Leaning into Leadership

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, Darrin explores the invisible backpack every principal carries and the important leadership work that often goes unnoticed. Drawing from his experiences as a principal, superintendent, and leadership coach, he shares three examples of the unseen work that makes an extraordinary difference: the conversations nobody hears, the decisions nobody understands, and the moments nobody remembers. But this episode isn't simply about the challenges of principalship. It's a celebration of the relationships, collective purpose, and privilege that make the work so meaningful. In this episode: The personal story behind Darrin's trip to the top of a mountain. The invisible backpack principals carry and why even the strongest leaders need support. Three important acts of leadership that rarely receive recognition. Why relationships remain one of the greatest rewards of school leadership. A challenge for superintendents to support the people who lead their schools. Two meaningful ways to celebrate National Principals Month. A question worth considering: Who helps the person everybody else comes to for help? Whether you're currently serving as a principal, supporting school leaders, or remembering a principal who made a difference in your life, this episode is a reminder that some of the most important leadership work happens when nobody is watching. During National Principals Month, take a moment to recognize someone whose leadership has made a difference. Be specific. Tell them about the conversation, decision, or moment that mattered. They might have no idea you still remember. This Episode Is Sponsored by Curriculum Leadership Institute and by HeyTutor We're excited to welcome Curriculum Leadership Institute (CLI) as our newest sponsor! Darrin has personally worked with CLI twice during his educational leadership career, first as a principal and again as a superintendent. CLI partners with districts to build sustainable curriculum systems, strengthen alignment, and provide teachers with the clarity they need to succeed. New districts can receive a 5% discount on their first year of service by mentioning Leaning Into Leadership. Learn more at https://cliweb.org or email [email protected]. HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, helping students receive targeted academic support. Learn more at https://heytutor.com. Keep leaning into leadership, keep making a difference, and have a Road to Awesome week!

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 of those environments, she has discovered one important constant: leadership is always human work. Darrin and Gaby dig into why relationships matter so much to team performance. High-performing teams don't have to be made up of best friends, but people do need to know one another, understand one another, and be willing to have honest conversations. Gaby shares how learning someone's origin story—and even acknowledging our own vulnerabilities and imperfections—can completely change the way a team works together. They also explore one of the biggest threats to healthy teams: the stories we create in our own heads. Darrin shares a story from his school leadership days about a colleague whose "thinking face" he initially interpreted as frustration or disagreement. That simple misunderstanding becomes a powerful example of how easily assumptions can turn into narratives—and how those narratives can quietly damage relationships. Gaby introduces the idea of Champion Conversations, intentional conversations designed to help people address unresolved issues rather than carrying old transgressions forward. She explains why teams sometimes need to clear the air before they can create a meaningful vision for the future. The conversation also explores agency, vulnerability, silos, honesty, and why leaders can't simply pile a new strategy on top of unresolved team dysfunction. As Gaby puts it, you can't create a compelling future "on top of the muck." If you lead a school, district, organization, department, or leadership team, this episode is an important reminder: the strength of your strategy will always be limited by the strength of the people trying to execute it together. In this episode: Why leadership and teamwork are fundamentally human work What Gaby means by a "champion team" Why connection can improve team performance The danger of operating in silos How assumptions and made-up narratives damage relationships Why vulnerability matters on leadership teams How Champion Conversations help teams clear old baggage Helping people recognize their agency instead of operating from victimhood Why honesty is essential to solving the right problems Creating a shared vision after rebuilding connection and trust What Gaby is doing right now to lean into leadership Connect with Gaby Jordan Learn more about Gaby's education work through Human Better EDU. You can also find Gaby on LinkedIn and Instagram and learn more about her corporate leadership work through Source Elements Group. This Episode Is Sponsored by HeyTutor HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers. Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com

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 challenged me, encouraged me, taught me something, and sharpened the iron along the way. We start with a simple question: What are you learning about yourself as a leader right now? That opens the door to a powerful conversation about moving from solving problems to developing people, learning to lead through influence, building leadership capacity in others, staying close to the work, adapting when circumstances change, and recognizing that leadership is always a long game. We also dig into how leaders continue to sharpen the iron. The answers range from surrounding yourself with people who challenge your thinking and intentionally building your network, to reading, listening, taking care of yourself, prioritizing family, staying curious, seeking feedback, and remaining humble enough to recognize that what worked yesterday may not work tomorrow. Then we turn the tables and look back at Leaning Into Leadership itself. Each guest shares an episode or conversation that has stayed with them—and hearing what they chose reminded me why I started this podcast in the first place. What began as an opportunity to grow a platform has become something much more meaningful: a place for me to learn alongside some remarkable people. We close with a lightning round built around three questions every leader should consider: What advice would you give someone beginning their leadership journey? How are you leaning into leadership right now? Who was the person who tapped you on the shoulder and helped you see something in yourself? That final question may be the most important one of the entire episode. Leadership rarely happens alone. Somewhere along the way, someone sees something in us. They encourage us. Challenge us. Open a door. Invite us to the table. Sometimes they see our potential before we do. Episode 300 is a celebration, but it is also a reminder of what leadership is really about: people, relationships, growth, and creating opportunities for others to become more than they thought possible. To every guest who has joined me over these first 300 episodes and every listener who has spent part of their week with Leaning Into Leadership—thank you. 300 down. We’ve got way more than 300 to go. This Episode Is Sponsored by HeyTutor HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers. Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com

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 inspired. His upcoming book, Too Damn Happy, draws from his own experiences along with positive psychology to explore practical ways people can flourish even in challenging, high-pressure environments. Darrin and Phil dig into the idea of “building in the good stuff.” Instead of waiting until after work or the weekend to do the things that fill us up, Phil challenges us to intentionally put small moments of joy into the workday itself. A song. A quick walk outside. A two-minute conversation with someone you care about. These aren't dramatic changes; they're small deposits that can make the work more sustainable. They also explore what happens when we give away our natural gifts. Those gifts aren't necessarily talents you can put on a résumé. They might be humor, listening, cooking, creativity, energy, calm, or simply being willing to admit when you don't know something. When we bring more of ourselves into our work and share those gifts with others, we create opportunities for connection — and give others permission to do the same. That leads Darrin and Phil into an important conversation about relationships. We spend a lot of time talking about educators getting to know their students, but relationships are a two-way street. When adults appropriately allow others to see who they really are, they can open the door for trust, vulnerability, and genuine human connection. And students are also watching how the adults around them interact with one another. Phil closes by sharing how he's leaning into leadership right now: giving his gifts and connecting great people with other great people. For him, leadership isn't simply about doing his own work well. It's about helping other people thrive too. In this episode: Why Phil left the classroom after 20 years The story behind Too Damn Happy Why happiness doesn't require ignoring the difficult parts of our work How to “build in the good stuff” throughout your day Why tiny shifts can make demanding work more sustainable Identifying and giving away your natural gifts How vulnerability opens the door to stronger relationships Why students notice the relationships adults model The difference between performative positivity and genuine flourishing How giving and connecting others can become an act of leadership This Episode Is Sponsored by HeyTutor HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers. Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com

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 needs underneath resistance. Drawing from her own experience as a teacher who resisted change, an instructional coach who initially struggled to create change, and eventually a leadership coach who became highly effective at working with educators experiencing resistance, Becca shares the research behind her five Catalyst Mindsets. Darrin and Becca explore: Why resistance is often the result of unmet needs rather than unwillingness or negativity The difference between a “resistant teacher” and a teacher experiencing resistance Why schools hire critical thinkers—and then sometimes expect them simply to comply The five Catalyst Mindsets: value, belonging, success, growth, and ownership Why generic strategies for dealing with resistance often miss the real problem The critical difference between compliance, buy-in, and true ownership Why agency is essential if leaders want people to own change How clarity around non-negotiables and professional judgment can immediately increase ownership Why leaders must explicitly tell people where they have permission to use their expertise How human-centered leadership can move change forward without going around people’s humanity One of the most practical takeaways from the conversation is something leaders can implement immediately: be crystal clear about what is non-negotiable and where people have the agency to exercise their professional judgment. When people understand where they have voice, choice, and the ability to make a meaningful impact, leadership can begin moving beyond compliance and toward genuine ownership. Becca also shares how she is personally leaning into leadership through shared leadership—developing others to lead the work rather than building something that depends entirely on her. Connect with Becca Silver Becca Silver is the CEO and founder of The Whole Educator and author of The Resistance Solution. Her work helps instructional coaches and educational leaders navigate resistance to change through a human-centered approach. Learn more about Becca, The Resistance Solution, the Resistance Solution Community, her Book Study Facilitator Training, and the Coaching the Whole Educator podcast through The Whole Educator. This Episode Is Sponsored by HeyTutor HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers. Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com