Why Windows 8 will be Microsoft’s biggest disaster since Windows Me

I feel sorry for Microsoft. They have some wicked smart people, and they seem to grok what the next big thing is going to be (they were seven years ahead of Apple in tablet computing), but they just can’t excute their way out of a wet paper bag. I have some suspicions of why this might be, which I’ll get to in a moment.

Right now Microsoft is busy snatching defeat out of the jaws of victory with Windows Phone. Developers are dropping the platform left and right, and Microsoft’s forced upgrade to Mango if you want to keep using the marketplace has left a lot of users (users who don’t have a PC to connect it to for the non-OTA update, for example) out in the cold.

But that’s just small potatoes. Microsoft’s big misstep is coming later this year. They call it Windows 8.

Microsoft, and CEO Steve Ballmer in particular, are very proud of Windows 8. I can understand why, but it’s not going to work out the way they think it will, and almost entirely to the decisions they’re making right now. Let me give you some examples of where Microsoft’s plans are incompatible with reality.

Microsoft finally caught on that people don’t want a full desktop user interface on a mobile device like a tablet or a phone. That was what they were doing wrong with tablets throughout most of the 2000s. But the big edge they think they have over Apple’s iPad is that people will be able to run the same apps, with the same look and feel, on their desktop and their tablet (and their phone, if rumors about Windows Phone 8 are to be believed). Only, that’s really not what they’re delivering. Microsoft’s computing infrastructure post-Win8 will be just as fragmented as Apple’s (with OS/X on some devices and iOS on others), but the difference is that while Apple is up front about that, Microsoft is trying to hide it, and it’s going to piss customers off.

Microsoft has done a horrible job branding the various incarnations of Windows 8. For example, this fall consumers are going to see two kinds of Windows tablets that look almost exactly the same. Both will be thin and sleek. Both will say Windows on them. Both will have the shiny new Metro user interface. But only one will really be Windows 8. That is, only one will be able to run legacy Windows applications as well as new Metro apps. But apart from a minor difference in the name of the OS (Windows 8 vs Windows RT), consumers won’t know the difference when they buy the tablets. Both tablets run “Windows” and I expect a lot of angry, confused consumers when they find out that their new Windows RT tablet won’t run their old copy of Quicken, the whole reason they bought the damn thing instead of an iPad in the first place.

Okay, so maybe tablet computing (arguably the future of personal computing for the masses) is going to be a mess because Microsoft insists on calling everything “Windows”. (And you can lay this confusing policy directly at the feet of Steve Ballmer, who makes the final call on all product naming decisions and who is still totally sold on the “Windows Everywhere” philosophy. Windows Phone might have done better if it had been called the XPhone and shared design branding with the Xbox, but Ballmer wouldn’t allow it.) What about laptops and desktops? You know, all the machines out there currently running Windows 7?

For these users, Windows 8 is going to feel like a slap in the face. The familiar desktop user interface is a second class citizen in Windows 8, because Microsoft insists on desktop users using Metro whether it makes sense or not.

I spent a few weeks with the Consumer Preview of Windows 8 (what we used to call a “beta” back in the day) and will probably take the upcoming Release Preview (what we used to call a “release candidate” or RC) next month when it’s available to the general public. And while I tried to embrace Metro, I kept going back to the desktop to get real work done. Only they’ve done away with the Start orb on the desktop taskbar, so I’d have to keep bouncing back to Metro to launch a program, only to go immediately back to the desktop UI. It was jarring and annoying. I managed to “fix” the problem by installing Start8, a wonderful little utility from the folks at Stardock, makers of Object Desktop and other nifty system enhancers I’ve used since my OS/2 days. Start8 gives you back your Start orb in Windows 8, negating the need to keep bouncing between environments if you do most of your work with desktop-grade apps. But I’d bet good money this utility won’t work in the Release Preview, or perhaps the actual released OS this fall.

Microsoft also recently announced that they’ve killed Aero, the “glass” effect on window chrome in Vista and Windows 7. Window title bars and other chrome in Windows 8 will be solid white, and completely flat with right angles, no shading, gradients, transparency or drop shadows. In a lot of ways, we’ve come full circle back to the user interface of Windows 3.0, for those of you old enough to remember it. This is done, they say, to better match the aesthetics of Metro and possibly even save battery life (though I doubt modern GPUs really notice the extra effort needed to render Aero’s effects).

What these changes mean, though, is that enterprise users are going to run screaming away from Windows 8. And keep in mind, enterprise is supposed to be Microsoft’s bread and butter. Not the consumer market, and certainly not tablet users. Enterprise desktops and laptops are supposed to be Microsoft’s unchallenged domain. And with Windows 8, they’re doing everything they can to alienate this group of change-adverse users in order to court a market that may not even exist (see arguments that there isn’t really a tablet market, but instead an iPad market). I’ve done a few enterprise migrations recently, and the vast, thundering majority of users I’ve worked with have had trouble adjusting to the differences between Windows XP and Windows 7. Windows 8, especially on desktops and laptops, is going to be so alien than I expect most IT departments to ignore it entirely and standardize on Windows 7 across the board.

So let’s recap. Because Microsoft won’t let Windows be Windows (so named because it was a windowing GUI, something Metro is not) and because of their insistence on calling things that are not Windows (Windows RT, Windows Phone, I’m shocked Ballmer hasn’t demanded to rename the Xbox “Windows Gaming”) Windows, Microsoft has hopelessly sabotaged:

  • Windows Phone, a platform that had a shot at being a viable third option after iOS and Android is sinking like a stone, and cramming essentially the full Windows RT kernel into a phone for Windows Phone 8 isn’t going to make it any better.
  • Windows RT, the ARM-based tablet OS that looks and acts just like its cousin on Intel-based Windows 8 tablets, only it doesn’t run the same software, guaranteeing a confused marketplace and further exodus to the simplicity of Apple’s “our way or the highway” iPad ecosystem.
  • Windows 8, built to appeal to a market that may not exist while simultaneously alienating virtually all of Microsoft’s current Windows customers.

I really do believe tablet computing will be the default way we interact with the internet in the years to come. But this perfect storm of failure (Hey, Ballmer, how about figuring out a way to sink Xbox and go for the Grand Slam?) will just ensure that Microsoft won’t be a part of it.

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