All of the big players are doing it.

Apple has Siri, Google has Google Now, Microsoft has Cortana, and China’s Baidu has Duer. Even smaller players are getting into the market, too. New York-based start-up has Amy and Andrew. These virtual assistants are designed to make your life easier. Some have personalities all their own, while others simply stick to business.

If Anna had gone and looked for that job, she wouldn’t have found it. It’s a role we invented 

But how do you inject humanity into technology? It’s not simply a matter of code and voice-over. Behind these assistants are writing teams crafting every word and phrase. And in many cases, those teams are anything but what you’d expect. Among their ranks: former poets, screenwriters, playwrights, and novelists who are being hired in increasing numbers to make virtual assistants come alive and, well, be more human.

Folklore to AI

At Harvard University, Anna Kelsey studied folklore and mythology but spent the bulk of her free time directing, producing, and managing plays. When she graduated, she thought she might pursue a career in theatre but wasn’t quite sure. She decided to move to New York. “New York is expensive and if you want to work in theatre, you still have to make money somehow,” said Kelsey, 24.

She found her way to the artificial intelligence (AI)-focused start-up and quickly moved up from AI trainer—where she annotated data extracted from scheduling related emails— to AI interaction designer, a position created by to design the dialogue model that determines Amy’s responses and to develop Amy’s voice.

“If Anna had gone and looked for that job, she wouldn’t have found it. It’s a role we invented,” said Stefanie Syman, the company’s head of communications.


For Kelsey, the liberal arts’ background has helped her succeed in her job: helping craft what Amy and Andrew, the company’s two virtual personal assistants, say to people in their email exchanges.


“A liberal arts’ education really teaches you about critical thinking, problem solving, and finding resolutions and pulling out meaning for different things and interpreting it,” she said. “You need to be excited about solving a problem that no one’s ever solved before, and that’s what we do here.”

A growth industry, for its part, recently raised $23m in new funding. Since 2010, funding for artificial intelligence start-ups has gone up nearly sevenfold: from $45m to $310m. And the market is expected to reach $11.1bn by 2024, according to technology research firm Tractica.

It’s further proof that technology groups are calling for creative thinkers. 

With all of that money will come the need for more writers and creative types to bridge the gap between technology and humanity.

“It’s further proof that technology groups are calling for creative thinkers,” said John Reed, senior executive director at Robert Half Technology. “As technology continues to intertwine with all industries, it will also continue to include professionals with various skill sets in order to create the most effective products and services possible.”

From TV to AI

Jonathan Foster, head of the writing team for Microsoft’s Cortana, began his career in film and television but said he always had a thing for tech. “Early on I was interested in the tech meets storytelling thing,” he said. Eventually he found himself at Microsoft, heading up the Xbox writing team. But it was his move to the Cortana team two years ago that made him feel he had really found his place – in the seemingly disparate worlds of AI and creative writing.

“Here we’re developing a personality, just like a screenwriter develops a character,” he said. “Whether it’s text or voice driven, it’s conversational interaction, which maps to the dialogue skillset I developed over years and years writing screenplays and before that, plays. It just kind of snapped into place for me.”

We’re developing a personality, just like a screenwriter develops a character.

Today, Foster leads a team of six in-house writers and another five writers spread around the globe. Surprisingly, humour has proven to be one of the hardest parts of Cortana’s personality to develop. Early on, it was decided that Cortana would have a “positive” personality, someone who left people feeling good after walking away from an interaction with her – but of course that also meant her humour needed to stay on the up and up. “It’s very difficult to stay positive with humour,” Foster said. “Because to be positive means you can’t throw anybody under the bus.”


For dilemmas like these, he calls on his team of writers, everyone from a poet in London, a screenwriter in Madrid, to a novelist in one of the offices down the hall.

 We are seeing an increasing need for infusing digital skills across the humanities.

It is crucial, he said, that artists who understand and appreciate the world of technology are brought into the field. “You have to love that part of it, you have to love the tech as a creative writer, because you’re going to be thrown into the thick of it,” Foster said. “The more immersed you are in that world, the better impact you are going to have on the writing. It requires the desire to understand a vast landscape.”

Universities taking note

As the demand for such hybrid interests increases at long-established tech companies and start-ups alike, universities are responding.

We are seeing an increasing need for infusing technology and digital skills across all disciplines including the humanities,” said Phil Ventimiglia, chief innovation officer at Georgia State University. “Every industry has been transformed as the result of technology.”

In response, the school launched the Digital Literacy Initiative in 2015. English Composition has been rethought to examine how learning the rhetoric of writing can also introduce students to creating a blog and designing a web page, according to Ventimiglia. The university is just one of many trying to infuse tech into humanities.

Too much of a good thing

I have the greatest respect for humans.

Of course, making virtual assistants and AI products too human can have its challenges. At, for instance, Andrew and Amy are so efficient and convincing in their email exchanges that some people have mistaken them for humans and suggested chatting by phone. One of Kelsey’s responsibilities has been to write the response to such a situation.

Meanwhile, at Microsoft, when asked if she is human, Cortana responds: “No, but I have the greatest respect for humans. You invented calculus and milkshakes.”

But, say experts, that might just be the price of successfully incorporating playwrights and poets into a very un-human world.

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