When you first launch Cortana, she runs through basic questions to learn about you — your name, your food preferences, what category of movie you like, and so on. After that, when the service is activated with Windows Phone's search button, you can swipe down to see a "proactive view" of information. It’s very similar to Google Now’s cards, with information on flights, sports results, stocks, and anything else Cortana has learned and jotted down in her Notebook. You can improve the Notebook by manually adding your personal interests, reminders, news, and other important data. It’s really a hub of information that turns into cards, and parts of it can be pinned as Live Tiles on the Start Screen or used to generate notifications in Windows Phone 8.1’s new Action Center, a notification hub similar to those found in iOS and Android. If, for example, your favorite football team just scored, Cortana can alert you. If you visit a foreign country you’ll be greeted with weather information, currency conversions, and maps. If you’re in a text or email message, Cortana will underline elements like "let’s meet at 8PM" to make it easy to set reminders or calendar appointments.

One of the most useful features of Cortana is its ability to trigger actions based on events, a little bit like the popular web service IFTTT. For instance, saying "Remind me the next time I call my wife that we need to talk about Kevin" will create a reminder that is triggered when you next go to call your wife or she calls you. It’s powerful, but Cortana even impresses during basic search queries. If you search for "What’s the best restaurant near me" you won’t get a big list of results like you do with Siri, you’ll get a single restaurant that’s rated the best in the area by Yelp users. "If you asked a real assistant, 'What is the best restaurant' and she held a page up to you, you would fire her and try to find another one," jokes Rob Chambers, principal group program manager of Bing. The difference is that if you had said "the best restaurants," plural, then you’d get a list thanks to Cortana’s understanding of the voice queries and their context. The truly impressive moment is when you’re simply able to say "call it" after asking for the best restaurant, or "give me directions" and Cortana understands you mean directions to the restaurant in your previous part of the query. It’s true multistep search, a way to layer query upon query to accomplish complex tasks by voice alone. It feels like the future.

In Windows Phone 8.1, Cortana appears as little more than an animated circle, but that doesn’t mean she doesn’t have a personality. Like any good assistant, and Apple’s Siri, Cortana’s personality shines through in daily use. Ask her, "Who’s your father?" and Cortana will reply, "Technically speaking, that’d be Bill Gates. No big deal." Other queries produce witty responses, and some answers make the circular character spring to life and animate with one of 16 emotions. Cortana won’t always respond with emotion and animations, but Microsoft envisions a future where she reacts visually to sports scores or other events — any good assistant knows to be pumped when a football team wins and furious when they lose, and so does Cortana now. "There's just more stuff we're gonna be able to do with the shape as we progress along this journey," explains Ash.