Marc Hughes

I am a developer from a bit west of Boston.

Scheduling meetings

11 Nov 2009

Scheduling meetings through outlook might be one of the worst practices I need to deal with on a daily basis.  It saves us a ton of time in the meeting-planning department but has huge drawbacks.

Problem number one, it's WAY too easy to schedule a meeting with someone.  Since the bar is lower, more meetings happen.  Since there's more meetings, they're often individually less valuable.  Since they're less valuable people don't treat them with the respect they deserve.  Nobody prepares beforehand.  Meeting agendas are the exception, not the rule.

Secondly, it's not an efficient way to schedule a meeting.  Wait, let me revise that slightly.  It's not an efficient way to schedule a set of meetings.  The normal process that is often used is to put everyone on an invitation.  Find a block of time everyone is available.  Book it.  Later, that process is repeated for the next meeting.  Even later it's repeated again.  Since different people go to different meetings, individual schedules get "fragmented".  Back in the days of personal assistants (or back then I guess the term was "secretaries"), they would handle the process of defragmenting schedules to make them make more sense.  This leads to situations when individuals have an hour meeting, an hour to work, an hour meeting, an hour to work, etc.  Without bigger blocks of time to work it's impossible to tackle certain problems.  Even worse, a high priority meeting might get pushed back because other meetings were scheduled earlier.

Combine those two problems, and it actually gets hard to book a meeting.  Since there are a lot of them.  And since there is fragmentation in people's schedules, finding an open block that everyone can join can be really hard to do.  This means scheduling happens further and further out.  If you need to talk about something with 10 people and the only time slot to get them all in a room is a week away, that sucks.

A side-effect of this is that when you receive a meeting request, you often really feel obligated to accept it.  Especially if the sender knows you have a free block of time.  That means you're not asking yourself  "Is me attending this meeting the best way for me to spend my time to advance/improve/help the organization?"  I think we should be asking that question all the time!

How to define an ideal solution?

If we're going to explore other options, it'd be helpful to have some evaluation criteria.  Here's what I would look for in a meeting scheduling system (in my order of priority).

  1. Ability to schedule meetings without conflicts.  (including resource and people conflicts)
  2. Schedule more important meetings sooner than less important ones.
  3. Minimize the number of chunks of free time each user has.  (In other words, maximize the average length of non-meeting time)  This one is really important for knowledge-workers.
  4. Encourage productive meetings.   (Clear purpose, set agenda, everyone comes prepared ... )
What other properties might an ideal solution have?

So what's one solution?

First, here's a technical solution.

The first problem of meetings being too easy to schedule is tough.  It really requires training people to act differently.  Without designing a technical solution that somehow discourages meetings, I'm not sure what to do about that.

The second problem could have a technical solution.  Imagine a "smart" scheduling system.  You need to schedule a meeting?  Submit the details of the meeting to some computer system.  Tell it

  1. Who needs to attend
  2. Any time constraints that must be upheld.
  3. What resources do you need.
  4. How important is it?
But the important thing is that you don't specify when it happens.  (There may be time-constraints for some meetings that do dictate a time.  Like if a client is arriving, it has to happen in a given time slot.  Or if there is a release planned for thursday, the release planning meeting must happen before thursday.)

Then the system is free to schedule that meeting whenever is "best" by some smart criteria.  It tries to maximize individual people's free time blocks.  It tries to schedule more important meetings sooner.  It moves existing meetings when new ones are scheduled so there's always an optimal solution planned.

The downside?  Meetings move.  It's hard to plan ahead.  Someone needs to develop a complex scheduling system.  The time that meetings happen becomes "voodoo magic" to some people.  It's possible to game the system.  It's not flexible.

Solution #2

Now, here's an organizational solution that I want to try out here at TSP.

1) Meetings that HAVE to happen at a certain date/time are scheduled as normal.  Got outsiders coming in?  Meeting to watch the pat's game?  Go ahead and schedule those as before through outlook.  Hopefully that's the minority of meetings for you.  (If you're the guy meeting with outside clients all day long, you're pretty much screwed any way you look at it.)  A certain class of exceptional or emergency-meeting falls in here too.

2) Got a meeting that doesn't HAVE to happen at a certain date/time?  You're not allowed to just schedule that through outlook.  Instead, at your daily scrum we schedule those as a group.  With one more constraint.  You only schedule meetings for tomorrow.  It's either important enough to schedule for tomorrow, or it isn't.  That's a much easier, concrete decision to make than scheduling a meeting next-week.  Some meetings lower on the priority list might not fit.  That's fine, try to get them on the list again tomorrow.

To actually create this schedule, you're likely looking at outlook as a group.


  1. You can intelligently schedule meetings.  Since you're only looking at a day at a time and you're considering all the meetings together it's easy.
  2. You get to decide which meetings are more important than others.
  3. You get to weigh the benefits of a meeting against non-meeting things.  It's easy to schedule a meeting a week in advance for a trivial matter.  It's really hard to schedule that meeting tomorrow if there's more important things to do.
  4. It makes people think about meetings and whether or not they have to happen.
  5. Since a meeting you're invited to is only ever a day away, it's more on your mind and you might prepare for it instead of being surprised by an outlook reminder.
Down sides:
  1. Boy does this require a lot of buy-in from everyone involved.
  2. Participants have limited time to prepare (The person calling the meeting has as much time as they need to prepare since they could just wait another day if needed)
  3. Since your group is scheduling a day in advance, it can be hard to get ahold of resources that other groups might be scheduling weeks in advance.  There's likely solutions to that, but I'll stay away from them for now.
I'd only consider using this for larger (4+ people) meetings.  Still feel free to have impromptu talks whenever they're needed.  Still feel free to try an resolve issues at the scrum, or by sticking around after your scrum.  In fact it might encourage a quick post-scrum discussion instead of a meeting.

Side-Note: I heard a rumor that Warren Buffet only schedules meetings a day in advance.  I have no idea if if is true or not.  But that's where I got the idea from.


Replace "Outlook" with any other "dumb" scheduling solution out there.  Lotus Notes?  Google Calendar?  Whatever.

Don't complain that I call it outlook and not Exchange or whatever the entire-system should be called.

My solution assumes you have a short daily meeting.  It would suck to have to introduce that if you don't.

What else?

There has to be better solutions to this.  What do you do?