To Calendly or not to Calendly? That is the real question.

Time management is a hot topic right now, as we get deeper into a new way of work and life and people continue to realize that there’s just too much going on and too many demands on their attention, and the only way to survive is to be more intentional about how you spend your time. Tech exec after tech exec has told me recently that they’re buying into the concept of time blocking, which means planning out every minute of your day — even the hour you want to spend watching TV, or the 30 minutes of goofing around on Reddit — as a way to make sure they’re allocating their time the way they want to.

But here’s the challenge with that: Hardly anybody actually has complete control over their time. We all have bosses, investors, board members, families, school schedules and a thousand other things to plan around.

That’s why the hot new feature in calendars is scheduling. Everybody’s suddenly looking for ways to make it easier to find a time that works for everyone. Calendly pioneered the idea, but Fantastical recently released its own scheduling tool, and three of the productivity apps folks are most excited about right now — Motion, Cron and Vimcal — all have it built in. Instead of the long back-and-forth to find a time that works, you just send a link or an automated message, click a button and boom you’re done.

This new kind of scheduling is a complicated dance, though. Some people find the whole idea rude, as if by sending you my Calendly link I’m saying “Oh, I’m quite busy, see if you can squeeze yourself into my extremely packed schedule but I don’t really care.” Sam Lessin briefly became the main character on Twitter after saying that he’ll never click your Calendly link. He called sending one “a ‘get in line’ move.” Is it more efficient? Sure. Is it still rude? Maybe.

I hate the calendaring dance, so I spent the last few weeks asking around to see if there’s a middle ground here, and it turns out there is. It’s simple, really: You offer a few times, and then end with “or, if it’s easier, just grab any time that works here” and send your link. Coffee next week? How about Monday at 11, Tuesday at 2, or just throw a time on my Calendly. Almost everyone I talked to agreed that that’s a decent middle ground, more efficient than the Calendar Battleship method of randomly guessing which hours might be free without seeming dismissive or rude.

That’s a better answer, I think, than even Calendly’s own suggestion. This is the script it suggests for users who don’t want to seem rude: “Feel free to share some times you’re available, or you can also pick from my Calendly if it’s easier.” Execs I asked said that still puts all the work on the other person; starting by offering a time or two goes even further toward meeting in the middle.

I ran the idea by Lessin to see if either approach would make him click a Calendly link. He said he agreed it’s a better strategy, but “I maintain that basically anyone is fully booked at all times with meetings, personal work time, family obligations, etc. so meeting with anyone is fundamentally about choosing to prioritize them over something else you could or should be doing.” Finding time to meet together isn’t about filling open spots on a calendar, he said, it’s about the constant and necessary refining of what you care about and want to do.

And that gets back to the bigger idea, one that is already starting to change the tools we use and the way we use them: After so many years of chasing ruthless efficiency, in the name of doing more and doing it faster, intentionality is the next big thing in productivity. There’s already not enough time for everything. All that’s left to do is get better at picking where to spend it.

You tell us

We asked for your thoughts on Calendly, and your best scheduling tips, and you responded! Here’s a thoughtful response from Sidecar Health’s Rob Banning:

“It really depends on the organization. Some have transparency rules where everyone's calendar is open and some default to blind calendars. We trend towards the former vs. the latter at Sidecar Health. I always include the agenda in the invite so people know what we're going to discuss and I always define what the meeting is going to accomplish: Brainstorm, Decision-making, Check-in are the three most used categories. I also try to schedule meetings for 25 minutes (for 30 minutes meetings) and 50 minutes (for those that would normally be scheduled for an hour). This gives people a few minutes in between meetings for bio-breaks, checking on their pets or kids, and to prep for the next meeting. People really appreciate the time and are more likely to be on time for their next meeting.

Scheduling apps like Calendly are incredibly helpful for scheduling, for instance, my CEO has a specific Calendly link that I use to schedule meetings with journalists — simply: Press avails. On the flip-side, when I receive a Calendly link from someone that's trying to sell me a product or service before we've had an initial conversation, I find it incredibly rude.

Since the pandemic started, I live and die by my calendar. Everyone I interact with on a regular basis knows that my calendar is ALWAYS up to date, so they have free reign to schedule meetings when needed without checking with me first.

The other thing we've adopted at our house (my husband and I both do PR and are on the phone/Zoom all day), I got my IT department to allow me to share my calendar externally so he can see when I'm free and vice versa — it's made scheduling things like contractors, housekeepers and general errands much simpler.”

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