Leaning into Leadership

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 years later, they reconnect to explore a leadership responsibility that can easily get buried beneath the daily demands of the job: intentionally building relationships with families. From scheduling positive calls home to taking academic support into an apartment complex clubhouse, Ted shares practical examples of meeting families where they are. They also discuss how to approach difficult conversations, create a welcoming front office, and make family engagement part of a district’s long-term direction. In this episode, we explore: Why parent organizations need a purpose beyond fundraising. How families’ own school experiences shape their expectations. Why positive calls home deserve a place on your calendar. Reaching families whose schedules make school involvement difficult. Starting conversations with a powerful question: “What are your hopes and dreams for your child?” Listening before moving into problem-solving mode. The role of office staff, bus drivers, and food service teams in building trust. Turning family engagement into an intentional district priority. A question to take back to your team: If a family only hears from us when something goes wrong, what can we change this week? Connect with Dr. Ted Huff Website: Leading with Parents Email: [email protected] LinkedIn: Search “Leading with Parents” Thank you to our sponsors HeyTutor — In-person, high-dosage tutoring for K–12 schools and districts, with recruiting, hiring, training, and supervision handled by HeyTutor. Curriculum Leadership Institute — A partner in aligning curriculum, instruction, and assessment across your district. Mention Leaning Into Leadership to receive 5% off your first year of partnership. Share this episode with a leader who could use a clear place to begin, and remember to rate, review, and subscribe.

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. Using classroom visits as a practical example, Darrin also discusses how roles, coverage, and shared expectations can create the conditions that help an administrative team follow through. Your midweek challenge: Finish this sentence: “Tomorrow, at this time, I will take this first action.” Put it on your calendar, ask for the support you need, and decide when you’ll return to the work. “You can take the work seriously without making the first step enormous.” Thank you to our sponsors: HeyTutor — In-person, high-dosage tutoring for K–12 schools and districts, with recruiting, hiring, training, and supervision handled by HeyTutor. Curriculum Leadership Institute — A partner in aligning curriculum, instruction, and assessment across your district. Mention Leaning Into Leadership to receive 5% off your first year of partnership. Share this episode with a leader who could use a clear place to begin, and remember to rate, review, and subscribe.

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. Whether you’re stepping into your first leadership role or have spent years in the principal’s office, this conversation offers an invitation to examine your habits and keep growing with intention. Connect with Dr. Christopher Jones Find Chris on Instagram at @drcsjones and explore his new book, The Leadership Riddle: A Leader’s Guide to Growing Without Losing Yourself. Revisit episode 42 for his first appearance on Leaning Into Leadership. Big Thanks to Our sponsors Curriculum Leadership Institute (CLI) partners with districts to develop an integrated curriculum system tailored to their needs, bringing clarity to teaching and learning and supporting the work through implementation. Mention Leaning Into Leadership for a 5% discount on your first year. Check them out at cliweb.org 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 at HeyTutor.com.

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 A leadership takeaway Every person we lead is carrying something. We may not know what it is, and we may never fully understand its weight. But when we shift our attention from making our presence known to recognizing the needs of those around us, we create the conditions for connection, trust, and stronger leadership. The goal isn't to avoid every storm. It's to build the capacity, relationships, and courage to face those storms together. Connect with Craig Woodall Visit CraigWoodall.com to learn more about Craig, explore his book Overcome, watch his TED Talk, and connect with him about speaking, coaching, and leadership. Connect with Darrin Learn more about leadership coaching, speaking, and the Road to Awesome at DarrinPeppard.com. Episode sponsors HeyTutor: Supporting schools and districts with high-impact, in-person tutoring in literacy and math. Learn more at HeyTutor.com. Curriculum Leadership Institute (CLI): Helping districts create aligned, sustainable curriculum systems through collaborative, relationship-based partnerships. Learn more at cliweb.org

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!