In case you haven't heard, Microsoft launched a completely new email service today, Outlook.com, replacing its long-tenured Hotmail service. What are you still doing here--go rush and claim your new email address! Wait, you're not in a hurry or need to switch from your existing email provider? Not surprising. Most of us are pretty content with our email accounts, whether it's Gmail, Yahoo mail, or even a privately hosted account tied to a custom domain. Web email interfaces aren't perfect, but that's why we use dedicated desktop and mobile email clients instead of just a web frontend. Third-party apps like Apple Mail and Sparrow (for now) make up for webmail's inefficiencies while Google, Yahoo, and even Microsoft make iterative improvements to the in-browser experience. What's more important is that the email address has become synonymous with personal identity on the web; more so than your Twitter handle or Facebook page, your email address is how you identify yourself to friends, contacts, and innumerable web services. It's an extremely personal association. But more importantly for companies like Google and Microsoft, it's also how you open yourself to their specific services like cloud storage and instant messaging. That's simple synergy.
So for Microsoft to convince the hundreds of millions of non-Hotmail users to adopt an Outlook.com email address, the service needs to be both compelling enough as an email experience to pull people away from what they're used to and comfortable with, and also provide an extremely easy way for users to retain the email-tethered identity that they've established (eg. importing their existing accounts). Based on my time with Outlook.com so far, the service doesn't quite hit the mark with either requirement.
Let's address the email user experience first, since that's one of Outlook.com's purported strengths. Outlook certainly looks different from Hotmail and its adherence to Microsoft's Metro design aesthetic is very apparent in the bold colors and generous line spacing. This is one hell of a clean interface, so much so that glancing back at Gmail makes Google's famously clean design sense look cluttered. In my meeting with Microsoft, Outlook's product manager called attention to the header layout, which takes up 60% fewer pixels than Gmail's, given that there is no omni-present search field or Google+ services toolbar. That reverence to the value of vertical space is in line with Microsoft's belief that computing is best done in the landscape orientation--as in Windows 8 desktops and tablets. Whether or not you believe that's the case, a more more efficient header is unquestionably a good thing.
Clutter reduction also comes in the form contextual buttons and menus. Icons and actions in the top Command Bar change depending on whether you've selected a message or have clicked through to the full email. Customizable "Quick Actions" also pop in if you mouse over messages in a folder. And when you're not actively selecting a message, the only button in the Command Bar will be to create a new email: the most useful action for an email service. All this contextual placement of actions feels intuitive and more importantly, invisible--actions are present and easy to find when I need them and subtly absent when I don't. This is good design--even the advertisement panel on the far right of the screen isn't obnoxious.
Outlook is also pretty clever in the way it handles email. Microsoft claims that 50 percent of email received by its users is newsletters, with social media updates and documents coming in a far distant second and third place in terms of quantity. That's a lot of Groupon offers and Amazon recommendations. So Outlook will supposedly intelligently parse your emails and tag them for sorting. The Quick View feature sorts your emails into categories, so you can view all emails with photo attachements or only shipping notifications, for example. And for newsletters, Outlook can perform a scheduled cleanup to delete old newsletters from individual senders and only keep the most recent one in your inbox. Microsoft will even help you unsubscribe to newsletters by contacting companies to get you of mailing lists, and block senders' addresses as a last resort.
So far so good. So where does Outlook get it wrong? With intelligent sorting and easily defined email rules, Microsoft is clearly paying attention to that 50+ percent of email that clutters up inboxes and makes "inbox 0" such an achievement. But I think it fails to cater to the way people actually use email these days--the emails that people actually send, receive, and care about. These may not account for 50 percent of the emails I receive on a daily basis, but are the ones I actually respond to and keep. From my experience, the majority of these emails are more telegrams than letters--a shift from verbose documents (which are better sent just as separate attached document files) to brief messages. Emails are more like conversations than ever, sitting in between the immediate urgency of instant messages and deliberate permanence of longform correspondences. That's why Facebook messages is so popular (and why its the same service as Facebook email) and possibly why mobile email use has grown at the expense of web-based email use. Quick and short emails allow the intimacy of a private conversation without the immediacy and constant attention demanded by an IM conversation.
Outlook doesn't seem to get that. Two features I immediately missed when using Outlook for an extended email exchange was the presence of emails' body text previewed in-line with the subject in the inbox (important to me for checking email at a glance) and the ability to instantly reply to (or forward) emails without leaving to a new page. In my opinion, the ease at which Gmail allows you to respond to conversations at the bottom of an email without sending you to a new "send email" page is one of its greatest strengths. That pop-in send field makes email threads feel more like conversations; loading a new page just to send a reply is an unnecessary inconvenience. This is something I hope Microsoft fixes as Outlook leaves its "preview" state.
So on to the issue of email identity. Even if Outlook.com is the most fluid, intuitive, smart, friendly--basically best--web-based email service in existence, the intrinsic value of an @outlook.com email address is minimal if all the services you use are connected to your existing email account. In the short run, the best Microsoft can hope for to convert the millions of Gmail users over is for Outlook.com to somehow be a better Gmail client than Google's own Gmail.com. That would be a huge coup for Microsoft--one-upping Google in user experience and getting to serve its own webmail ads to Gmail users. But for that to even have a chance of happening, Outlook has to make it extremely easy to import your existing account into its service. Right now, importing a Gmail account into Outlook is a three-step process, which isn't even visibly advertised to new users. Microsoft should shine an obnoxious light on this ability and make it a one-click process. And there should be no shame about it; new users should be shown a giant "click here to import your Gmail account" button when they log in for the first time. The transition process needs to be as seamless and painless as possible, not with imported emails filling up a separate folder all marked unread. Make users feel like they haven't left their existing email address--and associated identity behind. That's how you get users to convert and commit. Until then, Outlook.com is just another email account that users who are comfortable with their habits don't need.
The best thing to come from any new service is a reflective evaluation of how we use products in the real world; I am forced to consider whether my behavior is determined by practicality or just a byproduct of habit. Outlook may not be better than Gmail or Yahoo mail in every respect, but it is certainly different, and will force me to really think about how I use email. I'll be continuing to test Outlook.com as an alternative interface for my Gmail account for the next few weeks and report on my experience as Microsoft adds features and adapts the service to how people are actually using it. For now, there is no harm in signing up for an account and testing it out yourself--Microsoft makes it easy to close the account at any time from your Live profile page, and Hotmail users can switch back to the old layout if they really want to.