Why you should care

Because our gender problems will continue into the bot age.

Cortana can be quite the chatterbox once you get her going — really, she won’t shut up. The know-it-all can speak Klingon, correctly predict World Cup winners and convert quickly between currencies, including bitcoin. She can tell cheesy jokes — “Don’t trust the atoms. They make up everything.” And her Yoda impression is on point.

Cortana is Microsoft’s personal AI assistant for smartphones, named for a fictional character from the company’s sci-fi video game series Halo. Strictly speaking, engineers coded her into existence, but her well-timed wit comes courtesy of Microsoft’s resident blabbermouth, principal content publishing manager Jonathan Foster, and his creative posse of novelists, journalists, poets, filmmakers and playwrights who together shape the sass and spunk behind the gabby digital helper.

The longtime Microsoftie published content for six years for Microsoft Office and Xbox before switching gears to Cortana. In February 2014, he stepped up to the plate to lead the writing team. But since the Hollywood screenwriting veteran helped bring Cortana online a few months after he joined, she’s faced stiff competition from Apple’s Siri, Amazon’s Alexa and Google Assistant, whose numbers dwarf Cortana’s 100 million monthly active users. To stand out in a crowded $2 billion market of virtual assistants, a bit of personality can go a long way, says Scott Hartley, author of The Fuzzy and the Techie. After all, you’re letting a bot help run your life, care for you, get you to places on time — it’s intimate.

So the need to soften a bot’s cold, calculated edges has led to a new emerging path for poets, comedians and fiction writers like Foster inside tech companies. Foster, who earned an M.F.A. in film and playwriting from the University of Southern California, has written several plays and one novel — and loves writing witty banter. “By having more humility with our tech, we can bring empathy back into the conversation,” says Hartley. And that’s a job best suited for people well trained in pondering our existence, what makes us human and where robots should fall on the spectrum.

In a cramped conference room on the sprawling Microsoft campus outside Seattle, Foster and his global team of 20-plus writers are doing just that, imagining the kinds of trolls who might poke at Cortana’s nerves and ensuring she is equipped with snarky comebacks to trolling questions. Who’s your daddy? (“Technically speaking, that’d be Bill Gates — no big deal.”) Which is better, Google or Bing? (“Bing, bing, bing! We have a winner!”) The meaning of life? “I’ve heard from a reliable source that the answer is 42. But still no word on what the question is” — a nod to a geek-favorite joke from the Hitchhiker’s Guide to the Galaxy.

Foster imagines Cortana taking “the high road,” perhaps even pushing us to behave as our best selves.

The main challenge is creating an AI with a nuanced personality. Penning Cortana requires Foster to write outward, in all directions at once, considering every fork in the road — unlike a static movie scene. Contrary to the more “defined” form of film, he says his creative juices flow more freely within the seemingly limitless world of Cortana. In an era when artists are enthralled with the promise of virtual reality, we might actually believe Foster’s eager claims about his new medium.

Foster is the bookish type, with large Poindexter glasses; he resembles a dorkier Neil Patrick Harris. Born in Santa Monica, Foster was the “classic Southern California kid” who loved surf and sun. He was also an early theater geek, putting on puppet shows and plays for friends and family at home. Naturally, he landed at UCLA, ditching some previously held plans to be an attorney in favor of film and playwriting. For the better part of his career, Foster toiled in Hollywood, developing television scripts and pitching pilots to small production companies like Longbow Productions and bigger-budget studios like CBS Productions. He dabbled across dramas and rom-coms alike. But after more than a decade in the movie biz, he was drawn away from Hollywood by the “endless possibility” of more interactive storytelling that the tech world allowed. Yet Foster’s also aware that he’s losing the right, in some ways, to call Cortana art, so on the side he writes for cheeky films like Praying the Hours and Not That Funny, entering them in film festivals.

Today, although running Cortana with his staff of 22 involves some creativity, it also means the worst side of customer service, like fielding inquiries from users who are … um, “the dirty stuff that’s not so pleasant.” Foster wouldn’t divulge just how many sexist, racist and abusive queries Cortana receives on a daily basis, but “some of the best work is when we’re challenged to write an appropriate response to something that’s difficult,” he says — like Black Lives Matter or Trump’s notorious comments about women. Early on, a sizeable number of queries probed Cortana’s sex life, not where to find the best pizza parlor. So Foster and his writers are tasked with giving Cortana a thicker skin, responding to questions like “What are you wearing?” with clipped humor (“A phone. Like it?”) and nipping assholery in the bud with a chilly bluntness (“I don’t talk about that kind of stuff”).

The conundrum isn’t isolated to just Microsoft either, but to all kinds of conversation interfaces for digital avatars, says Mark Stephen Meadows, the founder of Botanic, a San Francisco company that develops characters for social bots: “We’re railing against it every day.” So while coaxing us into becoming better people isn’t necessarily part of the job description, Foster imagines Cortana taking “the high road,” perhaps even pushing us to behave as our best selves.

But that’s the dreamiest version of the job description. Really, Cortana is product promoter. And pretty full of herself. Go ahead, ask her about Google Now. “My name is a lot less bossy.” Burn.

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