An Imperfect Leader: The Superintendents and Leadership Podcast

I'm excited to share my conversation with Dr. Richard Ramos, Superintendent of the Miami Unified School District in Miami, Arizona. Dr. Ramos brings such heart to his work - lifting student voice, building true community partnerships, and embracing the beautiful messiness of leadership.

Here are the three big themes from our conversation:

• Student Agency & Community Collaboration: How a simple idea (a Business Partner Café) became a student-led space where young people host, present, and guide conversations with local business partners.

• Innovation & Project-Based Learning: A look inside Miami's Innovation Labs and how Dr. Ramos reframed summer school into an "Everyone Can Create" experience rooted in curiosity and strengths.

• Embracing Imperfection: A candid story about a costly mistake, a supportive superintendent, and the leadership lesson Dr. Ramos now carries with him: communicate, include others, and don't lead in isolation.

If you're passionate about student-centered learning and the human side of leadership, this episode will resonate.

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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 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.

In this episode, we are joined by Dr. Darren Kennedy, the High School Instructional Supervisor for Sumner County Schools (just outside Nashville, Tennessee). Dr. Kennedy, author of So You Think You Want to Be a Principal, 50 Voices from the Field, shares powerful insights on creating transformational change in school culture and academics.

Leaders, here are three things you will learn from this episode:

1. The power of focusing on Tier One Instruction over Intervention: Darren recounts his experience as a principal of a turnaround middle school where an initial heavy reliance on supplemental intervention programs resulted in only marginal progress. 
2. Why values must be a collective aspiration: Darren emphasizes that values and beliefs must be established through an inclusive, collaborative process with the administrative team to form a unified coalition. 
3. The essential need for Human-Centered Leadership: Understand that leading an organization involves working with humans, and longevity in leadership requires mastery of the "human side of the work." 

This episode is a must-listen for anyone responsible for student success and leader development.

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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 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.

------

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.

How do we prepare students to become empathic individuals and global citizens in an increasingly complex world?

Dr. Paul Freeman, Superintendent of Guilford Public Schools and Connecticut's Superintendent of the Year, joins An Imperfect Leader: The Superintendents and Leadership Podcast to discuss leading transformational change through confident vulnerability.

Dr. Freeman shares how Guilford's Portrait of a Graduate (POG) model guides instruction across all grade levels: developing students as adaptable learners, responsible collaborators, critical thinkers, effective communicators, empathic individuals, and global citizens.

💡 Highlights from the conversation:

• Making Thinking Visible: Moving from compliance to engagement.

• The Necessity of Discomfort: Encouraging deep, sometimes uncomfortable, conversations that build critical thinking.

• Commitment to Diversity, Equity, and Inclusion: Continuing to build a diverse, inclusive community through professional learning and material audits.

• Deliberate Practice: Partnering with Harvard's Ed Ethics team to help educators navigate complex discussions safely.

• After Action Review: Reflecting on lessons learned from retiring an offensive mascot and advancing social justice work.

Dr. Freeman embodies confident vulnerability. He embodies the courage to lead with both strength and humility. Tune in for a truly inspiring conversation!

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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

------- 

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.

------

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.

In this week's episode, we sit down with Dr. John Anzalone, Superintendent of the Camas School District (WA).

Dr. Anzalone shares his powerful reflections on leadership and what it truly means to lead with humility. Here are 3 lessons on imperfect leadership and courageous strategy we learned from John:

🌟 1. Establish a Clear North Star: Every financial decision should point back to one thing: students. 

💬 2. Lead with Courage and Vulnerability

🤝 3. Rebuild Trust from Within: 

🎙️ Key Takeaway:
Healthy systems are built on healthy relationships. Reflection, trust, and vulnerability aren't signs of weakness.Tthey're the heart of sustainable leadership.

Listen to the full conversation and let us know your thoughts via LinkedIn.

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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

------- 

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.

------

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.

I had the absolute pleasure of speaking with Dr. Deborah Wortham, nationally recognized educator, author of the bestseller Setting the Atmosphere, and CEO of Wortham Educational Enterprises.

Dr. Wortham shared powerful insights on how leaders move systems forward by focusing on culture, confidence, and consistency. If you're leading a system and striving to create the conditions for lasting transformation, here are 3 key takeaways:

✨ 1. Setting the Atmosphere & Belief-Driven Leadership: Dr. Wortham grounds her leadership in creating a cultural field that gives people permission to grow, develop, and succeed.

🤝 2. Collaborate in Circles, Not Silos: Dr. Wortham structures collaboration through concentric circles: Teacher Circle, Student Circle, etc because "one is too small a number to achieve greatness."

📚 3. Embrace a Learning Goal Orientation: Leadership means acknowledging imperfection and using it for growth. As Dr. Wortham reminds us: "It's okay not to know, but it's not okay not to know and not to learn."

🎧 Tune in to the full conversation for powerful stories, including the secret behind her daily rallying cry: "Smart is not something you are; smart is something you get."

#EducationalLeadership #SettingTheAtmosphere #Superintendent #SchoolCulture #LeadershipDevelopment #CollectiveEfficacy #LearningGoalOrientation #ImperfectLeader

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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

------- 

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.

------

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.

We recently had a powerful conversation with David K. Richards, nationally recognized education leader, innovator, CEO of Changemaker MicroSchools, and host of the Changemaker EDU podcast. The episode delves into an innovative model for educational leaders to consider.

Here are three key takeaways from our conversation:

1. Understanding the Micro School Model 

A microschool is defined by its intimacy. David envisions Changemaker MicroSchools as small learning environments, which can range anywhere from five to 150 students. 

2. Navigating Change: Disruption with Love

Introducing bold ideas often means navigating resistance and naysayers. David advises leaders to get clear on their purpose and strategy and to strive to disrupt with love. When people push back, it is important to understand that resistance often stems from fear and a need to maintain safety (the survival instinct). 

3. Embracing Vulnerability

Leadership is inherently imperfect. David stresses that effective leadership is an inside-out process that requires vulnerability. Leaders should resist the urge to pretend they know everything, especially in new roles. A powerful leadership tool is the simple phrase, "I don't know [the answer], but I will find out for you," which liberates the leader and earns respect. 

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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

------- 

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.

------

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.

What If AI Were Your Business Partner? How can school leaders use AI as a thought partner and collaborator?

The conversation around AI isn't about the future anymore, it's about now. This week's episode is a thought-provoking one. I sit down with Matt Leta, founder and CEO of FutureWorks, a serial entrepreneur, and a forward-thinking voice on AI in leadership and education.

Matt doesn't just talk about AI. He lives it. In this conversation, he shares how he launched a company with AI as his business partner, what he learned from the experience, and how those lessons connect to leadership, resilience, and systems thinking.

Here are three big takeaways from our conversation:

1. AI as a Thought Partner and Collaborator: Imagine treating AI not as a tool, but as a colleague. Matt shares how FutureWorks was built on this idea.

2. Resilience and Learning Through Failure: Matt opens up about nearly losing everything (an "eight-figure collapse") that he now calls his real MBA. His story is a powerful reminder that leadership requires both courage and reflection, especially in times of crisis.

3. Human Comfort and Change Management: Even the best technology fails if people aren't ready for it. We explore how to help teams move from curiosity to confidence.

This episode will stretch your thinking about what it means to lead—and learn—in the age of AI.

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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:

https://www.apccollab.com/

------- 

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.

------

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.

What does it really mean to lead for democracy in our schools today?

This week on An Imperfect Leader: The Superintendents and Leadership Podcast, I sit down with Dr. John Rogers of UCLA's School of Education and Information Studies for a powerful conversation on one of the biggest drains on schools today: culturally divisive conflict.

Dr. Rogers makes a clear distinction between healthy political debate and the anti-democratic conflict fueled by violent rhetoric and misinformation. His research reveals both the financial and human toll:

💸 One midsize district spent $1M in staff time grappling with divisive conflicts.
🕰️ Another saw public records requests quadruple, eating up thousands of wasted hours.
💔 In high-conflict districts, 94% of superintendents said staff health (mental and physical) was negatively impacted.

So what can school leaders do when the attacks often come from outside their circle of influence?

Dr. Rogers points to three essential moves:
✨ Reclaim the Narrative: Reinforce the mission of public education as fostering a diverse, multiracial democracy.
🤝 Build Bridges: Create schools as "social centers" that bring communities together to solve problems.
🧩 Embrace Imperfect Leadership: Engage in shared inquiry and lean on the collective wisdom of your team and community.

🎙️ This is a must-listen episode for every superintendent, principal, and educational leader navigating today's challenges.

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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:

https://www.apccollab.com/

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Superintendent Support Reimagined! 

Zach Taylor and I are creating a reflective, virtual Community of Practice designed exclusively for Superintendents and Senior District Leaders. While calling it An Imperfect Leadership Community of Practice makes sense, I keep advocating for Talk Supt 🙂.

Want to learn more? Check out our video here 👇 or visit:

https://imperfectleader.com/imperfect-leadership-community-of-practice/

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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.

------

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.

Thrilled to welcome Dr. Jason Radford, recently-retired Superintendent of Oldham County Schools (KY), to An Imperfect Leader: The Superintendents and Leadership Podcast. His journey is a terrific example of trust, strategy, and servant leadership.

Here are three big takeaways for all of us imperfect leaders:

✨ 1. Trust Through Transparency & Vulnerability: When trust was low and turnover high, Dr. Radford launched a "Rounding Roadshow" to connect with all 1,500 employees. In year one, he publicly shared the most critical feedback (including comments about himself). That honesty shifted the culture. By year three, 99%  said the district was on the right track.

📚 2. Strategy That Reaches the Student's Desk: Oldham County's strategic plan boils down to one clear promise: every student feels known, valued, supported, loved, and safe. 

🤝 3. Presence Heals: The Roadshows revealed staff were starved to hear directly from their superintendent. Showing up did more than close the gap between central office and schools. It created space for healing after the pandemic. Dr. Radford shared that the process healed him, too. 💙

A heartfelt thank you to Dr. Radford for modeling imperfect leadership with such honesty and care.

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/CJj3QFMHUrU?si=blO15MYOMeldlRpE

Instagram: https://www.instagram.com/animperfectleader/
Tiktok: https://www.tiktok.com/@animperfectleader 

Follow Co-host Jamie Almanzán on:

https://www.apccollab.com/

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Superintendent Support Reimagined! 

Zach Taylor and I are creating a reflective, virtual Community of Practice designed exclusively for Superintendents and Senior District Leaders. While calling it An Imperfect Leadership Community of Practice makes sense, I keep advocating for Talk Supt 🙂.

Want to learn more? Check out our video here 👇 or visit:

https://imperfectleader.com/imperfect-leadership-community-of-practice/

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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.

------

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.