The question of "is sending a Calendly link rude?" comes up often enough that the scheduling app has a whole blog post and ebook addressing it. The latest Twitter debate stems from a post by former Facebook VP Sam Lessin calling Calendly "The Most Raw / Naked Display of Social Capital Dynamics in Business."
Lessin, now a partner at VC firm Slow Ventures, argues that if you send someone a Calendly link, you're telling that person you're more important than them. When the sender is clearly a higher-up, like the "president of the US," then Calendly works. Otherwise, Lessin says he won't use it. "But just be clear about the social message I receive from you of your asserted self worth when you send me that link :)," he writes.
Others promptly weighed in, with one user calling it a "weirdly aggressive reaction to Calendly links." Overwhelmingly, people jumped in to defend Calendly. Users said the tool helps eliminate back-and-forth emails, and inspires focus. "The weirdest part of this Calendly discourse is it could have been solved with therapy," one user tweeted. Lessin's former Facebook colleague Dustin Moskovitz asked "who hurt you Sam". Marc Andreessen declared that anyone who disregards his Calendly links will be "permabanned from raising venture capital in Silicon Valley."
This has come up on Twitter before. Even in 2019, people were making fun of others taking offense at Calendly links. In September 2020, some people brought the debate into perspective by sharing Calendly's high revenue stats. Calendly's CEO Tope Awotona responded playfully to Lessin's post on Thursday, thanking him for an apparent spike in sign-ups.
Twitter drama aside, the company acknowledged that some people do feel sending a Calendly link implies a certain power dynamic. In an email to Protocol, Calendly communications manager Samantha Bosio noted that striking an approachable tone may help when emailing someone your scheduling link. “Feel free to share some times you’re available, or you can also pick from my Calendly if it’s easier," is one example. Overall, you want to emphasize that you're trying to respect the recipient's time.