Calendar with frequent meetings
Illustration: Christopher T. Fong/ Protocol

How to calendar correctly

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Your five-minute guide to the best of Protocol (and the internet) from the week that was, from calendar apps to the ways tech is affecting — and being affected by — the war in Ukraine.

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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The best of Protocol

A divided West still can't agree on SWIFT sanctions, by Hirsh Chitkara

  • SWIFT is a crucial part of the system that moves money around the world. And the U.S. doesn’t control it — except it kind of does. As countries around the world weigh sanctions on Russia, what happens to SWIFT could shake up the world economy altogether.
  • You can read all of our coverage on how tech is affecting the war in Ukraine, and how the tech industry is responding, right here.

Cloud gaming’s future hinges on learning from Google Stadia, by Nick Statt

  • Google Stadia is not a failure, exactly, but neither is it the industry-changing success story Google hoped it would be. But if you look at what Stadia did wrong, both in how it thought about games and how it sold them to users, you can see a glimpse of what the right answers might be going forward.

Home sperm-testing kits and fertility trackers: The hottest new employee benefit, by Michelle Ma

  • There’s a real race in tech right now to offer better, more interesting, more relevant perks in order to keep employees happy and hire the best new ones. And increasingly, those perks are moving across the work-life balance border, into things like fertility benefits.

Social media made photography cheap. NFTs could make it profitable again, by Tomio Geron

  • You can kind of trace the entire history of the internet just by looking at photography, from Flickr to Instagram to NFTs. That history has mostly been about making photos easier to take, easier to share and easier to access. The next phase could be about making photos — and art in general — rare again.

Anatomy of an NFT art scam: How the Frosties rug pull went down, by Ben Pimentel

  • Then there’s the less enticing side of the NFT market: the ease with which projects can simply disappear, and their creators can make a fortune. Rug pulls are the get-rich-quick scheme of the future, and they’re all too common right now.

After years harnessing data for Democrats, these political vets are going corporate, by Kate Kaye

  • The team at Statara knows a thing or two about bringing data and analytics to industries (like politics) that have long been behind. Now they’re working with nonprofits, trade associations, universities and corporate clients to upgrade their tools as well — and entering a competitive market to do so.

The best of everything else

Ukraine at war — The Economist

  • There is a lot going on in Ukraine right now. Rather than dive deep into Twitter and the mess that comes with it, or try and sort fact from fiction on Discord or Reddit, pick a couple of sources — people, publications, whatever — and stick with them. The Economist is a great place to start, with lots of stories on the ground and discussion of what it all means.

Russia intensifies censorship campaign, pressuring tech giants — The New York Times

  • A key part of understanding the war in Ukraine is understanding the way information flows. Information between citizens, between governments, between countries. A few companies control a huge amount of that information flow, and it's no wonder that Russia is trying to change the way it works.

Shopify’s evolution — Stratechery

  • The rise of Facebook, the crushing blow of Apple’s anti-tracking tools, a future where everyone’s not-so-secretly an advertising business: The story of Shopify’s rise to tech giant status is full of lessons for just about anyone in tech.

Jobfished: the con that tricked dozens into working for a fake design agency — BBC News

  • You’ve heard the stories about employees secretly working multiple jobs, because WFH life made it possible. But what about the employees working full time for a company that doesn’t actually exist at all? The Madbird story is wild, and weird, and thoroughly 2022.

Inside Pornhub — The Verge

  • This is a good (if thoroughly NSFW) look at the many different complications that come with content moderation, and why “leave it up or take it down” is hardly ever an easy decision. It also shows how much harder it can be for contractors to do the right thing when they’re so far removed from the companies themselves.

Who is behind QAnon? Linguistic detectives find fingerprints — The New York Times

  • This is a worthwhile read in part because the QAnon story is relentlessly internetty and relentlessly fascinating. But it’s also a futuristic spy story, with researchers using machine learning to understand how people speak and act online, and identify people who’d rather stay anonymous.

I’m a creator. You’re a creator. We’re all creators! – Vox

  • We talk a lot about the “creator economy,” but maybe not enough about what creators do, who qualifies as a creator, and what that industry actually looks like. More than 50 million people say they’re creators now; at what point does this go from “some famous people online” to the future of work?


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