A lot of what feels urgent in October is work that needed to start in September. This seven-point checklist helps Heads of School look ahead, catch what needs attention now, and make the school year easier to manage.
The start of a school year is busy, and there is no version of it that isn’t. You already know that.
What is easy to miss is that it is also one of the better moments in the year to sit down and look at what is coming. The term hasn’t taken on its own momentum yet, decisions are still relatively open, and there is usually a little more room to move things than there will be in a month.
An hour spent this way tends to save considerably more later, because a good deal of what turns into stress in October and November is simply work that needed to begin in September and didn’t.
Here are seven things worth going through before the term gathers pace.
Not just events. Put everything with a date attached to it in one view.
Board meetings. Reporting deadlines. Parent evenings. Tuition dates. Admissions activity. Professional development. Trips. Major communications. Anything leadership will need to prepare, approve or contribute to.
Then scan the whole period (rather than looking at one week at a time) to have a bigger picture and better perspective of what’s to come.
Once the dates are visible, identify the things that cannot simply be dealt with when they arrive. Some dates have two or three weeks of work behind them.
If a board meeting is in four weeks, when does the information for the report need to be ready?
If families need something by the end of the month, when does the team need to start preparing it?
If an event requires several departments, when does coordination need to happen?
For the biggest items, write down the next action, the date it needs to happen, and who is doing it.
A quick conversation can surface things that will never appear on your own checklist.
Ask each person responsible for a major area of the school:
What will you need from me before the end of September?
It might be an approval, decision, introduction, budget sign-off, piece of information or simply time to talk something through.
Finding that out now gives everyone more room to work. The aim is to catch the things that are easy to postpone until they suddenly become urgent.
September is full of recurring jobs that everyone knows need to happen. Sometimes, however, nobody has explicitly confirmed who is doing them.
For the important work coming up, make sure you can answer:
Who owns it? When does it need to happen? Who else needs to be involved?
You do not need a new project plan for every task. "Sarah’s doing the report, Marcus sends her the enrolment numbers by Friday" is usually enough.
Families are managing new schedules, activities, forms, payments, events and school information too.
Take a quick look at what they will need over the coming weeks.
A little anticipation here can make September easier for both families and the school office. Every question you answer in advance is one your office does not have to answer on the phone.
You have probably done this already, but September always shifts a few things.
Look at the student and family records, the timetable, the contact lists, and whether your new staff can actually get into the systems they need.
This does not need to become an audit.
Think of it as a final operational sweep before things start being used constantly.
Finally, look at your own calendar.
September will find ways to fill every empty space if you let it.
Reserve a few short blocks now for the work that is easy to postpone when the school gets busy: checking progress on upcoming deadlines, speaking with your leadership team, reviewing what is coming next and making decisions that require more time.
Almost everything that feels urgent in October is work that needed to start in September and didn’t. To avoid emergencies in the upcoming months, it’s worth taking even a little bit of time now to be better prepared for the demanding time ahead.
It’s also worth checking whether you’ve had the three conversations that belong at the start of a year: with your team, with your board, and with yourself. Look at what broke last year, what it cost, and whether you’re prepared to go through it again this year.