From Clippy to Cortana, Microsoft Tries to One-Up Competitors The software maker will debut a smarter interactive personal assistant.

June 5, 2014  -- From Clippy to Cortana, Microsoft has come a long way in its electronic personal assistance services.

Cortana, a digital personal assistant that is built into devices with Windows Phone 8.1, is Microsoft's answer to Apple's Siri, but, the company says, even smarter.

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The name comes from a character with AI (artificial intelligence) in the video game Halo. It's a far cry from the animated "Clippy" character that Microsoft introduced with Office 97 and retired in 2001, when Microsoft Office XP debuted.

When asked if Cortana would be available on other devices, Greg Sullivan, Microsoft's director of Windows Phone, said, "The system is designed to scale. The engine is in the cloud driven by Bing."

Want a reminder to tell your Dad to pick up his medication during his next phone call to you? Cortana can show you a reminder to do that when your phone rings.

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Anyone can use the voice search feature on Android-based Google phones to ask the question, "What are the best barbecue restaurants in New York City?" A Google phone will then show you a list of local restaurants, based on reviews by Google-owned Zagat.

Siri answered the same question with a list of 15 restaurants in the area, topped with Korean barbecue restaurants.

But if you ask Cortana the same question, your Microsoft phone responds with similar speed (using Yelp reviews), but then asks if you would like to narrow down the list with restaurants that take reservations.

Since 2008, Google has been “steadily been making updates” to the Google Search app with Voice Search, says a spokeswoman.

Another feature, Google Now, is a customizable Android service that culls information from your habits, such as commute cards with relevant traffic accidents, flight delays and “time to leave” reminders for scheduled events.

Apple did not respond to a request for comment.

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"The whole system itself is machine learning. It gets better with you," Sullivan said.

Microsoft's system is reminiscent of IBM's artificial intelligence system, Watson, which officially expanded into larger commercial uses earlier this year.

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Microsoft interviewed real-life personal assistants, who shared that the number one factor that allows them to do their job well is to get to know their clients and anticipate their needs.

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To set up your Cortana Beta version in your Windows phone, you are asked four questions, such as, "What are a couple of the most enjoyable parts of your everyday evenings? Pick two."

"She goes through those questions in order to begin her knowledge of you," Sullivan said, "and she stores that in her notebook."

He says what's unique to Microsoft's digital assistant is that a user can access and change Cortana's "notebook" about you: literally, a list of your "interests," "inner circle," "quiet hours" (when you don't want to be disturbed), reminders and more.

"That’s a real differentiator from the other systems out there," he said, adding that Cortana asks a user for permission to remember a preference or if you need a reminder.

"She’s not going to make assumptions. She will ask, 'Would you like more of this kind of information?' She can scan that flight itinerary to let you know if a flight is delayed, always in a way that you can manage."