The one-word question schools won't ask - Fine Point Communications

“Since the knowledge worker directs himself, he must understand what achievement is expected of him and why.”
— Peter Drucker, “The Effective Executive”

School communications offices never run out of tasks to perform. Even in the quietest part of summer, new requests flow in, where they join projects stacked up and waiting for attention.

In the middle of the school year, that flow is more like a flood of traditional projects, ongoing and new responsibilities and behind-the-scenes work.

Given all this, the first part of Peter Drucker’s charge — understanding the to-do list — presents little challenge to a communications director.

The other part, however? Here be dragons.

Why ask why

When the workload never really stops, the impulse may be to act first and worry about questions later.

Why does a given communications project need doing? The answer may seem evident: Because that’s what we always do.

Strategy suffocates in the cyclicality of school life. What the comms office has done once, it can expect to do again, and again, and again.

Drucker, the late business consultant and author, objected to this, positing that a director must always ask, “Is this still worth doing?”

“Every executive forever has to spend time, energy and ingenuity on patching up or bailing out the actions and decisions of yesterday, whether his own or those of his predecessors,” Drucker wrote.

A leader who fails to consider whether projects hold the same value today as when they began, Drucker continued, has consigned himself to “servitude to the past.”

An explosive question

It can be particularly hard in schools, and even risky, to ask “why?” about a project coming from another department.

The question can be heard as gatekeeping: The colleague may worry that, without a “proper” reply, communications will ignore the project request. Some may sense intransigence or passive resistance against another office’s authority.

For the person who just needs a task done to move ahead with their work, hearing comms ask “why?” can feel like Bartleby the Scrivener suddenly popped in for a chat.

At the same time, communications is not simply a rubber-stamp office. To perform its role in the school properly, it must push beyond basic details like what and when in order to understand the purpose and goal of the project.

Comms also needs to understand the priority of the request: Is this ask more pressing than other items already on the department’s to-do list?

Such conversations can uncover some broader confusion about communications’ role within the school. Clearing the air is valuable. But it will interrupt the process of getting things done.

Face the fear; do it anyway

Schools that have established a clear strategy for comms, including priorities for the department, tend to avoid this kind of uncertainty.

Not many campuses have reached this point, though. Here, asking “why?” can be an act of bravery.

Yes, the question may not be heard well; it may even provoke the listener.

But it also honors the reality that schools have limited capacities. Asking for the reasoning behind project requests helps use those capacities to best effect.

After all, that’s the real objective of our work. As Drucker reminds in “The Effective Executive,” the actions and decisions of today will decide the school’s future.

It’s easy to lose that understanding among the hurly-burly of communications work. But a director should always be steering toward that desired future.

Asking “why?” improves the wayfinding, and therefore the odds of institutional success.

Fine Point Off-Site update

In planning the Fine Point Off-Site, we decided our one-day conference should focus entirely on professional development. That’s why attendees will find no sponsors or exhibitors on the sidelines.

Similarly, our lineup of speakers comes from the world of independent schools — people who perform the same work as the audience.

This intentional program design makes our Feb. 25 event in Seattle more relevant and practical than any other conference on the calendar. Only the Off-Site devotes its entire schedule to improving as a communications director.

What’s more, the Off-Site features twice as many sessions on communications — in far less time — as does the much larger NAIS Thrive 2026 conference that kicks off the following day.

If you’re coming to NAIS, the Off-Site offers a great way to complement that investment and to make the most of your three days in Seattle.

Make plans to join us at the Westin Seattle on Feb. 25!

What’s new at Fine Point Communications

As 2025 winds down, we are closing out some large-scale projects: Fine Point produced two magazines this fall and provided interim communications leadership to a school as it searched for a permanent director.

And we counseled several schools on their emerging crisis communications needs, work that will extend for some into 2026.

Fine Point will take part this winter in a few conferences. If you’re coming to any of these events, please make a point of saying hello:

In late January, Fine Point Communications will sponsor the Heads Network’s Annual Conference for the third consecutive year. Our principal, Scott Butterworth, will attend the three-day conference.
On Feb. 4, Scott will present on crisis communications to the Small School Leaders Conference.
On Feb. 6, Scott will present on creativity in communications, development and admissions materials at the Educating Girls Symposium.
On Feb. 26-27, Scott and Fine Point associate Erin Dentmon will attend the NAIS Thrive 2026 conference, taking in the various sessions.