Work is a Verb
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Your Calendar Sorts Backwards
Two meetings get requested on the same Monday morning.
The first is thirty minutes on which vendor to use for the new company hoodies. Two people, neither of them senior. It lands on Tuesday afternoon.
The second is whether to correct the comp band on an engineering team that keeps losing people over it. It needs four people, two of whom run departments. The first slot where all four are free is three weeks out, long enough for another resignation to land before the meeting does.
Nobody chose that. No one sat down and decided hoodies should move three weeks faster than attrition.
Every organization runs a sorting function on its calendar: what gets talked about this week, what waits until next month. The input is how many calendars have to line up, multiplied by how full they already are. Importance is nowhere in it.
Importance runs the other way. The decisions that matter most need the most people in the room, and the most senior ones. The extreme case is the CEO. In a 2018 study, Porter and Nohria had assistants log every fifteen minutes of 27 large-company CEOs' time for thirteen weeks: three quarters of their working hours were scheduled in advance, and the most booked CEO left 3% open. That data predates remote work going mainstream. The time zones a remote company spans only narrow the window further, and that last step is our observation, not the study's.
Follow the arithmetic and the sort inverts. The more a decision matters, the further out it books.
The calendars doing the blocking are mostly not full of decisions. We set ourselves up for an awful day to stop other people from ruining our day. A full calendar is armor: proof of being needed, and the only polite way to stop anyone adding more.
What the waiting costs never shows up anywhere you would look. How many prospects opened your booking link, saw the first open slot weeks out, and closed the tab? The tools could measure it; I have never seen anyone ask. How many of your direct reports went to grab fifteen minutes, saw how buried you looked, and decided to handle it alone? They handled it worse than you would have, and you will never know.
None of this is an argument against meetings. Cutting volume is a real fix, and it even frees up slots. The ordering stays where it was. Async has the same ceiling: plenty of decisions should die quietly in a doc, and the ones that survive it are exactly the ones that need four calendars. And the standing leadership sync runs on the same sort: the agenda goes to whoever asked first, the slot stays fixed no matter what is waiting, and a long readout bumps exactly the item that needed the most time.
The problem is the pricing. Most calendars charge the same for every hour: nothing. The last free hour tomorrow costs a requester no more than a block three weeks out, so the scarce hour goes to whoever asked first and the four-calendar question waits behind the hoodies. Sell your last hour dearly.
So hold an hour back. The comp-band decision needed four calendars, and one person cannot unblock four. Get the handful of people who gate consequential decisions to hold the same two near-term slots every week, off every booking link they share. Now a four-calendar question has somewhere to land this week, and anyone who wants that time has to say what it is worth. A hoodie vendor cannot answer that. A comp band bleeding engineers can. It also gives your team something to decline with, which in my experience almost nobody can do without another meeting to point at.
The ask is joint, because armor only comes off together. Take it to whoever runs the leadership calendar and give it a boring name, decision hours, the kind nobody remembers to cancel. Four weeks in, report one number: days from raised to decided. The hoodies took a day. The comp band took three weeks. That gap is what you are shrinking.
Pick the most consequential open question at your company right now and find the date it is sitting on a calendar. Write down how long it has been waiting. That is your baseline. If there is no date, or the date is weeks out, no amount of hunting for a better slot will fix it. That is your sorting function, running exactly as built, on the one thing you wanted it to run fastest on.
