Three Conversations Every Head of School Should Have Before the New School Year

Before the new school year takes over, there is still time to look closely at what last year exposed. These three conversations help you capture what broke, what it cost, and what deserves attention this year.

There is a short window in late August when the previous school year already feels distant, but you can still remember what it took.

You can still remember the report that took half a day to assemble, the admissions information that had to be checked across three places, the spreadsheet someone rebuilt because the numbers did not match, the process that stopped because the one person who knew how it worked was away.

By the end of September, that memory is gone. A new school year takes over, and it needs your attention. The pace picks up, immediate priorities move to the top of the list, and the same workarounds quietly return because there is no longer much time to question them.

Whatever you leave unexamined now, you will work around until next June. Three conversations are enough to start changing that. Each is short, and each ends with something you can act on.

1. With your team

The question: What broke under load last year?

Start with the people who ran last year’s operations:

• your office manager,
• your registrar,
• whoever handles admissions,
• someone from the business office,
• a teacher involved in timetabling or reporting.

The goal is not a general conversation about what was difficult. Schools are complex organisations, and every year contains busy periods, unusual requests, and problems nobody could have prevented.

You are looking for the places where your processes stopped holding when demand increased.

Ask your team to think about the periods when the school was under the most operational pressure:

• admissions deadlines,
• enrolment and re-enrolment,
• fee collection,
• report cards,
• provincial reporting,
• parent communications,
• the start and end of term.

What happened when the volume increased?

• Which reports suddenly required manual work?
• Where did people copy information from one system into another?
• Which spreadsheets became essential?
• Where were staff waiting for someone else before they could continue?
• Which processes depended on one person knowing what to do?
• Where did families have to supply information the school already held?

Separate the inconvenience from the pattern. A one-off error may simply be a mistake. A process that repeatedly requires staff to export data, reconcile conflicting records or maintain an unofficial spreadsheet is something else. So is a task that works well for most of the year but becomes unmanageable every time the school reaches a predictable busy period.

Those are the issues to capture.

Do not finish the conversation with "we should improve that next year." Write the problems down while people still remember what happened. For each one, record:

• what staff were trying to do,
• what made the normal process difficult,
• what workaround they used,
• who was affected.

2. With your board

The question: What did it cost?

The list from your team tells you where the school struggled. Your board needs the same information in a form it can act on, which means putting a number against it.

Some costs are easy to find:

• overlapping subscriptions,
• overtime,
• temporary support,
• additional tools brought in to keep a process moving.

Others are absorbed quietly through staff time:

• hours spent re-entering information,
• reconciling records,
• rebuilding reports,
• chasing missing data,
• maintaining workarounds around systems that do not connect.

If you have not put a figure on those costs yet, we walked through a simple method to do it in The Hidden Costs of Fragmented Systems: What Your Workarounds Are Really Costing You. Start with a few recurring problems, estimate the staff hours they consume across the year, and apply a reasonable hourly cost. The result will not capture everything, but it will give you something concrete to discuss.

Once the cost is visible, the conversation changes. “This process is frustrating” is easy to defer. A recurring cost in staff time, software, and lost capacity is something the board can weigh against the cost of fixing it.

3. With yourself

The question: Am I prepared to repeat the last school year?

The third conversation is the shortest, but it is the one that determines whether anything happens next.

Look at the list, look at the cost, then ask yourself: if nothing changes, am I comfortable running another school year this way?

There may be good reasons to answer yes. Some problems are temporary. Some can be solved through clearer processes, better training or a small internal change. Other priorities may matter more this year, and a major system change may not be realistic yet.

But make that a conscious decision rather than letting September make it for you.

Because there is another possible answer. Perhaps the same issues appeared in 2024/25 and again in 2025/26. Perhaps your team has already refined the workaround as far as it will go. Perhaps the school has grown, but the processes supporting it have not. Perhaps something that once felt mildly inefficient now consumes enough staff time to become a genuine operational constraint.

If that is what your evidence shows, the question changes. It is no longer "Could this be better?" It becomes, "Is this the year we finally do something about it?"

That does not mean selecting new software tomorrow. It means giving the issue a real place on the school's agenda this year: investigating the problem, understanding the options, and working out what change would require.

Without that decision, it is very easy to spend another year managing what you already know is not working.

Three things to take into September

You do not need a completed transformation plan before the school year begins. You need enough clarity to stop last year's evidence disappearing beneath this year's workload:

1. Talk to your team and leave with a written record of what broke.
2. Talk to your board and leave with an estimate of what that friction cost.
3. Decide whether those are problems you are willing to absorb for another year.

September will bring plenty of new things to solve. The problems you already understand do not have to be among them.