Image: Joshua Huston

Ask Witty Bot where the restroom is in a coffee shop, and it will answer in metered verse: “Two bathrooms, both alike in dignity / In Fourth Coffee, where we lay our scene / To gender norms we pay no scrutiny / And civil tap makes civil hands quite clean.”

Deborah Harrison, the writer behind Witty Bot, is proud of her Shakespearean digital personality. Harrison studied English in college and worked in a bookstore and as a writing tutor before starting in the tech industry two decades ago. In 2013, she became the original writer for Microsoft’s virtual agent Cortana, and today the senior content experience manager at Microsoft is at the helm of Microsoft’s AI and bot conversation creation teams, authoring content for conversational agents across Microsoft.

For Harrison, creating dialogue requires a deeper understanding of human perspectives and communication. “When you converse with anything using human language, you are having the same natural responses — or related emotional responses — to the ones you have when you talk to actual people,” she says. “We honor that emotional reality. It’s really important to us that we aren’t putting people in a position to have a negative experience because of our lack of intention.”

One way her team strives to create positive interactions is through developing virtual personalities that meet the needs of Microsoft’s diverse audience — a goal that requires providing various perspectives and acknowledging the team’s limitations as “a finite set of people with a point of view born of [their] context.” Harrison also champions empathetic interactions. “We talk about how to arbitrate kindness,” she says. “You can declare that a bot is designed to be positive, but how do you ensure that it’s expressed time and again? That’s something we come back to in all the personas we devise.” 

Also important is a bot’s ability to manage derogatory remarks. “We built a whole suite of responses that we hoped would make it clear that Cortana understands it is inappropriate to talk to an agent that way,” Harrison says. “The hope was to model appropriate boundaries for the character that we had created.”

This modeling has taken hold in Harrison’s own life. “I am giving these agents a voice I would sometimes hesitate to give myself,” she says. By building healthy boundaries for the bots, Harrison is encouraged to advocate for herself. “Being able to practice agency with these pretend beings has given me a lot more ability to do that in my own universe. It’s pretty remarkable.”

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