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Leaning into Leadership: Daily Summaries Delivered
by Darrin Peppard
We all want to see successes in both our personal and professional lives. Often, that requires strong leadership. In a time when leadership can be more challenging than ever, this podcast is dedicated to cultivating leaders by elevating the voices of leaders and promoting positivity. Join Dr. Darrin Peppard, lifelong educator and best-selling author, for this mixed platform podcast (some solo, some guest interview) for inspiration and insight, and some great leadership stories from those are living it, excelling at it, and celebrating it. Together, let's lean into leadership.
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- 5 days ago33 min
Episode 280: Leadership in the Age of AI with Molly Rosen
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
- 1 weeks ago32 min
Episode 279: Burn the Script with Jo Lein
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
- 2 weeks ago17 min
Episode 278: Compliance Can Control a Team. Alignment Can Transform One.
What happens when strong leaders slowly stop speaking?In this reflective solo episode, Dr. Darrin Peppard explores the hidden cost of compliance-based leadership cultures and the long-term impact they can have on trust, alignment, and organizational health.Drawing from personal leadership experiences, conversations with leaders around the country, and John Maxwell’s “Law of the Lid,” Darrin unpacks what happens when high-capacity leaders find themselves working in environments driven more by control and compliance than collaboration and alignment.This episode is not about criticizing leaders. It’s about understanding how organizational cultures develop, why strong leaders sometimes disengage quietly, and how intentional alignment work can help teams rebuild trust and move forward together.In this episode, Darrin discusses:The difference between compliance-based and alignment-based leadershipJohn Maxwell’s “Law of the Lid” and how it impacts organizationsWhy strong leaders often become quieter instead of combativeThe emotional and cultural impact of low-trust leadership environmentsHow political behavior and silence slowly erode healthy cultureWhy leadership alignment matters more than forced complianceThe importance of creating trust, contribution, and shared ownershipHow leaders can still positively influence culture within their sphereKey Takeaways:Compliance may create short-term control, but alignment creates long-term health.Silence inside leadership teams is often a warning sign, not a sign of agreement.Healthy organizations allow honest dialogue, healthy tension, and contribution.Leadership culture outlives individual leaders—for better or worse.Alignment work is intentional work.SponsorThis episode is sponsored by HeyTutor.HeyTutor partners with schools and districts nationwide to provide evidence-based high-dosage tutoring support in Math and ELA while helping schools remain intentional about staff capacity and student support systems.Learn more here: HeyTutor
- 2 weeks ago49 min
Episode 277: Redefining Educator Professionalism with Dr. Nason Lollar
In this episode of Leaning Into Leadership, Darrin sits down with Dr. Nason Lollar to explore a topic often overlooked in leadership conversations—educator professionalism.Drawing from his book The Five Principles of Educator Professionalism, Nason introduces the TRUST framework, a practical approach to connecting individual behaviors with school culture.The conversation dives into how small, everyday actions—not just major incidents—shape the success, safety, and climate of a school.Key Topics:Why adult behavior—not student behavior—is often the real leadership challengeDefining professionalism as a contribution to school cultureThe TRUST framework:Teaching and learning firstRemain vigilant about safetyUnderstand communicationSeek personal balanceTake ownership of moraleThe difference between negatives vs. negativityWhy listening is one of the most overlooked leadership skillsMoving beyond “gotcha” leadership toward genuine supportThe power of acknowledgment in building staff moraleKey Takeaway:Professionalism isn’t about compliance—it’s about clarity, consistency, and contribution. When leaders define what matters and support their people well, culture improves—and so does everything else.Connect with Nason:Blog: nasonlollar.wordpress.comX: @nasonlollarFacebook: Nason Lollar, AuthorSponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan, don’t wait until the fall to build your support system.HeyTutor provides high-dosage tutoring in Math and ELA—handling recruitment, training, and management—so your team can focus on impact.Learn more at HeyTutor.comLet’s ConnectIf you’re working to move from planning to execution—and want to ensure your team stays aligned and focused throughout the year—Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.
- 3 weeks ago33 min
Episode 276: The Leadership TAP with Dr. Joy Karavedas
In this episode, Darrin sits down with Dr. Joy Karavedas to explore what it really means to develop leaders intentionally—and why that “tap on the shoulder” can be life-changing.Joy shares her journey into leadership and how her research revealed a powerful pattern: nearly every leader can point to a moment when someone saw their potential before they did.The conversation dives into:The importance of intentionally building a leadership pipelineWhy performance alone isn’t enough to identify future leadersThe reality of the “messy middle” and how leaders grow through itThe role of reflection in leadership development—and why most leaders skip itHow to give emerging leaders space to practice, fail, and growJoy also introduces her TAP framework:Trust – The foundation of leadership that must be earned dailyAuthenticity – Knowing who you are as a leader and showing up with confidencePerformance – The skills and execution that can be developed over timeOne of the biggest takeaways?A pat on the back might feel good—but a tap on the shoulder can change someone’s life.This episode is a powerful reminder that leadership development isn’t accidental—it’s intentional.Connect with Dr. Karavedas - https://drkaravedas.com/Sponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan, don’t wait until the fall to build your support system.HeyTutor provides high-dosage tutoring in Math and ELA—handling recruitment, training, and management—so your team can focus on impact.Learn more at HeyTutor.comLet’s ConnectIf you’re working to move from planning to execution—and want to ensure your team stays aligned and focused throughout the year—Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.
- May 3, 202631 min
Episode 275: From Compliance to Connection — Rethinking Classroom Engagement with Megan Diede
In this episode, Darrin sits down with Megan Diede to unpack one of the most pressing challenges in schools today: authentic student engagement.The conversation begins with a familiar frustration—classrooms full of students disengaged on devices—and quickly reframes the issue. It’s not about abandoning technology. It’s about being intentional and purposeful with instruction.Megan introduces a powerful shift in thinking:Engagement isn’t about activity—it’s about connection.Together, they explore what it means to move beyond compliance-driven teaching and into classrooms where students are actively connected to their learning.Key Takeaways:Why the “paper vs. tech” debate misses the pointThe real issue isn’t the tool—it’s how it’s used.Connection over complianceMegan defines connection as the intentional bridge between people and purpose—and explains how it transforms instruction.What engagement actually looks likeIt’s not always loud or busy. Sometimes it’s quiet, focused, and deeply meaningful.The role of leadership in creating risk-safe environmentsTeachers need permission—and support—to try, fail, and refine their instruction.Small instructional shifts that create big impactEngagement doesn’t require a complete overhaul—just intentional adjustments.The power of team connection (the “coconut story”)A simple moment of problem-solving revealed how connection fuels collaboration and reduces stress.How leaders and instructional coaches can support teachersThrough clarity, alignment, modeling, and ongoing—not one-time—support.Connect with Megan DiedeWebsite: https://www.integratedk12.comInstagram: https://www.instagram.com/megandiedeLinkedIn: https://www.linkedin.com/in/megandiedeFacebook: https://www.facebook.com/integratedk12Sponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan, don’t wait until the fall to build your support system.HeyTutor provides high-dosage tutoring in Math and ELA—handling recruitment, training, and management—so your team can focus on impact.Learn more at HeyTutor.com🎯 Let’s ConnectIf you’re working to move from planning to execution—and want to ensure your team stays aligned and focused throughout the year—Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.
- Apr 26, 202620 min
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 deeplyOthers:Struggled to see the fitDefaulted to old routinesOr simply didn’t follow throughSame expectations. Very different outcomes.4 Leadership Moves That Change Everything1. Make the Work VisibleIf the work matters, it must be seen.Without visibility, implementation becomes optional.2. Build Ongoing SupportTraining starts the work—it doesn’t sustain it.Coaching and follow-up are essential.3. Systematize FeedbackDon’t leave support up to initiative.Build regular check-ins and feedback loops into the system.4. Hold Leaders AccountableAlignment doesn’t happen by accident.It happens when leaders consistently lead the work.The Big LessonYour plan doesn’t fail because people didn’t understand it.It fails when you haven’t built the conditions for it to live throughout the year.Series RecapEpisode 270: Don’t wait until August—you’re already behindEpisode 271: Do the work now to prepare for successSponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan, don’t wait until the fall to build your support system.HeyTutor provides high-dosage tutoring in Math and ELA—handling recruitment, training, and management—so your team can focus on impact.Learn more at HeyTutor.com🎯 Let’s ConnectIf you’re working to move from planning to execution—and want to ensure your team stays aligned and focused throughout the year—Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.
- Apr 19, 202639 min
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 balconyFinal ThoughtThe best plans aren’t built on ambition alone.They’re built on:focus, intentional action, and consistent follow-throughAnd most importantly…They’re built with people—not just for them.Learn more about DigiCoach hereSponsor SpotlightThis episode is sponsored by HeyTutor.If improving student outcomes is part of your plan for next year, don’t wait until the fall to build your support systems.HeyTutor provides high-dosage tutoring in Math and ELA—both in-person and online—while handling recruitment, training, and management of tutors.Learn more at HeyTutor.comLet’s ConnectIf you’re working to turn your plan into real, actionable steps between now and August, Darrin can help.Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and momentum.
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About Leaning into Leadership
We all want to see successes in both our personal and professional lives. Often, that requires strong leadership. In a time when leadership can be more challenging than ever, this podcast is dedicated to cultivating leaders by elevating the voices of leaders and promoting positivity. Join Dr. Darrin Peppard, lifelong educator and best-selling author, for this mixed platform podcast (some solo, some guest interview) for inspiration and insight, and some great leadership stories from those are living it, excelling at it, and celebrating it. Together, let's lean into leadership.
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