Microsoft’s 13 worst missteps of all time

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Over the years, Microsoft’s made some incredibly good moves, even if they felt like mistakes at the time: mashing Word and Excel into Office; offering Sabeer Bhatia and cohorts $400 million for a year-old startup; blending Windows 98 and NT to form Windows 2000; sticking a weird Israeli motion sensor on a game box; buying Skype for an unconscionable amount of money. (The jury’s still out on the last one.)

Along the way, Microsoft has had more than its fair share of bad mistakes; 2012 alone was among the most tumultuous years in Microsoft history I can recall. This year you can bet that Redmond will do everything in its power to prove 2012 naysayers wrong. To do so, Microsoft must learn from the following dirty baker’s dozen of its most dreck-laden decisions, the ones that have had the very worst consequences, from a customer’s point of view.

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Windows 8 Deep Dive

Microsoft misstep No. 13: DOS 4.0
In July 1988, IBM and Microsoft released IBM DOS 4.0, and the wheels fell off with data-eating bugs, corrupted disks, and mismanaged memory. Fingers have been pointing ever since. Microsoft’s side says IBM botched the testing; IBM’s side says Microsoft shouldn’t have expected IBM DOS 4.0 to work on non-IBM hardware.

IBM shipped the partial-fix IBM DOS 4.01 in September, but Microsoft took two more months to ship the clearly identified, and differentiated, MS-DOS 4.01. Many people who bought new computers in late 1988 insisted on DOS 3.3, not 4.0 or 4.01. Customers didn’t know what to make of the new versions and largely stuck with the devil they knew, 3.3.

Microsoft misstep No. 12: The evil cuties Bob, Clippy, and Rover
Symbolized by a big yellow blob with nerdy glasses, Microsoft Bob — code-named “Utopia” — stands as the quintessential Microsoft failure by which all others must be measured. In a departure from the menu-based interface for Windows 95, which was released seven months after Bob, Microsoft Bob’s main screen looked like a cartoon living room, with graphic links to a word processor, finance application, calendar, Rolodex, checkbook, and other programs. Click on the grandfather clock’s face and the calendar program appeared. Click on the envelope and the email program sprang to life — Bob cut a special deal with MCI Mail whereby, for just $5 per month, a Bob owner could send up to 15 emails per month, absolutely free.

Customers could add tiles, er, shortcuts to new applications installed on their Bob-ified computer, and the shortcuts’ pictures would appear in the immersive Start menu, uh, cartoon living room, inside picture frames or shipping crates. The living room could be personalized with various colors, decorations, and themes. Stop me if this sounds too familiar.

The eponymous Bob himself looked a lot like Bill Gates — at least, as much as a smiley face with glasses can resemble the world’s greatest philanthropist. Microsoft Bob shipped with cartoon helpers bearing distinctive appearances and personalities: Scuzz the Rat (“Couldn’t care less about you. Seldom offers help.”); a dog named Rover (“Easy to work with, friendly and helpful. Tries to be your best friend.”); Chaos the Cat; Digger the worm; Shelly the turtle; Java the coffee-swigging dinosaur; and a half-dozen more.

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