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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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- Today13 min
Episode 283: Leadership Is the Intentional Creation of Conditions
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
- 3 days ago42 min
Episode 282: The New School Leader's Playbook with Erika Bare & Tiffany Burns
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
- 1 weeks ago25 min
Episode 281: Be the Light with Dr. Chris Culver
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
- 2 weeks 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
- 3 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
- 4 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
- May 17, 202649 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.
- May 10, 202633 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.
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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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