Intelligent Email

Our collective use (and abuse) of email has rendered it more of an endless game of whack-a-mole than an effective communication tool. The more email you send, the more you receive. And when compared with the plethora of real-time communication methods at our disposal—like texting or instant messaging—email feels sluggish. According to a 2012 Pew report, a scant 6 percent of teens use email daily, while 63 percent send texts.

Email giants like Microsoft, Yahoo, and Google have all gone back to the drawing board to find a fix, but to little avail. Microsoft just relaunched Hotmail as Outlook.com, replete with a less-cluttered interface, new forms of messaging like video chat, and better filters for separating personal messages from newsletters and junk mail. Yahoo is also in the process of releasing similar updates. A new crop of startups—like Boomerang, a Gmail plugin that allows you to schedule an email to be sent later, among other things—are also working to alleviate email-inflicted pains.

While these solutions chip away at the symptoms, none fix the underlying problem. Email in its current state is essentially a decision-fatigue engine, constantly prodding you with questions: Which message should you open now and which later? What’s the context? How do you know the sender? Anyone can email you anything at any time, and all those messages land in your inbox, urgent messages competing with coupons and newsletters.

Fixing email means finding a way to make these small but complex decisions for you. Gmail’s “priority inbox” scratches the surface by using machine learning to organize email according to relevance, so you’re less likely to miss something important in the incoming deluge. This type of machine learning—or narrow artificial intelligence, also used in products like Apple’s Siri—tracks specific factors, like a sender’s email address, in order to make decisions on your behalf, like highlighting messages from someone you email frequently. But since narrow AI is not yet sophisticated enough to match human decision making (if it were, we’d have larger philosophical questions to answer), it only works when given a fixed range of choices.

Asana, a newer “post-email application,” also uses narrow artificial intelligence. Brian Singerman, a partner in Silicon Valley’s well-revered Founders Fund—best known for its early investments in companies like Facebook and PayPal—says he invested in Asana because he believes a healthy marriage between machine learning and human design is the key to fixing email. That holy grail doesn’t exist yet. Till then, you’ve got mail.