Leaning into Leadership

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.

• Why many servant leaders become trapped in the Cycle of Chaos
• The difference between creating dependence and creating capacity
• How coaching conversations create lasting leadership growth
• Why systems and intentionality matter more than constant problem-solving
• The leadership question that can transform every meeting and conversation
• A new philosophy that connects coaching, ALIGN, leadership teams, and intentional leadership

• Great 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.

If 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.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

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.

• Why every school leader needs a trusted "work bestie"
• How preparation reduces anxiety before difficult conversations
• The planning process that leads to more effective communication
• Common mistakes leaders make during challenging meetings
• Strategies for working with frustrated parents and caregivers
• Why attacking the problem—not the person—is essential
• How to respond when someone asks, "Do you have a minute?"
• Practical ways to protect your calendar and prioritize instructional leadership
• Why saying "no" is sometimes the best leadership decision
• How intentional time management creates better leaders and healthier lives

Visit 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=LQQJ4d

Instagram https://www.instagram.com/connectingthroughconversation/

Linked In Erika Bare https://linkedin.com/in/erika-bare-6a72a6215

Linkedin Tiffany Burns https://linkedin.com/in/tiffany-burns-90a50a274

LinkedinCTC https://www.linkedin.com/company/connecting-through-conversation/

Twitter https://twitter.com/CTCPlaybook.com

Youtube https://www.youtube.com/@CTCPlaybook

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

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 belonging
• How kindness is a leadership strategy—not a weakness
• The connection between stress, burnout, and human connection
• The story behind Be the Light and its journey from darkness to hope
• The powerful "Light Manifesto" and what it means to choose kindness every day
• A memorable classroom story that illustrates the importance of perspective and self-compassion
• Three practical strategies you can implement immediately:
• The six-second pause
• Gratitude as a daily leadership practice
• Self-affirmation and the power of positive identity

Throughout 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.

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.

Dr. 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.

"Kindness is not one more thing. It is the thing that changes everything."

🌐 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

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.

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.

LinkedIn: 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

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.

• 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

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.

• 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

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.

• 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

• 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.

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

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.

• 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

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.

• Blog: 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

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.

Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.

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/

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

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.

Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.

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:

Together, they explore what it means to move beyond compliance-driven teaching and into classrooms where students are actively connected to their learning.

• Why the “paper vs. tech” debate misses the point
• The real issue isn’t the tool—it’s how it’s used.
• Connection over compliance
• Megan defines connection as the intentional bridge between people and purpose—and explains how it transforms instruction.
• What engagement actually looks like
• It’s not always loud or busy. Sometimes it’s quiet, focused, and deeply meaningful.
• The role of leadership in creating risk-safe environments
• Teachers need permission—and support—to try, fail, and refine their instruction.
• Small instructional shifts that create big impact
• Engagement 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 teachers
• Through clarity, alignment, modeling, and ongoing—not one-time—support.

• Website: https://www.integratedk12.com
• Instagram: https://www.instagram.com/megandiede
• LinkedIn: https://www.linkedin.com/in/megandiede
• Facebook: https://www.facebook.com/integratedk12

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

🎯 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.

Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.

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.

You 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.

Some educators:

• Collaborated and sought feedback
• Opened their classrooms
• Engaged students deeply

Others:

• Struggled to see the fit
• Defaulted to old routines
• Or simply didn’t follow through

Same expectations. Very different outcomes.

1. 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.

Your 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.

• Episode 270: Don’t wait until August—you’re already behind
• Episode 271: Do the work now to prepare for success

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

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.

Through coaching, leadership retreats, and team development, he supports leaders in building clarity, alignment, and lasting impact.