Goodbye, Hotmail; Hello, Outlook.com [REVIEW]

If you’ve been on the Internet for a long time, there’s a good chance Hotmail was your first email address. Launched in 1996, Hotmail was bought by Microsoft the following year, and the service has gone through myriad changes since then. Today, Microsoft is making its most radical change yet to the 16-year-old email service.

For starters, the Hotmail brand is toast. Microsoft is rebranding the service under the Outlook banner, moving the service to Outlook.com. The Hotmail site will still be there, and users won’t be forced to make the switch — yet — but the message is clear: Going forward, Microsoft email is called Outlook. You’ll still be able to keep your Hotmail address, and even use it as the one all your friends and family reply to, but your account will be an Outlook.com account.

Email Ads, the Microsoft Way

Also getting thrown out: the business model. Hotmail stood apart from other free-email services such as Gmail by building display ads into the page, forcing users to look at them. While the ads have been a (small) source of revenue for Microsoft, they’ve held back the service in many ways. Most notably: Hotmail arrived on mobile email apps late — and kicking and screaming — since once the service is integrated, display ads aren’t visible.

But now Microsoft is literally pushing those ads aside, replacing those display ads with Google-like keyword-based text ads that run along the right side of your message pane. Those ads will be tailored to you based on personal data, and they’ll get even more specific when you click on a message.

“Wait a second,” you say. “Isn’t this kind of ad targeting exactly what Microsoft criticized Google of doing in amusing ads like ‘Gmail Man.’” Absolutely true, but Microsoft gives itself a get-out-of-jail-free card: It will only serve you and ad within a message when it’s a newsletter or some other form of “official” communication (like from your bank). For person-to-person emails, the ads disappear in lieu of something else.

New Features

That being one of Hotm… er, Outlook’s most interesting new features: social integration. For whomever you’re conversing with, Outlook imports their most recent tweets and Facebook updates, along with links to profile pages. You can even Like, comment, retweet and @reply straight from the pane. Of course, it’ll only do this if you enable Outlook to scan for public content on either service, something you can disable later.

Microsoft was kind enough to give me an early look at the new Outlook and try out its new look and features. I must say, I like it. I also admire Microsoft’s moxie in throwing out both the Hotmail name and the existing business model. In a year filled with bold moves from the company, this doesn’t rank as the biggest, but both decisions feel like the right move.

The first thing you’ll notice after making the transition (by selecting “Upgrade to Outlook” in your Hotmail settings) is the new design. Hotmail, which evolved greatly over the last decade but retained the same overall look, has finally gotten an extreme makeover.

Clean Interface

Outlook’s austere blue-themed design will be recognizable to anyone who’s seen Windows Phone or Windows 8, and it makes the whole experience feel much more calm (Hotmail has always been the “noisiest” of the three major email services). And you can switch the blue color for something more to your liking at anytime.

Two great features about the new look: 1) It keeps things clean by offering you just one action item when you have nothing selected: compose a new message. And, 2) The layout is relatively tight compared to Gmail, minimizing the amount of “chrome,” navigation items and white space on the top of the page. You’re here to see email, so email is front and center.

Once you get past the layout, though, it becomes pretty clear that the general business of sending and receiving is pretty much the same. This is still email, after all. However, while using the Outlook preview I found that messages don’t quite come in as fast as on Hotmail. This could easily be because of the nature of the preview, but Microsoft might also have some optimizing to do after the transition.

Expectedly, you can launch Windows Live Messenger to start a chat at any time, and Microsoft says Skype support will be available at launch (it wasn’t during the preview period). With Skype integrated, you can start a Skype conversation with someone straight from an email. Once Microsoft completes its acquisition of Yammer, you’ll probably see similar functionality with that service.

Leaving Hotmail Behind

Hotmail was at times an albatross and a best-kept secret about Microsoft. After a long period of neglect, it improved greatly over the last few years, imitating the best features of its competitors while retaining features (like one-click rearranging) that keep fans of traditional email clients happy. As a result, Hotmail is still the web’s largest web-based email service, with 350 million users, according to comScore.

With the transition to Outlook, those users are in for a shock, but when they see what Microsoft’s got in store, I suspect many will see it as a pleasant surprise. Microsoft’s mail service has never been this clean or usable — or looked this similar to Gmail — before. The lack of clutter is greatly appreciated, and you have to give Microsoft credit for removing things like the big “SkyDrive” icon up top (we’re here for email, thanks).

It’s in the differences, though, where Outlook shines. The social integration is an excellent idea — after all, if I’m conversing with someone on email, what that person is sharing on social networks becomes more actionable than if I’m just seeing random things in a newsfeed. Suddenly realize in mid-sentence that it’d be better to talk to the person? Just use Skype.

With features like those, Microsoft’s web email service is much improved, and I’d even say superior to Gmail in many ways. If users are to have any issues, it’ll probably be with the Outlook name. The brand generates a lot of bad blood among users, and people inherently fear sweeping changes. At least in this case, things get better on the other side.

Thumbnail image courtesy of iStockphoto, PashaIgnatov

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