What if the problem in our schools isn’t a lack of voice, but a lack of connection?
In this episode, I had the opportunity to sit down with Dr. Matt Pitman, author of The Connection Conundrum, for a conversation that challenged many of the leadership norms we’ve inherited, especially the idea that effective leaders must remain stoic, distant, or emotionally neutral.
Matt makes a compelling case that this model is no longer serving our schools. Instead, he invites leaders to rethink community, voice, and presence; and to move from making people feel heard to making them feel truly held.
Here are three insights from our conversation that every leader should wrestle with:
🎧 3 Leadership Reflections Worth Your Time
1. From “Heard” to “Held”: Surveys and listening sessions are easy. Accountability is harder. Matt argues that voice only becomes authentic when leaders publicly explain how stakeholder input shaped a final decision. When people can see their fingerprints on the outcome, trust grows.
2. Lead as a Human, Not an Automaton: The era of the emotionless leader is over. Matt encourages leaders to start meetings by naming how they’re actually showing up. That small act of vulnerability allows teams to “be human together” before tackling the work.
3. The 30/70 Rule of Ambition: In a powerful moment of reflection, Matt shares a lesson learned the hard way: it’s fine to be 30% ambitious about what’s next, but 70% of your energy must be devoted to the people you lead right now.
This conversation is a timely reminder that connection isn’t soft leadership, it’s sustainable leadership.
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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://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: http://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.