Calendar software companies: for all our sakes, please make this one change

Ben Crothers
4 min readMay 31, 2021

Here’s a familiar scene for you, I’m sure.

You need to get stuck into that thing at work, but you check your inbox, to see if there’s anything urgent first. You wade through the latest wash of emails, and you find a meeting invitation:

Your garden variety calendar invitation, as seen in your inbox

The decision dance

Hmmm. You know the sender well, and there are other people invited too, but the details area is blank. You’re not totally sure about what this meeting is for.

Will you accept? You check your own calendar to see if there’s a conflict. You don’t have any other meetings at this time; you could go.

You sit there, with your cursor hovering over the Yes button.

There’s a ton of things you could do instead of going to this meeting. It’s going to cut a nice free space in your calendar in half. What’s it for? Why do you need to be there? “Just click Yes”, you tell yourself. “Get back to that thing I need to get cracking on. Figure it out later.”

Ah, but you made a promise to yourself not to let others control your time in your calendar! Who controls your time? You do!

You could message the sender over Slack (or Teams, or whatever it is you use to randomly tap each other on the shoulder all day), and find out. But that might trigger a conversation you really don’t have time for right now. There’s that thing you have to get to, right?

You hover your cursor over the Maybe button (or the Tentative button in other software) instead. You never use the Maybe button. What does it even mean? People barely ever reply Maybe to your calendar invitations. It seems so… indecisive? Passive-aggressive, even? When will they tell you Yes or No instead? Or do you have to follow them up, to get a Yes or No?

You look at the No button. You rarely use the No button. It seems so terse. So rude. So final. No.

While you’ve been gazing at this ambiguous proposition, this possibly presumptuous request for your time, a valuable minute has slipped by. Any head of steam you’d built up to get into that thing you needed to do has sadly subsided…

I don’t know about you, but this decision dance happens to me all. The. Time.

Practice good meeting hygiene

A part of good meeting hygiene is to always include an agenda in a meeting invitation, right? Or at least a clear reason for the meeting, and a clear reason why each recipient needs to be there.

But for loads of reasons, often there’s no reason given. No agenda. No useful title. Especially in those recurring meetings. It’s assumed you know, or it’s assumed you’ll come. Or, it’s assumed you’re the one who has to make the effort needed to work out what it’s for, and whether to accept or not.

The remedy: a new button

I’d like to short-circuit that whole decision dance routine, with one new button on those meeting invitations. Actually, not even a new button, just a replacement button.

Here it is:

Do you see it? I just want calendar software companies to replace the Maybe button with Why.

A Why button.

When you click the Why button, the sender gets an automatic email back, asking a very simple but very effective question: why? Then, the effort is on them to tell you the reason for the meeting, and the reason why you need to be there. Which is good meeting hygiene.

Hey, a guy can dream.

Who’s with me? ;)

A hack in the meantime

While us mere mortals wait for software to get better, you could always do this team productivity hack: agree as a team that whenever anyone wants to know why a meeting is happening, or why they’re invited, they can hit the Maybe button.

If you like this, please give it some applause 👏 Thank you!

If you want to know more about how to lead meetings better, and lead with meetings better, good news! I’m launching 4 online classes on how to do just that: 👉 brightpilots.com.

Head to brightpilots.com to learn more about new classes on how to lead high impact meetings

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Ben Crothers

Design strategist, educator, sketchnoter, facilitator, explainer, author of Presto Sketching. I like bringing out creativity in others.