Windows 8: The Seven Roads Not Taken

How should Microsoft have retooled itself for the era of tablets and touch interfaces? A few alternate-reality scenarios.

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In 1995, consumers in Sydney, Australia go gaga for Windows 95, Microsoft's most rapturously-received upgrade of all time

On Friday, I responded to Paul Thurrott's report that the first few weeks of Windows 8 sales have been disappointing by saying that Windows 8 is a long bet — and it therefore doesn't matter much what the early sales numbers look like. Bloggers John Gruber and MG Siegler referenced my post, and both said that Microsoft's strategy of combining Windows' traditional-PC interface with new touch-centric features is a mistake. Their thoughts are worth reading, and the market may well prove them correct.

Me, I've been studiously avoiding making any predictions about Windows 8's chances of success…except to say that I think it's going to take a while until we know whether Microsoft's big bet is going to pay off.

But here's a question that's worth pondering: If Windows 8 is a misbegotten idea, what should Microsoft have done instead? What should Windows 7's successor have looked like? What sort of products should the company offer for the era of touch interfaces and tablets? How should it position itself to do well in the post-PC years and decades to come?

I can think of seven alternate roads the company might have followed. (They're not all mutually exclusive.)

1. The plain ol' plain ol' road.

Microsoft could have released a Windows 8 that was to Windows 7 as Windows 7 was to Windows Vista: An improvement, but not a fundamental reimagining. Such a Windows 8 might have introduced some modest tweaks to make touch interfaces work better. But it wouldn't have demoted the old Windows interface in favor of an unrelated new look and feel; it wouldn't have eliminated the Start menu; it wouldn't have bifurcated into separate versions for x86 and ARM chips.

Advantages of this road: It wouldn't have confused or alarmed anybody.

Disadvantages of this road: This approach wouldn't have done much to reposition Windows for a world in which PCs are looking less and less like PCs.

2. The “Windows 7 Lion” road.

Apple upgrades OS X more frequently than Microsoft upgrades Windows, but it hasn't done anything too radical: The operating system is still a conventional desktop operating system for conventional personal computers, and doesn't support touchscreens. But both Lion and Mountain Lion have borrowed lots of features from iOS, including the Launchpad, full-screen mode, Notifications, App Store, AirPlay wireless video feature and more. They're all optional; if you liked OS X the way it was, you can use it the way you always did. Windows 8 could have done something similar, riffing on Windows Phone features in a relatively subtle manner.

Advantages: It sounds appealing to me!

Disadvantages: Apple has vast numbers of customers who know iOS and are ready to understand iOS-like features which show up in OS X. But Microsoft hasn't had much luck getting Windows users to buy Windows Phone handsets.

3. The Windows 1.0 road.

When Microsoft introduced the first version of Windows in 1985, it bore as little resemblance to DOS as Windows 8's new interface bears to old-school Windows. And anyone who ran both DOS and Windows lived in two different worlds with two radically different types of applications, much as Windows 8 users do. But for its first decade, Windows was an optional add-on to DOS — nobody used it unwillingly. Maybe Microsoft could have done something similar again, upgrading Windows in a more conventional manner, but simultaneously introducing an add-on which would give the operating system a simplified, touch-friendly front end.

Advantages: Nobody would feel like they were having something unfamiliar forced on them.

Disadvantages: A new Windows new interface as an extra-cost option might never become popular, let alone pervasive. (Then again, Windows 3.0 and Windows 3.1 were extra-cost options, and were blockbusters.)

4. The Windows Phone road.

During the 15 months in between the launch of Windows Phone 7 and the first public demo of Windows 8, lots of people thought that Microsoft should release a version of Windows Phone for tablets. Then the company revealed that it planned to give Windows itself a Windows Phone-like interface, and it became clear why it hadn't released a Windows Phone Tablet Edition. But maybe there's an alternate universe in which the company's tablet strategy was the same as Apple's: one operating system for phones and tablets, and one for computers. In this scenario, Windows tablets might look much like the Windows 8 and Windows RT models we're seeing, except they wouldn't offer the desktop and wouldn't be compatible with any legacy Windows apps.

Advantages: Windows Phone is an excellent operating system which might be pretty nifty on a tablet.

Disadvantages: Microsoft's having trouble convincing teeming masses of people to buy Windows Phone smartphones, so there's little evidence that they'd clamor for Windows Phone tablets.

5. The just-Surface road.

Right now, Microsoft isn't just introducing a wildly new version of Windows — it's also going into the PC business for the first time, with the tablets it calls Surface. The first version of Surface runs Windows RT, which is basically the same product as Windows 8, except it can't run traditional Windows apps except for the ones it comes bundled with: Office and Internet Explorer. Surface competes with other Windows RT tablets and with Windows 8 tablets, and the whole situation is kind of ugly and confusing. It's conceivable that it would have been cleaner if Windows just went on being Windows, and Surface was a new and unique Microsoft device, running an operating system that wasn't available on anything else.

Advantages: It would be easy to understand — and maybe Surface would get more attention if it were an idea unto itself rather than a Windows 8 offshoot.

Disadvantages: If Microsoft released an ambitious new software platform and didn't let its hardware-making partners use it, they might be even more ticked off than they are.

6. The something entirely new road.

Or, if you prefer, the Courier road. Instead of tackling the tablet conundrum by reworking Windows, in any form, Microsoft could have created something from scratch. Something that wasn't designed to replace Windows as we knew it. At least not yet.

Advantages: When a product starts off without any preconveived notions or existing customers, you can do whatever you want without fretting about ticking anyone off.

Disadvantages: Unless the idea was BIG, it probably wouldn't go anywhere. And it wouldn't answer an all-important question for Microsoft: What should Windows look like in 2012, 2013 and beyond?

7. The almost the same as what they did, with one big difference road.

If you upgrade to Windows 8, or buy a new Windows 8 PC, there's no way to cautiously dip your toe into the new-interface pool. The operating system boots into the Start screen, and it doesn't have the Start button and Start menu; it's willfully unfamiliar in a way that gives cautious consumers and businesses a reason to avoid it. Microsoft could have avoided this by (A) letting users configure Windows 8 to boot directly to the desktop; and (B) retaining the Start menu, at least as an option.

Advantages: Windows 8 users could acclimate themselves to the changes at their own pace.

Disadvantages: You know, I can't think of any. By shoving people directly into the new interface and withholding Windows' most familiar features, Microsoft took a pointlessly heavy-handed approach which denies its customers the ability to customize Windows to their own tastes. It's a move that's bad for Windows users. And if large numbers of those users respond by steering clear of Windows 8, it's bad for Microsoft.

Even if you find things in Windows 8 to admire, as I do, you may still come to the conclusion that a sizable percentage of Windows users should ignore it for the time being. (Last week, my father asked me if he should upgrade; I considered the matter for 1.37 seconds and then advised against it.) But Microsoft, and recently departed Windows honcho Steven Sinofsky, deserve credit for doing something. Something rather daring, actually. Rather than dithering, the company chose a road — and now it needs to figure out how the world's responding to its decision, and journey forth accordingly. What matters now is what happens next.