Leaning into Leadership

Afleveringen

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  Episode 291: Live Your Passion Out Loud 02.08.2026 15min

  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 TakeawaysPeople 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 LinkedInResources & 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 this link: https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTAConnect 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.
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  Episode 290: Before Staff Returns 26.07.2026 37min

  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.
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  Episode 289: The Blind Spots Holding Leaders Back 22.07.2026 12min

  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.
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  Episode 288: Building Belonging Through Microinclusions with Tom Walls 19.07.2026 38min

  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
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  Episode 287: Becoming the BISON - Leading Classrooms with Intention with Kim Gameroz 12.07.2026 35min

  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
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  Episode 286: Building the Bench - Growing the Next Generation of Leaders with Joshua Stamper 05.07.2026 46min

  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
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  Episode 285: The Future of School Leadership with Debra Wilson 28.06.2026 39min

  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
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  Episode 284: Great Schools Start with Great Leadership Teams 21.06.2026 47min

  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
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  Episode 283: Leadership Is the Intentional Creation of Conditions 17.06.2026 13min

  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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  Episode 282: The New School Leader's Playbook with Erika Bare & Tiffany Burns 14.06.2026 42min

  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 conversationsThe planning process that leads to more effective communicationCommon mistakes leaders make during challenging meetingsStrategies for working with frustrated parents and caregiversWhy attacking the problem—not the person—is essentialHow to respond when someone asks, "Do you have a minute?"Practical ways to protect your calendar and prioritize instructional leadershipWhy saying "no" is sometimes the best leadership decisionHow intentional time management creates better leaders and healthier livesMemorable 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 BurnsVisit 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=LQQJ4dInstagram https://www.instagram.com/connectingthroughconversation/Linked In Erika Bare https://linkedin.com/in/erika-bare-6a72a6215Linkedin Tiffany Burns https://linkedin.com/in/tiffany-burns-90a50a274LinkedinCTC https://www.linkedin.com/company/connecting-through-conversation/Twitter https://twitter.com/CTCPlaybook.comYoutube https://www.youtube.com/@CTCPlaybookSponsor 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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  Episode 281: Be the Light with Dr. Chris Culver 07.06.2026 25min

  Dr. Chris Culver returns to Leaning Into Leadership for a powerful follow-up conversation centered around his new book, Be the Light: The Science of Kindness and the Power of Belonging.If you enjoyed Chris's first appearance on Episode 214: The Science of Kindness, you're going to love where this conversation goes next. While Episode 214 explored the research behind kindness, this discussion takes a deeper look at how belonging, empathy, neuroscience, and intentional leadership can transform the cultures we create and the lives we touch.In this episode, Darrin and Chris explore:Why every person is wired for belongingHow kindness is a leadership strategy—not a weaknessThe connection between stress, burnout, and human connectionThe story behind Be the Light and its journey from darkness to hopeThe powerful "Light Manifesto" and what it means to choose kindness every dayA memorable classroom story that illustrates the importance of perspective and self-compassionThree practical strategies you can implement immediately:The six-second pauseGratitude as a daily leadership practiceSelf-affirmation and the power of positive identityThroughout the conversation, Chris reminds us that kindness isn't one more thing to add to our already overflowing to-do list—it is the thing that changes everything.New to Dr. Chris Culver?Be sure to go back and listen to Episode 214: The Science of Kindness, where we explore the research and foundations behind many of the ideas that inspired this new book. Together, these two conversations provide a powerful roadmap for leaders who want to build cultures rooted in connection, compassion, and belonging.About Dr. Chris CulverDr. Christopher Culver is an author, keynote speaker, educator, and founder of Orange Sparrow, where he helps organizations transform through The Science of Kindness. A former teacher, principal, and district leader, Chris blends neuroscience, vulnerability, and leadership to help people create cultures rooted in belonging, compassion, and connection.His newest book, Be the Light: The Science of Kindness and the Power of Belonging, provides research-backed insights and practical strategies for leaders, educators, and anyone looking to make a meaningful impact in the lives of others.Key Takeaway"Kindness is not one more thing. It is the thing that changes everything."Connect with Dr. Chris Culver🌐 Website: https://drchrisculver.com🧡 Orange Sparrow: https://orangesparrow.org📖 Be the Light: The Science of Kindness and the Power of Belonging📚 The Orange Sparrow's Journey (English/Spanish edition with companion curriculum)Previous Conversation with Dr. Chris Culver:🎙️ Episode 214: The Science of Kindness – Explore the research, neuroscience, and foundational principles that sparked the ideas expanded upon in Be the Light.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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  Episode 280: Leadership in the Age of AI with Molly Rosen 31.05.2026 33min

  What does leadership look like when the world is changing faster than ever before?In this episode of the Leaning Into Leadership podcast, Dr. Darrin Peppard sits down with Molly Rosen, Co-CEO of ProjectNext Leadership, for a powerful conversation about leadership transitions, succession development, organizational agility, and the growing impact of AI on leadership and workplace culture.Molly works with leaders across industries including tech, biotech, and entertainment, helping organizations prepare leaders for critical next-level roles. Together, Darrin and Molly explore why the skills that make someone successful in one role often do not transfer automatically into leadership — and why emotional intelligence, communication, humility, and adaptability matter now more than ever.The conversation dives into:The transition from “player” to “coach” leadershipWhy many leaders struggle to let go of their previous roleThe dangers of over-relying on technical expertiseSuccession development and building leadership pipelinesHow AI is reshaping organizations and leadership expectationsThe importance of organizational agilityWhy leaders must communicate vision without pretending to have all the answers“Sketch-based advocacy” and collaborative leadershipThe role of empathy and emotional intelligence during uncertainty and changeWhy leadership today is more about building teams than directing themMolly also shares her own leadership growth journey and the importance of prioritization and sequencing ideas as a leader.This episode is a must-listen for school leaders, organizational leaders, and anyone navigating leadership in rapidly changing environments.About Molly RosenMolly Rosen is Co-CEO of ProjectNext Leadership. She has worked with leaders in tech, entertainment, and biotech for over 20 years as an executive coach, facilitator, and consultant developing innovative talent systems.Her clients have included organizations such as Pixar, Airbnb, DocuSign, and Samsung, where she has helped leaders prepare for critical transitions and organizational change.Molly previously held leadership roles with BlessingWhite and Ninth House Network and holds an MBA from UCLA Anderson and a BA from UC Berkeley.Connect with Molly RosenLinkedIn: https://www.linkedin.com/in/mollyrosen/Website: https://www.projectnextleadership.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
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  Episode 279: Burn the Script with Jo Lein 24.05.2026 32min

  In this episode, Darrin sits down with leadership coach and new author Jo Lein to explore what really drives change in people and organizations—and why most coaching efforts fall short when they focus only on skills.Jo introduces the concept of Disruptive Mindset Coaching, challenging leaders to move beyond surface-level fixes and address the beliefs that shape behavior.Topics Covered:The difference between skill gaps and belief barriersWhy people aren’t “uncoachable”—they’re often operating from protective patternsThe three common patterns that show up in resistant behavior:DetachingSurrenderingOvercompensatingHow identity, values, and skill all influence leadership behaviorWhy systems in education are built on underlying beliefs—and how those beliefs shape outcomesThe danger of compliance culture in schoolsWhat it means to “burn the script” as a leaderHow leaders can create environments where innovation and growth are possibleAbout Jo Lein:Jo Lein is a leadership coach, writer, and educator who helps leaders break through limiting beliefs and transform practice. She is the author of Burn the Script, where she introduces her framework for Disruptive Mindset Coaching.Connect with Jo:TikTok & Instagram: @educoachbyjoSubstack: jolein.substack.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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  Episode 278: Compliance Can Control a Team. Alignment Can Transform One. 20.05.2026 17min

  What happens when strong leaders slowly stop speaking?In this reflective solo episode, Dr. Darrin Peppard explores the hidden cost of compliance-based leadership cultures and the long-term impact they can have on trust, alignment, and organizational health.Drawing from personal leadership experiences, conversations with leaders around the country, and John Maxwell’s “Law of the Lid,” Darrin unpacks what happens when high-capacity leaders find themselves working in environments driven more by control and compliance than collaboration and alignment.This episode is not about criticizing leaders. It’s about understanding how organizational cultures develop, why strong leaders sometimes disengage quietly, and how intentional alignment work can help teams rebuild trust and move forward together.In this episode, Darrin discusses:The difference between compliance-based and alignment-based leadershipJohn Maxwell’s “Law of the Lid” and how it impacts organizationsWhy strong leaders often become quieter instead of combativeThe emotional and cultural impact of low-trust leadership environmentsHow political behavior and silence slowly erode healthy cultureWhy leadership alignment matters more than forced complianceThe importance of creating trust, contribution, and shared ownershipHow leaders can still positively influence culture within their sphereKey Takeaways:Compliance may create short-term control, but alignment creates long-term health.Silence inside leadership teams is often a warning sign, not a sign of agreement.Healthy organizations allow honest dialogue, healthy tension, and contribution.Leadership culture outlives individual leaders—for better or worse.Alignment work is intentional work.SponsorThis 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
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  Episode 277: Redefining Educator Professionalism with Dr. Nason Lollar 17.05.2026 49min

  In this episode of Leaning Into Leadership, Darrin sits down with Dr. Nason Lollar to explore a topic often overlooked in leadership conversations—educator professionalism.Drawing from his book The Five Principles of Educator Professionalism, Nason introduces the TRUST framework, a practical approach to connecting individual behaviors with school culture.The conversation dives into how small, everyday actions—not just major incidents—shape the success, safety, and climate of a school.Key Topics:Why adult behavior—not student behavior—is often the real leadership challengeDefining professionalism as a contribution to school cultureThe TRUST framework:Teaching and learning firstRemain vigilant about safetyUnderstand communicationSeek personal balanceTake ownership of moraleThe difference between negatives vs. negativityWhy listening is one of the most overlooked leadership skillsMoving beyond “gotcha” leadership toward genuine supportThe power of acknowledgment in building staff moraleKey Takeaway:Professionalism isn’t about compliance—it’s about clarity, consistency, and contribution. When leaders define what matters and support their people well, culture improves—and so does everything else.Connect with Nason:Blog: nasonlollar.wordpress.comX: @nasonlollarFacebook: Nason Lollar, AuthorSponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan, don’t wait until the fall to build your support system.HeyTutor provides high-dosage tutoring in Math and ELA—handling recruitment, training, and management—so your team can focus on impact.Learn more at HeyTutor.comLet’s ConnectIf you’re working to move from planning to execution—and want to ensure your team stays aligned and focused throughout the year—Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.
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  Episode 276: The Leadership TAP with Dr. Joy Karavedas 10.05.2026 33min

  In this episode, Darrin sits down with Dr. Joy Karavedas to explore what it really means to develop leaders intentionally—and why that “tap on the shoulder” can be life-changing.Joy shares her journey into leadership and how her research revealed a powerful pattern: nearly every leader can point to a moment when someone saw their potential before they did.The conversation dives into:The importance of intentionally building a leadership pipelineWhy performance alone isn’t enough to identify future leadersThe reality of the “messy middle” and how leaders grow through itThe role of reflection in leadership development—and why most leaders skip itHow to give emerging leaders space to practice, fail, and growJoy also introduces her TAP framework:Trust – The foundation of leadership that must be earned dailyAuthenticity – Knowing who you are as a leader and showing up with confidencePerformance – The skills and execution that can be developed over timeOne of the biggest takeaways?A pat on the back might feel good—but a tap on the shoulder can change someone’s life.This episode is a powerful reminder that leadership development isn’t accidental—it’s intentional.Connect with Dr. Karavedas - https://drkaravedas.com/Sponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan, don’t wait until the fall to build your support system.HeyTutor provides high-dosage tutoring in Math and ELA—handling recruitment, training, and management—so your team can focus on impact.Learn more at HeyTutor.comLet’s ConnectIf you’re working to move from planning to execution—and want to ensure your team stays aligned and focused throughout the year—Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.
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  Episode 275: From Compliance to Connection — Rethinking Classroom Engagement with Megan Diede 03.05.2026 31min

  In this episode, Darrin sits down with Megan Diede to unpack one of the most pressing challenges in schools today: authentic student engagement.The conversation begins with a familiar frustration—classrooms full of students disengaged on devices—and quickly reframes the issue. It’s not about abandoning technology. It’s about being intentional and purposeful with instruction.Megan introduces a powerful shift in thinking:Engagement isn’t about activity—it’s about connection.Together, they explore what it means to move beyond compliance-driven teaching and into classrooms where students are actively connected to their learning.Key Takeaways:Why the “paper vs. tech” debate misses the pointThe real issue isn’t the tool—it’s how it’s used.Connection over complianceMegan defines connection as the intentional bridge between people and purpose—and explains how it transforms instruction.What engagement actually looks likeIt’s not always loud or busy. Sometimes it’s quiet, focused, and deeply meaningful.The role of leadership in creating risk-safe environmentsTeachers need permission—and support—to try, fail, and refine their instruction.Small instructional shifts that create big impactEngagement doesn’t require a complete overhaul—just intentional adjustments.The power of team connection (the “coconut story”)A simple moment of problem-solving revealed how connection fuels collaboration and reduces stress.How leaders and instructional coaches can support teachersThrough clarity, alignment, modeling, and ongoing—not one-time—support.Connect with Megan DiedeWebsite: https://www.integratedk12.comInstagram: https://www.instagram.com/megandiedeLinkedIn: https://www.linkedin.com/in/megandiedeFacebook: https://www.facebook.com/integratedk12Sponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan, don’t wait until the fall to build your support system.HeyTutor provides high-dosage tutoring in Math and ELA—handling recruitment, training, and management—so your team can focus on impact.Learn more at HeyTutor.com🎯 Let’s ConnectIf you’re working to move from planning to execution—and want to ensure your team stays aligned and focused throughout the year—Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.
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  Episode 274: If Everyone Was Pulling the Same Direction... 26.04.2026 20min

  In this final episode of the 3-part planning series, Darrin Peppard shifts from planning and preparation to something even more important—what happens when your plan meets reality.Through a candid story from his time as a superintendent implementing project-based learning, Darrin shares what worked, what didn’t, and the leadership lessons that emerged when execution didn’t match expectations.Because the truth is—most plans don’t fail in the planning phase.They fail in the implementation.Key TakeawaysPlanning Isn’t the Problem—Leadership IsYou can have the right plan, strong training, and full buy-in…and still see inconsistent results.The difference?How the work is led once the year begins.Same Plan, Different ResultsSome educators:Collaborated and sought feedbackOpened their classroomsEngaged students deeplyOthers:Struggled to see the fitDefaulted to old routinesOr simply didn’t follow throughSame expectations. Very different outcomes.4 Leadership Moves That Change Everything1. Make the Work VisibleIf the work matters, it must be seen.Without visibility, implementation becomes optional.2. Build Ongoing SupportTraining starts the work—it doesn’t sustain it.Coaching and follow-up are essential.3. Systematize FeedbackDon’t leave support up to initiative.Build regular check-ins and feedback loops into the system.4. Hold Leaders AccountableAlignment doesn’t happen by accident.It happens when leaders consistently lead the work.The Big LessonYour plan doesn’t fail because people didn’t understand it.It fails when you haven’t built the conditions for it to live throughout the year.Series RecapEpisode 270: Don’t wait until August—you’re already behindEpisode 271: Do the work now to prepare for successSponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan, don’t wait until the fall to build your support system.HeyTutor provides high-dosage tutoring in Math and ELA—handling recruitment, training, and management—so your team can focus on impact.Learn more at HeyTutor.com🎯 Let’s ConnectIf you’re working to move from planning to execution—and want to ensure your team stays aligned and focused throughout the year—Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.
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  Episode 273: Why Most School Plans Fail (And What to Do Instead) 19.04.2026 39min

  This month, we’ve been focused on one thing: building plans that don’t just sound good—but actually work.In this episode, Darrin is joined by Kathleen Beckham, Molly Dexter, and Brandon Mawhorter from digiCOACH for a real, unscripted conversation about what it takes to build—and execute—a plan that improves classroom instruction.This isn’t about theory.It’s about what actually moves the needle.Drawing from their experiences as educators, coaches, and system-level partners, Kathy, Molly, and Brandon share practical insights on focus, feedback, data, and the role of leadership presence in driving meaningful change.Key TakeawaysYou can’t focus on everythingThe best leaders narrow their priorities to 1–2 key areasMore than that creates noise and reduces impactClarity beats generalities“Improve instruction” isn’t a planLeaders must define what they expect to see in every classroom, every dayTeacher voice mattersGrowth happens through partnership, not directivesCollaboration builds buy-in and improves outcomesPresence is non-negotiableIf you’re not in classrooms, your plan won’t move forwardWhat gets calendared—and protected—gets doneData must lead to actionWalkthroughs without follow-up don’t create changeThe real impact comes from coaching conversations and feedback cyclesYou don’t have to do it aloneOutside partners bring perspective, accountability, and expertiseSometimes you need someone to pull you out of the weeds and back to the balconyFinal ThoughtThe best plans aren’t built on ambition alone.They’re built on:focus, intentional action, and consistent follow-throughAnd most importantly…They’re built with people—not just for them.Learn more about DigiCoach hereSponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan for next year, don’t wait until the fall to build your support systems.HeyTutor provides high-dosage tutoring in Math and ELA—both in-person and online—while handling recruitment, training, and management of tutors.Learn more at HeyTutor.comLet’s ConnectIf you’re working to turn your plan into real, actionable steps between now and August, Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and momentum.
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  Episode 272: 10 Leadership Moves You Can Make This Week 15.04.2026 21min

  In this mid-week episode, Darrin steps away from long-range planning to focus on something just as powerful—small, intentional actions leaders can take right now.With only weeks left in the school year, it’s easy to feel stuck in the daily grind. But meaningful leadership doesn’t require a new initiative or a perfect plan. It comes from clear priorities, consistent actions, and intentional choices.In this episode, Darrin shares 10 practical leadership moves you can implement immediately to:Improve performanceStrengthen cultureLead with greater clarityThese aren’t big strategies—they’re simple shifts that create real impact.In this episode, you’ll learn:Why clarity around your top priority changes everythingHow simple communication can reduce team anxietyThe power of strength-based walkthroughsHow to reclaim your time by eliminating what doesn’t matterA 5-minute coaching protocol that builds capacity across your teamWhy role clarity reduces chaos and increases momentumHow small moments of follow-through build trustThe importance of recognizing and reinforcing what you valueHow “balcony time” helps you break the Cycle of CHAOSWhy saying “no” is essential to leading with intentionKey Takeaway:Leadership doesn’t change because of one big initiative.It changes through small, consistent, intentional actions.Sponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan for next year, don’t wait until the fall to build your support systems.HeyTutor provides high-dosage tutoring in Math and ELA—both in-person and online—while handling recruitment, training, and management of tutors.Learn more at HeyTutor.comLet’s ConnectIf you’re working to turn your plan into real, actionable steps between now and August, Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and momentum.