Leaning into Leadership

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

  1. 4D AGO

    Episode 259: ALIGN - The Antidote to the Cycle of Chaos in Leadership Teams

    Ever left a leadership team meeting feeling like it was so productive—then realized a week later nothing really changed? In this solo episode, Darrin unpacks why that gap between effort and impact is rarely about commitment—and almost always about clarity. Building on his “Cycle of Chaos” episode, he shares the ALIGN Framework, a practical system for strengthening team dynamics and keeping teams focused on what matters most. In this episode, you’ll learn:Why strong teams drift into reactivity when clarity is missingHow alignment breaks the Cycle of Chaos—not just “working harder”The ALIGN Framework for healthier team dynamics:A — Agree on the Vision and Goals: Ensure everyone can name the top priorities in the same languageL — Language and Communication: Teams don’t just make decisions—they carry the messageI — Intentional Role Clarity: Clear ownership prevents duplication, avoidance, and frustrationG — Growth Through Cross-Training: Build continuity and empathy without eroding rolesN — Navigate with Intention: Protect focus, pause before adding initiatives, and stay anchored to priorities Reflection questions to take back to your team:If I asked each team member privately, would they name the same top three priorities?Are we clear on what gets communicated, who communicates it, and how it’s framed?Where might I be stepping in that’s keeping someone else from stepping up?Are we moving the goal forward—or just filling the calendar? Support for leaders and teamsIf you’re thinking, “This sounds like my team, but we’re struggling to get there,” Darrin invites you to reach out for coaching, team support, or a leadership team alignment retreat designed to reset vision, roles, and priorities. Connect with Darrin: darrinpeppard.com | roadtoawesome.net | @darrinmpeppard Thank you to our Amazing Sponsors This episode is brought to you by HeyTutor, delivering high-impact, research-based tutoring that supports students while reducing leadership overwhelm. Connect with them at HeyTutor.com This episode is also sponored by DigiCoach, helping leaders capture real-time instructional data, provide meaningful feedback, and build clarity through strong systems. Go to https://www.digicoach.com/ and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing.

    30 min

  2. JAN 25

    Episode 258: The Hidden Work - What Separates High Performers from Underachievers with Weston Kieschnick

    Weston Kieschnick has been in the work for a long time—as a classroom teacher, coach, author, and speaker—and this conversation feels like two colleagues reconnecting around what actually drives performance. We dig into Weston’s newest work and the idea that the gap between high performers and underachievers usually isn’t talent. It’s behavior—especially in the moments when adversity hits. In this episode, we explore:Why “hidden work” is the difference-maker when no one is watchingThe four performance pitfalls that derail people at every level:BlameExcusesSelf-deceptionGiving upThe flips that top performers lean into instead:OwnershipSolutionsTruthGritA Shark Tank green-room story with Barbara Corcoran that perfectly frames ownership vs. blameWhy feedback is the raw material for performance—and how self-deception blocks growthWeston’s take on “growability” and why self-awareness matters more than skill levelHow Weston is leaning into leadership right now: staying a learner, and learning from great leaders in every space Key takeawayWhen life gets hard, your default matters. You don’t rise to the level of your goals—you fall to the level of your patterns. This episode is a gut-check and a playbook. Connect with WestonFind Weston at WestonKieschnick.com and connect with him on social media to follow his work (and his “10-second truth” videos). Thank you to our Amazing Sponsors This episode is brought to you by HeyTutor, delivering high-impact, research-based tutoring that supports students while reducing leadership overwhelm. Connect with them at: https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA This episode is also sponored by DigiCoach, helping leaders capture real-time instructional data, provide meaningful feedback, and build clarity through strong systems. Go to https://www.digicoach.com/ and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing.

    41 min

  3. JAN 21

    Episode 257: Escaping the Cycle of Chaos

    Leadership doesn’t fall apart overnight. More often, it slowly drifts into a pattern that feels overwhelming, exhausting, and reactive. In this solo episode, Darrin introduces The Cycle of Chaos—a framework that helps leaders name what they’re experiencing and begin interrupting the patterns that keep them stuck in survival mode. Rather than offering quick fixes or productivity hacks, this episode invites reflection, clarity, and intentional leadership. In this episode, you’ll hear about:Why feeling busy doesn’t always mean you’re being effectiveHow constant reactivity increases cognitive load and erodes clarityThe five stages of the Cycle of Chaos:Constant ReactivityHigh Cognitive LoadAbsence of ClarityOverextensionSurvival Mode LeadershipWhy leaders stay stuck in the cycle—and why it’s not a failureHow clarity becomes the starting point for real change This conversation is a reminder that leaders don’t need to work harder—they need to lead clearer. SponsorsThis episode is brought to you by HeyTutor, delivering high-impact, research-based tutoring that supports students while reducing leadership overwhelm. Additional support comes from DigiCoach, helping leaders capture real-time instructional data, provide meaningful feedback, and build clarity through strong systems.

    25 min

  4. JAN 18

    Episode 256: Rethinking Intervention and Tutoring with Jennifer Sheffield

    School leaders everywhere are wrestling with the same challenge: How do we support students who are behind — without overwhelming teachers or relying on systems that don’t deliver results? In this episode of Leaning Into Leadership, Darrin Peppard sits down with Jennifer Sheffield, CEO of HeyTutor, for a grounded, practical conversation about what effective tutoring and intervention really look like in today’s schools. Jennifer brings a unique leadership lens — blending her background in law, governance, and education — to help leaders rethink how tutoring fits into MTSS, Tier 2 and Tier 3 supports, and daily school operations. In this episode, you’ll hear about:Why “tutoring” means very different things — and what defines high-impact tutoringThe biggest barriers schools face when implementing interventionsHow districts can address the human capital challenge without adding strain to teachersCreative push-in and pull-out models that work in middle and high schoolsWhy relationships and student champions matter as much as curriculumHow tutoring can become a pipeline for future educatorsWhat it means to lead with purpose, trust, and whole-person leadership Jennifer also shares a powerful personal story that shapes her leadership philosophy — reminding us that great leadership is ultimately about people, belief, and opportunity. Learn more:HeyTutor: https://www.heytutor.comContact Jennifer directly: jennifer@heytutor.com If you’re a school or district leader searching for intervention strategies that actually move the needle — this conversation will help you think differently. Episode Sponsors: This episode is sponsored by digiCOACH — an easy-to-use mobile platform that empowers school leaders to provide teachers with positive, actionable feedback tied to research-based instructional practices, with real-time data to support fidelity and instructional decision-making. Learn more at digicoach.com (mention the show for special partner pricing) This episode is also brought to you by HeyTutor - HeyTutor delivers customized, evidence-based, high-dosage Math and ELA tutoring to K–12 school districts nationwide. Their focus is on in-person tutoring, while also offering flexible online options — all tailored to meet diverse student needs and aligned with state standards. Head over to HeyTutor.com to learn more - tell them you heard about them on the Leaning into Leadership podcast.

    42 min

  5. JAN 12

    Episode 255: Angry Parents, Calm Leaders - A Framework for School Leaders

    In this special shared episode, Darrin Peppard and Dr. Frederick Buskey—host of The Assistant Principal Podcast—tackle a challenge leaders are facing more and more often: angry, escalated parent interactions. This conversation was sparked by a real question from the field—a leader Frederick supports reached out looking for guidance on how to handle parents when emotions are high. Together, Darrin and Frederick unpack a practical, grounded framework for what to do before, during, and after conflict shows up at your door. In this episode, you’ll hear:Why the best time to prevent angry parent blowups is before anything goes wrongHow leaders build “relationship capital” through proactive, positive contactWhy it matters to separate the student from the behavior (and how that changes everything)The value of student-written statements for clarity, due process, and aligned factsHow to make the parent call in a way that reduces defensiveness and keeps everyone groundedWhat to do when a parent escalates—and why listening is your strongest toolA powerful reminder: parents don’t always react to what happened—they react to feeling disrespectedThe bottom-line takeaway: It’s not about you—and remembering that makes it easier to listen Key takeawayWhen conflict rises, your job isn’t to “win” the conversation—it’s to protect dignity, stay calm, listen deeply, and build partnership forward. Episode Sponsors: This episode is brought to you by HeyTutor - HeyTutor delivers customized, evidence-based, high-dosage Math and ELA tutoring to K–12 school districts nationwide. Their focus is on in-person tutoring, while also offering flexible online options — all tailored to meet diverse student needs and aligned with state standards. Head over to HeyTutor.com to learn more - tell them you heard about them on the Leaning into Leadership podcast. This episode is also sponsored by digiCOACH — an easy-to-use mobile platform that empowers school leaders to provide teachers with positive, actionable feedback tied to research-based instructional practices, with real-time data to support fidelity and instructional decision-making. Learn more at digicoach.com (mention the show for special partner pricing)

    1h 13m

  6. JAN 4

    Episode 254: Hope Dealer with Dr. Mark Brown

    What does it mean to be a dealer in hope — not as the source of hope, but as someone who helps others discover it for themselves? In this first episode of 2026, Darrin sits down with longtime friend and colleague Dr. Mark Brown for a powerful conversation about leadership, hope, and intentional presence. Mark shares the story behind his “Hope Dealer” philosophy, why hope is for everyone (not just those in crisis), and how leaders can create cultures where people feel seen, supported, and empowered. As a first-year high school principal, Mark also reflects on the transition from assistant principal to principal, the importance of asking for help, and how modeling leadership behaviors matters more than any directive. The conversation closes with a reminder many leaders need to hear: taking care of yourself is not selfish — it’s essential. In this episode, you’ll hear about: What it really means to be a “Hope Dealer”Why leaders shouldn’t try to be the source of hope for othersLessons from Mark’s transition into the principalshipEmpowering others by asking for input — even when you don’t need itModeling leadership through presence, attitude, and behaviorWhy self-care is a leadership responsibility, not a luxury Connect with Dr. Mark Brown: Instagram: @heymarkbrownWebsite: www.markbrownedu.comBook: Hope Dealer: Leaning In to Lift Others This episode is sponsored by digiCOACH — an easy-to-use mobile platform that empowers school leaders to provide teachers with positive, actionable feedback tied to research-based instructional practices, with real-time data to support fidelity and instructional decision-making. Learn more at digicoach.com (mention the show for partner pricing) This episode is also brought to you by HeyTutor - HeyTutor delivers customized, evidence-based, high-dosage Math and ELA tutoring to K–12 school districts nationwide. Their focus is on in-person tutoring, while also offering flexible online options — all tailored to meet diverse student needs and aligned with state standards. Head over to HeyTutor.com to learn more - tell them you heard about them on the Leaning into Leadership podcast.

    33 min

  7. 12/28/2025

    Episode 253: A Look Back, A Look Forward, and Trends I'm Seeing for 2026

    As 2025 comes to a close, Dr. Darrin Peppard reflects on the year that was and what the work of leadership is asking of us as we head into 2026. In this year-end solo episode, Darrin invites both individual leaders and leadership teams to pause, reflect, and resist the urge to rush into the new year without clarity. Drawing from his work with leadership teams across the country, Darrin shares the key trends he’s seeing shape leadership in the year ahead—including the growing need for clarity, the non-negotiable role of culture, and the shift from compliance-driven leadership to coaching-focused practice. Darrin also reflects on his personal one-word theme for 2025 (Evolve) and looks ahead to 2026 with a renewed commitment to leading fiercely—with clear priorities, strong boundaries, and intentional focus. This episode is designed to be listened to individually or together as a leadership team, offering space for reflection, alignment, and forward momentum. This episode is sponsored by digiCOACH — an easy-to-use mobile platform that empowers school leaders to provide teachers with positive, actionable feedback tied to research-based instructional practices, with real-time data to support fidelity and instructional decision-making. Learn more at digicoach.com (mention the show for partner pricing) In This EpisodeWhy pausing to reflect matters before stepping into the new yearThe leadership trends shaping 2026The importance of clarity for leaders and leadership teamsWhy culture must remain a top priorityThe shift from compliance to coaching in effective leadershipOne-word reflection: Evolve (2025) and Fierce (2026) Connect & Continue the ConversationTo stay connected and receive reflective leadership insights in 2026, visit roadtoawesome.net and sign up for the newsletter. Go to darrinpeppard.com to learn more about Darrin's speaking, leadership workshops, and retreats. If you found this episode valuable, please subscribe to the podcast, leave a rating or review, and share it with other leaders or leadership teams who may benefit from this conversation.

    32 min

  8. 12/21/2025

    Episode 252: The Leader You're Not with Scott Borba

    This episode is sponsored by DigiCoach. Make walkthroughs meaningful. Simplify your coaching culture. Visit digiCOACH.com and mention Darrin for special partner pricing. In Episode 252 of Leaning Into Leadership, Darrin Peppard sits down with Scott Borba, superintendent–principal in California’s Central Valley and author of The Leader You’re Not. Together, they explore leadership identity, the cost of perfectionism, imposter syndrome, delegation, boundaries, and why sustainable leadership begins with self-awareness. This is a candid, reflective conversation for leaders at any stage — especially those feeling the weight of trying to do it all. Key Topics & TakeawaysWhy early-career leaders often fall into the “superhero” trapThe unique challenges of serving as both superintendent and principalHow COVID forced many leaders to confront identity, confidence, and callingThe importance of trusted mentors and leadership networksWhy perfectionism quietly fuels burnout and imposter syndromeHow delegation and asking better questions build leadership capacityThe cost of saying “yes” — and why boundaries are not selfishWhy leaders must stop comparing themselves to “Facebook leadership”The freedom that comes from knowing who you’re not as a leaderWhy legacy matters most at home — where leaders are not replaceable Memorable Moments“Trying to be the perfect leader kept me from growing.”“Every yes comes with a cost.”“You’re not replaceable at home — and that matters.”“Delegation isn’t weakness; it’s leadership.” About the Guest: Scott BorbaScott Borba is a superintendent–principal serving a small, rural school district in California’s Central Valley. With over 20 years in school leadership, Scott is deeply committed to relational leadership, mentorship, and sustainability in the profession. He is the author of The Leader You’re Not: Why It’s Just as Important as the Leader You Are, a reflective exploration of leadership identity, self-awareness, and letting go of unrealistic expectations. Scott also teaches in a university administrator preparation program and leads a countywide leadership network focused on connection, growth, and reducing burnout. Resources & Links📘 The Leader You’re Not by Scott Borbali...

    36 min
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About

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

Information

  • Creator
    Darrin Peppard
  • Years Active
    2022 - 2026
  • Episodes
    260
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Darrin Peppard
  • Show Website
    Leaning into Leadership

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