My partner works as a project manager, which is funny for a few reasons. One, because in my world of product management, there’s a palpable shudder when the job is confused with project management- PMs of the product variety should spend their time determining what to build, not managing the building process! Two, because nothing seems to stress this person more than what they refer to as “calendar games.” (Ironically, they’re pretty into other kinds of games, such as ridiculously complex board games or totally uncomplex retro arcade games).
Calendaring is a weirdly hard problem, for a technology that has been around at least since the industrial age and presumably far earlier. You have a calendar, I have one, and if we need to find a time when both of us are free, it seems pretty intuitive that simply laying one over the other would expose availability.
But there are complications, especially when there are more than two of us. For one thing, I might be in a different time zone. And offsets change and complicate things further (yet another reason why daylight savings is outmoded).
OK, but Calendly and similar services have basically solved this problem by letting you limit your availability not just by claimed slots, but also by your individual schedule. And Calendly works very well for one person choosing a time on another person’s calendar.
This still gets messy when say, you travel and you’re in another time zone, but that’s possible to deal with if annoying for either the person with the calendar or the developers trying to accommodate the traveler.
There’s another challenge, this time not so technical. We are, as a rule, very emotionally invested in the idea of “owning our own time.”
Every day in my meditation practice space, I hear, “Time just is,” but it’s still quite hard to turn over the perceived control of that time to someone else. Conversely, and as reflected by a social media controversy, some people take affront at being asked to select times based on when another person is available, with the idea that whoever set up the calendar is enforcing their own boundaries as an act of dominance. Anger is a boundary energy, as they say, so it’s no surprise people get irritable when it comes to trying to converge into mutual time without feeling controlled in one way or another.
Along with this generalized frustration, we also tend to not want to have the same personal and work calendars, nor make plans the same way with work and personal contacts. For example, I tried to make a Calendly event for a friend but discovered we were meeting within business hours, unless I could figure out how to block things on my ‘work calendar’ that are personal, many of which are not as specifically time blocked, like “going out with a friend.” And it could get very awkward if people at your work can see what’s on your calendar.
But for those of us who find services such as Calendly a welcome relief from sending emails back and forth, it feels mysterious why there’s been almost zero innovation in finding times for multiple people to meet. Partly this is a function of the aforementioned power dynamics- who gets to be the one determining the time for everyone? Because if it’s not one person, then things just return to endless group email chains with one person inevitably coming in at the last minute to spoil everything.
Partly though, it’s something else, which is that there is no, as far as I know, service that can look at multiple people’s calendars across different organizations and calendar clients and let you know when everyone is free. I am guessing there may be some complexities in the technology that make this hard- but I mean, really? Up to 10 people’s calendar on a given week should be within the capability of an not-too-complicated algorithm to evaluate. (No, you tell me- how hard is this, really?)
Perhaps the last piece of the problem is that while people may have space in their calendar or have meetings booked, there’s another wrinkle- what I might loosely characterize as FOMO. Yes, I may have a meeting booked but if something more compelling comes along I might want to move it. As a Calendly user, I’m often caught by mildly irritating surprise when someone reschedules an hour before we were to meet, leaving me with a 45 minute gap that doesn’t lend itself to actually getting things done. But as a researcher, I quickly gave up on any rebooking or even no-show resentment since it’s a fact of life. Still, when you have multiple people in a meeting and a key person develops a conflict, it quickly becomes everyone’s headache. But even this seems much better to give to AI than to have to spend additional time negotiating a new slot.
I propose we have an AI that is granted more limited views of people’s schedules, maybe for just enough time to cross reference a week and surface availabilities, with rules input by the players about how to choose the preferred time among what’s possible. I suppose if you wanted to get really fancy, it could even figure out travel time and factor that in.
Could this work? I am guessing the APIs are available if we can have Calendly connections with the various clients. So how about it? Surely, we can surpass Doodle and make meeting as easy as just showing up?
I predict that as we figure out calendar games, we’ll also move away from separate productivity tools and have planning, goal setting, tasks all live in the calendar. Right now this is pretty terrible on Google Calendar, but someone will come along and make this new category of time-management exciting. Or we’ll end up working for our robot overlords when they figure out how to schedule us. Either way, I won’t be filling in Doodles.