Leaning into Leadership

Darrin Peppard
  • 4.9 (31)
  • SELF-IMPROVEMENT
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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. 5D AGO

    Episode 274: If Everyone Was Pulling the Same Direction...

    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 deeply Others: Struggled to see the fitDefaulted to old routinesOr simply didn’t follow through Same expectations. Very different outcomes. 4 Leadership Moves That Change Everything1. Make the Work Visible If the work matters, it must be seen. Without visibility, implementation becomes optional. 2. Build Ongoing Support Training starts the work—it doesn’t sustain it. Coaching and follow-up are essential. 3. Systematize Feedback Don’t leave support up to initiative. Build regular check-ins and feedback loops into the system. 4. Hold Leaders Accountable Alignment 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 success 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.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.

    21 min

  2. APR 19

    Episode 273: Why Most School Plans Fail (And What to Do Instead)

    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 balcony Final ThoughtThe best plans aren’t built on ambition alone. They’re built on: focus, intentional action, and consistent follow-through And most importantly… They’re built with people—not just for them. Learn more about DigiCoach here Sponsor Spotlight This 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.com Let’s Connect If 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.

    39 min

  3. APR 15

    Episode 272: 10 Leadership Moves You Can Make This Week

    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 clarity These 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 intention Key Takeaway:Leadership doesn’t change because of one big initiative. It changes through small, consistent, intentional actions. Sponsor Spotlight This 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.com Let’s Connect If 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.

    22 min

  4. APR 12

    Episode 271: Planning Isn’t Enough—Here’s What to Do Before August

    What Has to Be True by August?In Part 2 of this 3-part series on planning for the upcoming school year, Darrin shifts the focus from planning to preparation. You already know what you want to accomplish next year—but what are you doing right now to make that success possible? This episode challenges leaders to stop waiting for August and instead take intentional steps today that set the foundation for a strong start. Key TakeawaysPreparation > Planning Planning identifies the goal. Preparation makes success possible. Ask yourself: What has to be true by August for this to work? Start the Work Now Don’t wait for a full rollout in the fall. Begin building: LanguageExpectationsEarly repsSo the work feels familiar—not new—when the year begins. Take Inventory Before August Use a protocol like Start, Stop, Continue, Consider to: Gather input from your teamSurface what’s working (and what’s not)Create clarity and shared ownership When people feel heard, they’re far more likely to commit. Unpack the Backpack Give your team the opportunity to: Let go of what’s no longer serving themProtect what’s workingAvoid adding “one more thing” to an already full plate Leading Through TurnoverNot every team is fully in place right now—and that’s okay. Progress doesn’t stop just because people change. You can still: Clarify core priorities and non-negotiablesDocument your directionProtect what’s already workingBuild clear onboarding into your vision and goals Don’t wait for the perfect team—create clarity that any team member can step into. The Bottom LineBetween now and August, your job is not to create more. It’s to: Take actionGather inputCreate claritySet conditions for success So when the year begins, you’re not starting from scratch—you’re building on momentum. 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.com Let’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.

    22 min

  5. APR 6

    Episode 270: If Your Plan Starts in August, You May Already Be Behind

    This week kicks off a three-part solo series focused on one critical question: How do we actually plan for success in the coming school year? April is a time when leaders are deep in planning—budgets, staffing, schedules, and resources are all coming together. But too often, we focus on what we’re going to do without fully thinking through how we set our teams up for success. In this episode, Darrin challenges a common leadership assumption—that the work starts in August—and introduces a different way of thinking. Because August isn’t the starting line. It’s the reveal. In This EpisodeWhy so many leadership teams delay their real work until AugustThe danger of treating the start of the school year as the starting pointHow lack of clarity shows up immediately when the year beginsA powerful shift in thinking: “What must be true by August?”An introduction to backward mapping as a leadership strategyA simple exercise you can use right now to begin planning differently Key TakeawayGreat leaders don’t wait for August to get started. They use the time leading up to the school year to build clarity, align their teams, and create momentum—so when the year begins, they’re ready. Try ThisPick one initiative or priority for next year and ask yourself: What are three things that must be true by August for this to succeed? Your answers will reveal exactly where your focus should be right now. What’s Coming NextNext week, we tackle a real challenge many leaders face: What do you do when your team is in transition and August really is when everyone comes together? Even in times of change, there are steps you can take now to set yourself up for success. Sponsor Spotlight: HeyTutorStrong leadership requires focus—and that’s hard to maintain when leaders are pulled into operational work that can be handled by the right partners. That’s why Darrin highlights the work of HeyTutor, a sponsor of the Leaning Into Leadership podcast. HeyTutor provides: High-quality, evidence-based math and ELA tutoringFull program management (recruiting, training, scheduling)Clear data tracking through an easy-to-use dashboard Their support helps leadership teams stay focused on what matters most—leading people and improving outcomes. Learn more: heytutor.com

    13 min

  6. MAR 29

    Episode 269: The Cost of Misalignment—and How to Get Your Team Back on Track

    In this episode of the Leaning Into Leadership podcast, Dr. Darrin Peppard takes on a challenge that quietly impacts even the strongest leadership teams: misalignment. You can have talented, committed leaders who care deeply about their work—and still feel like something is off. Conversations feel unclear. Decisions take longer than they should. Initiatives pile up without traction. That’s misalignment. And while it may not be loud or obvious, it comes at a cost. In this episode, Darrin breaks down: What misalignment really looks like in leadership teamsThe hidden costs, including decision fatigue, staff confusion, and lost timeA personal leadership story that reshaped his understanding of alignmentWhy alignment doesn’t happen during the work—it must be built intentionally Darrin also shares a practical tool you can use immediately with your team: Start. Stop. Continue. Consider.This simple protocol helps leadership teams: Identify what needs to be addedEliminate what’s no longer alignedProtect what’s workingThink strategically about what’s next Whether used in a leadership retreat or a focused team session, this process creates the clarity and shared direction teams need to move forward together. Key takeaway: Your team doesn’t need to work harder. They need to work together—on the right things, in the right way. 🔗 Resources & LinksBlog: Start, Stop, Continue, Consider ProtocolConnect with Darrin: darrin@roadtoawesome.netLearn more about leadership retreats and team development Thank you to our Amazing Sponsors This episode is sponored by DigiCoach, helping leaders capture real-time instructional data, provide meaningful feedback, and build clarity through strong systems. Go to digicoach.com and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing. This episode is also brought to you by HeyTutor, delivering high-impact, research-based tutoring that supports students while reducing leadership overwhelm. Connect with them at HeyTutor.com

    25 min

  7. MAR 22

    Episode 268: When Leaders Become the Bottleneck (and How to Get Out of the Way) with Brooke Dukes

    In this episode, Darrin sits down with Brooke Dukes to explore a challenge that many leaders face—but often don’t recognize: Becoming the bottleneck. We talk about how this happens unintentionally, why it’s so common among high-performing leaders, and how it ultimately limits both team growth and organizational success. Brooke brings a powerful perspective to this conversation. As the founder of Success by Design Club and creator of OZ, an AI-powered leadership coach, she has spent over two decades working with leaders at the highest levels—including Fortune 500 organizations—helping them break free from burnout and lead with clarity and confidence. Together, we dig into the dangers of “superhero leadership,” the hidden cost of control, and why stepping in to help can actually hold your team back. Most importantly, we explore what it really takes to shift—from being the center of every decision to building systems and structures that allow your team to step up and thrive. If you’ve ever felt overwhelmed, stretched thin, or like everything depends on you… this conversation is for you. Key TakeawaysHow leaders unintentionally become the bottleneckThe danger of “superhero leadership”Why helping can actually hurt your teamThe role of systems in scaling leadershipHow to build trust, clarity, and accountabilityWhy burnout is often a systems issue—not a personal failure About Brooke DukesBrooke M. Dukes is the founder of the Success by Design Club and creator of OZ, an AI-powered leadership coach designed to help leaders grow without burning out. With over 20 years of experience in executive leadership, sales, and consulting—including work as a Fortune 500 executive and global strategist—Brooke helps CEOs, founders, and visionaries build businesses that actually work for them. Her work blends behavioral science, Human Design, and real-world strategy to restore clarity, confidence, and calm in leadership. She is also the creator of the GRACe™ Communication Framework and Culture Compass™ Diagnostic, a #1 best-selling author, host of the Burn On, Not Out podcast, and a sought-after speaker known for her honest and heart-forward approach. 🔗 Connect with BrookeWebsite: brookmdukes.comPodcast: Burn On, Not OutSocial: @BrookMDukes Get Darrin's weekly blog here Thank you to our Amazing Sponsors This episode is sponored by DigiCoach, helping leaders capture real-time instructional data, provide meaningful feedback, and build clarity through strong systems. Go to digicoach.com and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing. This episode is also brought to you by HeyTutor, delivering high-impact, research-based tutoring that supports students while reducing leadership overwhelm. Connect with them at HeyTutor.com

    37 min

  8. MAR 18

    Episode 267: Listener Question - Managing Parent Communication Without Losing Your Day

    One of the most rewarding parts of hosting Leaning Into Leadership is hearing from listeners who are doing the work every day. In this episode, Darrin responds to a question from a first-year principal in upstate New York who asked a challenge many school leaders face: How do you stay responsive to parents while still leading the school effectively? Parent emails, phone calls, and concerns can quickly fill a leader’s day. Without systems in place, communication can pull leaders into a reactive cycle that leaves little time for the work that matters most. Drawing from his own experience as a principal and from insights shared on the podcast, Darrin explores how leaders can break free from the Cycle of CHAOS and build systems that protect their time while strengthening communication with their school community. Along the way, he shares practical strategies that help leaders communicate clearly, set expectations, and stay focused on their highest priorities. This episode also highlights an idea shared by Rae Hughart in Episode 199 and connects to leadership lessons from Darrin’s book Road to Awesome: The Journey of a Leader. At the heart of the conversation is a powerful reminder for every leader: "Stop sacrificing the important on the altar of the urgent." Resources Mentioned: Road to Awesome: The Journey of a Leader School Leader Weekly Planner Episode 199 – Rae Hughart 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 digicoach.com and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing.

    25 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
    275
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Darrin Peppard
  • Show Website
    Leaning into Leadership

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