Build 2019: Head of Cortana discusses what’s coming next for the digital assistant

It’s no secret that Microsoft’s Cortana virtual assistant, which first became available on Windows Phone 8.1 five years ago, is lagging behind its competitors which include the Google Assistant, Alexa, and Siri. While the service does integrate well with Windows 10 and Office 365, there is still a lot left to be desired.

For example, it doesn’t integrate very well with iOS and Android devices, as it can’t launch apps, change settings, or interact with other apps in the same way that the Google Assistant and Siri can. Everything, including alarms and reminders, are done locally within the app as opposed to the phone’s built in system apps.

Cortana’s chief Andrew Shuman was able to provide a little insight as to the future of Microsoft’s virtual assistant. In an interview with The Verge, Shuman stated they are “finding those places where Microsoft can really add a lot of value.” Microsoft 365 continues to be one of those places Shuman has in mind, going on to further explain that, “I think that what we’ve been really working on over the last year is how we can better embed Cortana across Microsoft 365 experiences and really delight users, especially those users who really are on board, so we have to understand their calendar, their tasks, their work documents, their interfacing with their close collaborators.”

Microsoft has also been working to improve the conversational experience with Cortana, so that users can interact with her more naturally as opposed to reciting commands. The company acquired Semantic Machines almost a year ago, which uses machine learning to bring conversational AI to the table, allowing users to interact with the assistant much more effortlessly.

Google has already integrated conversations into Google Home devices by allowing them to continue listening for a brief time after the first command is issued. Furthermore, Google’s I/O keynote yesterday also appeared to have shown off a more natural conversational experience, which will allow users to quickly give multiple commands without having to say “hey Google” each time.

For Cortana, is clear that there is a lot of work that needs to be done in this area to allow the assistant to better understand the context of more complicated commands. According to Dan Klein, a Microsoft technical developer who co-founded semantic machines: “That would be shattered across dozens of different skills in the standard approach. The key thing here is context, and the idea that everything you say and everything you do is bridging together.”

Shuman also suggested that Cortana will be able to learn about user’s important projects, deadlines, and meetings by leveraging machine learning. “We can learn from the files you’re sharing or the titles even of your files, or the subject of your emails. And I don’t mean this in a creepy way, I mean this in a data resource way that these algorithms can learn, eyes off,” he stated.

In any case, Cortana has never been the ideal assistant for those who aren’t heavily invested in Microsoft’s ecosystem. The company knows this, and that’s why it’s now focusing more on users who rely on Microsoft services every day.

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How do you think Microsoft can improve Cortana?