Leaning into Leadership

In Episode 262, we explored the hidden cost of distraction and how trust, psychological safety, and connection erode when leaders aren’t fully present. This is Part 2 of our three-part series on leadership presence.

In this episode, Darrin focuses on why distraction keeps happening — and how to intentionally break through the cycle of overwhelm.

Chaos isn’t loud.

It’s cumulative.

It’s the stacking of interruptions, back-to-back meetings, unresolved conversations, decision fatigue, and carrying problems that aren’t yours to carry. When leaders operate in survival mode, presence becomes nearly impossible.

In this episode, you’ll learn:

1. Why overwhelm — not incompetence — is the real issue
2. The difference between chaos being loud vs. cumulative
3. How to engineer margin into your leadership
4. The importance of calendar integrity
5. Why decision discipline protects your leadership capacity
6. How to clarify your Top Three priorities each week
7. How to use a simple 15-Minute Weekly Presence Audit

Plus, Darrin shares a free resource:

📥 The School Leaders Weekly Planner — a tool designed to help you schedule your priorities, build margin, and protect your presence. Download the free planner using the link here.

Reflection Question:

What on your calendar right now is stealing margin from the moments that matter most?

Find one thing. Change one thing. Break the chaos. Build the margin. Protect the moments.

Next up in Episode 264: The interpersonal work that makes leadership presence genuine and authentic.

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

This episode kicks off a powerful three-part series on leadership presence.

In Part 1, Darrin explores the hidden cost of distraction and how leaders unintentionally erode trust, psychological safety, and emotional connection when they are not fully present.

Through personal stories from his time as a high school principal, Darrin shares moments of realization when distraction cost him relational depth — and what those experiences taught him about culture and leadership.

In this episode, you’ll learn:

1. Why presence is not “soft” — it’s culture work
2. The three things that erode when leaders aren’t fully present
3. The difference between productivity and true leadership impact
4. Why leadership is about stabilizing people, not just solving problems
5. A simple 60-Second Reset you can use before your next important conversation

Reflection Question:

Where this week does someone need the fully present version of you?

This episode sets the foundation for Part 2, where we’ll explore how to intentionally create margin and break the patterns that keep leaders stuck in distraction.

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 https://www.digicoach.com/ and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing.

In Episode 261, I’m coming to you on location from Edmond, Oklahoma, where I had the opportunity to sit down with my friend Joe Beckman at the OASSP conference.

Joe has spent more than 20 years traveling the world with one simple mission: reclaim human connection.

And if we’re honest, that mission has never been more urgent. Loneliness is at an all-time high. Belonging and self-worth feel fragile. Technology is louder than conversation. So what does that mean for school leaders?

In this conversation, Joe challenges us to rethink where connection lives on our priority list. It’s not one more thing on the plate.

It is the plate.

We talk about:

1. Why connection must be the foundation of leadership
2. The powerful “Chinette plate” analogy and what it means for culture
3. How storytelling builds trust and opens students’ minds
4. Why vulnerability accelerates connection in classrooms
5. The Big Tobacco → Big Tech comparison and what leaders must understand
6. How adults must model healthy tech boundaries
7. Why conferences and networks matter in fighting leadership isolation
8. The courage required to lean into difficult conversations

Joe also shares how he is personally leaning into leadership right now by stepping into uncomfortable spaces and using his voice where it matters most.

If you care about culture…If you care about your people… If you care about leading well in a distracted world…

This episode is for you.

Connect with Joe: www.joebeckman.com

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 https://www.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

In this episode of Leaning Into Leadership, I’m joined by George Couros, one of the most influential voices in education around innovation, culture, and human-centered leadership.

George and I dig into his leadership journey — not from a place of “having it all figured out,” but from a place of learning out loud. We talk about how blogging helped him find his voice, not just share it, and why writing, reflection, and vulnerability matter more than ever for leaders.

We also explore the ideas behind George’s newest book, Forward Together: Moving Schools from Conflict to Community in Contentious Times, including:

1. Why trying to “win” arguments often pushes people further away
2. The reality that somebody hates you — and why that shouldn’t drive your leadership
3. The balance between comfort and challenge in professional learning (the “warm bath / cold shower”)
4. How leaders can move communities forward during polarized, emotionally charged times

We close with a powerful reflection on leadership and self-care, as George shares how prioritizing his health has changed not only how he leads — but how he models leadership for his own kids.

This is an honest, thoughtful, and deeply human conversation about what leadership really looks like right now.

You can learn more about George at his website

Grab his new book on Amazon

Here is the link to the blogpost I referenced in the show

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 https://www.digicoach.com/ and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing.

Ever left a leadership team meeting feeling like it was so productive—then realized a week later nothing really changed?

In this solo episode, Darrin unpacks why that gap between effort and impact is rarely about commitment—and almost always about clarity. Building on his “Cycle of Chaos” episode, he shares the ALIGN Framework, a practical system for strengthening team dynamics and keeping teams focused on what matters most.

1. Why strong teams drift into reactivity when clarity is missing
2. How alignment breaks the Cycle of Chaos—not just “working harder”
3. The ALIGN Framework for healthier team dynamics:
4. A — Agree on the Vision and Goals: Ensure everyone can name the top priorities in the same language
5. L — Language and Communication: Teams don’t just make decisions—they carry the message
6. I — Intentional Role Clarity: Clear ownership prevents duplication, avoidance, and frustration
7. G — Growth Through Cross-Training: Build continuity and empathy without eroding roles
8. N — Navigate with Intention: Protect focus, pause before adding initiatives, and stay anchored to priorities

1. If I asked each team member privately, would they name the same top three priorities?
2. Are we clear on what gets communicated, who communicates it, and how it’s framed?
3. Where might I be stepping in that’s keeping someone else from stepping up?
4. Are we moving the goal forward—or just filling the calendar?

If you’re thinking, “This sounds like my team, but we’re struggling to get there,” Darrin invites you to reach out for coaching, team support, or a leadership team alignment retreat designed to reset vision, roles, and priorities.

Connect with Darrin: darrinpeppard.com | roadtoawesome.net | @darrinmpeppard

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 https://www.digicoach.com/ and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing.

Weston Kieschnick has been in the work for a long time—as a classroom teacher, coach, author, and speaker—and this conversation feels like two colleagues reconnecting around what actually drives performance.

We dig into Weston’s newest work and the idea that the gap between high performers and underachievers usually isn’t talent. It’s behavior—especially in the moments when adversity hits.

1. Why “hidden work” is the difference-maker when no one is watching
2. The four performance pitfalls that derail people at every level:
3. Blame
4. Excuses
5. Self-deception
6. Giving up
7. The flips that top performers lean into instead:
8. Ownership
9. Solutions
10. Truth
11. Grit
12. A Shark Tank green-room story with Barbara Corcoran that perfectly frames ownership vs. blame
13. Why feedback is the raw material for performance—and how self-deception blocks growth
14. Weston’s take on “growability” and why self-awareness matters more than skill level
15. How Weston is leaning into leadership right now: staying a learner, and learning from great leaders in every space

When life gets hard, your default matters. You don’t rise to the level of your goals—you fall to the level of your patterns. This episode is a gut-check and a playbook.

Find Weston at WestonKieschnick.com and connect with him on social media to follow his work (and his “10-second truth” videos).

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: https://heytutor.com/?utm_source=RTA&utm_medium=RTA&utm_campaign=RTA

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 https://www.digicoach.com/ and tell them you heard about them here on the Leaning into Leadership podcast for special partner pricing.

Leadership doesn’t fall apart overnight. More often, it slowly drifts into a pattern that feels overwhelming, exhausting, and reactive.

In this solo episode, Darrin introduces The Cycle of Chaos—a framework that helps leaders name what they’re experiencing and begin interrupting the patterns that keep them stuck in survival mode.

Rather than offering quick fixes or productivity hacks, this episode invites reflection, clarity, and intentional leadership.

1. Why feeling busy doesn’t always mean you’re being effective
2. How constant reactivity increases cognitive load and erodes clarity
3. The five stages of the Cycle of Chaos:
4. Constant Reactivity
5. High Cognitive Load
6. Absence of Clarity
7. Overextension
8. Survival Mode Leadership
9. Why leaders stay stuck in the cycle—and why it’s not a failure
10. How clarity becomes the starting point for real change

This conversation is a reminder that leaders don’t need to work harder—they need to lead clearer.

This episode is brought to you by HeyTutor, delivering high-impact, research-based tutoring that supports students while reducing leadership overwhelm.

Additional support comes from DigiCoach, helping leaders capture real-time instructional data, provide meaningful feedback, and build clarity through strong systems.

School leaders everywhere are wrestling with the same challenge:

How do we support students who are behind — without overwhelming teachers or relying on systems that don’t deliver results?

In this episode of Leaning Into Leadership, Darrin Peppard sits down with Jennifer Sheffield, CEO of HeyTutor, for a grounded, practical conversation about what effective tutoring and intervention really look like in today’s schools.

Jennifer brings a unique leadership lens — blending her background in law, governance, and education — to help leaders rethink how tutoring fits into MTSS, Tier 2 and Tier 3 supports, and daily school operations.

1. Why “tutoring” means very different things — and what defines high-impact tutoring
2. The biggest barriers schools face when implementing interventions
3. How districts can address the human capital challenge without adding strain to teachers
4. Creative push-in and pull-out models that work in middle and high schools
5. Why relationships and student champions matter as much as curriculum
6. How tutoring can become a pipeline for future educators
7. What it means to lead with purpose, trust, and whole-person leadership

Jennifer also shares a powerful personal story that shapes her leadership philosophy — reminding us that great leadership is ultimately about people, belief, and opportunity.

1. HeyTutor: https://www.heytutor.com
2. Contact Jennifer directly: [email protected]

If you’re a school or district leader searching for intervention strategies that actually move the needle — this conversation will help you think differently.

Episode Sponsors:

This episode is sponsored by digiCOACH — an easy-to-use mobile platform that empowers school leaders to provide teachers with positive, actionable feedback tied to research-based instructional practices, with real-time data to support fidelity and instructional decision-making.

Learn more at digicoach.com (mention the show for special partner pricing)

This episode is also brought to you by HeyTutor - HeyTutor delivers customized, evidence-based, high-dosage Math and ELA tutoring to K–12 school districts nationwide. Their focus is on in-person tutoring, while also offering flexible online options — all tailored to meet diverse student needs and aligned with state standards.

Head over to HeyTutor.com to learn more - tell them you heard about them on the Leaning into Leadership podcast.

In this special shared episode, Darrin Peppard and Dr. Frederick Buskey—host of The Assistant Principal Podcast—tackle a challenge leaders are facing more and more often: angry, escalated parent interactions.

This conversation was sparked by a real question from the field—a leader Frederick supports reached out looking for guidance on how to handle parents when emotions are high. Together, Darrin and Frederick unpack a practical, grounded framework for what to do before, during, and after conflict shows up at your door.

1. Why the best time to prevent angry parent blowups is before anything goes wrong
2. How leaders build “relationship capital” through proactive, positive contact
3. Why it matters to separate the student from the behavior (and how that changes everything)
4. The value of student-written statements for clarity, due process, and aligned facts
5. How to make the parent call in a way that reduces defensiveness and keeps everyone grounded
6. What to do when a parent escalates—and why listening is your strongest tool
7. A powerful reminder: parents don’t always react to what happened—they react to feeling disrespected
8. The bottom-line takeaway: It’s not about you—and remembering that makes it easier to listen

When conflict rises, your job isn’t to “win” the conversation—it’s to protect dignity, stay calm, listen deeply, and build partnership forward.

Episode Sponsors:

This episode is brought to you by HeyTutor - HeyTutor delivers customized, evidence-based, high-dosage Math and ELA tutoring to K–12 school districts nationwide. Their focus is on in-person tutoring, while also offering flexible online options — all tailored to meet diverse student needs and aligned with state standards.

Head over to HeyTutor.com to learn more - tell them you heard about them on the Leaning into Leadership podcast.

This episode is also sponsored by digiCOACH — an easy-to-use mobile platform that empowers school leaders to provide teachers with positive, actionable feedback tied to research-based instructional practices, with real-time data to support fidelity and instructional decision-making.

Learn more at digicoach.com (mention the show for special partner pricing)

What does it mean to be a dealer in hope — not as the source of hope, but as someone who helps others discover it for themselves?

In this first episode of 2026, Darrin sits down with longtime friend and colleague Dr. Mark Brown for a powerful conversation about leadership, hope, and intentional presence. Mark shares the story behind his “Hope Dealer” philosophy, why hope is for everyone (not just those in crisis), and how leaders can create cultures where people feel seen, supported, and empowered.

As a first-year high school principal, Mark also reflects on the transition from assistant principal to principal, the importance of asking for help, and how modeling leadership behaviors matters more than any directive. The conversation closes with a reminder many leaders need to hear: taking care of yourself is not selfish — it’s essential.

In this episode, you’ll hear about:

1. What it really means to be a “Hope Dealer”
2. Why leaders shouldn’t try to be the source of hope for others
3. Lessons from Mark’s transition into the principalship
4. Empowering others by asking for input — even when you don’t need it
5. Modeling leadership through presence, attitude, and behavior
6. Why self-care is a leadership responsibility, not a luxury

Connect with Dr. Mark Brown:

1. Instagram: @heymarkbrown
2. Website: www.markbrownedu.com
3. Book: Hope Dealer: Leaning In to Lift Others

This episode is sponsored by digiCOACH — an easy-to-use mobile platform that empowers school leaders to provide teachers with positive, actionable feedback tied to research-based instructional practices, with real-time data to support fidelity and instructional decision-making.

Learn more at digicoach.com (mention the show for partner pricing)

This episode is also brought to you by HeyTutor - HeyTutor delivers customized, evidence-based, high-dosage Math and ELA tutoring to K–12 school districts nationwide. Their focus is on in-person tutoring, while also offering flexible online options — all tailored to meet diverse student needs and aligned with state standards.

Head over to HeyTutor.com to learn more - tell them you heard about them on the Leaning into Leadership podcast.