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’s 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. 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?

Halo Cortana

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



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