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. 2: Management musical chairs

I'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 6

Microsoft'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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