Write the Perfect Email to Anyone With This Creepy Site

When my editor Joe told me to write this story, I knew with algorithmic certainty how to respond: “Done. Absolutely. It’s taken care of.”
I got this advice from Crystal, a site that promises to help you understand how best to talk to any particular person. All you have to do is pick the subject. Crystal will then slurp up public data from around the web, run it through “proprietary personality detection technology,” and spit out a detailed report on that person’s preferred style of communicating. It’s one part oppo research, one part algorithmic astrology. It’s definitely creepy, perhaps useful, and almost certainly a look at how we’ll communicate in the future.
In the case of my editor, Crystal’s dossier was surprisingly accurate: “Joe is an achiever: fast-paced, ambitious, and persuasive, so get to the bottom line and don’t feel insulted by a direct or blunt comment.” When speaking to him, it told me to use words like “done,” “absolutely,” and “it’s taken care of.” In email, it recommended limiting my message to three sentences and stating my purpose clearly in the first line. After all, Crystal informed me, “it does not come naturally to Joe to be accommodating and forgiving with his time.”

Like anything that cultivates an association with magic, Crystal is less impressive once you know how it works. If someone were looking you up, the site would start by examining things you’ve written publicly—social media profiles being a primary source—and analyzing factors like writing style and sentence structure. Then it processes what others have written about you. Using those data points, the site identifies you as one of 64 communicative types, which the company has adapted from well-known personality frameworks. Crystal doesn’t really know you, in other words, it just knows what you’re like.

According to co-founder Drew D’Agostino, that can be enough. “The beauty of these frameworks is that, if you know one bit of data about a person and you’re accurate about it, you can make really good assumptions about how they’re likely to communicate,” he says. Building the model required considerable experimentation, but given a certain volume of writing, “we figured out a few algorithms that really nailed it,” D’Agostino says. In my experience, the results seemed a mix between useful characterizations and fortune cookie-like truisms.

It wasn’t immediately obvious what to do with the technology, but D’Agostino and company eventually arrived at an answer: email. Beyond letting you look up reports on individuals, paying customers get access to a Chrome extension that puts Crystal’s oracular advice right in your inbox. While emailing D’Agostino to arrange an interview, I noticed a new ochre button in my Gmail compose window. It bore an exhortation: “Be brief.” I was startled, then followed its instruction.

There’s a lot of anxiety involved in sending email, D’Agostino says. It can be hard to know what sort of greeting to use, or whether to include a joke. Crystal tries to remove some of that ambiguity. Clicking the “Be brief” button pulled up more detailed suggestions, providing specific phrases to use and avoid in that particular scenario. Crystal even goes so far as to offer a fully-written email template, algorithmically derived for the recipient.

That of course is the dream implicit in all this: A button that sends the perfect email every time. Indeed, a number of artists have explored the contours of this queasy future in recent months. A browser extension by Joanne McNeil fills emails with exclamation points and smileys, automating the “emotional labor” required in today’s cheerful correspondence. Lauren McCarthy and Kyle McDonald took these ideas a step further with Pplkpr, an app that uses biometric signals sort the real life acquaintances that invigorate you from those that aren’t worth your time.

Pplkpr is satire—it’s funded by the Andy Warhol Foundation for the Visual Arts—but it seems like an artifact from a plausible, perhaps even likely future. Marshall McLuhan once said artists are always the first to figure out how technology will change culture, and there are signs we’re headed in Pplkpr’s direction. Increasingly, we meet partners on dating sites, paired by algorithms. Our phones become ever more adept at parsing conversations and suggesting programmed replies.

D’Agostino says he built Crystal because he wanted to technologically enhance his emotional intelligence. And such a tool probably could be helpful, say for knowing the person you’re sending a job application to hates wordy emails. But surely there’s a point at which algorithmically informed communication curls back around, mobius-strip style, and we end up even more remote and unknowable to each other than we were when we started.