Leaning into Leadership

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.In this episode, we explore:Why “hidden work” is the difference-maker when no one is watchingThe four performance pitfalls that derail people at every level:BlameExcusesSelf-deceptionGiving upThe flips that top performers lean into instead:OwnershipSolutionsTruthGritA Shark Tank green-room story with Barbara Corcoran that perfectly frames ownership vs. blameWhy feedback is the raw material for performance—and how self-deception blocks growthWeston’s take on “growability” and why self-awareness matters more than skill levelHow Weston is leaning into leadership right now: staying a learner, and learning from great leaders in every spaceKey takeawayWhen 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.Connect with WestonFind 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 SponsorsThis 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=RTAThis 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.In this episode, you’ll hear about:Why feeling busy doesn’t always mean you’re being effectiveHow constant reactivity increases cognitive load and erodes clarityThe five stages of the Cycle of Chaos:Constant ReactivityHigh Cognitive LoadAbsence of ClarityOverextensionSurvival Mode LeadershipWhy leaders stay stuck in the cycle—and why it’s not a failureHow clarity becomes the starting point for real changeThis conversation is a reminder that leaders don’t need to work harder—they need to lead clearer.SponsorsThis 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.In this episode, you’ll hear about:Why “tutoring” means very different things — and what defines high-impact tutoringThe biggest barriers schools face when implementing interventionsHow districts can address the human capital challenge without adding strain to teachersCreative push-in and pull-out models that work in middle and high schoolsWhy relationships and student champions matter as much as curriculumHow tutoring can become a pipeline for future educatorsWhat it means to lead with purpose, trust, and whole-person leadershipJennifer also shares a powerful personal story that shapes her leadership philosophy — reminding us that great leadership is ultimately about people, belief, and opportunity.Learn more:HeyTutor: https://www.heytutor.comContact Jennifer directly: [email protected] 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.In this episode, you’ll hear:Why the best time to prevent angry parent blowups is before anything goes wrongHow leaders build “relationship capital” through proactive, positive contactWhy it matters to separate the student from the behavior (and how that changes everything)The value of student-written statements for clarity, due process, and aligned factsHow to make the parent call in a way that reduces defensiveness and keeps everyone groundedWhat to do when a parent escalates—and why listening is your strongest toolA powerful reminder: parents don’t always react to what happened—they react to feeling disrespectedThe bottom-line takeaway: It’s not about you—and remembering that makes it easier to listenKey takeawayWhen 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:What it really means to be a “Hope Dealer”Why leaders shouldn’t try to be the source of hope for othersLessons from Mark’s transition into the principalshipEmpowering others by asking for input — even when you don’t need itModeling leadership through presence, attitude, and behaviorWhy self-care is a leadership responsibility, not a luxuryConnect with Dr. Mark Brown:Instagram: @heymarkbrownWebsite: www.markbrownedu.comBook: Hope Dealer: Leaning In to Lift OthersThis 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.