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/

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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.

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.

This week, our guest is Lars Clemensen, the Superintendent of Hampton Bays Union Free School District and President of NYSCOSS. Lars shares profound insights on leadership, community connection, and what it truly means to prepare students for a dynamic future.

This episode offers lessons for all educational leaders. Here are three things we encourage you to listen for:

💡 Schools as the "Future Business" and Community Investment: Lars describes schools as being "in the future business" and emphasizes that budget expenses should be seen as investments in a stronger community, not just costs.

💡 Mastering Crisis Communication with Transparency: Lars offers a candid "after-action review" of his leadership during COVID-19. He reflects on the critical importance of a disciplined, transparent communication plan and the order of informing stakeholders to maintain trust and prevent groups from feeling devalued.

💡 Intentional, Child-Centered Career Development: Learn about Hampton Bays' innovative approach to student pathways, moving beyond a "scavenger hunt" for diplomas.

This conversation is a powerful reminder of a superintendent's belief in opportunity and how meaningful relationships are essential for effective leadership, especially when navigating 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/

--------

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.

New school year is in full swing for many and is just weeks away for others! As leaders, we often strive for perfection, but what if embracing imperfection is our greatest strength?

In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast, we're honored to host Dr. Eric Knost, a former superintendent with 34 years of experience in the education field, including 17 years as a superintendent and deputy superintendent in three different school districts.

Eric shares his journey, emphasizing that prioritizing people, honesty, and vulnerability are the true hallmarks of effective leadership. This episode offers profound insights for all school leaders:

• Learn why Eric believes “imperfection defines perfection” in leadership, and how embracing your humanistic qualities makes you more real and impactful.
• Discover the power of human connection and relationships, exemplified by his own bus driver, Mr. Roberts.
• Hear how he passionately advocates for people-centered cultures over compliance-driven ones, believing bureaucracy should be removed from education when possible.
• Gain insights from his “500-year flood” experience, where vulnerability transformed his leadership and fostered a deeper sense of belonging with his community and staff.

This episode is a must-listen for school leaders seeking to cultivate empathy, compassion, and authentic connection in their districts this coming year. Tune in and prepare to lead with heart.

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

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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.