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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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- 6 days ago19 min
Episode 307: Accountability Isn't Punishment - How Great Leaders Grow People
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:Have I been absolutely clear about what needs to change and what successful performance looks like?Have I intentionally provided the support and follow-through that could help this employee improve?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."Thank You to Our SponsorsCurriculum 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.HeyTutorHeyTutor 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=RTAConnect With DarrinExplore 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!
- 1 weeks ago33 min
Episode 306: When the School Calls, What Do Parents Expect? with Dr. Ted Huff
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 HuffWebsite: Leading with ParentsEmail: tedhuff@leadingwithparents.orgLinkedIn: Search “Leading with Parents”Thank you to our sponsorsHeyTutor — 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.
- 2 weeks ago17 min
Episode 305: It’s the Start That Stops Most People
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.
- 2 weeks ago39 min
Episode 304: The Leadership Riddle - Growing Without Losing Yourself with Dr. Christopher Jones
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 JonesFind 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 sponsorsCurriculum 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.orgHeyTutor 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.
- 3 weeks ago32 min
Episode 303: Facing the Storm - Leadership, Loss, and the Power to Overcome with Craig Woodall
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, OvercomeWhy rediscovering your purpose matters when life and leadership become overwhelmingThe difference between "Here I Am" and "There You Are" leadershipHow small, intentional daily habits can help us build resilienceWhy taking care of yourself is essential to taking care of othersWhat the buffalo can teach us about facing adversity togetherHow a strong school culture helped Craig lead through the uncertainty of COVID-19The deeply personal experiences that brought Craig face-to-face with the events of September 11Why Craig's next chapter is focused on helping others find hope and overcome their own challengesA leadership takeawayEvery 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 WoodallVisit 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 DarrinLearn more about leadership coaching, speaking, and the Road to Awesome at DarrinPeppard.com.Episode sponsorsHeyTutor: Supporting schools and districts with high-impact, in-person tutoring in literacy and math. Learn more at HeyTutor.com.Cu
- Oct 4, 202625 min
Episode 302: The Work Nobody Sees - A Thank You to School Principals
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 HeyTutorWe'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 info@cliweb.org.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!
- Sep 27, 202629 min
Episode 301: Building Champion Teams - Connection Before Performance with Gaby Jordan
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 workWhat Gaby means by a "champion team"Why connection can improve team performanceThe danger of operating in silosHow assumptions and made-up narratives damage relationshipsWhy vulnerability matters on leadership teamsHow Champion Conversations help teams clear old baggageHelping people recognize their agency instead of operating from victimhoodWhy honesty is essential to solving the right problemsCreating a shared vision after rebuilding connection and trustWhat Gaby is doing right now to lean into leadershipConnect with Gaby JordanLearn 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 HeyTutorHeyTutor 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
- Sep 23, 20261h 9m
Episode 300: Leadership Lessons From the People Who Helped Shape the Journey
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 HeyTutorHeyTutor 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
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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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