Leaning into Leadership

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  Episode 298: The Resistance Solution with Becca Silver 13.09.2026 38dk

  What if resistance isn’t something leaders need to overcome?In Episode 298 of the Leaning Into Leadership Podcast, Darrin sits down with Becca Silver, CEO and founder of The Whole Educator and author of The Resistance Solution, for a powerful conversation about what is really happening when educators push back against change.Becca challenges leaders to stop labeling people as “resistant” and instead recognize that resistance is an experience people move through. Rather than relying on compliance, consequences, or generic advice like “build better relationships,” she introduces a human-centered approach that helps leaders understand the unmet needs underneath resistance.Drawing from her own experience as a teacher who resisted change, an instructional coach who initially struggled to create change, and eventually a leadership coach who became highly effective at working with educators experiencing resistance, Becca shares the research behind her five Catalyst Mindsets.Darrin and Becca explore:Why resistance is often the result of unmet needs rather than unwillingness or negativityThe difference between a “resistant teacher” and a teacher experiencing resistanceWhy schools hire critical thinkers—and then sometimes expect them simply to complyThe five Catalyst Mindsets: value, belonging, success, growth, and ownershipWhy generic strategies for dealing with resistance often miss the real problemThe critical difference between compliance, buy-in, and true ownershipWhy agency is essential if leaders want people to own changeHow clarity around non-negotiables and professional judgment can immediately increase ownershipWhy leaders must explicitly tell people where they have permission to use their expertiseHow human-centered leadership can move change forward without going around people’s humanityOne of the most practical takeaways from the conversation is something leaders can implement immediately: be crystal clear about what is non-negotiable and where people have the agency to exercise their professional judgment.When people understand where they have voice, choice, and the ability to make a meaningful impact, leadership can begin moving beyond compliance and toward genuine ownership.Becca also shares how she is personally leaning into leadership through shared leadership—developing others to lead the work rather than building something that depends entirely on her.Connect with Becca SilverBecca Silver is the CEO and founder of The Whole Educator and author of The Resistance Solution. Her work helps instructional coaches and educational leaders navigate resistance to change through a human-centered approach.Learn more about Becca, The Resistance Solution, the Resistance Solution Community, her Book Study Facilitator Training, and the Coaching the Whole Educator podcast through The Whole Educator.This Episode Is Sponsored by HeyTutorHeyTutor 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
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  Episode 297: Stop Accepting “That’s Just the Way It Is” 06.09.2026 33dk

  What happens when growth doesn’t solve your problems—but actually makes them bigger?In Episode 297 of Leaning Into Leadership, Dr. Darrin Peppard sits down with entrepreneur, Marine veteran, and business leader Ron Nussbaum for a conversation about entrepreneurship, problem solving, challenging the status quo, and what it really takes to build something that matters.Ron shares the story behind BuilderComs and the realization that changed the way he thought about growth: if you scale your organization without solving the problems already inside it, you’re simply scaling those problems too.That lesson reaches far beyond entrepreneurship.Darrin and Ron explore why leaders sometimes become comfortable tolerating things that are merely “okay,” why challenging the status quo doesn’t mean changing everything, and why one of the most important questions a leader can ask is, “What problem are we actually trying to solve?”Ron also shares the thinking behind Ask a Shop Owner, a platform designed to give small business owners actionable guidance and accountability when they encounter real-world business challenges.The conversation closes with an important reality about entrepreneurship and leadership: every meaningful pursuit involves trade-offs. The goal isn’t to avoid them. It’s to intentionally choose the trade-offs that move you toward the life, organization, and outcomes you actually want.In this episode:Why leaders need to stop scaling problemsChallenging “that’s just the way we’ve always done it”Finding the real problem before searching for solutionsWhy growth can magnify existing organizational weaknessesTurning experience and knowledge into actionable plansThe role accountability plays in creating resultsWhy entrepreneurship requires uncomfortable trade-offsChoosing freedom, stability, and the outcomes that matter mostExpanding the reach of your leadershipRon’s challenge is simple but powerful: don’t accept a problem simply because everyone else has learned to live with it. Challenge it. Solve it. Then scale the solution.This Episode Is Sponsored by HeyTutorHeyTutor 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
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  Episode 296: Beyond Compliance - Building Classrooms Where Students Want to Engage 30.08.2026 35dk

  What if the goal of great teaching isn’t getting students to comply, but creating the conditions where they genuinely want to engage?In this episode of Leaning Into Leadership, Dr. Darrin Peppard sits down with educator, school leader, author, and founder of Terry Leadership Group, Kendall Terry, for a conversation about what happens when schools stop focusing primarily on what teachers are doing and start paying closer attention to what students are actually learning.Kendall shares his experience helping build Clayton-Bradley Academy from its early years and the unique opportunity that came with designing educational systems from the ground up. Rather than inheriting decades of “this is how we’ve always done it,” Kendall and his colleagues were able to ask a different question: What does research tell us about how the brain learns, and how should that change what happens in our classrooms?That question eventually helped shape the Learning-Centered School Model, where the learner—not the teacher, the curriculum, or the test—is at the center of instructional decisions. Kendall and Darrin explore what that actually looks like in practice, from something as simple as welcoming every student into the classroom to making learning relevant, interactive, safe, and meaningful.The conversation then moves into Kendall’s BRACE Framework, five conditions that can dramatically influence engagement:B — Belonging: Students and teachers need to know they are valued and that their voices matter.R — Relevance: Learners need to understand what they are learning and why it matters.A — Agency: Students and teachers need autonomy, ownership, and opportunities to create, try, fail, and try again.C — Challenge: Learning should stretch people appropriately while providing the support necessary for success.E — Engaged Response: Learning isn’t a one-and-done transaction. Students need opportunities to respond, receive feedback, revisit their thinking, and continue until they reach mastery.For school leaders, BRACE also provides another powerful opportunity: shifting classroom walkthroughs and instructional feedback away from simply looking for compliance and toward identifying the conditions that produce authentic student engagement. As Kendall points out, students can comply because they don’t want to get in trouble—or they can engage because the learning experience is meaningful enough that they actually want to participate. Those are very different outcomes.Darrin and Kendall also dig into SMART habits and an important leadership truth: goals give us a destination, but habits determine whether we ever get there.The challenge isn’t deciding that we want greater belonging, stronger engagement, or improved student achievement. The challenge is determining what we will actually do on a Tuesday afternoon when the fire drill just ended, students are bouncing off the walls, and the big strategic goal is the furthest thing from our minds.Kendall suggests starting incredibly small. Want to increase belonging? Build the habit of greeting every student by name. Then connect the behavior to a predictable trigger: If class is beginning, then I will greet every student who enters my classroom by name.Small. Repeatable. Intentional.And over time, potentially transformational.Finally, Kendall answers the question every guest on Leaning Into Leadership receives: How are you leaning into leadership right now?His answer is one every leader should consider: listening.Not listening while preparing the next response. Not listening long enough to tell someone why they're wrong. But listening with the genuine intention of understanding another person's perspective, experience, and situation.Because belonging begins when people believe their voice actually matters.In This EpisodeWhy student learning—not teacher performance—should be at the center of instructional decisionsHow brain research can influence everyday classroom practiceWhy greeting students and creating predictability matter more than we sometimes realizeThe difference between student compliance and genuine engagementKendall's BRACE Framework for increasing engagementHow belonging, relevance, agency, challenge, and engaged response work togetherWhy leaders can use BRACE to strengthen classroom walkthroughs and feedbackThe limitations of setting goals without intentionally developing habitsHow small, repeatable habits can create significant changeWhy leaders need to listen to understand instead of listening to respondConnect with Kendall Terry:Terry Leadership Group and the BRACE resources are available through Kendall's website, and he also shares his work on LinkedIn, Facebook, and Instagram.This Episode Is Sponsored by HeyTutorHeyTutor 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.
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  Episode 295: Who Takes Care of the Leader? with Melissa Doman 23.08.2026 43dk

  Leadership comes with expectations. Be steady. Be available. Support your people. Make the difficult decisions. Carry the pressure.But what happens when the person everyone looks to for support needs support too?In this episode of Leaning Into Leadership, Darrin sits down with organizational psychologist, former therapist, and author Melissa Doman for an honest and practical conversation about leadership mental health, communication, emotional intelligence, and what sustainable leadership actually looks like.Melissa challenges the idea that leaders should simply absorb the pressure that comes with the role. Instead, she argues that organizations need to humanize leaders and give them permission to communicate their needs, acknowledge their capacity, and access the same resources they are expected to provide for everyone else.Darrin and Melissa explore the popular idea that “leaders eat last” and why servant leadership can become unhealthy when leaders interpret service as sacrificing themselves for everyone around them. Sustainable leadership requires leaders to care for others and manage their own emotional and cognitive capacity.The conversation gets incredibly practical as Melissa introduces the idea of communicating capacity — being able to tell your team honestly where you are and what you can realistically handle. If you're operating at 30 or 40 percent on a particular day, your team doesn't need you to pretend you're at 100. They need clarity about what they can expect from you.Darrin and Melissa also discuss:Why emotional intelligence, communication, and constructive conflict should be considered core professional developmentWhy policies and procedures aren't enough if people haven't learned how to communicate effectivelyThe danger of practicing servant leadership to your own detrimentHow leaders can give team members permission to speak up when something seems differentWhy curiosity is more productive than immediately judging a leader's behaviorHow to communicate your capacity without using it as an excuse for poor performanceThe difference between mission-critical priorities and manufactured emergenciesStephen Covey's circles of control, influence, and concernCreating personal mental well-being non-negotiables that actually work for youWhy leadership peer-support networks should exist inside organizationsThe importance of leaders modeling the use of the resources they encourage their employees to useWhy leadership can become incredibly lonely — and why leaders need other leaders who understand what it means to “sit in the chair”Melissa also shares insights from her book Cornered Office: Why We Need to Talk About Leadership Mental Health, along with the upcoming Wiley re-release of Yes, You Can Talk About Mental Health at Work: Here's Why (and How to Do It Really Well).And because this is Leaning Into Leadership, the conversation somehow also includes salsa dancing, inflatable Velociraptors, ABBA…and the first-ever Chewbacca impression in podcast history. Well, at least in this podcast's history.About Melissa DomanMelissa Doman is an organizational psychologist, former therapist, author, speaker, and consultant who teaches organizations, leaders, and employees the practical skills needed to talk about mental health, communication, and team dynamics at work. Her clients range from global organizations to professional sports teams, mid-sized companies, and small businesses around the world.Her latest book, Cornered Office: Why We Need to Talk About Leadership Mental Health, explores the often-overlooked emotional and cognitive realities of leadership and challenges organizations to include leaders in conversations and systems designed to support workplace mental health.Connect with MelissaWebsite: melissadoman.comLinkedIn: Melissa DomanInstagram: @thewanderingmelMentioned in This EpisodeCornered Office: Why We Need to Talk About Leadership Mental Health (link)Yes, You Can Talk About Mental Health at Work: Here's Why (and How to Do It Really Well) — re-releasing from Wiley on September 29, 2026.This Episode Is Sponsored by HeyTutorHeyTutor 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.
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  Episode 294: 5 Leadership Traps to Avoid as the School Year Begins 19.08.2026 22dk

  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 arriveLetting urgency rewrite your prioritiesAssuming everyone understood the opening-day messageTrying to solve every problem personallyWaiting too long to address something you already know isn't rightAt 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 EpisodeWhy presence matters more than performative visibilityHow the urgent can quietly replace your real leadership prioritiesWhy your calendar tells the truth about what you valueThe difference between communicating a message and creating clarityHow solving every problem can actually weaken the people around youWhy servant leadership is about empowerment, not doing everything for othersThe difference between grace and avoidanceWhy addressing small issues early protects the culture you're trying to createHow to recognize leadership drift before it becomes your new normalKey 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 HeyTutorHeyTutor 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.
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  Episode 293: The Human Side of Leadership with Stacy Nation 16.08.2026 33dk

  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 practicesWhy relationships are a critical resiliency factorCreating environments where adults can regulate and perform at their bestWhy supporting people does not mean lowering expectationsWhat leaders should understand about the reasoning and emotional brainWhy Stacy encourages leaders to replace “Why?” with “Help me understand”Using shared language around regulation throughout a schoolMoving from reactive responses to proactive supportWhy leaders need to live—not simply model—the practices they expect from othersStacy 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.orgInstagram: Stacy G NationFacebook: Stacy Nation / Stacy G NationLinkedIn: Stacy NationYouTube: Search Stacy Nation or Stacy YorkBook: What Really Happens in Therapy Behind Closed Doors: A Guided Journey to HealingSponsor 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: heytutor.comConnect 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 292: Why Not? A Leadership Mindset That Changes Everything 09.08.2026 25dk

  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 EpisodeThe 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 GuestsBradlee SkinnerInstagram/Facebook/TikTok/X: @BradleeWSkinnerDJ Brand: @DJPhonyStarkMelissa SkinnerFacebook: Ms. Melissa SkinnerInstagram: @IncredibleSkinnerTikTok: @MrsMamaSkinnerSponsor 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: 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 291: Live Your Passion Out Loud 02.08.2026 15dk

  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 37dk

  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 12dk

  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 38dk

  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 35dk

  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 46dk

  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 39dk

  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 47dk

  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 13dk

  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 42dk

  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 25dk

  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 33dk

  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 32dk

  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