What the Most Honest Leaders I Know Say About Their Own Weaknesses

One of the things I respect most about strong school leaders is the ones who can look at their own practice with real honesty. Not performative humility. Not self-deprecating humor to deflect. Actual, clear-eyed honesty about where they’re falling short and why.

The leaders I’ve seen grow the fastest in this work all share one thing in common: they know which practice they’re doing well and which one they keep pushing to the side when the week gets heavy.

For most of the leaders I talk to, the practice that gets pushed aside most often is individual connection. The one-on-one conversations. The hallway check-ins. The honest question asked to one person before the staff meeting starts. That’s the work that gets squeezed first when the day fills up, and it’s also the work that matters most for how teachers feel about being in that building.

Here’s why I think this happens. Individual connection is not urgent the way a parent call is urgent. It doesn’t have a deadline the way a report does. It doesn’t feel like a task that can be crossed off a list. So when something urgent arrives, which it always does, the connection work moves down the priority list.

But the cost of that accumulates. When teachers don’t feel individually seen by their leader, they start to disengage slowly. Not dramatically. Not all at once. Just a little less initiative here, a little less willingness to take a risk there, a little more quiet in the staff meeting where you used to hear their voice.

The most honest thing a leader can do right now is ask: which of the people I’m responsible for haven’t I had a real conversation with in the last two weeks? And then go have that conversation. Today. Before the next urgent thing arrives.

That’s not a leadership program. That’s a decision.