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Cortana is a disembodied voice on WP8 based on the Halo character

Windows Phone is still a distant third to Apple and Android in the smartphone market, but Microsoft is hoping to change that with the introduction of Windows Phone 8.1— and more importantly its personal digital assistant Cortana.

Microsoft claims that Cortana isn't like your average virtual assistant. She's supposed to be a little wittier, more personable, and capable of learning more about you than Siri or Google Now.

After using Cortana for a week and speaking with Microsoft's Marcus Ash, Partner Group program manager, it's clear that the company's got a lot riding on the success of its new virtual assistant.



But there are still several obstacles in Microsoft's way. Besides the competition from Apple and Google, virtual assistants still haven't really become a mainstream part of a smartphone user's everyday routine.

We sat down with Ash to talk about how Microsoft created Cortana, its plans for the future and its strategy in facing the competition.

Business Insider: Microsoft interviewed real-life personal assistants when creating Cortana. What was the strategy behind that?

Marcus Ash: If you want to make a real humanistic connection with that technology, the best thing you can do is find a set of humans that do the job we think this phone should be able to do. We [asked] them, 'What do you do to really make the person that you work for happy? What types of [tasks] do they ask you to do?’

The other area we were focusing on was how much personality we should attribute to this assistant. These machine learning systems need a lot of data. So if you don’t ask the right questions, then you’re not going to get the right data, and then the system can’t train itself. So it never really gets better.

You need a pleasant sounding voice. You need to make sure that voice sounds as human as you can possibly make it.

You need to make sure that voice sounds as human as you can possibly make it.

We need to make sure that the voice actually has human sounding phrases to say. When you ask a question that you would ask a normal person, the system should respond the same way a person would respond. So we really thought of all those problems.

So we thought let’s go talk to people who have these personal assistant jobs where we could get a flavor for how much of their personality comes through on the job. We examined the dynamic between the person that's being assisted versus the assistant.

BI: In what other ways did you study real personal assistants?

MA: We interviewed these people that had these high-stress jobs, meaning they were assisting people who were celebrities where it really matters that you’re getting things right. I think it was somewhere between five and seven assistants that we interviewed over the course of one week. And we had them keep a journal, and we looked through those journals and we looked back and did exit interviews.

We asked them tell us about the relationship with the person [he or she] worked for. We said, tell me the types of things you do for them. Tell me how much they have to ask you to do things for you versus how proactive you are. That’s where we got a lot of insight.

BI: So what was the most important thing you found through that process?

View photos Cortana More

Lisa Eadicicco

How Cortana looks on a Windows Phone

MA: It’s all about trust. This person tells me very private information. And this person expects me to keep this private information between us. They didn’t go into details, but you can imagine the kinds of things that an assistant that follows that type of person around might see or hear. If the person doesn’t trust me, then I can’t do my job effectively because I’ll be limited in the information that I get from that person.

I just had this idea that the personal assistant knows the person [they’re assisting] so well that they can anticipate things. I just wouldn’t have guessed that it was so rigorous. One person pulled out her journal. She called it her bible of this particular person.

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