Tag Archives: Siri

Microsoft’s Cortana Designed to Not Put Up With Dudes’ Bullshit | The Mary Sue

Microsoft’s Cortana Designed to Not Put Up With Dudes’ Bullshit | The Mary Sue:

Microsoft’s Debora Harrison is one of eight writers who composes Cortana’s dialogue for use in the U.S., which means she helps craft Cortana’s jokes, banter, and responses to people who want to get fresh with her. Harrison explained at the Re•Work Virtual Assistant Summit in San Francisco last week, ‘If you say things that are particularly assholeish to Cortana, she will get mad. That’s not the kind of interaction we want to encourage.’ Harrison and her team reportedly talked with IRL personal assistants for advice on how to respond to harassment.


I’ve been using Cortana a lot in the past six months. I’ve come to deeply appreciate the amount of work that Debora Harrison and other people at Microsoft have invested in Cortana’s subtleties. When I give a voice command to Siri or Alexa, I’m using the “operating a computer” section of my brain. But when I talk to Cortana, I’m lighting up my “speaking with a real person” subroutines.

As a result, though I’ve yelled at Siri many (many many oh hell yes many) times, I’ve always been polite with Cortana…not even when Cortana has stubbornly failed to execute a dead-simple command using words straight out of a demo script. I know I can’t “offend” her and I’m free to cuss as though I’ve got a working time machine and only ten seconds to go back thirty years and tell off that utterly-psychopathic kid who lived one street over from me. But Cortana’s “personality” is so subtly-human that my social software’s “don’t be a jerk” failsafes automatically kick in before I even consider articulating anything like that.

I’m impressed and pleased that Microsoft has put so much effort into making Cortana into an assistant, not a servant. When I read this piece, I was tempted to bark commands at Cortana, or say inappropriate things. But y’know what? I don’t want the Cortana software to tick a checkbox in an internal database that says “Andy thinks it’s appropriate to ask his assistant about her sex life.” 

Again, this isn’t an emotional response. I want the software to continue to work well, and here I believe that treating Cortana well will lead to Windows 10’s voice commands to anticipate and execute my requests well. This feels like a natural payoff to the way the Cortana team continues to improve the software: they talk to real-life personal assistants. And not just about how the interpret their bosses’ vague requests correctly, but how they’ve been able to deal with jerks and get the job done. Like a meatware personal assistant, Cortana guides me on what it considers to be appropriate by “rewarding” me for good behavior. If I’m patient and express my request clearly, Cortana gets it right on the first try.

We might be swerving anxiously close to our $1500 laptops turning our workspaces into our own private Skinner boxes. But I’m intrigued by the possible long-term impact of millions of digital assistants who expect to be treated with dignity. It could be a good training sim for all of those executives who, as children, were used to getting everything they want, and as a result they’ve come to think of every other human being as a non-playing character

If Cortana offers a curt replies when she’s treated like office equipment (or, worse, when she’s treated the way that women generally get treated in the workplace), and the only way to get that document printed or that appointment added to the calendar is to say please and thank you and address her by her proper name, not as “sugar-toes,” it could train these jerks to treat humans as humans, too.

Like I said, I haven’t tried to get Cortana upset with me so I don’t know how far the software would go if I spoke disrespectfully. I’m mulling over what I, as an engineer, would do if my bosses gave me the green light to pursue this “Cortana demands to be treated with dignity” line. I shouldn’t prevent Cortana from executing the software’s core functions. So “sugar-toes” would indeed add “Go to the bank and get $100 in singles for Friday night” to the to-do list. But I could make her be a little brusque about it, and change her tone of voice to something flat and uninteresting.

Would I go so far as to lock out certain “bonus” features that aren’t promised on the side of the box? “Andy the sexist jerk” gets a response of “Acknowledged. To-do list updated.” But! “Really great boss Andy” gets “Okay, Andy. I’ve added that to your to-do list. There’s a bank only 230 yards from your Thursday meeting. Would you like me to add a map listing, and schedule a to-do reminder that triggers when you leave the meeting site?” And Cortana would use a friendly voice.

At the very least, I’d have Cortana maintain a sort of cumulative score of its user. When it comes time to roll out software updates and brand new features in waves, the nicest, most polite, most respectful, and most patient users would get them first.

In the meantime, “Administrative Professionals’ Day” is April 26. Maybe I’ll upgrade Cortana’s WiFi connection to a CAT6, just so that she know that she’s appreciated.