In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast, Peter Stiepleman sits down with Josh Reppun, host and Global Community Director of What School Could Be. Josh, a former history teacher turned educational innovator, shares his journey of challenging traditional education models. Through his work with the What School Could Be initiative, Josh is helping lead the conversation on student-driven learning and community involvement in education reform.

Josh’s story is one of transformation, from teaching in Hawaii to curating conversations with educators worldwide. He explores how creative, real-world learning can redefine the future of education and the importance of collaboration among educators to bring about meaningful change.

If you’re a school leader, educator, or someone passionate about empowering communities through education, don’t miss this thoughtful and inspiring conversation with Josh Reppun.

Key Takeaways from the Episode:

1. Josh Reppun discusses how schools are embracing new, student-centered approaches to learning to foster deeper engagement.

2. Why integrating real-world challenges into the curriculum prepares students for the workforce and beyond.

3. How bringing together educators, students, and local communities can drive educational transformation.

4. Josh shares how the What School Could Be podcast is helping elevate innovative educators and new ideas in education.

5. Josh reflects on how setbacks in his career have shaped his leadership approach and commitment to education reform.

Listening Links:
Spotify: https://open.spotify.com/show/26Y4nEEwL9mLzrxUh17NWf
Apple: https://podcasts.apple.com/us/podcast/an-imperfect-leader-the-superintendents/id1644897856
Podcast Site: https://imperfectleader.com/podcasts/

Follow Our Guest Josh Reppun on:
LinkedIn: https://www.linkedin.com/in/joshreppun/
Instagram: https://www.instagram.com/joshreppun/
What School Could Be Podcast: https://wscbpodcast.com/

Follow the Host Peter Stiepleman on:
LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/
Website: https://imperfectleader.com/
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 https://www.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 https://imperfectleader.com/

In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I sit down with Dr. Justin Irish, Superintendent of the Anacortes School District in Washington and a former principal at Edmonds School District. Dr. Justin Irish shares how systems thinking, co-design, and meaningful partnerships have helped his district navigate mental health challenges, budget shortfalls, and equity conversations.

We discuss his strategic approach to transparent budgeting, the importance of shared decision-making, and the lessons he learned through vulnerability and community engagement. From establishing mental health supports across schools to leading the redesign of the highly capable program during the pandemic, Dr. Justin Irish demonstrates the power of authentic, human-centered leadership.

If you’re a school leader, educator, or someone passionate about empowering communities through education, don’t miss this thoughtful and inspiring conversation with Dr. Justin Irish.

Key Takeaways from the Episode:

• Strategic Partnerships for Student Wellness – Dr. Justin Irish explains how his district built cross-sector collaborations with hospitals and foundations to support students' mental health.

• Building Systems of Predictable Support – How a tiered model (MTSS) helps identify and meet students’ academic and emotional needs.

• Transparent and Inclusive Budget Planning – Lessons from implementing zero-based budgeting and community-led advisory councils to navigate financial constraints.

• Redesigning the Highly Capable Program – Why listening, pausing, and co-designing with stakeholders helped reshape a controversial decision into a shared solution.

• The Value of Vulnerable Leadership – Dr. Justin Irish reflects on the importance of acknowledging mistakes and leading with humility to build trust and connection.
  
  

Listen to the full episode to hear how Dr. Justin Irish is making a lasting impact on education and building stronger, more connected school communities.

Listening Links:
Spotify: https://open.spotify.com/show/26Y4nEEwL9mLzrxUh17NWf
Apple: https://podcasts.apple.com/us/podcast/an-imperfect-leader-the-superintendents/id1644897856
Podcast Site: https://imperfectleader.com/podcasts/

Follow Our Guest Dr. Justin Irish on:
LinkedIn: https://www.linkedin.com/in/justin-irish-379b0135b/
Anacortes School District: https://www.asd103.org/

Follow the Host Peter Stiepleman on:
LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/
Website: https://imperfectleader.com/
Instagram:https://www.instagram.com/animperfectleader/
Tiktok: https://www.tiktok.com/@animperfectleader

--------------------------------------------------------------------------------
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 https://www.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 https://imperfectleader.com/

In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I sit down with Michelle Caulfield, Superintendent of the Corning-Painted Post Area School District in Corning, New York. Michelle shares how her district is expanding access to opportunities by centering student voice, investing in innovative programs, and building a culture of connection and belonging.

We discuss how inclusive, student-led clubs are transforming school culture, how unique programs like drone soccer and unified sports are engaging students in new ways, and how Michelle is leading with empathy while navigating challenges like recruitment and budget constraints. She also shares lessons learned about listening, showing up, and what it means to be an imperfect leader.

If you're a school leader, educator, or someone interested in shaping the future of education, don't miss this thoughtful conversation with Michelle Caulfield.

Key Takeaways from the Episode:

• Michelle explains how Corning’s schools are expanding student voices by encouraging students to lead initiatives, shape clubs, and participate in district planning.

• She shares how innovative programming like drone soccer and unified sports helps meet diverse student needs and creates new opportunities for connection and engagement.

• Michelle discusses what she learned about community communication after a failed budget vote, and how she rebuilt trust through personal outreach and deeper listening.

• She describes how the district is improving hiring by holding on-the-spot job fairs, training interviewers on bias awareness, and building relationships with teacher preparation programs.

• Michelle reflects on the challenges of perfectionism in leadership and the importance of slowing down, listening to understand, and showing up with consistency and care.

Tune in to hear how Michelle Caulfield is leading with empathy, courage, and a commitment to growing opportunities for all students.

Listening Links:
Spotify: https://open.spotify.com/show/26Y4nEEwL9mLzrxUh17NWf
Apple: https://podcasts.apple.com/us/podcast/an-imperfect-leader-the-superintendents/id1644897856
Podcast Site: https://imperfectleader.com/podcasts/

Follow Our Guest Michelle Caulfield on:

District Website: https://www.corningareaschools.com/
Facebook: https://www.facebook.com/CPPSchools/
Instagram: https://www.instagram.com/cppschools/

Follow the Host Peter Stiepleman on:

LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/
Website: https://imperfectleader.com/
Instagram:https://www.instagram.com/animperfectleader/
Tiktok: https://www.tiktok.com/@animperfectleader

--------------------------------------------------------------------------------
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 https://www.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 https://imperfectleader.com/

In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I sit down with Moises Morgenstern, co-founder and CEO of Empat Speech, a leading platform that connects schools with experienced speech-language pathologists (SLPs). Moises shares how his company is improving access to speech therapy using technology, addressing the nationwide shortage of SLPs, and supporting schools in providing high-quality speech-language services.

We discuss how telehealth speech therapy is transforming support for students, particularly in rural communities where access to in-person specialists is limited. Moises discusses the importance of bilingual speech therapy, strategies for managing caseloads in schools, and how AI-enhanced solutions are helping improve student outcomes through personalized learning.

If you're a school leader, educator, or someone interested in shaping the future of education, don't miss this insightful conversation with Moises Morgenstern.

Key Takeaways from the Episode:

• Expanding Access to Speech Therapy – How Empat Speech helps schools connect with licensed SLPs, even in rural or underserved communities.

• Personalized Support – The role of technology in tracking student progress and enhancing speech therapy outcomes.

• Flexible Solutions for Schools – How virtual therapy helps schools reduce staffing challenges, supplement in-house SLPs, and provide individualized services.

• The Importance of Bilingual Support – How Empat Speech offers bilingual speech-language pathologists to meet the needs of diverse student populations.

• Lessons in Leadership – Moises shares insights on navigating challenges, prioritizing relationships, and building long-term solutions for education.

Listen to the full episode to hear how Moises Morgenstern is reshaping speech therapy accessibility and leveraging technology to support student success.

Listening Links:
Spotify: https://open.spotify.com/show/26Y4nEEwL9mLzrxUh17NWf
Apple: https://podcasts.apple.com/us/podcast/an-imperfect-leader-the-superintendents/id1644897856
Podcast Site: https://imperfectleader.com/podcasts/

Follow Our Guest Moises Morgenstern on:

• LinkedIn: https://www.linkedin.com/in/moises-morgenstern/

• Empat Speech Website: https://www.empatspeech.com/

Follow the Host Peter Stiepleman on:

LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/
Website: https://imperfectleader.com/
Instagram:https://www.instagram.com/animperfectleader/
Tiktok: https://www.tiktok.com/@animperfectleader

--------------------------------------------------------------------------------
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 https://www.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 https://imperfectleader.com/

In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I'm joined by Damian McBeath, Principal of the John Wallis Church of England Academy. As an experienced school leader and author, Damian brings a wealth of knowledge on education reform, leadership, and the evolving role of schools in shaping students beyond academics.

During our discussion, Damian and I discussed how schools can foster whole-child development through experiential learning and why reducing digital distractions has become essential for student engagement. We also discuss his experience testifying before the UK Parliament on phone-free policies and the cultural transformation his school has undergone.

If you're a school leader, educator, or someone interested in shaping the future of education, don't miss this insightful conversation with Damian McBeath.

• The Expanding Horizons Initiative – Damian explains how structured experiential learning opportunities help students develop life skills, emotional intelligence, and resilience.

• The Impact of Phone-Free Schools – Lessons from implementing a mobile phone ban, how students and teachers have responded, and the broader implications for education policy.

• Leadership & Cultural Shifts – The importance of building trust, engaging stakeholders, and leading change with transparency and empathy.

Listen to the full episode to hear my conversation with Damian McBeath about his leadership journey and the transformative policies shaping education today.

Listening Links:
Spotify: https://open.spotify.com/show/26Y4nEEwL9mLzrxUh17NWf
Apple: https://podcasts.apple.com/us/podcast/an-imperfect-leader-the-superintendents/id1644897856
Podcast Site: https://imperfectleader.com/podcasts/

Follow Our Guest Damian McBeath on:
LinkedIn: https://www.linkedin.com/in/damian-mcbeath-82903583/
Twitter: https://x.com/damianmcbeath
Website: https://uk.bettshow.com/speakers/damian-mcbeath

Follow the Host Peter Stiepleman on:
LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/
Website: https://imperfectleader.com/
Instagram:https://www.instagram.com/animperfectleader/
Tiktok: https://www.tiktok.com/@animperfectleader

--------------------------------------------------------------------------------
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 https://www.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 https://imperfectleader.com/

In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I'm joined by Dr. Curtis Cain, Superintendent of the Rockwood School District and 2022's National Superintendent of the Year. With decades of experience in educational leadership, Dr. Cain offers deep insights into navigating the complexities of leading a major school district through unprecedented times.

During our discussion, Dr. Cain and I explored what constitutes effective leadership in the ever-evolving landscape of education. We explore the critical roles of trust and accountability in maintaining team cohesion and morale during crises.

If you're an educator or leader seeking insights into resilience and community trust, don't miss this essential conversation with Dr. Curtis Cain!

Here are the key takeaways:

👉🏼 Adaptive Leadership in Challenging Times: Dr. Cain highlights the importance of flexibility and resilience in adapting to new educational technologies during the pandemic.
👉🏼 The Human Side of Education: Emphasizing emotional and community support, Dr. Cain discusses the need for educators to connect deeply with students' well-being.
👉🏼 Cultivating Leadership and Emotional Intelligence: Dr. Cain underscores the critical role of empathy and responsiveness required in effective leadership.
👉🏼 Embracing Technological Advancements: We discuss the rapid integration of digital tools in education, likening it to historic innovations and enhancing learning for digital fluency.

🎧 Listen to the full episode to hear my conversation with Dr. Curtis Cain about his journey and strategic insights on transformative leadership and technology in education.

Listening Links:
Spotify: https://open.spotify.com/show/26Y4nEEwL9mLzrxUh17NWf
Apple: https://podcasts.apple.com/us/podcast/an-imperfect-leader-the-superintendents/id1644897856
Podcast Site: https://imperfectleader.com/podcasts/

Follow Our Guest Dr. Curtis Cain on:
Linkedin: https://www.linkedin.com/in/curtis-cain-9b757441/
Twitter: https://x.com/rockwoodsupt

Follow the Host Peter Stiepleman on:
LinkedIn: https://www.linkedin.com/in/peter-stiepleman-76004819a/
Website: https://imperfectleader.com/
Instagram:https://www.instagram.com/animperfectleader/
Tiktok: https://www.tiktok.com/@animperfectleader

--------------------------------------------------------------------------------
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 https://www.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 https://imperfectleader.com/