Scheduling always seems to be an issue with tabletop games. Whether physical or virtual, finding a time when five or six people can get together at the same place at the same time gets harder and harder as you get older, it seems. I feel like I should have some clever insight into scheduling game sessions by now, but I really don't -- for the most part it comes down to scheduling for a particular weeknight and setting quorum, or the number of people you need to run session.
I have tried open-ended scheduling, where we sit down at the end of the session, take out our calendars, and try to find the next three-hour hole in our schedules. I have found this to be a tedious process, and it usually ends up yielding a similar result to a weeknight scheduling, if only because our schedules, at least in the circles I run in, tend to be roughly weekly-oriented. I imagine that if everybody in the game diligently kept an online calendar of when they were and were not free, this could be made easier or even automated, but I have a feeling few people have a Google Calendar or Outlook Calendar or similar that up to date.
My group uses Google Calendar for our scheduling; after each session, I get a quick check of who can make the next week, and if we won't hit quorum, who can make the next week, and so on. Right now quorum for our group is four -- I'll drop one person and still run, but if we loose two for a particular session, I move the session. I then send out the invite for the next session, so everybody has it on their calendars and I can track RSVP's. It is a simple system, and I sometimes forget to send out the invites immediately, but so far that's the system we've used and its worked pretty well so far.
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