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How ‘book a time on my calendar’ became one of the most aggressive things you can say at work

February 4, 2022, 12:00 AM UTC

On Jan. 26, investor and entrepreneur Sam Lessin shared some thoughts on Twitter about the scheduling app Calendly and the general practice of booking yourself into someone’s calendar via an emailed link.

Calling the practice the most “raw/naked display of social capital dynamics in business,” Lessin wrote, “When someone sends you a Calendly link and asks you to slot yourself on their calendar, they are telling you that you are less important than them…It’s a ‘Get in line’ move.”

The tweet goes on to say that meetings require a nuanced back-and-forth between two parties to delicately consider priorities on each end, and ultimately mutually shift calendars to finally align. The comments that followed ranged from utter ignorance that anyone could take offense at receiving a link, to a spirited embrace of the power move. “Notice with immediate effect: Anyone who disregards my Calendly links will be permabanned from raising venture capital in Silicon Valley,” wrote @pmarca. “If it’s decided that @calendly links are socially distasteful, there is always the back up method of horse mounted couriers waving white flags of truce,” noted @alhemmingsen. (In case you missed it, hop on Twitter and search @calendly or @lessin and you’ll find yourself deep in this rabbit hole too.) Calendly CMO Patrick Moran says that at one point someone, somewhere, was tweeting the word Calendly every six seconds. And, in fact, Moran’s team posted in response a Brady Bunch–type meme of themselves eating popcorn as they watched the Twitter aftermath of Lessin’s post unfold—and thanking him for the spike in sign-ups.

The back-and-forth continued for days. And it’s no surprise why. In a few short years many of us have gone from feeling in total control of our own calendars to instead accepting they are a semipublic entity, on which meetings can suddenly materialize in any time block left open. While some among us spend our days jumping from Zoom to Zoom every half hour, others must block out “fake” meetings in order to preserve time for, you know, work. In most cases, notes Gustavo Razzetti, founder at Fearless Culture, a Chicago-based culture consultancy, “meetings can be a sign of how we control people.” After all, time is arguably the most precious resource any of us have, and the dance required to match schedules to borrow, share, or claim time with anyone at this point can trigger all sorts of dynamics.

Scott Stiles has been working at Microsoft since before the advent of Outlook in 1992. He is now the VP of product management for Outlook at Microsoft and says these questions are at the heart of his day-to-day. “It’s been exciting to see the evolution,” says Stiles. “The internet broke everything loose. Outlook has evolved over the years. At its core, there’s this belief that there is unique value in a tool for you to keep organized and get things done. I’ve had an amazing time working through the shift toward multi-device, multimodal, work-from-anywhere. Personal time is just blending in.” Stiles’s perspective on meetings, how we schedule them and what that means in terms of our relationships and interactions, is certainly unique given his ability to consider how it started and where it’s going. “It’s transformational to schedule a meeting with a group of people you know are really busy, while on your phone, standing in line at the supermarket,” he says.

Calendly, meanwhile, was founded by sales guy Tope Awotona in 2013, who was looking to make his back-office work of meeting-making easier. Now it’s used by more than 10 million people in 116 countries, especially in the context of meetings for the purpose of sales and recruiting. Moran says that while it makes the scheduling a bit more efficient, the user experience piece Stiles mentions is key. “It’s easy to solve the thing Lessin was talking about,” says Moran. “You start with human. And then you think, ‘I better put some words around this thing. Hey, here’s my link but feel free to offer times that work for you or send me your link.’ What is that? Twenty words?”

Razzetti agrees, adding that by sharing a link you’re giving people options. Just as easily, he says, the response could be a request for flexibility or compromise: “For example, I have a link that I only use for clients in Europe that shows I’m available 6:30 to 8:00 a.m. CT. I’d never take meetings so early, unless for European people. So I’m using Calendly with flexibility, not as ‘my way or the highway.’” 

Professor Cait Lamberton teaches marketing at the University of Pennsylvania’s Wharton School of Business and has done a fair bit of research on dignity and respect in the workplace. She says the Calendly debate gets deep into the heart of whether or not we feel valued in any given work relationship. “We feel we are treated with respect when we are seen and heard and have both agency and control,” says Lamberton. “When people have their email set up to immediately shoot back a link for their calendar without interaction, you get a response that started the Twitter uproar.” Context and communication, she says, are incredibly valuable, as they can speak to the nature of a relationship and address the purpose and urgency attached to a meeting. “It can feel very disrespectful,” she says. “That’s why it’s your responsibility to engage your own agency and make sure the interactions are happening in a way where everyone feels good about the outcome.”

Of course, for some the larger point isn’t who clicks whose link to book a meeting, it’s that technology is enabling more unneccessary meetings. Ethan Eismann, SVP of design at Slack, agrees. “Meetings can be extraordinarily draining. It’s almost antihuman. The majority of meetings you don’t need to be in. Can we do meetings in a different way? There’s going to be a revolution in productivity,” he says. (He also noted that before our call he took three meetings while walking in his neighborhood then saw a virtual huddle and jumped in and out of that.)

Both Calendly and Zillow have given up their formal brick-and-mortar office spaces, allowing employees to work from anywhere. To combat meeting fatigue and protect focus time, both companies keep internal meetings to a specific block of hours each day (noon to 5 p.m. EST at Calendly and 1 to 5 p.m. EST at Zillow). “Let’s respect that we don’t always want to be on,” says Meghan Reibstein, VP of organizational operations at Zillow. “There’s time we should collaborate and there are ways to work that don’t involve meetings. It is okay to control your schedule.” Zillow also ended 2021 with two weeks of quiet, when employees were encouraged to cancel any meetings they had. “This was huge internally for people to just say no,” says Reibstein.

In Razzetti’s work, he has seen businesses limit the number of people in meetings (Amazon’s rule that no meeting can exist with more people than two pizzas can feed), enforce a silent first 15 minutes to build in time for everyone to read any necessary briefs before it begins, place bans on PowerPoints and bulleted slides, and even build physical spaces in the office that encourage spontaneous brainstorms and conversations over coffee or in passing that abandon a preconceived meeting structure (Ikea has a striking open stairwell where this often happens).

In the absence of that protective admin monitoring your schedule, says Stiles, there’s an individual responsibility to balance the technological piece with the need for boundaries. Also important, says Stiles: keeping on top of your preferences on when you’re available for internal or external meetings, using thoughtful language around scheduling apps or links, and building in time when you’re just not available for any subset of potential meetings. Overall, says Razzetti, meetings “should be the last resource” to land on after considering if the work can be done asynchronously, or you can leverage Slack or another messaging platform to share ideas or accomplish a goal. “It’s a mindset,” he says. “Meetings are the symptom of something bigger: Are we trying to do everything, or are we focused on something important? When you say no to a meeting you can say yes to do more meaningful work. Who is guilty, the one who sent the invite or the person who accepted it?”

As for Lessin, his tweet prior to the one about Calendly referenced taking a meeting from an ice bath—perhaps making that move a close second for the most naked display of social capital dynamics in business.

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