The meeting had existed for eleven months before anyone asked why. Every Monday at nine, the same seven people, the same hour, and somewhere around month four the preparation had stopped, the lateness had become habit, and one person had started booking over it and sending apologies that fooled nobody. The agenda said “weekly business review”. What it was actually for, no one could quite say any more.
That is not the unusual part. The unusual part is that someone eventually noticed. Most meetings are held. Very few are designed, a distinction that sounds like semantics until you have sat through enough of them. Holding a meeting means finding a slot, pulling in whoever seems relevant, and writing a title vague enough that no one questions whether it should exist. Designing one starts somewhere else entirely: what needs to be true at the end of this hour that is not true at the start? That single question settles everything else, who is in the room, how long they are there, what they should have read first, and whether there is any point gathering at all. Chiefs of Staff sit through a disproportionate share of meetings, and watch a disproportionate share produce the wrong thing or nothing, and after enough of those you get a clear eye for where it goes wrong. Chief of Staff meeting design starts with one diagnosis: most meetings fail because nobody decided what kind of meeting they were running before they ran it.
The three things a meeting can do
A meeting does one of three jobs well, and every meeting that reaches for all three does none of them:
- It makes a decision. That needs a proposal on the table before anyone arrives. The pre-read is not optional; it is the thing that turns a debate into a decision. Fellow.ai’s 2026 research found teams that send structured, decision-focused pre-reads are 2.3 times more likely to leave with a clear conclusion.1 Skip the pre-read and the meeting usually produces another meeting.
- It builds shared understanding. That needs a clear picture of what is being shared, why it matters, and what people are meant to do with it. “Weekly update” answers none of those three.
- It strengthens the relationships that hold a team together under pressure. Most organisations never book this one on purpose, which is part of why their trust problems keep compounding in the background. People who do not understand each other make worse decisions together.
The diagnostic is not “what should we talk about”. It is: what type of meeting is this, and does everything in the structure serve that type? If you cannot answer the first part, the meeting probably should not happen.
Why the default keeps winning
Most recurring meetings start with good intent and survive on inertia. The monthly leadership meeting was genuinely useful in the first quarter, when the team was new and needed a shared view of priorities; six months on, the people know each other, the priorities have moved, and the format has not. Nobody cancelled it, because cancelling feels like a statement and nobody wanted to make one. That is what makes calendars so hard to change from the inside: adding a meeting takes one decision, removing one takes a negotiation. The Chief of Staff is often the only person placed to have it, close enough to the principal to see the cost and far enough from any one team not to feel personally implicated. Microsoft’s data shows Teams meetings up 192% since 2020, and a 2026 survey of 182 senior managers found 71% call their meetings unproductive.2 Those numbers describe a design problem, not a scheduling one.
What to do this week
Pick one recurring meeting in your principal’s calendar and ask three things. What is this meeting designed to produce, as a specific output and not “discussion” or “review”? Could that output come another way, a written decision, a fifteen-minute call, an async thread? And if it must happen, what would need to be true before it starts for it to actually work? If you cannot answer the first, the meeting has no design. That is recoverable, but it has to be named before it can be fixed.
There is a particular kind of leader who believes a full calendar is the same as productive leadership. The meetings are running, the team is engaged, something is happening. What rarely gets counted is the cost: the hours nobody has left for the thinking that made the meetings worth running in the first place. The Chief of Staff usually sees that cost before anyone else. What matters is whether the observation ever makes it onto the agenda.
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