Windows 8.1 Is the First Rough Draft of ‘One Microsoft’

How a theoretically minor upgrade portends an entire company's new direction.

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You can’t judge a book by its cover — or a software product by its version number. That’s always been particularly true of Microsoft Windows. The most famous releases sport plenty of visible change and important-sounding names such as Windows 3.0, Windows 95 and Windows Vista. But the versions of Windows that do the most to improve the lives of people who use them are often those whose very names tell you that they’re about refinement rather than revolution: Windows for Workgroups 3.11, Windows 98 Second Edition, Windows XP SP3.

Today, Microsoft is releasing Windows 8.1, a free update arriving slightly less than a year after Windows 8 did. (Windows 8 users can download from the Windows Store.) It’s another one of those versions of Windows whose significance belies the version number. That’s in part because it polishes up a lot of things about Windows 8 that needed polishing. But it’s also because Windows 8.1, more than most Windows updates, is a preview of where the whole Microsoft mothership is headed.

What was most important in Windows 8 stared you right in the face. It was the radically new user interface — originally known as Metro, a moniker it’s been unable to shake — which blew up three decades of Windows conventions in favor of something more modern and touch-centric. It was such an epoch-shifting gambit that it’s not the least bit surprising that the world is still figuring out how to react to it.
It’s also no shocker that there was a need for a Windows 8.1 — an update with a meaningful number of features that might have been in Windows 8, but weren’t. “I always love that question — ‘why can’t I have everything now?'” says Gabe Aul, director of product management for Windows and such a Microsoft veteran that he worked on the aforementioned Windows for Workgroups, which shipped in 1993. “Some things take time to do.”

With a look and feel that aren’t a major departure from Windows 8, Windows 8.1 is about more subtle change. Everyone fixates on the fact that Microsoft brought back the Start button, but that’s only a medium-sized whoop, especially since it takes you to the new user interface that many Start-button loyalists still regard warily.

No, the single most significant thing about 8.1 may be the way it deeply embeds multiple Microsoft products — like SkyDrive, Bing and Xbox — into the Windows experience. They’re there as services that help nudge Windows, one of the world’s most venerable pieces of conventional software, further into the cloud. That matters in and of itself. But it’s also among the first tangible results of “One Microsoft,” the company’s attempt to behave like a single focused, fast-moving team that happens to be rather large — rather than the disparate assemblage of self-interested fiefdoms it’s often been accused of being.

Windows 8.1 isn’t a product of the massive reorganization Steve Ballmer announced in a memo on July 11. Work on the update began in earnest right after Windows 8 shipped on October 26, 2012, and ended less than six weeks after Microsoft employees found Ballmer’s missive in their inboxes. It’s the next version of Windows — whatever it is, and whenever it arrives — that will have been developed under the new corporate structure, which, among other things, creates unified operating-system and device groups.
Yet Windows 8.1 is very much in sync with the overarching goals of the reorg as Ballmer described them:

We are rallying behind a single strategy as one company — not a collection of divisional strategies. Although we will deliver multiple devices and services to execute and monetize the strategy, the single core strategy will drive us to set shared goals for everything we do. We will see our product line holistically, not as a set of islands. We will allocate resources and build devices and services that provide compelling, integrated experiences across the many screens in our lives, with maximum return to shareholders. All parts of the company will share and contribute to the success of core offerings, like Windows, Windows Phone, Xbox, Surface, Office 365 and our EA offer, Bing, Skype, Dynamics, Azure and our servers. All parts of the company will contribute to activating high-value experiences for our customers.

Now, Microsoft smooshing together products, platforms and brands is nothing new. (Exhibit A: the legal case known as United States v. Microsoft, set into motion when Windows first got joined at the hip with Internet Explorer.) But for years, it usually did so by treating everything, reflexively, as an extension of Windows. That led to such exercises in muddy branding as Bing’s predecessor, the Google competitor called Windows Live Search — which didn’t seem to have anything to do with Windows.
This time it’s different. Windows 8.1 flips the proposition: Now Windows feels like an extension of everything else Microsoft is doing.
A few examples:

  • It’s now as simple to store stuff in SkyDrive, Microsoft’s online storage service, as on your hard drive. Windows 8.1 caches SkyDrive data so it’s available when you’re not connected to the web, and uses Smart Files to conserve space, especially on devices with limited storage, such as tablets.
  • Bing Smart Search melds results from your hard drive with ones from Microsoft’s search engine — and, when you search for something music-related, from the Xbox Music service.
  • The Mail app borrows features from webmail, including Sweep, which lets you train it how to automatically handle messages of a certain type — such as ones from a particular person — as they arrive.
  • Integration with the upcoming Xbox One will let you start watching a video on the console or a Windows 8.1 PC, pause it, then pick up where you left off on the other device.

In many ways, these features are the culmination of an effort to blur together software and services that began years ago, after Microsoft shipped the good-but-resolutely-traditional Windows 7. “A lot of it, foundationally, was in Windows 8,” Chris Jones, corporate vice president for operating system services, says of the technologies that make it possible. But the Windows 8.1 incarnations of services such as SkyDrive and Bing are more sophisticated, and they feel more like operating-system features than their relatively superficial Windows 8 predecessors.

One glance at Windows 8’s all-new touch interface told you that Microsoft was trying to reinvent its 28-year-old operating system for the age of smartphones and tablets. But Windows 8.1’s emphasis on services reflects the modern era just as much, and Microsoft readily acknowledges that Windows is learning tricks from newer platforms.

“It used to be that what you had on your hard drive was bigger than what you could have in the cloud,” says Jones, speaking of the SkyDrive integration. “Now what you have in the cloud might be bigger. It’s very similar to the shift that happened with e-mail. You started connecting your phone to a very large cloud inbox.”

Much more than in Windows 8, the new features are also beginning to set up Windows to become something that can get better on an ongoing basis, more like a web service than a piece of boxed software. Over time, for example, Bing Smart Search can provide more and more customized results for different types of content, without any software upgrade. We can ship updates to the search experience every day,” says Kieran Snyder, a group program manager for Bing who was formerly part of the Windows team. “Having been with Windows for seven or eight years, that’s not something I thought we would see Windows embrace.”

Just from a branding standpoint, it’s fascinating to see Microsoft bring its other properties into Windows in such a prominent way. In Microsoftland, search is now synonymous with Bing; both gaming and music are universally tied to Xbox. It’s very much an intentional strategy, and strikingly different from the days when the Windows brand trumped everything else. “Search is one of the great unifiers across devices,” says Snyder of Bing’s high-profile place within Windows 8.1. “We do see value to coalescing around a great search brand.”

And then there’s that “One Microsoft” question: Is Windows 8.1 the product of a Microsoft that’s better at cross-team collaboration than it’s been in the past? If so, did that result in a better operating system?
The people who I spoke with at the company say that they were working hard to be “One Microsoft” even before the reorganization formalized the vision. Already, they contend, there’s been a massive increase in the quantity and quality of dialogue between people who in the past would have focused on their own priorities and checked in with each other only once in a while.

“We talk to Kieran daily,” says Aul about his Bing colleague Snyder. In the past, he says, communications between the operating-system and search areas were handled with “a group-sync meeting with the Bing leadership team once a month.”

“It was a pretty new thing to have everyone in the same room designing,” says Snyder of the Windows 8.1 development process. Before, she says, separate teams would develop bits and pieces of a new product autonomously, then try to retrofit them after the fact. Which led to colleagues having to tell each other things like “This isn’t right for touch, you need to go back and redesign it.”

Then there’s the team responsible for Microsoft’s Surface tablets. They’re in constant contact with other groups, too: For instance, the improved camera in the new Surface needed new software. But as usual when discussing Surface, Microsoft is careful to say that it’s not favoring its own PC hardware arm over the likes of HP, Lenovo and Dell. “The teams have worked together very closely together, while still trying to maintain a relationship that we’d be comfortable having with other [manufacturers],” says Aul.

Of course, it’s tough for anyone outside Microsoft to have an informed opinion of what’s going on in some conference rooms in Redmond. But even for us outsiders, it’s pretty obvious that the company is making a good-faith effort to make its major platforms and services — like Windows, Windows Phone, Xbox and Bing — make sense as a matched set, with a single design aesthetic and many commonalities in features. Getting everyone marching in the same direction might still be tough, but at least it’s clear that the company has one destination in mind for everybody.

The more that Microsoft’s various groups have common interests, the more that the reorg’s emphasis on teamwork might leave everybody’s skills rubbing off on everybody else in a mutually beneficial way. Snyder says that’s already happening: “Bing has gotten much better at understanding modern design. Windows has learned much more about machine learning.”

Even if you’re impressed by what’s new in Windows 8.1, as I largely am, there’s only so much you can divine about Microsoft’s future from its digital tea leaves. The company, after all, is about to undergo even more epochal change as it gets a new CEO and swallows up a gigantic hardware maker. The company still has to contend with a PC business that’s in decline, and Windows Phone 8, though nice, remains in distant third place in a smartphone market that may only have room for two big winners. Still, this update is the most tangible evidence so far of what “One Microsoft” is all about  — and it would be nice to think that it’s a rough draft of bigger things to come.