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Why Calendly Isn’t Evil

A dramatic tweet started off a battle of two minds

Francesco D'Alessio
2 min readJan 28, 2022

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This week, Sam Lessin kicked off on a topic that sparked much drama in the productivity space, something you don’t often see — with a deep dive into why he believes Calendly is a disrespectful tool.

💬 Why he isn’t wrong

The thing is, in premise, I actually agree with him. The act of sending a Calendly/or any other tool, as a one-way matching of your time is a little bit one-sided.

Don’t get me wrong, I like Calendly and most other calendar arrangers, they do us a great service in helping us find slots that help us get work done.

But I do believe that we need to make availability sharing more 2-way, and right now we’re actually at a cross roads to how we can do that without going full machine learning. There are alternatives to Calendly, but none that fully considers time — that isn’t a team tool (Clockwise does offer team AI management).

📣 His delivery was awful

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