This email plugin made accurate judgments on my ideal email and now I'm shook

As part of technology startups’ never-ending quest to automate all of our messy, personal interactions, there are now artificially-intelligent plugins promising to advise us on how to write better emails to our colleagues. Does your colleague need long, winding intros before you ask that favor — or do they prefer you to get straight to the point?

First developed in 2014, and gaining wider attention now, Crystal is an application that can integrate with your calendar, LinkedIn, and inbox. It promises to have data-driven answers to these kinds of murky questions. On its website, it says it analyzes “public data to tell you how you can expect any given person to behave, how he or she wants to be spoken to, and perhaps more importantly, what you can expect your relationship to be like.”

Once you’ve allowed it look at your email messages and contacts, you let Crystal’s “proprietary personality detection technology” become part-nosy detective, part-grammar teacher to look up your public content, writing style, and sentence structures, and make judgments about what you like.

Trying it out

The best way to test Crystal’s claims, I decided, would be to test it on myself. With some trepidation for what it would reveal, I signed up with my work email and let Crystal’s algorithms into my life.

Culling through every public social media post it could find, articles and blog posts I’ve written, and the DISC Personality Assessment I took, Crystal’s algorithm sorted me into one of 64 “communication types” adapted from personality frameworks. Crystal’s dossier judged that I was “very social, compassionate, trustworthy” and I wanted “a stable environment (avoiding confrontation if possible).”

Although these assessments made me sound like a shelter dog looking for my forever home, they were not wrong. I wondered which tweet or personal blog post gave me away. I am indeed “relationship-oriented,” and if someone wants me to respond quickly in an email for career advice, it’s best to leverage interests and relationships we have in common.

Crystal’s pro-tips for people who want to have successful emails interactions with me?

• “Point out personal connections like common friends or interests”
• “Use a sentence to express appreciation for her time”
• “Add non-essential but friendly lines like ‘hope you’re doing well”

All of these statements were true, but I was unsettled to see these interpersonal cues broken down so mechanically and transactionally.

How many people using Crystal were writing non-essential lines to throw me a bone in my daily interactions?

Pretty good, not perfect

Crystal’s judgment wasn’t completely right. I am definitely not a “natural planner,” but then again — like astrology — Crystal doesn’t present its advice as hard facts. Even in its disclaimer, Crystal notes that its judgments are intended more as a guide than a factual answer: “Statements in the personality profile are not intended to be factual—they are a combination of estimated personality insights intended to provide a ‘best guess’ about a person’s preferred communication style.”

If you fork over money for a paid Crystal subscription, you can use its Email Coach extension. Through this feature, you get more concrete, real-time advice on how to draft emails to contacts as it looks up publicly available data on them to give you the best research on how to reply to them.

With generational and cultural differences at play in the workplace, employees are right to worry about having their tone and meaning misunderstood in communications. There are office etiquette guides to Slack and real-time spellcheck plug-ins dedicated to helping anxious workers present their best, curated self at work.

If writing networking emails to strangers makes you anxious, having Crystal on your side can feel like the boost needed to get your tone right. But as for me, it’s also a reminder that if you want to know who someone is beyond their AI-selected assessment profile and computer-assisted emails, it’s better to meet them face-to-face.