The Tightrope of Leadership with Dr. Larry Cuban
Tue Feb 03 2026
Leadership isn't about finding the perfect solution. It's about learning from the daily grind of complexity.
In this week's episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I had the chance to speak with Dr. Larry Cuban, former superintendent, Stanford professor, and author.
A few insights that stayed with me, especially for leaders working in high-stakes environments:
1️⃣ Conflict isn't a failure, it's the work: Dr. Cuban shared that he couldn't recall a single conflict-free day as a superintendent. Leadership is a constant balancing act (boards, unions, families, and communities all pulling at once).
2️⃣ Be a "good enough" leader: Burnout often comes from chasing an ideal that doesn't exist. Dr. Cuban argues for being good enough (not mediocre), but well-matched to your context.
3️⃣ Excellence can't be mandated: Lasting improvement doesn't come from top-down pressure. It comes from tapping into the wisdom of people doing the work every day. For school leaders, that often means buffering teachers from noise so they can teach, reflect, and grow.
Leadership leaves scars. Systems resist change. And progress is rarely linear. But as Dr. Cuban reminds us, it's the effort to adapt that defines a leader's legacy.
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Follow Host Peter Stiepleman on:
LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/
Website: https://imperfectleader.com/
YouTube (video of conversation):
https://youtu.be/VkKiXpczSEAhttps://www.youtube.com/@animperfectleaderleadershi5144/featured
Instagram: https://www.instagram.com/animperfectleader/
Tiktok: https://www.tiktok.com/@animperfectleader
Follow Co-host Jamie Almanzán on:
Connect with APC Leadership Collaborative for support in navigating complex leadership situations: https://www.apccollab.com
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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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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.
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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.
More
Leadership isn't about finding the perfect solution. It's about learning from the daily grind of complexity. In this week's episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I had the chance to speak with Dr. Larry Cuban, former superintendent, Stanford professor, and author. A few insights that stayed with me, especially for leaders working in high-stakes environments: 1️⃣ Conflict isn't a failure, it's the work: Dr. Cuban shared that he couldn't recall a single conflict-free day as a superintendent. Leadership is a constant balancing act (boards, unions, families, and communities all pulling at once). 2️⃣ Be a "good enough" leader: Burnout often comes from chasing an ideal that doesn't exist. Dr. Cuban argues for being good enough (not mediocre), but well-matched to your context. 3️⃣ Excellence can't be mandated: Lasting improvement doesn't come from top-down pressure. It comes from tapping into the wisdom of people doing the work every day. For school leaders, that often means buffering teachers from noise so they can teach, reflect, and grow. Leadership leaves scars. Systems resist change. And progress is rarely linear. But as Dr. Cuban reminds us, it's the effort to adapt that defines a leader's legacy. ------- Follow Host Peter Stiepleman on: LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/ Website: https://imperfectleader.com/ YouTube (video of conversation): https://youtu.be/VkKiXpczSEAhttps://www.youtube.com/@animperfectleaderleadershi5144/featured Instagram: https://www.instagram.com/animperfectleader/ Tiktok: https://www.tiktok.com/@animperfectleader Follow Co-host Jamie Almanzán on: Connect with APC Leadership Collaborative for support in navigating complex leadership situations: https://www.apccollab.com ------- An Imperfect Leader is sponsored by IXL. Boost learning with a platform proven to deliver results. IXL gives educators a complete K–12 curriculum and personalized learning plans that adapt to every student. Trusted by over 1 million teachers and 96 of the top 100 school districts, IXL helps schools outperform on state tests, and helps teachers focus on what matters most. IXL: Powerful data. Personalized learning. Real progress. Discover what IXL can do for your school at IXL.com/imperfect ------- An Imperfect Leader is sponsored by Yondr. Schools around the world are seeing the damaging effects of phones on student engagement, social development, and mental health. Yondr has developed a unique product and program to allow schools to become phone-free, from arrival to dismissal. Learn why 1 Million Students use Yondr every day. MINIMIZE DISTRACTIONS. MAXIMIZE LEARNING POTENTIAL. Go to overyondr.com to learn more. ------ The Mosaic Project, one of our favorite organizations, has over 25 years of experience empowering students to celebrate differences, communicate assertively, and resolve conflicts peacefully at their outdoor school. Their innovative SEL curriculum is now available to An Imperfect Leader listeners at a 10% discount through their new documentary film-based Mosaic Classroom Project! The Project's ready-to-use lesson plans include film, original music, "gametivities", and real conversations. We're proud to partner with The Mosaic Project in helping educators build inclusive, peaceful learning communities! Just mention An Imperfect Leader during the onboarding process to receive the 10% discount. Learn more about The Mosaic Classroom Project. ------ Think differently. Think in systems. Reach out to The Waters Center for Systems Thinking to learn more about how systems thinking capacity building can strengthen your team and organization. Homepage: www.waterscenterst.org Thinking Tools Studio: https://thinkingtoolsstudio.waterscenterst.org ------ An Imperfect Leader: Leadership in (After) Action is supported by ILAA, LLC, a firm dedicated to supporting aspiring, new, and established leaders. For more information, please find them at imperfectleader.com. Music for An Imperfect Leader was written and arranged by Ian Varley. Sam Falbo created our artwork, a wood-print inspired daruma doll butterfly.