Episode 275: From Compliance to Connection — Rethinking Classroom Engagement with Megan Diede

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” leadership * Why many leaders struggle to let go of their previous role * The dangers of over-relying on technical expertise * Succession development and building leadership pipelines * How AI is reshaping organizations and leadership expectations * The importance of organizational agility * Why leaders must communicate vision without pretending to have all the answers * “Sketch-based advocacy” and collaborative leadership * The role of empathy and emotional intelligence during uncertainty and change * Why leadership today is more about building teams than directing them Molly 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 ROSEN Molly 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 ROSEN LinkedIn: https://www.linkedin.com/in/mollyrosen/ [https://www.linkedin.com/in/mollyrosen/] Website: https://www.projectnextleadership.com/ [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 [https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA ]

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 barriers * Why people aren’t “uncoachable”—they’re often operating from protective patterns * The three common patterns that show up in resistant behavior: * Detaching * Surrendering * Overcompensating * How identity, values, and skill all influence leadership behavior * Why systems in education are built on underlying beliefs—and how those beliefs shape outcomes * The danger of compliance culture in schools * What it means to “burn the script” as a leader * How leaders can create environments where innovation and growth are possible ABOUT 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 [https://www.amazon.com/Burn-Script-Thinking-Transform-Practice/dp/B0GZZVYDQV/ref=tmm_pap_swatch_0?_encoding=UTF8&dib_tag=se&dib=eyJ2IjoiMSJ9.OV0mUdNI4qxolPa81DQIaUF9bl-5YwwjMPC4WaCdTPGBejWSjF8z0888JSuu6ktYnYT4P7Pzr7ZEsdOrCej2yx78dpjvfpnIPXPHX2rSBymlSLqlzxwDc2Bx1qqfOgwtXzzhZ9573-0BPlfpGAy00ncuIBMN9F_BKdMvc7N15msqs9q5fdKwrMcYlKUAPf2vsdR4cTKcknJnwG-aobvk10XykdNxrY9vq2fYAjRC3KI.li6rfa6R1IlEvByQpjl14uvqe9D5fl88QrWcyUGRCp4&qid=1779314267&sr=8-1], [https://www.amazon.com/Burn-Script-Thinking-Transform-Practice/dp/B0GZZVYDQV/ref=tmm_pap_swatch_0?_encoding=UTF8&dib_tag=se&dib=eyJ2IjoiMSJ9.OV0mUdNI4qxolPa81DQIaUF9bl-5YwwjMPC4WaCdTPGBejWSjF8z0888JSuu6ktYnYT4P7Pzr7ZEsdOrCej2yx78dpjvfpnIPXPHX2rSBymlSLqlzxwDc2Bx1qqfOgwtXzzhZ9573-0BPlfpGAy00ncuIBMN9F_BKdMvc7N15msqs9q5fdKwrMcYlKUAPf2vsdR4cTKcknJnwG-aobvk10XykdNxrY9vq2fYAjRC3KI.li6rfa6R1IlEvByQpjl14uvqe9D5fl88QrWcyUGRCp4&qid=1779314267&sr=8-1] where she introduces her framework for Disruptive Mindset Coaching. CONNECT WITH JO: * TikTok & Instagram: @educoachbyjo * Substack: jolein.substack.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 [https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA ]

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 leadership * John Maxwell’s “Law of the Lid” and how it impacts organizations * Why strong leaders often become quieter instead of combative * The emotional and cultural impact of low-trust leadership environments * How political behavior and silence slowly erode healthy culture * Why leadership alignment matters more than forced compliance * The importance of creating trust, contribution, and shared ownership * How leaders can still positively influence culture within their sphere KEY 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. SPONSOR 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 [https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA ]

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 [https://www.amazon.com/Five-Principles-Educator-Professionalism-Rebuilding/dp/B0D8YB5VSH/ref=sr_1_1?crid=1VH3IIZ04NGF8&dib=eyJ2IjoiMSJ9.0prqA89oMvSnzu65rP7rWw.cZEFG5sjOBZU8MqP7xGMhWE8UvHnNMycHaTR92WI38E&dib_tag=se&keywords=nason+lollar&qid=1778876207&sprefix=nason+lolla%2Caps%2C202&sr=8-1], 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 challenge * Defining professionalism as a contribution to school culture * The TRUST framework: * Teaching and learning first * Remain vigilant about safety * Understand communication * Seek personal balance * Take ownership of morale * The difference between negatives vs. negativity * Why listening is one of the most overlooked leadership skills * Moving beyond “gotcha” leadership toward genuine support * The power of acknowledgment in building staff morale KEY 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.com [https://nasonlollar.wordpress.com/] * X: @nasonlollar * Facebook: Nason Lollar, Author Sponsor Spotlight This 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 [https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA] Let’s Connect If 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 [https://darrinpeppard.com/]. Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.

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 pipeline * Why performance alone isn’t enough to identify future leaders * The reality of the “messy middle” and how leaders grow through it * The role of reflection in leadership development—and why most leaders skip it * How to give emerging leaders space to practice, fail, and grow Joy also introduces her TAP framework: * Trust – The foundation of leadership that must be earned daily * Authenticity – Knowing who you are as a leader and showing up with confidence * Performance – The skills and execution that can be developed over time One 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/ [https://drkaravedas.com/] Sponsor Spotlight This 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 [https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA ] Let’s Connect If 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 [https://darrinpeppard.com/]. Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.