so many teams want to move fast but are stuck in the trap of "the first calendar slot that works for everyone is next Thursday at 2pm so we'll kick things off then"

- Brie Wolfson on Twitter

Loaded calendars are a cancer lurking inside of software companies. If I had a dollar for every time someone's daily update alluded to wall-to-wall meetings, I'd be sitting on a beach instead of writing on this blog.

If there's one concept that this industry struggles with, it's opportunity cost. We believe that because we can, we should. So we say yes to everything, not realizing all of the possibility lost because we're going with the flow.

So we go with the flow until we find ourselves paralyzed by a laissez faire attitude towards time. Regular 1:1s become the norm. Everything has to get run through a committee. We find ourselves in meetings about meetings. The workday is filled with metawork, everyone knows it, but nobody is willing to raise their hand and say "this is wrong".

I'm reminded of Shopify's 2023 memo to employees, where they enforced a "calendar purge" in order to free up time to do the work that matters.

"The best thing founders can do is subtraction,” Chief Executive Officer Tobi Lutke, who co-founded the company, said in an emailed statement. “It’s much easier to add things than to remove things. If you say yes to a thing, you actually say no to every other thing you could have done with that period of time. As people add things, the set of things that can be done becomes smaller. Then, you end up with more and more people just maintaining the status quo.” 

Also relevant, from Paul Graham's Maker Schedule, Manager Schedule:

When you're operating on the manager's schedule you can do something you'd never want to do on the maker's: you can have speculative meetings. You can meet someone just to get to know one another. If you have an empty slot in your schedule, why not? Maybe it will turn out you can help one another in some way.

Business people in Silicon Valley (and the whole world, for that matter) have speculative meetings all the time. They're effectively free if you're on the manager's schedule. They're so common that there's distinctive language for proposing them: saying that you want to "grab coffee," for example.

Speculative meetings are terribly costly if you're on the maker's schedule, though. Which puts us in something of a bind. Everyone assumes that, like other investors, we run on the manager's schedule. So they introduce us to someone they think we ought to meet, or send us an email proposing we grab coffee. At this point we have two options, neither of them good: we can meet with them, and lose half a day's work; or we can try to avoid meeting them, and probably offend them.

Graham's solution is regularly scheduled office hours, which sounds nice in principle, but doesn't feel scalable. Inevitably, people will want more access and more information and more connectedness. Office hours will begin happening daily, then multiple times per day, until someone decides that dedicated recurring meetings are the better option.

One more link for the road: Alex Komoroske's Coordination Headwinds deck.