Microsoft's 13 worst missteps of all time

DOS 4.0, Zune, and Windows 8 are but a few of the landmarks among 25 years of failures Redmond-style

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Microsoft misstep No. 5: Windows 8

Windows 8 is turning out to be a misstep of unprecedented proportions. The fundamental problem, as many of us at InfoWorld have described repeatedly, is the Jekyll-and-Hyde nature of the Frankenstein interface. Clearly, with Windows sales heading deeply down and the entire PC hardware industry going with it, Microsoft had to do something. Relegating the old-fashioned Windows desktop to a tile on a new mobile phone app hasn't done the trick.

Or maybe we're all wrong and Windows 8 will breathe new life into the PC industry. In another six months, we should know for sure.

Microsoft misstep No. 4: Windows 8 branding

There's nothing inherently wrong with Windows 8 -- it's a noble (if flawed) attempt at bringing Windows into a more mobile future. There's plenty inherently wrong with Microsoft branding. When you bring the two together, the combination's absolutely lethal.

Please. I spent a whole day trying to come up with a worse name than "Windows RT." I couldn't do it. Microsoft could call the Metro-side-of-Windows-8-plus-Office-2013-RT just about anything, and it would be better than Windows RT.

So many people right now are so confused about the differences between Windows RT and Windows 8 that we won't hear the end of it for another decade -- or longer. Customers who buy a Windows RT tablet, thinking they were getting Windows, will be sorely upset. I bet the return rate for Windows RT tablets at the retail level goes well into double digits, simply because of the naming confusion.

Then there's Metro: immersive, Modern UI, Windows Store. I don't even know what to call it any more. I can imagine telling my Aunt Mildred that she needs to get a Modern UI Calculator from the Windows Store. I mean, Microsoft itself stopped using the term "UI" nearly a decade ago: It's always UX. You can call Metro apps "Windows Store apps," but not all apps in the Windows Store run on the Metro side (for example, Office 2013 is in the Windows Store). And not all Metro apps originate in the Windows Store -- the Metro Xbox Music app, for example, isn't really a Windows Store Xbox Music app because you don't download or install it from the Windows Store.

There's another Win8 branding inanity as predictable as tomorrow's sunrise. The next version of Windows will probably be called Windows 9 -- cool. Here's what I want to know: What will the next version of Windows RT be called? Windows 9 RT? Windows RT 2.0? Windows SU?

Microsoft misstep No. 3: Missed opportunities in the cloud

In the mid-1990s, Windows senior VP Jim Allchin and Internet Platform and Tools division senior VP Brad Silverberg crossed swords many times, with Silverberg pumping for faster expansion into the cloud and Allchin more intent on building on Windows' success. Allchin won, Silverberg left, and by 1999 the die had been cast.

In the mid-2000s, Windows president Steve Sinofsky and Microsoft Chief Software Architect Ray "of course we're in a post-PC world" Ozzie also had their differences of opinion, with Ozzie pushing hard to expand quickly in the cloud, and Sinofsky more intent on building on Windows' success. Sound familiar? Sinofsky won, Ozzie left, and by 2010, Microsoft had lost its second high-level visionary cloud advocate.

In the intervening 10 years, Microsoft embraced the cloud, but did so with one foot firmly entrenched in Windows and the other in Office. Innovative cloud designs, like Mesh, have been tossed aside, while me-too cloud products like SkyDrive garnered a big budget.

Microsoft's foray into the online advertising market, with the Bing search engine, hasn't gone particularly well in spite of Microsoft's successful attempt to stack the deck in Bing's favor on new Windows computers.

Perhaps the biggest cloud shortcoming for Microsoft, at least from a consumer point of view, is its inability to build an ecosystem that comes anywhere close to the Apple, Android, or even Amazon offerings. Apple's taken an enormous lead in the consumer cloud, with Android scurrying to catch up, and Microsoft not yet in the running.

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