Leaning into Leadership

What do you do when a talented employee keeps making the same mistakes? How many conversations do you have before deciding it's time to move on?

In this solo episode of Leaning Into Leadership, Dr. Darrin Peppard challenges the idea that employee accountability should be synonymous with punishment. Instead, he explores how leaders can use clarity, intentionality, and consistent feedback to help struggling employees grow while maintaining high expectations.

Drawing from his experience as a school leader, Darrin shares the story of an enthusiastic, talented employee whose tendency to act before understanding the full picture repeatedly created problems for the team. Rather than giving up on that employee, Darrin continued coaching, reinforcing expectations, and intentionally recognizing improvement. Eventually, that employee became one of the strongest members of the team and went on to lead a team of their own.

The lesson? Holding someone accountable doesn't have to mean giving up on them.

In this episode, you'll discover:

• Why accountability should focus on development, not simply punishment or compliance.
• How to recognize the difference between an employee's potential and their current performance.
• Why repeating the same corrective conversation may not produce different results.
• How clarity and intentionality create the foundation for meaningful improvement.
• Why recognizing progress is just as important as addressing mistakes.
• How to balance compassion for an individual employee with responsibility to the entire team.
• When continued performance concerns may require more formal action.

Three questions to take to the balcony:

1. Have I been absolutely clear about what needs to change and what successful performance looks like?
2. Have I intentionally provided the support and follow-through that could help this employee improve?
3. Am I recognizing their growth, or am I only noticing their mistakes?

Great leadership isn't about ignoring poor performance or lowering expectations. It's about creating the conditions where people can do their best work while holding them responsible for meeting the standards that matter.

"Don't confuse holding someone accountable with giving up on them."

Curriculum Leadership Institute (CLI)

CLI helps school districts build clarity, consistency, and sustainable systems for curriculum leadership. Darrin has personally worked with CLI as both a principal and superintendent.

Visit https://cliweb.org to learn more. Mention the Leaning Into Leadership podcast to receive a 5% discount on your first year of services.

HeyTutor

HeyTutor partners with schools and districts to provide high-quality tutoring and academic support in English language arts and mathematics, helping students receive individualized instruction and achieve stronger learning outcomes.

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

Explore leadership speaking, coaching, workshops, and retreats at https://darrinpeppard.com.

Discover more resources, books, and leadership insights at https://roadtoawesome.net.

If this episode resonated with you, share it with another leader who might be navigating a difficult employee conversation. And don't forget to follow, rate, and review Leaning Into Leadership.

Keep building the next mile of your Road to Awesome!

When a parent sees your school’s number on their phone, what do they expect to hear?

That answer might tell you something important about the relationship you’ve built.

In episode 306 of Leaning Into Leadership, Dr. Ted Huff joins Darrin for a conversation about moving family engagement beyond fundraising and building partnerships grounded in trust, listening, and shared hopes for students.

Ted brings 31 years of experience as a teacher, assistant principal, and principal. He and Darrin first connected in Washington, D.C., in 2016 while representing their states as Principals of the Year. Ten years later, they reconnect to explore a leadership responsibility that can easily get buried beneath the daily demands of the job: intentionally building relationships with families.

From scheduling positive calls home to taking academic support into an apartment complex clubhouse, Ted shares practical examples of meeting families where they are. They also discuss how to approach difficult conversations, create a welcoming front office, and make family engagement part of a district’s long-term direction.

In this episode, we explore:

• Why parent organizations need a purpose beyond fundraising.
• How families’ own school experiences shape their expectations.
• Why positive calls home deserve a place on your calendar.
• Reaching families whose schedules make school involvement difficult.
• Starting conversations with a powerful question: “What are your hopes and dreams for your child?”
• Listening before moving into problem-solving mode.
• The role of office staff, bus drivers, and food service teams in building trust.
• Turning family engagement into an intentional district priority.

A question to take back to your team:

If a family only hears from us when something goes wrong, what can we change this week?

Connect with Dr. Ted Huff

Website: Leading with Parents

Email: [email protected]

LinkedIn: Search “Leading with Parents”

Thank you to our sponsors

HeyTutor — In-person, high-dosage tutoring for K–12 schools and districts, with recruiting, hiring, training, and supervision handled by HeyTutor.

Curriculum Leadership Institute — A partner in aligning curriculum, instruction, and assessment across your district. Mention Leaning Into Leadership to receive 5% off your first year of partnership.

Share this episode with a leader who could use a clear place to begin, and remember to rate, review, and subscribe.

You know the work matters. You want to get into classrooms, address that difficult conversation, or revisit the priorities your team identified back in August. So what keeps getting in the way of beginning?

In this special midweek episode of Leaning Into Leadership, Darrin Peppard shares a conversation with a principal during a coaching visit in Omaha, Nebraska. One observation—“It’s the start that stops most people”—becomes a challenge to examine the leadership work we keep putting off.

The Cycle of Chaos gives leaders plenty of obvious starting points: answer the phone, respond to the parent, handle the hallway issue. But the work connected to your purpose often requires you to create the starting point yourself. Darrin explores how clarity and intentionality help turn that intention into action.

Three moves to help you begin:

• Name the thing you’re putting off. Get specific about the work and identify what makes it difficult to start.
• Make the first action clear and manageable. Choose one useful action that fits into your day and moves the work forward.
• Give the start somewhere to lead. Plan your next step, reflect on what you learn, and build follow-through into your leadership practice.

Using classroom visits as a practical example, Darrin also discusses how roles, coverage, and shared expectations can create the conditions that help an administrative team follow through.

Your midweek challenge: Finish this sentence: “Tomorrow, at this time, I will take this first action.” Put it on your calendar, ask for the support you need, and decide when you’ll return to the work.

“You can take the work seriously without making the first step enormous.”

Thank you to our sponsors:

HeyTutor — In-person, high-dosage tutoring for K–12 schools and districts, with recruiting, hiring, training, and supervision handled by HeyTutor.

Curriculum Leadership Institute — A partner in aligning curriculum, instruction, and assessment across your district. Mention Leaning Into Leadership to receive 5% off your first year of partnership.

Share this episode with a leader who could use a clear place to begin, and remember to rate, review, and subscribe.

Being busy can feel like progress. Having answers can feel like confidence. Keeping your door open can feel like good leadership. But when was the last time you stopped to question whether those habits are helping you lead?

Dr. Christopher Jones returns to Leaning Into Leadership after first joining the show in episode 42. A veteran high school principal, Chris brings honest stories and practical ideas from his new book, The Leadership Riddle: A Leader’s Guide to Growing Without Losing Yourself.

Together, Darrin and Chris explore the stages of leadership development through an unexpected lens: the riddle of the Sphinx. From crawling through the unfamiliar challenges of a new role to finding your stride and supporting the leaders coming behind you, each stage requires reflection, humility, and a willingness to keep learning.

Chris also challenges the belief that effective leaders must always have an open door. He shares why protecting time to think is essential to serving your school well—and how to help your team understand the purpose behind that boundary.

The conversation turns personal as Chris recounts receiving an anonymous, hurtful card when leaving a school. His experience opens a discussion about responding to criticism, recognizing patterns in feedback, and asking what you might need to learn before allowing defensiveness to take over.

In this episode, we discuss:

• Adapting to a changing environment while holding on to your core values.
• Why leaders cannot skip the uncomfortable stages of learning.
• The danger of mistaking momentum for continued progress.
• Helping new administrators feel safe admitting what they don’t know.
• Protecting thinking time and communicating that boundary with your staff.
• Considering the source, frequency, and substance of criticism.
• How mentoring other leaders prompts you to reexamine your own practices.
• Building a legacy through the support you give and the support you accept.

Whether you’re stepping into your first leadership role or have spent years in the principal’s office, this conversation offers an invitation to examine your habits and keep growing with intention.

Connect with Dr. Christopher Jones

Find Chris on Instagram at @drcsjones and explore his new book, The Leadership Riddle: A Leader’s Guide to Growing Without Losing Yourself. Revisit episode 42 for his first appearance on Leaning Into Leadership.

Big Thanks to Our sponsors

Curriculum Leadership Institute (CLI) partners with districts to develop an integrated curriculum system tailored to their needs, bringing clarity to teaching and learning and supporting the work through implementation. Mention Leaning Into Leadership for a 5% discount on your first year. Check them out at cliweb.org

HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers. Learn more at HeyTutor.com.

What does it mean to face life's most difficult storms rather than run from them? And how do the challenges we experience personally shape the way we show up as leaders?

In this powerful and deeply personal episode of Leaning Into Leadership, Darrin sits down with longtime friend, fellow University of Wyoming doctoral graduate, and retired high school principal Craig Woodall, author of Overcome.

Craig spent 30 years in public education, including his final 12 years as principal of Rocky Mountain High School in Colorado. But his story extends far beyond the hallways of a school. On September 11, 2001, Craig lost his brother in the attacks on the World Trade Center. That unimaginable loss, followed by the deaths of his parents and years of navigating grief, fundamentally changed his understanding of himself, his purpose, and his leadership.

In this conversation, Craig shares how he learned to stop avoiding grief and begin building the capacity to carry it. He talks about the daily habits that helped him rediscover purpose, the importance of taking care of ourselves while caring for others, and why some of the most powerful leadership lessons come from our most difficult experiences.

Darrin and Craig also explore the difference between two kinds of leaders: the "Here I Am" leader who enters a room focused on themselves, and the "There You Are" leader who enters looking for opportunities to connect, support, and serve others.

The conversation takes another powerful turn as Craig shares the buffalo analogy that helped shape his philosophy of overcoming adversity. Rather than running from an approaching storm, buffalo turn toward it and face it together. It's a lesson Craig carried into his leadership during the COVID-19 pandemic, when a strong school culture, consistent communication, and a shared sense of purpose helped his staff navigate extraordinary uncertainty.

Craig also reflects on two unforgettable stories from Overcome: his visits to Guantanamo Bay to observe proceedings related to the September 11 attacks, and the final phone conversation he shared with his brother just days before the tragedy.

This is an episode about grief, certainly. But more than that, it's about hope, resilience, relationships, and the extraordinary capacity we have to grow through the challenges life puts in front of us.

In this episode, you'll hear about:

• How Craig's personal journey of loss and grief became the foundation for his book, Overcome
• Why rediscovering your purpose matters when life and leadership become overwhelming
• The difference between "Here I Am" and "There You Are" leadership
• How small, intentional daily habits can help us build resilience
• Why taking care of yourself is essential to taking care of others
• What the buffalo can teach us about facing adversity together
• How a strong school culture helped Craig lead through the uncertainty of COVID-19
• The deeply personal experiences that brought Craig face-to-face with the events of September 11
• Why Craig's next chapter is focused on helping others find hope and overcome their own challenges

A leadership takeaway

Every person we lead is carrying something. We may not know what it is, and we may never fully understand its weight. But when we shift our attention from making our presence known to recognizing the needs of those around us, we create the conditions for connection, trust, and stronger leadership.

The goal isn't to avoid every storm. It's to build the capacity, relationships, and courage to face those storms together.

Connect with Craig Woodall

Visit CraigWoodall.com to learn more about Craig, explore his book Overcome, watch his TED Talk, and connect with him about speaking, coaching, and leadership.

Connect with Darrin

Learn more about leadership coaching, speaking, and the Road to Awesome at DarrinPeppard.com.

Episode sponsors

HeyTutor: Supporting schools and districts with high-impact, in-person tutoring in literacy and math. Learn more at HeyTutor.com.

Curriculum Leadership Institute (CLI): Helping districts create aligned, sustainable curriculum systems through collaborative, relationship-based partnerships. Learn more at cliweb.org

What happens when the person everyone turns to needs someone to turn to?

October is National Principals Month, and Dr. Darrin Peppard is sharing one of his most personal leadership stories yet.

During his years as a high school principal, Darrin once drove to the top of a mountain for one simple reason: he needed somewhere he could scream. It was a moment that reflected the emotional weight of leading a school, carrying confidential information, navigating difficult decisions, and supporting an entire school community.

In this special solo episode of Leaning Into Leadership, Darrin explores the invisible backpack every principal carries and the important leadership work that often goes unnoticed.

Drawing from his experiences as a principal, superintendent, and leadership coach, he shares three examples of the unseen work that makes an extraordinary difference: the conversations nobody hears, the decisions nobody understands, and the moments nobody remembers.

But this episode isn't simply about the challenges of principalship. It's a celebration of the relationships, collective purpose, and privilege that make the work so meaningful.

In this episode:

• The personal story behind Darrin's trip to the top of a mountain.
• The invisible backpack principals carry and why even the strongest leaders need support.
• Three important acts of leadership that rarely receive recognition.
• Why relationships remain one of the greatest rewards of school leadership.
• A challenge for superintendents to support the people who lead their schools.
• Two meaningful ways to celebrate National Principals Month.

A question worth considering:

Who helps the person everybody else comes to for help?

Whether you're currently serving as a principal, supporting school leaders, or remembering a principal who made a difference in your life, this episode is a reminder that some of the most important leadership work happens when nobody is watching.

During National Principals Month, take a moment to recognize someone whose leadership has made a difference. Be specific. Tell them about the conversation, decision, or moment that mattered.

They might have no idea you still remember.

This Episode Is Sponsored by Curriculum Leadership Institute and by HeyTutor

We're excited to welcome Curriculum Leadership Institute (CLI) as our newest sponsor!

Darrin has personally worked with CLI twice during his educational leadership career, first as a principal and again as a superintendent. CLI partners with districts to build sustainable curriculum systems, strengthen alignment, and provide teachers with the clarity they need to succeed.

New districts can receive a 5% discount on their first year of service by mentioning Leaning Into Leadership.

Learn more at https://cliweb.org or email [email protected].

HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, helping students receive targeted academic support.

Learn more at https://heytutor.com.

Keep leaning into leadership, keep making a difference, and have a Road to Awesome week!

What separates a group of talented people from a truly great team?

In Episode 301 of Leaning Into Leadership, Darrin sits down with executive coach and global educator Gaby Jordan to explore what it takes to build what she calls champion teams—teams grounded in connection, honesty, trust, and a shared commitment to something bigger than themselves.

Gaby brings a unique perspective to leadership. After practicing law for 15 years in Midtown Manhattan, she transitioned into business, executive coaching, and eventually education. Today, her work spans corporate organizations and educational settings from K–12 schools to universities. Across all of those environments, she has discovered one important constant: leadership is always human work.

Darrin and Gaby dig into why relationships matter so much to team performance. High-performing teams don't have to be made up of best friends, but people do need to know one another, understand one another, and be willing to have honest conversations. Gaby shares how learning someone's origin story—and even acknowledging our own vulnerabilities and imperfections—can completely change the way a team works together.

They also explore one of the biggest threats to healthy teams: the stories we create in our own heads. Darrin shares a story from his school leadership days about a colleague whose "thinking face" he initially interpreted as frustration or disagreement. That simple misunderstanding becomes a powerful example of how easily assumptions can turn into narratives—and how those narratives can quietly damage relationships.

Gaby introduces the idea of Champion Conversations, intentional conversations designed to help people address unresolved issues rather than carrying old transgressions forward. She explains why teams sometimes need to clear the air before they can create a meaningful vision for the future.

The conversation also explores agency, vulnerability, silos, honesty, and why leaders can't simply pile a new strategy on top of unresolved team dysfunction. As Gaby puts it, you can't create a compelling future "on top of the muck."

If you lead a school, district, organization, department, or leadership team, this episode is an important reminder: the strength of your strategy will always be limited by the strength of the people trying to execute it together.

In this episode:

• Why leadership and teamwork are fundamentally human work
• What Gaby means by a "champion team"
• Why connection can improve team performance
• The danger of operating in silos
• How assumptions and made-up narratives damage relationships
• Why vulnerability matters on leadership teams
• How Champion Conversations help teams clear old baggage
• Helping people recognize their agency instead of operating from victimhood
• Why honesty is essential to solving the right problems
• Creating a shared vision after rebuilding connection and trust
• What Gaby is doing right now to lean into leadership

Connect with Gaby Jordan

Learn more about Gaby's education work through Human Better EDU. You can also find Gaby on LinkedIn and Instagram and learn more about her corporate leadership work through Source Elements Group.

This Episode Is Sponsored by HeyTutor

HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers.

Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com

Three hundred episodes.

For this milestone edition of Leaning Into Leadership, I wanted to do something different. Instead of looking back by myself, I invited six incredible leaders—and people who have become an important part of my own journey—to join me for a conversation about leadership, growth, relationships, and the people who help us become better versions of ourselves.

Joining me for Episode 300 are Jason Ryan, Katie Kinder, Todd Bloomer, Bentli Lewis, Josh Tovar, and Brandon Beck. Every one of them has appeared on the podcast before. More importantly, every one of them has challenged me, encouraged me, taught me something, and sharpened the iron along the way.

We start with a simple question: What are you learning about yourself as a leader right now?

That opens the door to a powerful conversation about moving from solving problems to developing people, learning to lead through influence, building leadership capacity in others, staying close to the work, adapting when circumstances change, and recognizing that leadership is always a long game.

We also dig into how leaders continue to sharpen the iron. The answers range from surrounding yourself with people who challenge your thinking and intentionally building your network, to reading, listening, taking care of yourself, prioritizing family, staying curious, seeking feedback, and remaining humble enough to recognize that what worked yesterday may not work tomorrow.

Then we turn the tables and look back at Leaning Into Leadership itself. Each guest shares an episode or conversation that has stayed with them—and hearing what they chose reminded me why I started this podcast in the first place.

What began as an opportunity to grow a platform has become something much more meaningful: a place for me to learn alongside some remarkable people.

We close with a lightning round built around three questions every leader should consider:

• What advice would you give someone beginning their leadership journey?
• How are you leaning into leadership right now?
• Who was the person who tapped you on the shoulder and helped you see something in yourself?

That final question may be the most important one of the entire episode.

Leadership rarely happens alone. Somewhere along the way, someone sees something in us. They encourage us. Challenge us. Open a door. Invite us to the table. Sometimes they see our potential before we do.

Episode 300 is a celebration, but it is also a reminder of what leadership is really about: people, relationships, growth, and creating opportunities for others to become more than they thought possible.

To every guest who has joined me over these first 300 episodes and every listener who has spent part of their week with Leaning Into Leadership—thank you.

300 down. We’ve got way more than 300 to go.

This Episode Is Sponsored by HeyTutor

HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers.

Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com

What if flourishing at work didn't require a massive life overhaul?

In this episode of Leaning Into Leadership, Darrin welcomes back speaker, educator, and soon-to-be author Phil Januszewski for a high-energy conversation about happiness, relationships, and the small choices that can make demanding work more sustainable.

After 20 years in the classroom, Phil stepped away from teaching to speak full time — or, as he puts it, he “quit my job to help other teachers not quit theirs.” His work now takes him across the country helping educators and other service-oriented professionals feel less tired and more inspired. His upcoming book, Too Damn Happy, draws from his own experiences along with positive psychology to explore practical ways people can flourish even in challenging, high-pressure environments.

Darrin and Phil dig into the idea of “building in the good stuff.” Instead of waiting until after work or the weekend to do the things that fill us up, Phil challenges us to intentionally put small moments of joy into the workday itself. A song. A quick walk outside. A two-minute conversation with someone you care about. These aren't dramatic changes; they're small deposits that can make the work more sustainable.

They also explore what happens when we give away our natural gifts. Those gifts aren't necessarily talents you can put on a résumé. They might be humor, listening, cooking, creativity, energy, calm, or simply being willing to admit when you don't know something. When we bring more of ourselves into our work and share those gifts with others, we create opportunities for connection — and give others permission to do the same.

That leads Darrin and Phil into an important conversation about relationships. We spend a lot of time talking about educators getting to know their students, but relationships are a two-way street. When adults appropriately allow others to see who they really are, they can open the door for trust, vulnerability, and genuine human connection. And students are also watching how the adults around them interact with one another.

Phil closes by sharing how he's leaning into leadership right now: giving his gifts and connecting great people with other great people. For him, leadership isn't simply about doing his own work well. It's about helping other people thrive too.

In this episode:

• Why Phil left the classroom after 20 years
• The story behind Too Damn Happy
• Why happiness doesn't require ignoring the difficult parts of our work
• How to “build in the good stuff” throughout your day
• Why tiny shifts can make demanding work more sustainable
• Identifying and giving away your natural gifts
• How vulnerability opens the door to stronger relationships
• Why students notice the relationships adults model
• The difference between performative positivity and genuine flourishing
• How giving and connecting others can become an act of leadership

This Episode Is Sponsored by HeyTutor

HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers.

Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com

What if resistance isn’t something leaders need to overcome?

In Episode 298 of the Leaning Into Leadership Podcast, Darrin sits down with Becca Silver, CEO and founder of The Whole Educator and author of The Resistance Solution, for a powerful conversation about what is really happening when educators push back against change.

Becca challenges leaders to stop labeling people as “resistant” and instead recognize that resistance is an experience people move through. Rather than relying on compliance, consequences, or generic advice like “build better relationships,” she introduces a human-centered approach that helps leaders understand the unmet needs underneath resistance.

Drawing from her own experience as a teacher who resisted change, an instructional coach who initially struggled to create change, and eventually a leadership coach who became highly effective at working with educators experiencing resistance, Becca shares the research behind her five Catalyst Mindsets.

Darrin and Becca explore:

• Why resistance is often the result of unmet needs rather than unwillingness or negativity
• The difference between a “resistant teacher” and a teacher experiencing resistance
• Why schools hire critical thinkers—and then sometimes expect them simply to comply
• The five Catalyst Mindsets: value, belonging, success, growth, and ownership
• Why generic strategies for dealing with resistance often miss the real problem
• The critical difference between compliance, buy-in, and true ownership
• Why agency is essential if leaders want people to own change
• How clarity around non-negotiables and professional judgment can immediately increase ownership
• Why leaders must explicitly tell people where they have permission to use their expertise
• How human-centered leadership can move change forward without going around people’s humanity

One of the most practical takeaways from the conversation is something leaders can implement immediately: be crystal clear about what is non-negotiable and where people have the agency to exercise their professional judgment.

When people understand where they have voice, choice, and the ability to make a meaningful impact, leadership can begin moving beyond compliance and toward genuine ownership.

Becca also shares how she is personally leaning into leadership through shared leadership—developing others to lead the work rather than building something that depends entirely on her.

Becca Silver is the CEO and founder of The Whole Educator and author of The Resistance Solution. Her work helps instructional coaches and educational leaders navigate resistance to change through a human-centered approach.

Learn more about Becca, The Resistance Solution, the Resistance Solution Community, her Book Study Facilitator Training, and the Coaching the Whole Educator podcast through The Whole Educator.

This Episode Is Sponsored by HeyTutor

HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers.

Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com