Meetings are hard, and no software can handle it


Meetings, the cause and solution for all work-related problems, amirite?

But seriously, arranging and then actually holding meetings with others, plus a dash of follow-ups, is how things get done in many professions, including software leadership. I have yet to find a single piece of software, or even a suite, that handles all the steps. So why does software fail at this task so badly?

Let’s look more closely at the workflow of scheduling, and eventually conducting, a meeting. To keep it simple, let’s say it’s a 1:1 meeting. Group meetings are even more complicated, and this article is long enough already. And, no, this isn’t a Pandemic Special. Pretty much everything here applies to in-office meetings as much as fully-remote.

Step 1. Prior to meeting, especially with someone outside your usual work circles, it’s a good idea to reach out in advance and give a heads-up A) that you’ll be scheduling a meeting soon, B) to feel out some mutually advantageous times, C) then to negotiate something sooner than the first open slot, two months out, D) to provide a high-level idea of the topic, and E) to point them at any materials they should get familiar with in preparation for the meeting. These days it usually means Slack or maybe Microsoft Teams, but (thankfully!) not everyone is available online 100% of the time. If your workmate isn’t online when you are, then you have an open loop about reaching out. Fire up your TODO app of choice…

You could argue that this step isn’t strictly necessary. After all, that’s what the calendar system, say Outlook, is for, right? People’s calendars should already be up to date (hint: they’re not), and the meeting invitation can spell out everything else they’ll need. Right? The problem is, unless there’s a power differential, not everyone will accept your meeting requests. I mean, the Director of Engineering could probably blast a meeting onto any engineer’s calendar, but a power move is likely to create friction, if not panic. Because your goal isn’t the meeting itself—it’s a greater outcome for which the meeting is a stepping stone. In fact, if you do have a power dynamic in relation to someone, please take extra care to gently guide your invitees into a productive meeting.

Step 2. With preparation done, now you can send a meeting invitation. In a perfect world, the invitation quickly switches into the “Accepted” state and stays there. Or maybe it doesn’t. There may be further negotiation about new proposed times, places, topics, priorities, or anything else. If you’re like me, your invitation will have camouflaged itself into a dense thicket of wall-to-wall blue boxes on your calendar, and it’s quite difficult to keep track of which meetings are actually accepted and which ones might be waiting on you to confirm something, especially when your next few weeks might have dozens of these Schrödinger maybe-meetings.

To the calendar app, the fundamental unit of value is a block of time. People and ideas are incidental.

But hold up, we missed a step.

Step 1.5? For effective meetings, the meeting sender should provide a crisp agenda adhering to a strict timeline. For some recipients, this will be a make-or-break factor in whether they’ll accept the meeting. So this is another reason for the pre-approach—if there’s no possible way a meeting will ever work out logistically, you save the time of having carefully crafted an agenda. So between steps (1) and (2) it looks like we get another TODO entry. Or maybe an annotation on an existing entry? Hmm.

To the TODO app, the fundamental unit of value is the task, or possibly subtask, which must be in a state of either 0% or 100% completion. Moving backward (“oops, that meeting just got un-accepted”) is poorly handled, if at all.

Step 3—except that we’re deep enough into this Finite State Machine that it barely makes sense to continue numbering steps—happens a few days or weeks later, when you can’t even remember which folks you have or haven’t scheduled with already. Projects change. Ideas mature. Chance encounters reshape your relationship with the project, and sometimes a meeting can cease being needed. And there’s no easy way to tell at-a-glance who is or isn’t already scheduled. C’mon. Raise your hand if you’ve ever started scheduling a new meeting with someone, only to find out that you already had one elsewhere on the calendar…

Step 4ish. Finally the meeting. At this point you’re almost glad to actually be in a meeting. Almost. This is the part that calendar apps seem to have been designed around. This is also where, five minutes into the designated time, you discover that the other person never accepted the meeting, or somehow declined without sending a notice your way, or got pre-empted by a meeting with the Director of Engineering, or is out sick, etc. If that happens, you get to start the whole process over again, starting with tracking down and updating all the related calendar items, emails, and TODO entries.

Otherwise, thanks to your crisp advance agenda, the meeting goes swimmingly, and you set aside the last few minutes for Next Steps, which end up on their TODO list, or yours. Which by this point is has so many items, that things start getting lost.

Steps 5+: Follow-ups. To be continued…

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