Inside Windows Cortana: The Most Human AI Ever Built by @tynanwrites

Inside Windows Cortana: The Most Human AI Ever Built by Dan Tynan Tech Columnist

Tony Stark had Jarvis. Luke Skywalker had C3PO. And, if Microsoft has its way, very soon you’ll have Cortana.

Like Apple’s Siri or Amazon’s Alexa, Cortana lets you talk to your devices as if they were people. And, like those two voice-driven interfaces, she can understand what you’re saying and respond in a way that feels almost human.

But unlike those other virtual entities, Cortana will work across PCs as well as phones. And it will do far more than just retrieve information; Microsoft wants Cortana to be the Alfred to your Batman — handling your communications, managing your calendar, and attending to your needs.

On July 29, when Microsoft begins releasing the latest version of its operating system, the world’s 1.5 billion Windows users will have access to one of the most human-like artificial intelligence interfaces ever made.

But Cortana presented a unique challenge to Microsoft’s developers: How do you imbue a series of bloodless algorithms with a human personality? What form should that personality take? How clever should it be? How nice? And can you persuade people to fall in love with it?

To find out, we spent time with the team behind Microsoft’s daring experiment and with Cortana herself. This is her story.

Jarvis 1.0

A few years ago, when Microsoft was struggling to give consumers a reason to buy its phones, it did what Microsoft always does: It held focus groups. From those groups it learned something essential about what users wanted, according to Marcus Ash, group program manager for Microsoft’s Cortana and search teams.

While having constant access to information is good, the focus folks said, having a device that actually does things for you is better. Instead of something that could display all the flights from San Francisco to New York on a particular day, for example, customers wanted one that would book the flight, pick an aisle seat in business class, and order them a kosher meal — all on its own.

That became the design goal: a digital personal assistant that would set Microsoft’s devices apart from everyone else’s. The early name for this concept was Jarvis, named for Tony Stark’s virtual valet.

The first question the Microsoft team had to answer: How should the ideal personal assistant act? To find out, Microsoft interviewed a half-dozen high-powered assistants to Hollywood executives and technology CEOs. All of them had one thing in common: extremely detailed knowledge about the boss, usually contained in a notebook that rarely left the assistant’s hands. Not merely their bosses’ schedules or the list of people whose calls they were trying to avoid, but also things like whether they preferred veggie burgers to sirloin steak, dinner jazz to R&B, or town cars to taxis.

To do the job well, the assistant had to be able to use that knowledge to anticipate the boss’s desires and make decisions on his or her behalf, says Ash. To work as intended, Cortana will need to read your email and manage your schedule. She’ll need to know which sports teams you follow, the stocks you track, where you went on vacation, and dozens of other personal details. It’s an intimate relationship requiring enormous amounts of trust.

“Cortana can’t be very helpful if she doesn’t know anything about you,” explains Ash. But Microsoft believes the key to trust lies in transparency. Users will to be able to see what data Cortana collects, what she does with it, and then have the opportunity to say “no thanks,” he adds.

The chit chat

Convincing users to extend that level of trust to a faceless digital entity was the second challenge facing the Cortana team. For Cortana to have any chance of success, she needed a personality. So Microsoft hired a team of writers to create one.

Every morning at 10 a.m., Jonathan Foster assembles his team in Building 50 at Microsoft’s North Campus. The team includes a screenwriter, a playwright, a novelist, and an essayist. On the wall, a screen displays a query Cortana has received that can’t be answered via simple search results.

The team’s job, for the next hour or two: come up with human-like dialogue that makes Cortana seem like more than just a series of clever algorithms. Microsoft calls this brand of quasi-human responsiveness “chit chat.”

Most of these questions aren’t seeking information; instead, they’re testing the limits of Cortana’s intelligence and/or patience — in other words, they’re pure entertainment. Users want to know what she thinks; they want to see whether she’ll respond with shock or outrage or confusion.

Like writers for a TV sitcom, members of the chit-chat team go around the table trying to out-do each other with witty responses. It is, Foster admits, a great job. But it’s not an easy one.

“Our No. 1 priority is for people to walk away from their experience feeling good,” he says.

But even a seemingly innocuous question like, “Do you like dogs?” can generate a nearly infinite range of responses, most of which will likely offend someone. If Cortana says dogs are her favorite animals, you risk drawing the ire of the Internet’s legions of cat lovers. If she says she prefers Schnauzers, you alienate fans of Labradoodles.



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