Episode 257: Escaping the Cycle of Chaos

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 parent, handle the hallway issue. But the work connected to your purpose often requires you to create the starting point yourself. Darrin explores how clarity and intentionality help turn that intention into action. Three moves to help you begin: Name the thing you’re putting off. Get specific about the work and identify what makes it difficult to start. Make the first action clear and manageable. Choose one useful action that fits into your day and moves the work forward. Give the start somewhere to lead. Plan your next step, reflect on what you learn, and build follow-through into your leadership practice.

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: the riddle of the Sphinx. From crawling through the unfamiliar challenges of a new role to finding your stride and supporting the leaders coming behind you, each stage requires reflection, humility, and a willingness to keep learning. Chris also challenges the belief that effective leaders must always have an open door. He shares why protecting time to think is essential to serving your school well—and how to help your team understand the purpose behind that boundary. The conversation turns personal as Chris recounts receiving an anonymous, hurtful card when leaving a school. His experience opens a discussion about responding to criticism, recognizing patterns in feedback, and asking what you might need to learn before allowing defensiveness to take over. In this episode, we discuss: Adapting to a changing environment while holding on to your core values. Why leaders cannot skip the uncomfortable stages of learning. The danger of mistaking momentum for continued progress. Helping new administrators feel safe admitting what they don’t know. Protecting thinking time and communicating that boundary with your staff. Considering the source, frequency, and substance of criticism. How mentoring other leaders prompts you to reexamine your own practices. Building a legacy through the support you give and the support you accept.

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 September 11, 2001, Craig lost his brother in the attacks on the World Trade Center. That unimaginable loss, followed by the deaths of his parents and years of navigating grief, fundamentally changed his understanding of himself, his purpose, and his leadership. In this conversation, Craig shares how he learned to stop avoiding grief and begin building the capacity to carry it. He talks about the daily habits that helped him rediscover purpose, the importance of taking care of ourselves while caring for others, and why some of the most powerful leadership lessons come from our most difficult experiences. Darrin and Craig also explore the difference between two kinds of leaders: the "Here I Am" leader who enters a room focused on themselves, and the "There You Are" leader who enters looking for opportunities to connect, support, and serve others. The conversation takes another powerful turn as Craig shares the buffalo analogy that helped shape his philosophy of overcoming adversity. Rather than running from an approaching storm, buffalo turn toward it and face it together. It's a lesson Craig carried into his leadership during the COVID-19 pandemic, when a strong school culture, consistent communication, and a shared sense of purpose helped his staff navigate extraordinary uncertainty. Craig also reflects on two unforgettable stories from Overcome: his visits to Guantanamo Bay to observe proceedings related to the September 11 attacks, and the final phone conversation he shared with his brother just days before the tragedy. This is an episode about grief, certainly. But more than that, it's about hope, resilience, relationships, and the extraordinary capacity we have to grow through the challenges life puts in front of us. In this episode, you'll hear about: How Craig's personal journey of loss and grief became the foundation for his book, Overcome Why rediscovering your purpose matters when life and leadership become overwhelming The difference between "Here I Am" and "There You Are" leadership How small, intentional daily habits can help us build resilience Why taking care of yourself is essential to taking care of others What the buffalo can teach us about facing adversity together How a strong school culture helped Craig lead through the uncertainty of COVID-19 The deeply personal experiences that brought Craig face-to-face with the events of September 11 Why Craig's next chapter is focused on helping others find hope and overcome their own challenges

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.

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