In the past few weeks, I’ve watched strong, capable leaders work tirelessly to fix individual issues in their schools. The problem isn’t effort.The problem isn’t commitment.The problem isn’t even leadership skill. The problem is that many of these fixes never stop to ask a bigger question: What is this doing to the system as a […]
I’ve lost count of how many times I’ve walked out of a leadership team meeting feeling pretty good about the conversation—only to realize a week later that very little had actually changed. The meeting wasn’t bad. In fact, it felt productive. People were engaged. Notes were taken. Decisions were made. But then the week unfolded. […]
Over the years, I’ve noticed a leadership pattern that shows up far more often than most people are willing to admit. And the tricky part is this: it almost always comes from a good place. Just this week, I worked with a leader who genuinely cares about her people. She’s capable, hardworking, and deeply invested […]
There are few moments in leadership that linger quite like an angry parent conversation. The phone call you replay on the drive home.The meeting that tightens your chest before you even sit down.The email you reread three times, wondering how things escalated so quickly. This blog—and the podcast episode that sparked it—exists because these moments […]
I remember a conversation with a school leader not long ago that has stayed with me. It wasn’t dramatic.There was no crisis unfolding in real time. No angry phone call. No emergency meeting. Just a quiet pause. She leaned back in her chair, exhaled, and said,“I don’t even know why I’m so tired. I just […]
Each year, I spend time choosing one word to guide how I want to show up as a leader. Not a resolution.Not a checklist.A posture. As I looked ahead to 2026, one word kept surfacing for me—quietly at first, then with increasing clarity.If you listened to Leaning Into Leadership Episode 253, you heard me unpack […]
Over the course of 2025, I’ve spent a lot of time sitting at leadership team tables. Tables where the agenda is full and the conversations move quickly.Tables where leaders show up prepared, committed, and deeply invested in their schools and organizations. And no matter where I am, I keep noticing the same thing. Leadership teams […]
As the holiday season approaches, I know many leaders are arriving here tired. Not the “I need a nap” kind of tired—but the deeper kind. The kind that comes from carrying responsibility, making hard decisions, supporting people through challenges, and holding it together even when you weren’t sure how much more you had to give. […]
Earlier today, I was talking with one of the leaders I support. She paused for a moment, took a breath, and said quietly but honestly,“Darrin, I’m tired. My teachers are tired. Behaviors are up, people’s patience is down… we are tired.” Her words weren’t dramatic. They weren’t complaining. They were simply true.And the truth landed […]
This past week, I sat with nearly every leader I’m currently coaching. Some were tired. Some were overwhelmed. Some were fired up and ready for the next challenge. But almost all of them had one thing in common: They hadn’t slowed down long enough to really reflect on their year. In each conversation, I gave […]
