Episode 250: Flipping the Mic - Lessons from 250 Episodes of Leaning Into Leadership

This episode is sponsored by DigiCoach

Make walkthroughs meaningful. Simplify your coaching culture. Visit digiCOACH.com and mention Darrin for special partner pricing.

For this milestone episode, the script gets flipped. Longtime friends and frequent guests Todd Bloomer and Dominic Armano take over the show and interview host Dr. Darrin Peppard about the lessons he’s learned from 250 episodes and a lifetime in school leadership.

They dig into leadership clarity, time management, burnout, support systems, and why relationships will always matter more than perfect paperwork. You’ll hear practical advice for current principals, assistant principals, and aspiring leaders who are wondering, “Am I in the right seat?” or “Am I ready for the next step?”

In this episode, we explore:

• Reaching 250 episodes
• What Darrin has learned from starting the podcast in 2022 and pushing past the “most podcasts die by episode 10” barrier.
• How consistency, clarity, and curiosity have shaped the show.
• Coaching, walkthroughs, and making feedback part of the job
• Why leaders must get crystal clear on what they care about and what they’re looking for in every classroom.
• How to shift from “gotcha” feedback to curious, growth-focused conversations with teachers.
• For principals who haven’t been in classrooms enough
• Using the Eisenhower Matrix to separate what’s truly important from what just feels urgent.
• A simple exercise with sticky notes to analyze where your time really went this semester.
• How to build systems and delegation so you can focus on instruction and culture.
• Support systems & avoiding burnout as a leader
• The critical role of a great secretary/admin assistant in protecting your time and priorities.
• Why every leader needs people outside their building—coaches, mentors, colleagues—to call when things get heavy.
• The power of a trusted circle at home and how podcasts can be “free PD” that keeps you growing.
• For assistant principals who are struggling or ready for more
• What to do when you’re coming home thinking, “Did I make a mistake?”
• Reflective questions Darrin uses with leaders:
• What have you learned about yourself as a leader?
• What’s actually going well (even if it doesn’t feel like it)?
• How to think about your trajectory if you’re ready for the next role.
• If Darrin could wave a magic wand…
• The one administrative task he’d eliminate: the bureaucracy of evaluation.
• What evaluation could look like if it was purely about coaching, growth, and support rather than compliance.
• Advice for new principals starting mid-year
• Why your first job isn’t to “fix” everything—it’s to build relationships and listen.
• How to learn the subculture of your new school community before making big moves.
• Seeing the rest of the year as your “learning runway” before truly leading in year one.
• The teacher Darrin would rather mentor
• Given the choice, why he’ll always choose the relationship-rich but disorganized teacher over the hyper-organized teacher who struggles to connect with kids.
• How systems can be taught, but genuine connection with students is much harder to create from scratch.
• How Darrin is leaning into leadership right now
• His commitment to finding every possible avenue to pour into leaders—whether or not they hold a formal title.
• Helping leaders find clarity, act with intention, and walk in their purpose.

For more visit darrinpeppard.com