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: jennifer@heytutor.com

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.

As 2025 comes to a close, Dr. Darrin Peppard reflects on the year that was and what the work of leadership is asking of us as we head into 2026. In this year-end solo episode, Darrin invites both individual leaders and leadership teams to pause, reflect, and resist the urge to rush into the new year without clarity.

Drawing from his work with leadership teams across the country, Darrin shares the key trends he’s seeing shape leadership in the year ahead—including the growing need for clarity, the non-negotiable role of culture, and the shift from compliance-driven leadership to coaching-focused practice.

Darrin also reflects on his personal one-word theme for 2025 (Evolve) and looks ahead to 2026 with a renewed commitment to leading fiercely—with clear priorities, strong boundaries, and intentional focus. This episode is designed to be listened to individually or together as a leadership team, offering space for reflection, alignment, and forward momentum.

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)

1. Why pausing to reflect matters before stepping into the new year
2. The leadership trends shaping 2026
3. The importance of clarity for leaders and leadership teams
4. Why culture must remain a top priority
5. The shift from compliance to coaching in effective leadership
6. One-word reflection: Evolve (2025) and Fierce (2026)

To stay connected and receive reflective leadership insights in 2026, visit roadtoawesome.net and sign up for the newsletter. Go to darrinpeppard.com to learn more about Darrin's speaking, leadership workshops, and retreats.

If you found this episode valuable, please subscribe to the podcast, leave a rating or review, and share it with other leaders or leadership teams who may benefit from this conversation.

This episode is sponsored by DigiCoach. Make walkthroughs meaningful. Simplify your coaching culture. Visit digiCOACH.com and mention Darrin for special partner pricing.

In Episode 252 of Leaning Into Leadership, Darrin Peppard sits down with Scott Borba, superintendent–principal in California’s Central Valley and author of The Leader You’re Not. Together, they explore leadership identity, the cost of perfectionism, imposter syndrome, delegation, boundaries, and why sustainable leadership begins with self-awareness.

This is a candid, reflective conversation for leaders at any stage — especially those feeling the weight of trying to do it all.

1. Why early-career leaders often fall into the “superhero” trap
2. The unique challenges of serving as both superintendent and principal
3. How COVID forced many leaders to confront identity, confidence, and calling
4. The importance of trusted mentors and leadership networks
5. Why perfectionism quietly fuels burnout and imposter syndrome
6. How delegation and asking better questions build leadership capacity
7. The cost of saying “yes” — and why boundaries are not selfish
8. Why leaders must stop comparing themselves to “Facebook leadership”
9. The freedom that comes from knowing who you’re not as a leader
10. Why legacy matters most at home — where leaders are not replaceable

1. “Trying to be the perfect leader kept me from growing.”
2. “Every yes comes with a cost.”
3. “You’re not replaceable at home — and that matters.”
4. “Delegation isn’t weakness; it’s leadership.”

Scott Borba is a superintendent–principal serving a small, rural school district in California’s Central Valley. With over 20 years in school leadership, Scott is deeply committed to relational leadership, mentorship, and sustainability in the profession.

He is the author of The Leader You’re Not: Why It’s Just as Important as the Leader You Are, a reflective exploration of leadership identity, self-awareness, and letting go of unrealistic expectations. Scott also teaches in a university administrator preparation program and leads a countywide leadership network focused on connection, growth, and reducing burnout.

1. 📘 The Leader You’re Not by Scott Borba

This episode is sponsored by DigiCoach. Make walkthroughs meaningful. Simplify your coaching culture. Visit digiCOACH.com and mention Darrin for special partner pricing.

In this powerful and deeply personal conversation, Darrin sits down with longtime friend and colleague Dr. Danny Steele to explore what it truly means to lead with heart, clarity, and purpose. Danny reflects on his 31-year career in education, the mentors who shaped him, the mistakes that taught him, and the passion that continues to fuel his work supporting educators today.

Together, they dig into:

• Danny’s early leadership missteps and the moment he realized his job was to serve teachers first.
• The concept of “passion drift”—why educators lose their edge and how leaders can help them get it back.
• Why administrators must redefine their light bulb moments to sustain joy and impact.
• The insecurities that quietly derail leadership—and how vulnerability becomes the antidote.
• How to lead instructional improvement without being an expert in every subject area.
• Key ideas from Danny’s brand-new book, The Instructional Leader in You: 10 Strategies for Every School Leader, including why curiosity must come first and why leaders must prioritize learning over teaching.
• Practical, reflective questions every leader can ask themselves to grow in 2025 and beyond.

This episode is a masterclass in humility, clarity, and the power of leading from a place of authenticity. Whether you're a principal, assistant principal, district leader, or teacher-leader, this conversation will leave you challenged and inspired.

• Danny’s Website: SteeleThoughts.com
• Danny on Social Media: @SteeleThoughts
• Email Danny: danny@steelethoughts.com
• Get Danny’s New Book: The Instructional Leader in You