Three Practices That Keep School Leaders Proactive
I was listening to a podcast recently where the host shared this quote: “Unspoken expectations are premeditated resentments.” Five words. Brutal honesty.
The quote is often attributed to American author Neil Strauss. I can’t speak to the rest of his work, but I can speak to this: those five words explain a lot about school leadership, especially when it comes to planning.
I have lost track of how many times I’ve rolled into a week and thought, “Oh, crap. That’s this week?”
Graduation. Open house. Teacher contracts. Accreditation paperwork. The budget draft that was absolutely going to get started earlier this year.
Every time it happened, I would tell myself, “Write this down so you remember earlier next time.” And every time, I didn’t.
In the world of school leadership, you are pulled in a million different directions. You have call lists to review, sub schedules to coordinate, chapel to prep for, discipline issues to handle, parent emails to respond to, teams to coach, and, let’s be honest, lightbulbs to change and puke to clean up…And this is all before lunch on a Wednesday.
Planning rarely feels urgent. Until it is.
A wise teammate of mine once said, “Your urgency is not my emergency.” If only the calendar agreed.
The calendar does not care that you meant to start the budget in January. It does not care that enrollment “felt steady.” It does not care that you were hoping for a slower spring. It simply turns the page.
And there it is, the event, the deadline, the season, staring back at you like it hasn’t been on the calendar for twelve straight months. Here’s the hard truth: schools don’t resent unpredictable crises. They resent predictable ones that were never spoken out loud.
If enrollment season, hiring windows, budget drafts, and accreditation cycles live in the world of unspoken expectations, resentment isn’t far behind. Not because the events are bad, but because the scramble is exhausting.
There is a difference between reactivity and living in the moment proactively.
Reactive leadership means worrying about the scotch tape peeling off the wall because it was thrown up fifteen minutes before the first guests walked through the door.
Proactive leadership means walking into the same event with margin. You’re able to enjoy the conversations, the families, and the purpose behind it all.
Same event. Very different experience.
So what do we actually do about it?
First, appoint a professional look-ahead-er. Every team has one. The person who already lives three weeks ahead of everyone else. Empower them. Give them permission to interrupt. Let them be annoying. Their job is to lift your head out of the weeds and point to the oncoming freight train you can’t see yet. Great leaders don’t carry the calendar alone. They learn to recognize the hidden strengths sitting around the table and empower them accordingly. Not every leader is wired to live three months ahead, and that’s okay.
Note: The art of leadership is recognizing that you can’t do it all. This art builds a team that collectively sees what you miss. Delegation isn’t weakness. It is stewardship. Being self-aware enough to know your own blind spots allows you to intentionally develop the strengths of your time. When this happens, the entire organization gains margin. For this reason, delegation is a core part of our School Leader Partnership, because healthy leadership is rarely accidental.
Second, protect planning time like it matters. Put it on the calendar. Defend it. If it doesn’t get scheduled, it doesn’t exist. A small, consistent investment of time prevents the full-blown Titanic moment later.
Build an internal calendar. Most schools focus on the visible calendar–the one shared with families a year in advance. We post it proudly. We color-code it. We distribute it before we’ve even fully recovered from the current year.
But there’s another calendar. The internal one. The unsexy, nitty-gritty cycle of enrollment timelines, staffing conversations, budget drafts, accreditation benchmarks, contract deadlines, reporting windows, and board reviews. That internal calendar is the one that determines whether the visible one feels joyful… or chaotic.
Unspoken expectations become premeditated resentments. Spoken expectations–planned, chunked, and owned–become leadership.
Graduation will happen in May. It always does. The question isn’t whether it’s coming.
The question is whether you’ll be shocked by it again.
Questions for Reflection
Who on my team is naturally wired to see around corners and have I actually empowered them to speak up when they see something coming? If not, what would it look like this week to formally give them permission to interrupt, challenge, or flag future risks?
Where in my calendar does planning happen right now? If someone looked at my schedule for the next month, would they see protected planning time?
What are the three to five most important internal deadlines or processes that should live on our internal calendar, but currently only live in people’s heads? Who will own documenting and maintaining that internal calendar so the organization gains margin?
The School Leader Partnership is a four-month, semester-length partnership designed to strengthen leadership sustainability. Over the course of one semester, leaders gain a clear view of their current reality and implement practical systems that allow them to move from reactive mode into proactive, confident leadership with board alignment built in. Learn more here or by scheduling a free, 30-minute consultation with our team.
