On Message with Ben Gross

Intuitively, it isn’t obvious that calendaring is a hard problem. But after using (and being forced to use) various calendaring schemes, and sitting through lots of team meetings to discuss Exchange, Meeting Maker, WebCalendar, iCal, Yahoo! and other free services too numerous to mention, I’m convinced that it’s hard for small groups to agree on a process, and that most of the software that is supposed to help is badly flawed.

Every system I have seen is slow, or has a proprietary component, or doesn’t mirror how people work, or lacks a good permissions system, or doesn’t offer the view that someone needs, or can’t support the kind of give and take negotiation that is always involved in scheduling. Calendaring is highly personal, and yet all systems ask us to conform to someone else’s way of thinking. Sometimes the benefits outweigh the discomfort of adopting a particular system, but someone is always made unhappy when a system is imposed.

That said, here is another system based on a rather amusing little hack. I’m not sure I’ll use it much, but it should be suggestive for developers. Group calendaring is a nightmare; whoever can fix it is likely to do well, and a lowest common denominator approach like this does seem like the way to go.

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