Award-winning author, dynamic keynote speaker, trusted advisor, & workplace tech expert 


On Calendly Etiquette

When egos, tech, and the desire for efficiency collide.
Feb | 2 | 2022


Feb | 2 | 2022
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In Reimagining Collaboration, I tell the tale of a possible collaboration that never got off the ground. TL;DR: Another individual didn’t want to use my YouCanBookMe page to, you know, book time with me. Note that he insisted that we continue to use e-mail to hit a moving target.1

At least I’m not alone. It turns out that mine is hardly the only kerfuffle involving contemporary scheduling tools.

The Calendly Conundrum

Protocol published a timely piece on that very subject. The maelstrom that Facebook (Meta?) VP Sam Lessin recently caused on Twitter served as the story’s background:

Exhibit A that social media doesn’t exactly lend itself to nuance, but I digress.

At a high level, a person from Company A needs to meet with someone from Company B. Seems innocent enough, right? Yes, but it turns out that there’s often an unspoken power dynamic or flat-out pissing contest taking place.

The Seinfeldeque subtext is often: You want me to use your tool? Who the hell are you?

This is but one of the many issues that plague interorganizational communication and collaboration.

For years, I have happily used others’ scheduling apps because of the time they save. (In keeping with the Hub-Spoke Model of Collaboration, I stitch together Calendly with Zoom and Slack. #practicewhatyoupreach) At the same time, though, I’m not completely oblivious. I understand how my obsession desire for optimal efficiency could put some folks off. Regardless of my benign intent, I can see how a person could balk at having to use my scheduling tool.


To that end and in an effort to have my cake and eat it too, I modified my response about a year ago: To make scheduling as easy as possible, please look at my [Calendly link] and book a time. Alternatively, if you use a similar scheduling tool, shoot me a link.

I find that the second sentence diffuses any potential tension. I’m happy to report zero dustups since that minor tweak. As Homer Simpson once said, “Well, Marge. Self-improvement has always been a passion of mine. Bring on the swear jar.”

Here’s a typical response to my new approach:

Wonderful! Just set up some time for tomorrow. Looking forward to it!

Problem solved.



  1. I’ve since moved to Calendly.

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