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.