As Elena shared, "What you can do of greatest benefit to the world is attend to your own healing." 🔹 Focus on Your Sphere of Control: When external pressures feel overwhelming, resilience is built by going deeper into what you can influence. 🎯 🔹 Presence Is the Greatest Gift: So many leaders default to "fix-it mode." But the most impactful thing you can offer is being fully present with the people you serve. 🤍 🔹 Embrace Your Imperfection: Perfection is, in Elena's words, "absurd and unattainable." Authentic leadership lives in humility, honesty, and being human. As Elena beautifully said during the episode: "The biggest gift you can give is to be absolutely present… The main thing is that you're showing up, that you're here." 🎧 Listen to the full episode to explore how moving beyond compliance and leading from the heart can change both you and the communities you serve. ------- Follow Host Peter Stiepleman on: LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/ Website: https://imperfectleader.com/ YouTube (video of conversation): https://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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    58 mins
  • Dr. Bryan Luizzi: When Leadership Doesn't Go as Planned (Remastered)

    Dr. Bryan Luizzi: When Leadership Doesn't Go as Planned (Remastered)
    Dec 30 2025
    The latest episode of An Imperfect Leader features Dr. Bryan Luizzi, Superintendent of New Canaan Public Schools, and it's a powerful reminder that leadership is less about having the answers and more about having the courage to step forward. From Connecticut classrooms to teaching and leading in Jordan, Bryan and I explore what it means to lead people in moments of uncertainty and change. 🎧 Three leadership themes to listen for: 1. Leading with "Yes" (and Courage, Not Recklessness): Bryan shares how a "lead with yes" mindset shaped his career and opened doors to unexpected opportunities. 2. Balancing Stewardship and Innovation: Great leaders honor what works while still pushing forward. Bryan tells the story of New Canaan's transformation of a 1970s planetarium into The Dome, an immersive learning space where students create, not just consume. 3.Why Imperfection Matters: Perfection freezes leaders. Excellence invites learning. Bryan reflects on a major leadership misstep after returning from Finland and the hard lesson of confusing a technical fix with adaptive change. 👂 What leaders should listen closely for: • A good idea, poorly implemented, is a bad idea. • Why real leadership means involving people with you, not deciding for them. • How authenticity and truth-telling rebuild trust after failure. This episode is an honest look at learning in public and leading with humility and heart. 🎙️ Listen now and reflect on what it means to lead imperfectly. ------- Follow Host Peter Stiepleman on: LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/ Website: https://imperfectleader.com/ YouTube (video of conversation): https://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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    40 mins
  • Richard Lemons on Why You Can't Talk People Into Change and What Actually Works

    Richard Lemons on Why You Can't Talk People Into Change and What Actually Works
    Dec 23 2025
    This week, I had the privilege of sitting down with Dr. Richard Lemons, Executive Director of Partners for Educational Leadership, for a conversation that every system-level leader should spend time with. Richard has spent decades helping leaders tackle the hardest work in education: changing systems without losing our humanity. Here are three themes leaders should listen for: 1. You Can't Talk People Into New Mental Models: Richard reminds us that deeply entrenched beliefs about schooling aren't shifted by better arguments or smarter PowerPoints. They change through radically different experiences that disrupt assumptions and invite reflection. 2. Student Voice Cuts Through Ideology: When adults stop debating and truly listen to students, clarity emerges. Student voice has the power to quiet political noise and re-anchor leaders in purpose and moral urgency. 3. Imperfect Leadership Is the Only Way Forward: Richard reframes leadership growth as living in a space of being consciously imperfect (aware of what we don't know and open to learning). This episode is a gift for superintendents, central office leaders, and anyone trying to lead systemic change while staying grounded in values. ------- Follow Host Peter Stiepleman on: LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/ Website: https://imperfectleader.com/ YouTube (video of conversation): https://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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    1 hr and 3 mins
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