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Leaning into Leadership

Leaning into Leadership

Hosted by Darrin Peppard

ManagementEducationInterviews guests

Episodes

293

Latest episode

Aug 2026

Language

EN

About the show

We all want to see successes in both our personal and professional lives. Often, that requires strong leadership. In a time when leadership can be more challenging than ever, this podcast is dedicated to cultivating leaders by elevating the voices of leaders and promoting positivity. Join Dr. Darrin Peppard, lifelong educator and best-selling author, for this mixed platform podcast (some solo, some guest interview) for inspiration and insight, and some great leadership stories from those are living it, excelling at it, and celebrating it. Together, let's lean into leadership.

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August 19, 202622 min

Episode 294: 5 Leadership Traps to Avoid as the School Year Begins

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 quietly derail their best intentions during the opening weeks of school. Darrin explores why presence is different from simply being visible, how the Cycle of Chaos can allow urgency to rewrite your priorities, and why communicating something once doesn't mean people understand it. He also challenges leaders to stop solving every problem themselves and to recognize the important difference between giving someone grace and simply avoiding a necessary conversation. The five leadership traps: Retreating to your office once students arrive Letting urgency rewrite your priorities Assuming everyone understood the opening-day message Trying to solve every problem personally Waiting too long to address something you already know isn't right At the center of the episode is one question every school leader should consider as the year gets underway: Is the leader you're becoming in September the same leader you intended to be at the beginning of August? You probably won't lose your school year in the first few weeks. But you can establish habits during those weeks that you'll spend the rest of the year trying to undo. Be intentional now. Protect what matters. And go have a Road to Awesome year. In This Episode Why presence matters more than performative visibility How the urgent can quietly replace your real leadership priorities Why your calendar tells the truth about what you value The difference between communicating a message and creating clarity How solving every problem can actually weaken the people around you Why servant leadership is about empowerment, not doing everything for others The difference between grace and avoidance Why addressing small issues early protects the culture you're trying to create How to recognize leadership drift before it becomes your new normal Key Takeaways “You can't recognize what you never see.” “Your calendar is going to tell the truth about your priorities long before your mission statement ever will.” “Don't confuse delivering a message with creating clarity.” “Don't just solve problems. Build problem-solvers.” “What we tolerate teaches a lesson.” “Clarity early is almost always easier than making corrections later.” 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 .

August 16, 202633 min

Episode 293: The Human Side of Leadership with Stacy Nation

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, caring relationship—which makes relationship-building far more than a “soft” leadership skill. The conversation also turns toward the adults in our schools. Are teachers able to meet their own basic needs during the day? What happens after a difficult interaction with a student? Do leaders create conditions that help adults regulate themselves before asking them to help students do the same? Stacy makes the case that supporting adults and maintaining high expectations are not competing ideas. Darrin and Stacy also dig into neuroscience and leadership, including the difference between the reasoning and emotional functions of the brain, why certain questions can immediately create defensiveness, and how leaders can communicate differently when emotions are running high. Stacy shares the story behind her book, What Really Happens in Therapy Behind Closed Doors: A Guided Journey to Healing , and how her experiences as a therapist, military member, parent, and someone navigating her own family story shaped the work. Finally, the conversation comes back to leadership: creating shared language around emotional regulation, moving from reactive to proactive approaches with students, and recognizing that meaningful change requires more than a one-day training. In this episode, you’ll hear about: The difference between trauma-informed and trauma-restorative practices Why relationships are a critical resiliency factor Creating environments where adults can regulate and perform at their best Why supporting people does not mean lowering expectations What leaders should understand about the reasoning and emotional brain Why Stacy encourages leaders to replace “Why?” with “Help me understand” Using shared language around regulation throughout a school Moving from reactive responses to proactive support Why leaders need to live—not simply model—the practices they expect from others Stacy sums up her approach to leadership beautifully near the end of the conversation: leadership changes when what we teach becomes integrated into how we actually live and lead. Connect with Stacy Nation: Website: gobeyou.org Instagram: Stacy G Nation Facebook: Stacy Nation / Stacy G Nation LinkedIn: Stacy Nation YouTube: Search Stacy Nation or Stacy York Book: What Really Happens in Therapy Behind Closed Doors: A Guided Journey to Healing Sponsor Spotlight This episode is proudly sponsored by HeyTutor. HeyTutor partners with school districts across the country to provide high-dosage tutoring in mathematics and English language arts. Their comprehensive approach—including recruiting, training, scheduling, and managing tutors—allows educators to focus on what they do best while accelerating student learning. Learn more by visiting: heytutor.com Connect with Darrin If this episode challenged your thinking, I'd love to hear from you. What's one piece of feedback that changed the way you lead? Connect with me on LinkedIn or visit https://darrinpeppard.com/ to continue the conversation. If you enjoyed this episode, please subscribe, leave a review, and share it with another leader who could benefit from this message.

August 9, 202625 min

Episode 292: Why Not? A Leadership Mindset That Changes Everything

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. Together they share the philosophy that has begun shaping every area of their lives and why that simple mindset shift has opened doors they never imagined. Along the way, they discuss: How one small decision can completely change your future. Why educators should never underestimate the impact of seemingly ordinary moments. Melissa's powerful "Dot" tradition that reminds students they matter. The leadership culture behind the Savannah Bananas and Fans First Entertainment. What schools can learn about creating unforgettable experiences. Why high expectations are one of the greatest gifts leaders can give. How embracing mistakes creates healthier organizations. The difference between living with "What If?" and living with "Why Not?" Whether you're leading a school, a business, or your own family, this episode is a reminder that leadership often begins by saying yes to opportunities before you're completely ready. In This Episode The selfie that unexpectedly changed Bradlee's career. Building a classroom where every student feels seen. Lessons from the Savannah Bananas' culture of intentional leadership. Why "Plus the Experience" is a leadership principle every organization should embrace. Creating environments where people are encouraged to learn through failure. Living a life guided by "Why Not?" Connect with Today's Guests Bradlee Skinner Instagram/Facebook/TikTok/X: @BradleeWSkinner DJ Brand: @DJPhonyStark Melissa Skinner Facebook: Ms. Melissa Skinner Instagram: @IncredibleSkinner TikTok: @MrsMamaSkinner Sponsor Spotlight This episode is proudly sponsored by HeyTutor . HeyTutor partners with school districts across the country to provide high-dosage tutoring in mathematics and English language arts. Their comprehensive approach—including recruiting, training, scheduling, and managing tutors—allows educators to focus on what they do best while accelerating student learning. Learn more by visiting: https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA Connect with Darrin If this episode challenged your thinking, I'd love to hear from you. What's one piece of feedback that changed the way you lead? Connect with me on LinkedIn or visit https://darrinpeppard.com/ to continue the conversation. If you enjoyed this episode, please subscribe, leave a review, and share it with another leader who could benefit from this message.

August 2, 202615 min

Episode 291: Live Your Passion Out Loud

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 students was impossible to ignore—and why that same authentic energy is exactly what every leader should bring to their team. This episode is an invitation to stop hiding what matters most and begin leading with genuine conviction. Because while people may respect competence, they are inspired by leaders who care deeply and aren't afraid to show it. In this episode, you'll learn: Why authentic passion is one of a leader's greatest strengths. How your enthusiasm gives others permission to care. The difference between delivering a polished message and speaking from conviction. Why reconnecting with passions outside of work makes you a better leader. A simple challenge to help you inspire your staff before the school year begins. Key Takeaways People don't follow perfection—they follow conviction. Passion is contagious, but so is indifference. Your staff needs more than your plans; they need to see what truly matters to you. The passions that restore you personally often strengthen you professionally. Leadership isn't about managing your passion—it's about modeling it. Resources & Links • Learn more about Road to Awesome • Connect with Dr. Darrin Peppard on LinkedIn Resources & Links • Learn more about Road to Awesome • Connect with Dr. Darrin Peppard on LinkedIn Sponsor Spotlight This episode is proudly sponsored by HeyTutor . HeyTutor partners with school districts across the country to provide high-dosage tutoring in mathematics and English language arts. Their comprehensive approach—including recruiting, training, scheduling, and managing tutors—allows educators to focus on what they do best while accelerating student learning. Learn more by visiting this link: https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA Connect with Darrin If this episode challenged your thinking, I'd love to hear from you. What's one piece of feedback that changed the way you lead? Connect with me on LinkedIn or visit https://darrinpeppard.com/ to continue the conversation. If you enjoyed this episode, please subscribe, leave a review, and share it with another leader who could benefit from this message.

July 26, 202637 min

Episode 290: Before Staff Returns

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 another opening-week checklist, this conversation focuses on the mindset, habits, and intentional leadership practices that shape school culture throughout the entire year. In this episode, you'll discover: Why preparing yourself matters more than preparing the building How to identify the three priorities that should drive your leadership Why leadership team alignment creates consistency and trust How to design opening experiences that inspire teachers instead of overwhelming them Practical strategies to protect your calendar from the "cycle of chaos" Why your presence during difficult moments shapes culture more than your plans Three reflection questions every principal should answer before staff returns Whether you're entering your first year as a principal or your twentieth, this episode will help you begin the school year with greater clarity, intentionality, and purpose. Key Takeaway: "You are not preparing the building. You are preparing yourself and your leadership team to lead the people who will make the building successful." Resources & Links • Learn more about Road to Awesome • Connect with Dr. Darrin Peppard on LinkedIn Sponsor Spotlight This episode is proudly sponsored by HeyTutor . HeyTutor partners with school districts across the country to provide high-dosage tutoring in mathematics and English language arts. Their comprehensive approach—including recruiting, training, scheduling, and managing tutors—allows educators to focus on what they do best while accelerating student learning. Learn more by visiting the link above. Connect with Darrin If this episode challenged your thinking, I'd love to hear from you. What's one piece of feedback that changed the way you lead? Connect with me on LinkedIn or visit https://darrinpeppard.com/ to continue the conversation. If you enjoyed this episode, please subscribe, leave a review, and share it with another leader who could benefit from this message.

July 22, 202612 min

Episode 289: The Blind Spots Holding Leaders Back

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 may see things you cannot, and why trusted coaches, mentors, and colleagues are so essential to continued growth. If you're committed to becoming a more intentional leader, this conversation will challenge you to stop asking, "How am I doing?" and start asking, "What am I not seeing?" In This Episode Why one sentence from a superintendent transformed Darrin's leadership The difference between our intentions and the experience others have with us Why leadership breakthroughs come from awareness—not simply learning more The coaching conversation that revealed the real source of one leader's overwhelm How organizational systems become invisible over time Why every leader has blind spots The difficult truth about feedback and positional leadership Why coaches don't exist to fix leaders—they help leaders see How servant leadership can unintentionally become a bottleneck The one question every leader should ask someone they trust Memorable Quotes "Learning adds information. Awareness changes perspective. Perspective changes behavior." "Your staff knows what your blind spots are, but they may not feel it is okay to point them out." "Leadership isn't about becoming perfect. It's about becoming more aware." "Leadership isn't limited by what we know. It's often limited by what we don't yet know about ourselves." "Sometimes the first condition we need to create is one where we can see ourselves more clearly." Resources & Links Learn more about Road to Awesome: https://roadtoawesome.net Connect with Dr. Darrin Peppard on LinkedIn Learn more about HeyTutor: https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA Sponsor This episode is proudly sponsored by HeyTutor . HeyTutor partners with school districts across the country to provide high-dosage tutoring in mathematics and English language arts. Their comprehensive approach—including recruiting, training, scheduling, and managing tutors—allows educators to focus on what they do best while accelerating student learning. Learn more by visiting the link above. Connect with Darrin If this episode challenged your thinking, I'd love to hear from you. What's one piece of feedback that changed the way you lead? Connect with me on LinkedIn or visit RoadToAwesome.net to continue the conversation. If you enjoyed this episode, please subscribe, leave a review, and share it with another leader who could benefit from this message.

July 19, 202638 min

Episode 288: Building Belonging Through Microinclusions with Tom Walls

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 immediately. Among the topics discussed: Why great culture is built through consistent daily rituals—not occasional big moments The surprising leadership power of a simple handshake How repetition creates belonging and shared identity Why relationships—not lesson plans—became the most rewarding part of Tom's teaching career The importance of helping people feel seen, heard, and valued Why leaders should embrace finesse over force when influencing others How asking better questions uncovers the hidden learning gaps our students and staff may have Whether you're a teacher, coach, principal, superintendent, or organizational leader, this conversation is a reminder that leadership often isn't about doing more—it's about being more intentional with the moments you already have. About Tom Walls Tom Walls is a veteran educator, football coach, and leadership speaker with more than 30 years of experience building student-led classrooms and championship-caliber football programs. His upcoming book, Coach Like a Teacher, Teach Like a Coach , explores how proven teaching strategies and coaching principles can be used to develop stronger classrooms, teams, and school communities. Tom presents internationally on leadership, team building, student engagement, and organizational culture. Connect with Tom LinkedIn: http://linkedin.com/in/tom-wallsleadership Substack: http://thomaswalls.substack.com Connect with Darrin Peppard Website: https://roadtoawesome.net LinkedIn: https://www.linkedin.com/in/darrinmpeppard Learn more about coaching, consulting, keynote speaking, and leadership development opportunities through Road to Awesome. Sponsor Spotlight: This episode is sponsored by HeyTutor . HeyTutor partners with schools and districts nationwide to provide evidence-based high-dosage tutoring support in Math and ELA while helping schools remain intentional about staff capacity and student support systems. Learn more here: HeyTutor.com

July 12, 202635 min

Episode 287: Becoming the BISON - Leading Classrooms with Intention with Kim Gameroz

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, emotional safety, and consistent routines help students—and educators—thrive. Whether you're a classroom teacher, instructional coach, principal, or district leader, this conversation offers practical ideas you can implement immediately. In this episode you'll hear: Why intentional leadership starts with predictable experiences The story behind Becoming the BISON How teachers can use feelings to guide classroom expectations Why consistency creates emotional safety Practical strategies for smoother classroom transitions Supporting neurodiverse learners through intentional systems Building teacher confidence through community and coaching Lessons Kim has learned growing two successful education businesses Why leaders should focus on creating conditions where teachers can do their best work Connect with Kim Gameroz Website: https://www.kimgameroz.com/ Instagram: @kimgameroz Teaching Inside Out: @teaching_inside_out Facebook Community: Becoming the BISON Book: Becoming the BISON Connect with Darrin Peppard Website: https://roadtoawesome.net LinkedIn: https://www.linkedin.com/in/darrinmpeppard Learn more about coaching, consulting, keynote speaking, and leadership development opportunities through Road to Awesome. Sponsor Spotlight: This episode is sponsored by HeyTutor. HeyTutor partners with schools and districts nationwide to provide evidence-based high-dosage tutoring support in Math and ELA while helping schools remain intentional about staff capacity and student support systems. Learn more here: HeyTutor.com

July 5, 202646 min

Episode 286: Building the Bench - Growing the Next Generation of Leaders with Joshua Stamper

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 matters most. From there, the conversation turns toward a question every organization should be asking: Who are we intentionally preparing to lead next? Darrin and Joshua share their own “tap on the shoulder” moments — those pivotal conversations where someone saw leadership potential in them before they saw it in themselves. They discuss why leaders have a responsibility to identify potential early and create pathways for others to grow. They also explore why building leaders requires far more than assigning tasks. Covering events, managing duties, or checking off responsibilities does not develop leadership capacity. True leadership development happens when aspiring leaders are given authentic experiences, meaningful conversations, coaching, feedback, and opportunities to sit alongside current leaders. In this episode, Darrin and Joshua discuss: Why leaders have a moral obligation to grow future leaders The power of identifying leadership potential early Why a simple “tap on the shoulder” can change someone’s career trajectory How to create meaningful growth opportunities for aspiring leaders Why leadership development must move beyond tasks and titles The importance of mentoring and coaching through mistakes Helping aspiring leaders gain confidence before they step into the role Why instructional leadership experiences are critical preparation How leaders can build a stronger bench for the future Great leaders don’t just create followers. They create more leaders. If we want stronger schools, stronger organizations, and stronger cultures, we have to stop waiting for leaders to appear — and start intentionally developing them. Connect with Joshua Stamper Website: joshstamper.com Podcast: Aspire to Lead Book/Work: The Language of Behavior Connect with Dr. Darrin Peppard Website: darrinpeppard.com Road to Awesome: roadtoawesome.net

June 28, 202639 min

Episode 285: The Future of School Leadership with Debra Wilson

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 can adapt to changing family expectations, navigate increasing complexity, and create meaningful educational experiences that prepare students for an uncertain future. In This Episode Debra's journey from attorney to education leader The evolution of school leadership over the past 25 years Why leadership teams have become more important than ever The role of alignment in successful schools and organizations How demographic shifts are impacting education What leaders should be considering about AI and the future of learning The importance of creating meaningful educational experiences Why today's students need schools to think differently A powerful leadership lesson about seeking perspective and support How leaders can build systems that create long-term success Key Takeaway "Nobody leads by themselves." As schools become increasingly complex, leaders who build aligned teams, seek diverse perspectives, and focus on creating intentional experiences for students and families will be best positioned to thrive. About Debra Wilson Debra P. Wilson serves as President of the National Association of Independent Schools (NAIS). Prior to becoming president in 2023, she served as President of the Southern Association of Independent Schools (SAIS) and spent nearly two decades at NAIS as General Counsel, leading advocacy efforts, supporting schools through crises, and advancing best practices in governance and leadership. Connect with Debra Wilson LinkedIn: https://www.linkedin.com/in/debrapwilson/ National Association of Independent Schools: https://www.nais.org/ NAIS LinkedIn: https://www.linkedin.com/company/nais/ New View EDU Podcast: https://www.nais.org/resource-center/nais-podcasts/new-view-edu Connect with Darrin Peppard Website: https://roadtoawesome.net LinkedIn: https://www.linkedin.com/in/darrinmpeppard Learn more about coaching, consulting, keynote speaking, and leadership development opportunities through Road to Awesome. Sponsor Spotlight: This episode is sponsored by HeyTutor. HeyTutor partners with schools and districts nationwide to provide evidence-based high-dosage tutoring support in Math and ELA while helping schools remain intentional about staff capacity and student support systems. Learn more here: HeyTutor.com

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