Best and worst browser launch
In September 1997, Internet Explorer 4 launched, cementing Microsoft's browser dominance and ultimately killing Netscape Navigator as a competitor. With the introduction of IE4, Microsoft also tied Internet Explorer more deeply to Windows. This came back to haunt the company when it was sued by both the U.S. government and the European Union for anticompetitive behavior, including using Windows to force people to use Internet Explorer instead of competing browsers.
Worst interface
Go to any list of the worst software ever written, and 1995's Microsoft Bob will be on it. Designed for Windows 3.1 and later Windows 95, it was supposed to be a user-friendly interface to help nontechies use computers. Instead, it was so cloyingly cute that, in comparison, photos of big-eyed puppies appear to be deep and meaningful. (As Harry McCracken wrote in a PC World review, "It seems to be aimed at a six-year-old who has personal finances to manage.")
Bob was also confusing to navigate; sucked up system resources, reducing computers to a crawl; and was widely derided in the general and tech press. Users stayed away in droves.
Microsoft Bob was overseen for a time by Melinda French, who was Bill Gates' girlfriend at the time and later became his wife.
If you want to see Bob in action yourself, check out this video of Bob. (Warning: The video contains extreme stupidity, horrendous interface design and a nonstop stream of intense monotony.)
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.