Smartest market targeting
Microsoft's earliest products were for individual users, rather than for IT departments, but the company knew that ultimately it would have to sell products aimed at enterprises if it wanted to thrive. On June 11, 1996, the company launched Microsoft Exchange Server, which was originally written to handle Microsoft's internal e-mail. (Previously the company used a Xenix-based e-mail system.)
Exchange Server was first released as Version 4.0, apparently to continue the numbering convention of the earlier Microsoft Mail product, which was at Version 3.5. Exchange has since expanded to include other communications functions such as mobile device syncing and e-mail/voice-mail consolidation, and it has become a cornerstone of corporate IT departments.
Best hire
Love him or loathe him, there is no doubt that Steve Ballmer's hard-driving, relentless style and laser focus through the years have helped Microsoft become the world's most successful software company.
Ballmer, who knew Gates from their Harvard days, came to Microsoft in June 1980 as one of the young company's few employees with real-world business experience. He had worked for Procter & Gamble after graduation and had attended Stanford Business School for one year before joining Microsoft.
Worst waste of visionary talent
Ray Ozzie is one of the technology industry's true visionaries. He worked on the first spreadsheet, VisiCalc, and developed the Lotus Symphony office suite. And that was only the prelude: He launched Iris Associates, which developed the software that would become Lotus Notes, and later Groove Networks, which developed the collaboration software Groove Virtual Office (now called Microsoft Office Groove).
In April of 2005, Microsoft bought Groove and Ozzie became Microsoft's chief technical officer. In June 2006, he was promoted to chief software architect, a title previously held by Bill Gates.
Many industry watchers had high hopes for Ozzie's influence at Microsoft, but he has done little to change the company's direction, software or culture, particularly when it comes to his specialty, collaboration. Beyond adding Groove to the Office suite, Microsoft has done little to develop it, sell it or make it central to the company's strategy. The upcoming version of Office for the Web doesn't even have basic synchronization features, and the "Live" brand is a mess, consisting of an odd mishmash of downloadable software and Web-based services, with no real connection between them.
Why hasn't Ozzie made his mark? Some people (including yours truly) postulate that there's a dog-eat-dog culture at Microsoft, with too many people protecting too much turf, and he's never managed to adapt.
Weirdest company spokesperson
Most companies like their public faces to be sober, measured and thoughtful -- but then, most companies don't have Steve Ballmer at the helm. Although he's been a boon for the company overall, Ballmer has also been prone to public fits of behavior that at times appear to channel Pee Wee Herman on acid.
The most well-known of these is the infamous "Monkey Boy dance" in which, center stage at a conference, Ballmer danced, howled, screamed and generally acted the madman to show his enthusiasm for Microsoft. Another YouTube favorite is the "Developers" video, which captured him soaked with sweat, screaming "Developers, developers, developers, developers..." until his voice gave out.
Best company spokesperson
Bill Gates -- his geekiness and intelligence eventually won over the press, and he became a near-ubiquitous magazine cover boy before his retirement in June 2008.
Worst PR disaster
In February 2008, extremely embarrassing internal documents were released in what's known as the Vista "junk PC" lawsuit. The class-action suit against Microsoft charged that the company misled consumers into buying Windows XP computers that were marked "Windows Vista Capable" -- even though those PCs couldn't run the most important features of the then-new operating system.
Over several months, internal Microsoft documents became part of the suit, including one from an unnamed employee, who wrote in an e-mail, "Even a piece of junk will qualify" to be called Windows Vista-capable. And in another e-mail message, Mike Nash, who is now a corporate vice president for Windows product strategy, wrote, "I PERSONALLY got burnt.... Are we seeing this from a lot of customers?... I now have a $2,100 e-mail machine."
Jim Allchin, who at the time of the Vista-capable PC push was the co-president of Microsoft's Platforms and Services Division, wrote in an e-mail, "We really botched this.... You guys have to do a better job with our customers."
Later e-mails revealed that Microsoft may have launched the marketing scheme in order to help Intel sell low-end chips that were not capable of running the full version of Vista.