Give Good Email

Calendly use seems to provoke strong feelings – especially so on Twitter – and a recent tweet from Sam Lessin complaining about Calendly etiquette as a “naked display of social capital dynamics” reminded me of my longstanding thesis that human interactions cannot simply be “solved” with technology. In fact, I think Sam’s particular issue has little to do with the mechanics of Calendly almost everything to do with the ability to carry on polite human interaction via email and the internet.

I was long hesitant to embrace Calendly for fear of the exact perception issues that Sam outlines (and which many a tweet has railed against), but I’ve since come to the conclusion that Calendly is actually a very fine piece of technology that can make scheduling a great deal more pleasant for all involved – provided it’s used with just a little common sense and consideration for our fellow humans.

The tool is not the problem here. What we have is PEBKAC: Problem Exists Between Keyboard And Chair. (hint: the problem is you. Good news, though – you can also be the solution)

If I launch a Calendly at you in an email with little or no context expecting you to insert yourself into my Very Busy and Important Schedule, then of course I risk coming off as nakedly self-serving and impolite, and deservedly so.

There’s a straightforward solution here that I’m a little surprised so many Calendly haters seem to either overlook or be incapable of arriving at on their own: just give good email!

It seems many people have forgotten (or never learned?) how far some basic etiquette and polite writing will get you in life.

I regularly use Calendly, including in situations where I’m unquestionably the party with “lower status.” The difference is that I don’t just toss a link at people. Instead, I make it clear that I’m happy to defer to a time of their choosing, while offering my Calendly link as a faster option. Usually my emails include something like:

Feel free to propose a time that works best for you, or you can use my Calendly link if that’s faster and not too impersonal.

The surprising thing is that almost everyone, including those of “higher status” or from whom I presumably need/want something, chooses the Calendly link. It’s just more efficient in most cases!

I’m now fortunate to also have a wonderful exec admin who helps me with scheduling logistics, but even so I will often give folks the option of using Calendly or interacting with my EA to find a mutually agreeable time. Most still choose the link. Frankly, I find an unceremonious or curt handoff to a human EA for scheduling is even more off-putting than a carelessly deployed Calendly link. I see the former as an even more naked power play; basically “talk to this obviously lower status person for scheduling because I can’t be bothered with such mundanity.” Again, it’s a pitfall easily avoided by just giving good email and politely looping in an assistant with a little bit of empathy and/or humility.

For the productivity-obsessed for whom hand-crafted emails are too much, technology can help scale empathy. I have a few Superhuman “snippets” (pre-written phrases) which I can insert with just a couple keystrokes. Voilá! I’ve powered through my inbox and channeled my inner Emily Post. C’est magique.

If we ever find ourselves trying to find a mutually agreeable time to meet, feel free to send me your Calendly link. I promise I won’t be offended. :-)