In this episode of the Leaning Into Leadership podcast, Darrin sits down with fellow high school principal and podcast host Jeff Linden, Principal of Hastings High School in Nebraska. With a shared passion for culture and leadership, Jeff and Darrin dive into what it really takes to build a thriving school environment—especially for those stepping into leadership roles for the first time.

Jeff opens up about his unconventional path to school leadership, including his service in the U.S. Army Reserves, a career in coaching, and his early days as a rookie head football coach and math teacher. He shares what inspired his transition to administration and how a single conversation set him on a leadership journey grounded in systems thinking and relationship building.

Topics covered include:

• The power of systems to reduce chaos and create consistency
• A 60-90-30 day transition plan for new school leaders
• How to foster collective buy-in to support schoolwide accountability
• Jeff’s approach to culture-first leadership and his school’s cell phone policy journey
• Why listening is a non-negotiable skill for new administrators
• How podcasting helps Jeff sharpen his leadership skills

If you're stepping into school leadership—or looking to sharpen your systems and culture-building strategies—this episode is packed with insight and practical takeaways. Plus, Jeff shares how his podcast, Educational Leadership with Principal JL, is helping leaders grow and connect.

📩 Connect with Jeff:

• Email: the.principal.jl@gmail.com
• Podcast: Educational Leadership with Principal JL (available on all major platforms)
• Social Media: Find his handles through his podcast page
• More contact info: https://dot.cards/principal_jl

Jeff Linden is the Principal of Hastings High School in Nebraska and the host of t the Educational Leadership with Principal JL podcast. With over 17 years in education, Jeff brings a wealth of experience as a teacher, coach, and school leader. A military veteran, Jeff’s leadership is grounded in discipline, systems thinking, and a passion for building strong school culture. He holds multiple advanced degrees in leadership and curriculum and is committed to empowering educators, supporting student success, and fostering collaborative school communities.

In this episode of Leaning Into Leadership, Darrin sits down with Joe LaTorre, a middle school English teacher, team coordinator, and founder of the Bridges program in Long Island, NY. Joe shares how looping, relationship-building, and culturally responsive practices help him build classroom communities rooted in trust and student empowerment. They dive deep into the origin and impact of Bridges, a student leadership and cultural exchange initiative, and explore how educators can go beyond curriculum to foster belonging and long-term engagement.

Joe and Darrin discuss everything from rethinking first-day icebreakers to helping students tackle real-world issues like mental health and community leadership. You’ll hear stories about students taking charge, serving their communities, and building relationships that last beyond the school walls. If you’re looking for actionable ways to build student agency and school culture—this episode delivers.

🎧 About Joe LaTorre:

Joe LaTorre’s unconventional journey—from finance to an unexpected stint with the Teletubbies—ultimately led him to his true calling: education. What began as a passion for inspiring a love of reading and writing grew into a mission to equip students and adults with the skills and mindsets needed to thrive in an ever-changing world. Through leadership development, innovation, and a focus on purpose, his work challenges apathy and unlocks potential.

As the founder of Bridges, a partnership between two Long Island school districts, Joe has helped teenagers develop leadership and communication skills to shape their futures. A two-time New York State Teaching Award winner, he has led district-wide initiatives, presented at regional and national forums, and been featured in multiple media outlets. Known for bringing people together and fostering cultures of success, Joe continues to explore new ways to create transformative educational experiences.

📱 Follow Joe on Instagram: @TheJoeLaTorre

🌐 Learn more at: www.JosephLaTorre.net

In this fourth installment of our special NASSP Principal of the Year series, Darrin sits down with Terita Walker, principal of Denver East High School and one of three finalists for NASSP’s 2025 National High School Principal of the Year award.

Walker has transformed East into a school where inclusivity, student empowerment, and academic excellence thrive. With nearly two decades at the school, she reflects on her growth as a leader, the intentional systems she's built to elevate student voice, and how she's making time to deeply connect with teachers post-pandemic.

This episode explores how school culture is built through trust, visibility, and authenticity—and why Terita believes joy is found in the journey.

About Terita Walker

Walker is the principal of Denver East High School in Colorado. Through intentional leadership and a deep commitment to equity, she has fostered a culture where students and staff thrive. She regularly engages with East’s 90+ affinity groups, hosts monthly coffee chats, co-leads community events, and credits the school’s success to the collective work of students, staff, families, alumni, and district partners.

In this third episode of our NASSP National Principal of the Year Finalist series, we head to Ketchikan, Alaska, where Sherilynn Boehlert serves as the principal of Schoenbar Middle School. Sheri shares her inspiring leadership journey—from growing up in a family of educators to leading a Blue Ribbon elementary school and now impacting lives at the middle level.

With honesty and humor, Sheri unpacks her leadership “survival can”—the key tools and values that have helped her build continuity, shared leadership, and school-wide improvement. She discusses the power of relationships, the importance of hiring for fit and culture, and how her team’s deep trust has fueled meaningful change.

Plus, we hear about Schoenbar’s legendary student survival trip, an experience unlike any other that not only connects students to nature—but serves as a powerful metaphor for leadership.

This episode is filled with truth bombs, laughter, and deep insight into what it means to lead with heart in challenging and beautiful places.

Guest Bio:

Sherilynn Boehlert is the principal of Schoenbar Middle School in Ketchikan, Alaska. Previously, she served as the school’s assistant principal and was the principal of Point Higgins Elementary School, which was named a National Blue Ribbon School under her leadership. Boehlert is a graduate of Arizona State University West’s Leadership for Educational Entrepreneurs program and is deeply committed to student-centered decision-making, inclusive leadership, and data-driven practices that build strong, collaborative environments.

Connect with Schoenbar Middle School:

📘 Facebook: Schoenbar Middle School

🌐 Website: Ketchikan Gateway Borough School District

Episode Summary:

Teacher evaluation has long been a source of frustration—for both educators and administrators. In this episode of the Leaning Into Leadership podcast, I sit down with Craig Randall, the developer and author of Trust-Based Observations, to reimagine what teacher observation can and should look like.

Craig shares how shifting the focus from ratings to relationships not only supports teacher growth but also transforms school culture. We talk about why most traditional evaluation models actually hinder innovation, how to build psychologically safe spaces for professional learning, and what it takes to move from a compliance-based mindset to one of curiosity, collaboration, and trust.

You’ll also hear:

• The 9 key pedagogical focus areas of the TBO system
• How to navigate time and legal constraints with TBO
• Why great teachers still need—and crave—strong feedback
• What Brene Brown’s “trust marbles” have to do with better instructional leadership
• How leaders can model the exact mindset they want teachers to bring to their classrooms

Whether you’re a district leader, principal, or aspiring administrator, this episode will challenge your assumptions and offer a clear path to better, more human-centered instructional leadership.

Craig Randall is the developer and author of Trust-Based Observations. Over the past 30+ years, he has worked in education as a counselor, coach, teacher, and principal. Today, Craig trains school leaders around the globe in the TBO system—a framework that replaces fear-based evaluations with trust-driven feedback, resulting in stronger instruction, teacher innovation, and school cultures rooted in psychological safety.

Craig is also the host of the 20 Minutes of Teaching Brilliance (On the Road with Trust-Based Observations) podcast, where he highlights real conversations with classroom teachers about what makes great teaching and learning come alive. He frequently speaks at education conferences and is currently working on his second book.

📘 Learn more at: trustbased.com

📧 Contact: craig@trustbased.com

🎙️ Podcast: 20 Minutes of Teaching Brilliance

📱 Connect:

• X/Twitter: @TrustBasedCraig
• LinkedIn: Craig Randall
• Facebook + Instagram: Craig Randall
• Bluesky: @trustbasedcraig.bsky.social

In this inspiring episode of Leaning Into Leadership, we continue our NASSP National Principal of the Year series with Tony Cattani, a finalist for the 2025–2026 National High School Principal of the Year. For 18 years, Tony has led Lenape High School in Medford, NJ, where he's created a thriving school culture grounded in trust, reflection, and instructional growth.

Tony shares how his leadership journey evolved from managing to truly leading, and how a single conference keynote transformed his outlook. We dive into his groundbreaking peer observation model that has generated more than 3,000 teacher visits, fostered collective efficacy, and built a culture where everyone grows together. From collegiality cafes to popcorn lesson invitations, Tony’s story is a masterclass in empowering educators and redefining professional development.

This conversation is packed with actionable leadership insights, a healthy dose of humility, and yes—a metaphor involving Buffalo chicken dip that perfectly sums up what it means to lead with purpose and pride.

Learn more about NASSP's Principal of the Year program at https://www.nassp.org/news/nassp-announces-national-principal-of-the-year-finalists/

In this powerful kickoff to our NASSP Principal of the Year finalist series, Dr. Damon Lewis of Ponus Ridge STEAM Academy in Norwalk, CT shares his incredible leadership journey—from paraeducator to transformational middle school principal. Under his leadership, chronic absenteeism dropped from 31% to 8%, equity-driven initiatives expanded access to gifted and accelerated programs, and eighth-grade PSAT scores outpaced national, state, and district averages.

Dr. Lewis discusses the culture shift at his school, his “so what, now what” mindset, and why proper preparation, intentional systems, and relentless focus on every student have made the difference. He also opens up about how his personal story fuels his mission—and how being a national finalist is a platform for advocacy, equity, and excellence in public education.

Key Topics:

• Vision-driven leadership and systems thinking
• Accelerating achievement while addressing inequity
• Listening as a leadership superpower
• The impact of culturally responsive leadership
• Why excuses build bridges to nowhere

Learn more about NASSP's Principal of the Year program at https://www.nassp.org/news/nassp-announces-national-principal-of-the-year-finalists/