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

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 [https://joshstamper.com/] Podcast: Aspire to Lead [https://joshstamper.com/aspire-episodes/] Book/Work: The Language of Behavior [https://joshstamper.com/books/] CONNECT WITH DR. DARRIN PEPPARD Website: darrinpeppard.com [https://darrinpeppard.com/] Road to Awesome: roadtoawesome.net [https://roadtoawesome.net/]

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/ [https://www.linkedin.com/in/debrapwilson/] National Association of Independent Schools: https://www.nais.org/ [https://www.nais.org/] NAIS LinkedIn: https://www.linkedin.com/company/nais/ [https://www.linkedin.com/company/nais/] New View EDU Podcast: https://www.nais.org/resource-center/nais-podcasts/new-view-edu [https://www.nais.org/resource-center/nais-podcasts/new-view-edu] CONNECT WITH DARRIN PEPPARD Website: https://roadtoawesome.net [https://roadtoawesome.net/] LinkedIn: https://www.linkedin.com/in/darrinmpeppard [https://www.linkedin.com/in/darrinpeppard] 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 [https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA ]

Episode 284: Great Schools Start with Great Leadership Teams

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 [https://lgms.ocss-va.org/] 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 allowed both staff and students to thrive. This conversation is an honest look at leadership in action—the successes, the struggles, and the systems that make sustainable excellence possible. IN THIS EPISODE, YOU'LL HEAR: * Why trust is the foundation of every successful leadership team * How vulnerability and accountability strengthen leadership * The importance of role clarity and intentional communication * Practical systems that reduced discipline referrals by nearly 30% * Why supporting teachers leads directly to better student outcomes * How coaching accelerated growth and prevented burnout * The value of reflection, feedback, and continuous improvement * Why leadership teams need a "safe space" to process challenges together KEY TAKEAWAYS Leadership is a team sport. Strong leadership isn't about having all the answers—it's about building relationships, communicating clearly, holding high expectations while providing high support, and creating systems that allow everyone to do their best work. Throughout the conversation, Marlene, Rocio, and Christina demonstrate that the intentional creation of trust doesn't just make leadership more enjoyable—it makes schools more effective. MEMORABLE QUOTES "The team has to be strong for the school to be successful." "If we're asking teachers to do something, they deserve to understand the why." "High expectations only work when they're matched with high support." "The more clarity we bring, the more efficiently our school can run." CONNECT WITH DR. DARRIN PEPPARD If this episode resonates with you, share it with another leader who believes that leadership teams have the power to transform schools. Subscribe to Leaning Into Leadership wherever you listen to podcasts and learn more about leadership coaching [https://darrinpeppard.com/training/], keynote speaking [https://darrinpeppard.com/speaking/], and the ALIGN Framework at Road to Awesome. Because leadership isn't about doing more. It's about intentionally creating the conditions where other people can do their best work. For leadership coaching, keynote speaking, leadership retreats, and weekly leadership insights, visit roadtoawesome.net [https://roadtoawesome.net/] or darrinpeppard.com [https://darrinpeppard.com/] 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 [https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA ]

Episode 283: Leadership Is the Intentional Creation of Conditions

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 [https://darrinpeppard.edublogs.org/2026/06/13/nothelping/], Darrin challenges traditional assumptions about servant leadership, delegation, coaching, and what it really means to support the people we lead. Instead of measuring leadership by how much we carry, this episode invites listeners to rethink leadership through the lens of clarity, coaching, systems, intentionality, and growth. IN THIS EPISODE YOU'LL DISCOVER: * Why many servant leaders become trapped in the Cycle of Chaos * The difference between creating dependence and creating capacity * How coaching conversations create lasting leadership growth * Why systems and intentionality matter more than constant problem-solving * The leadership question that can transform every meeting and conversation * A new philosophy that connects coaching, ALIGN, leadership teams, and intentional leadership KEY TAKEAWAYS * Great leaders create conditions instead of collecting responsibilities. * Coaching is one of the greatest acts of servant leadership. * Every meeting, conversation, expectation, and decision creates conditions that shape culture. * Leaders escape the Cycle of Chaos when they stop doing everyone else's work and focus on developing people instead. MEMORABLE QUOTES > "Leadership is the intentional creation of conditions where other people can do their best work." > "The Cycle of Chaos happens when leaders stop creating conditions and start doing everybody else's work." > "Sometimes the most servant-hearted thing we can do is ask another question instead of providing another answer." > "Maybe leadership isn't measured by how much we carry. Maybe it's measured by how much capacity we create in others." CONNECT If this episode challenged your thinking, share it with another leader, leave a review, and subscribe to the podcast. For leadership coaching, keynote speaking, leadership retreats, and weekly leadership insights, visit roadtoawesome.net [https://roadtoawesome.net/] or darrinpeppard.com [https://darrinpeppard.com/] 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 [https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA ]

Episode 282: The New School Leader's Playbook with Erika Bare & Tiffany Burns

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 trusted support network, protecting your time, and leading with intentionality rather than reacting to every urgent issue. Whether you're stepping into your first assistant principal role, becoming a building principal, or mentoring a new leader, this episode is packed with immediately actionable advice. IN THIS EPISODE, YOU'LL LEARN: * Why every school leader needs a trusted "work bestie" * How preparation reduces anxiety before difficult conversations * The planning process that leads to more effective communication * Common mistakes leaders make during challenging meetings * Strategies for working with frustrated parents and caregivers * Why attacking the problem—not the person—is essential * How to respond when someone asks, "Do you have a minute?" * Practical ways to protect your calendar and prioritize instructional leadership * Why saying "no" is sometimes the best leadership decision * How intentional time management creates better leaders and healthier lives MEMORABLE QUOTES > "Action is the antidote to anxiety." > "School leadership is not a solo sport." > "Never sacrifice the important at the altar of the urgent." > "You are worth so much more than a minute." CONNECT WITH ERIKA BARE & TIFFANY BURNS Visit Connecting Through Conversation for resources, blog posts, free planning guides, and information about their books and professional learning opportunities. Facebook https://www.facebook.com/profile.php?id=100090370647418&mibextid=LQQJ4d [https://www.facebook.com/profile.php?id=100090370647418&mibextid=LQQJ4d] Instagram https://www.instagram.com/connectingthroughconversation/ [https://www.instagram.com/connectingthroughconversation/] Linked In Erika Bare https://linkedin.com/in/erika-bare-6a72a6215 [http://linkedin.com/in/erika-bare-6a72a6215] Linkedin Tiffany Burns https://linkedin.com/in/tiffany-burns-90a50a274 [http://linkedin.com/in/tiffany-burns-90a50a274] LinkedinCTC https://www.linkedin.com/company/connecting-through-conversation/ [https://www.linkedin.com/company/connecting-through-conversation/] Twitter https://twitter.com/CTCPlaybook.com [https://twitter.com/CTCPlaybook.com] Youtube https://www.youtube.com/@CTCPlaybook [https://www.youtube.com/@CTCPlaybook] 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 [https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA ]