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

By Woody Leonhard, InfoWorld |  Software, Microsoft

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 cloudIn 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.

Microsoft misstep No. 2: Management musical chairsI've talked about the Microsoft management musical chairs in a series of InfoWorld Tech Watch posts, most recently "Game of thrones: The men who would be Ballmer." Suffice it to say that all of the people capable of providing a steady transition from the reign of Ballmer have left the company.

Jim Allchin. Brad Silverberg. Paul Maritz. Nathan Myhrvold. Greg Maffei. Pete Higgins. Jeff Raikes. J Allard. Robbie Bach. Bill Veghte. Ray Ozzie. Bob Muglia. Steve Sinofsky. They're all legends, in their own way, and Microsoft had many more.

We still have some luminaries. Andy Lees survived the Sinofsky purge. Paul Maritz is still around, having spent years at VMware. Bill Veghte's at HP. There are others still at Microsoft, but most lack the experience to play in that league.

The lack of senior management depth may turn out to be Microsoft's biggest misstep in the early 2010s.

Microsoft misstep No. 1: Internet Explorer 6Microsoft's greatest misstep of all time? Internet Explorer 6. Consider:

Chances are good that more Windows computers have been infected via Internet Explorer 6 than by any other vector. Flash and Adobe Reader may come close, but IE6 is up there. ActiveX, IE6's evil toady, deserves its own ring in developer hell.

In the process of deploying IE6, Microsoft ran afoul of U.S. antitrust laws. The repercussions of the DoJ action resonated throughout Microsoft's product line for more than a decade, driving all sorts of design decisions that were at least partially influenced by antitrust concerns.

Microsoft lost an enormous amount of public goodwill over IE6. It's as if, suddenly, the average Windows user started to understand that their computer was at risk because of a bad piece of Microsoft software. Web developers did, and do, hate IE6, with its fussy quirks, outright bugs, and absolute disdain for anything reeking of a standard.

Microsoft took more than five years to ship an upgrade -- most likely the biggest misstep of all.

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