Leaning into Leadership

Are we really empowering student voice, or are we simply giving students opportunities to talk?

That's one of the central questions in this episode of Leaning Into Leadership, recorded on location at Shoreham-Wading River High School in New York.

Darrin sits down with his friend Frank Pugliese, a veteran educator entering his 30th year in education and his 10th year as principal of Shoreham-Wading River High School.

The conversation follows two days of leadership development and professional learning in Shoreham-Wading River, including a powerful student leadership experience facilitated by Darrin and Dr. Brandon...

What if the most powerful leadership moments aren't the big decisions, major initiatives, or important meetings, but the small interactions we create every single day?

In this episode of Leaning Into Leadership, Dr. Darrin Peppard welcomes Ryan Tiffin, author of Chasing Magic: How Experience Changes Lives and Shapes Leaders, for a conversation about the power of intentional leadership, creating meaningful experiences, and recognizing that you don't need a title to make a difference.

Ryan's professional journey has taken him from photography and DJing to marketing, Disney, Cinemark, and leading teams across a variety of industries...

What do you do when a talented employee keeps making the same mistakes? How many conversations do you have before deciding it's time to move on?

In this solo episode of Leaning Into Leadership, Dr. Darrin Peppard challenges the idea that employee accountability should be synonymous with punishment. Instead, he explores how leaders can use clarity, intentionality, and consistent feedback to help struggling employees grow while maintaining high expectations.

Drawing from his experience as a school leader, Darrin shares the story of an enthusiastic, talented employee whose tendency to act before understanding the full picture...

When a parent sees your school’s number on their phone, what do they expect to hear?

That answer might tell you something important about the relationship you’ve built.

In episode 306 of Leaning Into Leadership, Dr. Ted Huff joins Darrin for a conversation about moving family engagement beyond fundraising and building partnerships grounded in trust, listening, and shared hopes for students.

Ted brings 31 years of experience as a teacher, assistant principal, and principal. He and Darrin first connected in Washington, D.C., in 2016 while representing their states as Principals of the Year. Ten...

You know the work matters. You want to get into classrooms, address that difficult conversation, or revisit the priorities your team identified back in August. So what keeps getting in the way of beginning?

In this special midweek episode of Leaning Into Leadership, Darrin Peppard shares a conversation with a principal during a coaching visit in Omaha, Nebraska. One observation—“It’s the start that stops most people”—becomes a challenge to examine the leadership work we keep putting off.

The Cycle of Chaos gives leaders plenty of obvious starting points: answer the phone, respond to the par...

Being busy can feel like progress. Having answers can feel like confidence. Keeping your door open can feel like good leadership. But when was the last time you stopped to question whether those habits are helping you lead?

Dr. Christopher Jones returns to Leaning Into Leadership after first joining the show in episode 42. A veteran high school principal, Chris brings honest stories and practical ideas from his new book, The Leadership Riddle: A Leader’s Guide to Growing Without Losing Yourself.

Together, Darrin and Chris explore the stages of leadership development through an unexpected lens: th...

What does it mean to face life's most difficult storms rather than run from them? And how do the challenges we experience personally shape the way we show up as leaders?

In this powerful and deeply personal episode of Leaning Into Leadership, Darrin sits down with longtime friend, fellow University of Wyoming doctoral graduate, and retired high school principal Craig Woodall, author of Overcome.

Craig spent 30 years in public education, including his final 12 years as principal of Rocky Mountain High School in Colorado. But his story extends far beyond the hallways of a school. On Sep...

What happens when the person everyone turns to needs someone to turn to?

October is National Principals Month, and Dr. Darrin Peppard is sharing one of his most personal leadership stories yet.

During his years as a high school principal, Darrin once drove to the top of a mountain for one simple reason: he needed somewhere he could scream. It was a moment that reflected the emotional weight of leading a school, carrying confidential information, navigating difficult decisions, and supporting an entire school community.

In this special solo episode of Leaning Into Leadership...

What separates a group of talented people from a truly great team?

In Episode 301 of Leaning Into Leadership, Darrin sits down with executive coach and global educator Gaby Jordan to explore what it takes to build what she calls champion teams—teams grounded in connection, honesty, trust, and a shared commitment to something bigger than themselves.

Gaby brings a unique perspective to leadership. After practicing law for 15 years in Midtown Manhattan, she transitioned into business, executive coaching, and eventually education. Today, her work spans corporate organizations and educational settings from K–12 schools to universities. Across all...

Three hundred episodes.

For this milestone edition of Leaning Into Leadership, I wanted to do something different. Instead of looking back by myself, I invited six incredible leaders—and people who have become an important part of my own journey—to join me for a conversation about leadership, growth, relationships, and the people who help us become better versions of ourselves.

Joining me for Episode 300 are Jason Ryan, Katie Kinder, Todd Bloomer, Bentli Lewis, Josh Tovar, and Brandon Beck. Every one of them has appeared on the podcast before. More importantly, every one of them has...

What if flourishing at work didn't require a massive life overhaul?

In this episode of Leaning Into Leadership, Darrin welcomes back speaker, educator, and soon-to-be author Phil Januszewski for a high-energy conversation about happiness, relationships, and the small choices that can make demanding work more sustainable.

After 20 years in the classroom, Phil stepped away from teaching to speak full time — or, as he puts it, he “quit my job to help other teachers not quit theirs.” His work now takes him across the country helping educators and other service-oriented professionals feel less tired and more inspir...

What if resistance isn’t something leaders need to overcome?

In Episode 298 of the Leaning Into Leadership Podcast, Darrin sits down with Becca Silver, CEO and founder of The Whole Educator and author of The Resistance Solution, for a powerful conversation about what is really happening when educators push back against change.

Becca challenges leaders to stop labeling people as “resistant” and instead recognize that resistance is an experience people move through. Rather than relying on compliance, consequences, or generic advice like “build better relationships,” she introduces a human-centered approach that helps leaders understand the unmet need...

What happens when growth doesn’t solve your problems—but actually makes them bigger?

In Episode 297 of Leaning Into Leadership, Dr. Darrin Peppard sits down with entrepreneur, Marine veteran, and business leader Ron Nussbaum for a conversation about entrepreneurship, problem solving, challenging the status quo, and what it really takes to build something that matters.

Ron shares the story behind BuilderComs and the realization that changed the way he thought about growth: if you scale your organization without solving the problems already inside it, you’re simply scaling those problems too.

That lesson reache...

What if the goal of great teaching isn’t getting students to comply, but creating the conditions where they genuinely want to engage?

In this episode of Leaning Into Leadership, Dr. Darrin Peppard sits down with educator, school leader, author, and founder of Terry Leadership Group, Kendall Terry, for a conversation about what happens when schools stop focusing primarily on what teachers are doing and start paying closer attention to what students are actually learning.

Kendall shares his experience helping build Clayton-Bradley Academy from its early years and the unique opportunity that came with designing ed...

Leadership comes with expectations. Be steady. Be available. Support your people. Make the difficult decisions. Carry the pressure.

But what happens when the person everyone looks to for support needs support too?

In this episode of Leaning Into Leadership, Darrin sits down with organizational psychologist, former therapist, and author Melissa Doman for an honest and practical conversation about leadership mental health, communication, emotional intelligence, and what sustainable leadership actually looks like.

Melissa challenges the idea that leaders should simply absorb the pressure that comes with the role. Instead, she argues that organizations need...

The beginning of a school year brings an energy that is hard to match. The building is ready, staff members are reconnecting, priorities have been established, and leaders walk into the year determined to lead with clarity and intentionality.

Then the students arrive.

Suddenly the emails pile up, meetings fill the calendar, parent concerns emerge, staffing challenges demand attention, and the urgent begins competing with what you said mattered most.

In this special midweek episode of Leaning Into Leadership, Dr. Darrin Peppard challenges school leaders to recognize five common leadership traps that can...

Episode 293 of Leaning Into Leadership is a conversation about something every leader needs to understand: we lead humans, and humans bring their experiences, emotions, stress, and trauma with them to work.

Darrin sits down with licensed clinical social worker, speaker, author, and military leader Stacy Nation to explore what trauma-informed—and ultimately trauma-restorative—leadership can look like in schools.

Stacy challenges leaders to move beyond simply knowing that trauma exists and begin creating environments built around safety, connection, relationships, and restoration. As she explains, one of the most important resiliency factors is having a positive, cari...

Sometimes the biggest opportunities in life begin with the smallest moments.

For Bradlee Skinner, it started with a selfie at a Savannah Bananas game. That one interaction eventually led him from the classroom to becoming a plaza DJ for the Savannah Bananas and Texas Tailgators. But this conversation isn't really about baseball—it's about leadership, courage, relationships, and choosing to say "Why Not?" instead of asking "What If?"

Joining Darrin are Bradlee and Melissa Skinner, two incredible educators who have built careers around creating meaningful experiences for students while embracing growth, creativity, and intentional leadership. To...

As leaders prepare to welcome staff back for a new school year, many spend hours refining presentations, updating strategic plans, and perfecting opening-day messages. But what if the most powerful thing your staff needs isn't a polished speech—it's your passion?

In this personal birthday episode, Dr. Darrin Peppard shares how a day spent Jeeping through Rocky Mountain National Park, Grand Lake, and the Colorado mountains reminded him of the importance of reconnecting with the things that make us come alive. That experience led him to reflect on a conversation with a school administrator whose passion for st...

As another school year begins, principals across the country are busy preparing classrooms, finalizing schedules, reviewing procedures, and checking countless items off their opening-week to-do lists.

But what if the most important preparation has nothing to do with the building?

In this solo episode, Dr. Darrin Peppard challenges school leaders to stop asking, "Is the school ready?" and begin asking, "Am I ready?"

Drawing from his own experiences as a principal, superintendent, and leadership coach, Darrin shares five commitments that will help leaders prepare themselves before they prepare everyone else. Rather than offering...

Leadership growth isn't always about discovering a new strategy. More often, it's about becoming aware of something that has been true all along.

In this solo episode, Dr. Darrin Peppard shares two defining leadership stories that changed the way he thinks about coaching, feedback, and personal growth. From a simple conversation with a superintendent that forever changed his communication style to a coaching experience that revealed the hidden system keeping a leader overwhelmed, this episode explores one powerful truth:

Awareness changes everything.

You'll discover why every leader has blind spots, why your team...

Relationships don't happen by accident. The strongest classrooms, teams, and organizations are built through intentional habits that communicate one simple message: You matter here.

In Episode 288 of Leaning Into Leadership, Darrin sits down with veteran educator, football coach, and leadership speaker Tom Walls to discuss the power of what he calls microinclusions—small, repeatable actions that create belonging, trust, and buy-in without requiring hours of preparation.

Drawing from more than 30 years of experience in classrooms and on football fields across the United States and Canada, Tom shares practical strategies that any leader can begin using im...

What if one of the most powerful leadership lessons isn't found in the principal's office—but inside a classroom?

In this episode, Dr. Darrin Peppard sits down with educator, author, and Teaching Inside Out founder Kim Gameroz to discuss why intentionality—not simply strategy—is what transforms classrooms, educators, and school culture.

Kim shares the inspiration behind her book Becoming the BISON, explains why bison run into storms instead of away from them, and introduces her powerful framework:

Be Intentional So Others Notice.

Together, Darrin and Kim explore how predictable systems, emotio...

Leadership isn’t just about the impact you create today. It’s about the leaders you prepare for tomorrow.

In this annual shared episode, Dr. Darrin Peppard sits down with fellow leadership coach, author, and podcast host Joshua Stamper for a powerful conversation about one of the most important responsibilities of leadership: developing the next generation of leaders.

Darrin and Joshua begin by reflecting on transitions, stress, and the reality every leader faces — even the best plans encounter challenges. The difference is whether leaders have the clarity and intentionality to stay focused on the work that m...

What does effective school leadership look like in a rapidly changing world?

In this episode of Leaning Into Leadership, Darrin Peppard sits down with Debra Wilson, President of the National Association of Independent Schools (NAIS), for a thoughtful conversation about leadership, organizational alignment, AI, demographic shifts, and the future of education.

Drawing on more than two decades of experience supporting school leaders, Debra shares why today's educational challenges require leaders to move beyond the traditional "hero leader" model and embrace the power of strong leadership teams.

Together, Darrin and Debra explore how schools...

What does it take to build a leadership team that truly works?

In this episode of Leaning Into Leadership, Dr. Darrin Peppard sits down with Marlene Rombach, Rocio Rhoads, and Christina Shires—the leadership team at Locust Grove Middle School in Locust Grove, Virginia—to reflect on their first year leading together.

With a first-year principal, a first-year assistant principal, and an assistant principal stepping into a significantly expanded role, this team faced enormous challenges from day one. Yet through intentional communication, trust, coaching, and a commitment to shared leadership, they built a culture that allo...

What if leadership isn't about carrying more?

What if the true responsibility of a leader isn't solving every problem but intentionally creating the conditions where other people can do their best work?

In this special solo episode of Leaning Into Leadership, Dr. Darrin Peppard reflects on a week of leadership coaching, keynote speaking, and executive development that led him to articulate a philosophy that has quietly guided his work for years.

Building on the response to his recent blog, I Thought I Was Helping - A Perspective on Servant Leadership, Darrin challenges traditional...

Landing your first leadership position is exciting...until reality sets in.

The meetings, the emails, the difficult conversations, the angry parents, and the constant interruptions can quickly pull new administrators away from the work they were most excited to do: leading people and supporting learning.

In this episode of Leaning Into Leadership, Dr. Darrin Peppard is joined by Erika Bare and Tiffany Burns, experienced school leaders and co-authors, for a practical conversation about surviving—and thriving—in your first years of school leadership.

Together they share strategies for preparing for difficult conversations, building a tr...

Dr. Chris Culver returns to Leaning Into Leadership for a powerful follow-up conversation centered around his new book, Be the Light: The Science of Kindness and the Power of Belonging.

If you enjoyed Chris's first appearance on Episode 214: The Science of Kindness, you're going to love where this conversation goes next. While Episode 214 explored the research behind kindness, this discussion takes a deeper look at how belonging, empathy, neuroscience, and intentional leadership can transform the cultures we create and the lives we touch.

In this episode, Darrin and Chris explore:

What does leadership look like when the world is changing faster than ever before?

In this episode of the Leaning Into Leadership podcast, Dr. Darrin Peppard sits down with Molly Rosen, Co-CEO of ProjectNext Leadership, for a powerful conversation about leadership transitions, succession development, organizational agility, and the growing impact of AI on leadership and workplace culture.

Molly works with leaders across industries including tech, biotech, and entertainment, helping organizations prepare leaders for critical next-level roles. Together, Darrin and Molly explore why the skills that make someone successful in one role often do not transfer...

In this episode, Darrin sits down with leadership coach and new author Jo Lein to explore what really drives change in people and organizations—and why most coaching efforts fall short when they focus only on skills.

Jo introduces the concept of Disruptive Mindset Coaching, challenging leaders to move beyond surface-level fixes and address the beliefs that shape behavior.

Topics Covered:

What happens when strong leaders slowly stop speaking?

In this reflective solo episode, Dr. Darrin Peppard explores the hidden cost of compliance-based leadership cultures and the long-term impact they can have on trust, alignment, and organizational health.

Drawing from personal leadership experiences, conversations with leaders around the country, and John Maxwell’s “Law of the Lid,” Darrin unpacks what happens when high-capacity leaders find themselves working in environments driven more by control and compliance than collaboration and alignment.

This episode is not about criticizing leaders. It’s about understanding how organizational cultures develop, why stro...

In this episode of Leaning Into Leadership, Darrin sits down with Dr. Nason Lollar to explore a topic often overlooked in leadership conversations—educator professionalism.

Drawing from his book The Five Principles of Educator Professionalism, Nason introduces the TRUST framework, a practical approach to connecting individual behaviors with school culture.

The conversation dives into how small, everyday actions—not just major incidents—shape the success, safety, and climate of a school.

Key Topics:

In this episode, Darrin sits down with Dr. Joy Karavedas to explore what it really means to develop leaders intentionally—and why that “tap on the shoulder” can be life-changing.

Joy shares her journey into leadership and how her research revealed a powerful pattern: nearly every leader can point to a moment when someone saw their potential before they did.

The conversation dives into:

In this episode, Darrin sits down with Megan Diede to unpack one of the most pressing challenges in schools today: authentic student engagement.

The conversation begins with a familiar frustration—classrooms full of students disengaged on devices—and quickly reframes the issue. It’s not about abandoning technology. It’s about being intentional and purposeful with instruction.

Megan introduces a powerful shift in thinking:

Together, they explore what it means to move beyond compliance-driven teaching and into classrooms where students are actively connected to their learning...

In this final episode of the 3-part planning series, Darrin Peppard shifts from planning and preparation to something even more important—what happens when your plan meets reality.

Through a candid story from his time as a superintendent implementing project-based learning, Darrin shares what worked, what didn’t, and the leadership lessons that emerged when execution didn’t match expectations.

Because the truth is—most plans don’t fail in the planning phase.

They fail in the implementation.

Key Takeaways

Planning Isn’t the Problem—Leadership Is

You can have t...

This month, we’ve been focused on one thing: building plans that don’t just sound good—but actually work.

In this episode, Darrin is joined by Kathleen Beckham, Molly Dexter, and Brandon Mawhorter from digiCOACH for a real, unscripted conversation about what it takes to build—and execute—a plan that improves classroom instruction.

This isn’t about theory.

It’s about what actually moves the needle.

Drawing from their experiences as educators, coaches, and system-level partners, Kathy, Molly, and Brandon share practical insights on focus, feedback, data, and the role of leader...

In this mid-week episode, Darrin steps away from long-range planning to focus on something just as powerful—small, intentional actions leaders can take right now.

With only weeks left in the school year, it’s easy to feel stuck in the daily grind. But meaningful leadership doesn’t require a new initiative or a perfect plan. It comes from clear priorities, consistent actions, and intentional choices.

In this episode, Darrin shares 10 practical leadership moves you can implement immediately to:

These aren’t big strategies—they’re simple shift...

What Has to Be True by August?

In Part 2 of this 3-part series on planning for the upcoming school year, Darrin shifts the focus from planning to preparation.

You already know what you want to accomplish next year—but what are you doing right now to make that success possible?

This episode challenges leaders to stop waiting for August and instead take intentional steps today that set the foundation for a strong start.

Key Takeaways

Preparation > Planning

Planning identifies the goal. Preparation makes success possible.

As...

This week kicks off a three-part solo series focused on one critical question:

How do we actually plan for success in the coming school year?

April is a time when leaders are deep in planning—budgets, staffing, schedules, and resources are all coming together. But too often, we focus on what we’re going to do without fully thinking through how we set our teams up for success.

In this episode, Darrin challenges a common leadership assumption—that the work starts in August—and introduces a different way of thinking.

Because August i...