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Leaning into Leadership: Daily Summaries Delivered
by Darrin Peppard
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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- 1 weeks ago37 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 buildingHow to identify the three priorities that should drive your leadershipWhy leadership team alignment creates consistency and trustHow to design opening experiences that inspire teachers instead of overwhelming themPractical strategies to protect your calendar from the "cycle of chaos"Why your presence during difficult moments shapes culture more than your plansThree reflection questions every principal should answer before staff returnsWhether 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 LinkedInSponsor SpotlightThis 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 DarrinIf 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.
- 1 weeks ago12 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 EpisodeWhy one sentence from a superintendent transformed Darrin's leadershipThe difference between our intentions and the experience others have with usWhy leadership breakthroughs come from awareness—not simply learning moreThe coaching conversation that revealed the real source of one leader's overwhelmHow organizational systems become invisible over timeWhy every leader has blind spotsThe difficult truth about feedback and positional leadershipWhy coaches don't exist to fix leaders—they help leaders seeHow servant leadership can unintentionally become a bottleneckThe one question every leader should ask someone they trustMemorable 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 & LinksLearn more about Road to Awesome: https://roadtoawesome.netConnect with Dr. Darrin Peppard on LinkedInLearn more about HeyTutor: https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTASponsorThis 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 DarrinIf 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.
- 2 weeks ago38 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 momentsThe surprising leadership power of a simple handshakeHow repetition creates belonging and shared identityWhy relationships—not lesson plans—became the most rewarding part of Tom's teaching careerThe importance of helping people feel seen, heard, and valuedWhy leaders should embrace finesse over force when influencing othersHow asking better questions uncovers the hidden learning gaps our students and staff may haveWhether 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 WallsTom 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 TomLinkedIn:http://linkedin.com/in/tom-wallsleadershipSubstack:http://thomaswalls.substack.comConnect with Darrin PeppardWebsite: https://roadtoawesome.netLinkedIn: https://www.linkedin.com/in/darrinmpeppardLearn 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
- 3 weeks ago35 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 experiencesThe story behind Becoming the BISONHow teachers can use feelings to guide classroom expectationsWhy consistency creates emotional safetyPractical strategies for smoother classroom transitionsSupporting neurodiverse learners through intentional systemsBuilding teacher confidence through community and coachingLessons Kim has learned growing two successful education businessesWhy leaders should focus on creating conditions where teachers can do their best workConnect with Kim GamerozWebsite: https://www.kimgameroz.com/Instagram: @kimgamerozTeaching Inside Out: @teaching_inside_outFacebook Community: Becoming the BISONBook: Becoming the BISONConnect with Darrin PeppardWebsite: https://roadtoawesome.netLinkedIn: https://www.linkedin.com/in/darrinmpeppardLearn 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
- 4 weeks ago46 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 leadersThe power of identifying leadership potential earlyWhy a simple “tap on the shoulder” can change someone’s career trajectoryHow to create meaningful growth opportunities for aspiring leadersWhy leadership development must move beyond tasks and titlesThe importance of mentoring and coaching through mistakesHelping aspiring leaders gain confidence before they step into the roleWhy instructional leadership experiences are critical preparationHow leaders can build a stronger bench for the futureGreat 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 StamperWebsite: joshstamper.comPodcast: Aspire to LeadBook/Work: The Language of BehaviorConnect with Dr. Darrin PeppardWebsite: darrinpeppard.comRoad to Awesome: roadtoawesome.net
- Jun 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 EpisodeDebra's journey from attorney to education leaderThe evolution of school leadership over the past 25 yearsWhy leadership teams have become more important than everThe role of alignment in successful schools and organizationsHow demographic shifts are impacting educationWhat leaders should be considering about AI and the future of learningThe importance of creating meaningful educational experiencesWhy today's students need schools to think differentlyA powerful leadership lesson about seeking perspective and supportHow leaders can build systems that create long-term successKey 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 WilsonDebra 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 WilsonLinkedIn: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-eduConnect with Darrin PeppardWebsite:https://roadtoawesome.netLinkedIn:https://www.linkedin.com/in/darrinmpeppardLearn 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
- Jun 21, 202647 min
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 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 teamHow vulnerability and accountability strengthen leadershipThe importance of role clarity and intentional communicationPractical systems that reduced discipline referrals by nearly 30%Why supporting teachers leads directly to better student outcomesHow coaching accelerated growth and prevented burnoutThe value of reflection, feedback, and continuous improvementWhy leadership teams need a "safe space" to process challenges togetherKey TakeawaysLeadership 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 PeppardIf 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, keynote 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 or darrinpeppard.comSponsor 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
- Jun 17, 202613 min
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, 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 ChaosThe difference between creating dependence and creating capacityHow coaching conversations create lasting leadership growthWhy systems and intentionality matter more than constant problem-solvingThe leadership question that can transform every meeting and conversationA new philosophy that connects coaching, ALIGN, leadership teams, and intentional leadershipKey TakeawaysGreat 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."ConnectIf 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 or darrinpeppard.comSponsor 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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About Leaning into Leadership
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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