Episode 4: Break the Rules (On Purpose) — Leading Beyond the Rulebook

What if the rules you’ve been following aren’t actually serving your people anymore? In this episode, we dig into why the best leaders don’t blindly follow rules—they question them, challenge them, and replace them with values and expectations that build stronger schools.

We’ll look at how rules often start with good intentions but can quickly shift into tools of control that stifle culture. You’ll hear stories of innovators like Steve Jobs, Rita Pierson, Taylor Swift, and the founders of Airbnb—leaders who weren’t reckless, but intentional about breaking the rules to create something better.

From there, we’ll walk through powerful mindset shifts: moving from rules to quotes to live by, from control to shared expectations, from compliance to cultural norms, and from “no exceptions” to intentional, humane ones. Plus, we’ll share practical strategies like running a “rule audit” with students, using the “Why?” test, and challenging yourself to condense every school rule down to just three universal expectations.

By the end, you’ll be ready to trade rule management for culture building—and maybe even ask yourself: Which rules in my school don’t make sense anymore?

Because rules might belong in board games, but in leadership? They’re meant to be challenged.