An accumulation of blunders under Steve Ballmer's leadership may have hit a tipping point this year, leading to Friday's groundshaking announcement that Bill Gates' former right hand and heir, as well as Microsoft's fiercest cheerleader, will step down as CEO within the next 12 months.
In recent years, Ballmer has been the target of critics over a variety of issues, including their dissatisfaction with the company's stock performance, Google's dominance in search advertising, the perception that Microsoft reacted late to cloud computing and its weak position in the tablet and smartphone OS markets.
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"There have been a whole series of market shifts that Microsoft has either missed entirely or misjudged their importance," said Al Gillen, an IDC analyst.
Rebecca Wettemann, a Nucleus Research analyst, said Ballmer should have exited the stage several years ago, because he has lacked the vision to see market fluctuations and failed to properly execute on opportunities.
"This gives Microsoft a chance to start a new chapter and hire a CEO who has vision to lead the market, and not follow it, which is what Microsoft has been doing," she said. "It must be someone who isn't looking just at how we move people to the next version of Office, but how we innovate to drive value to customers."
Most recently, Ballmer has been in hot water over Windows 8, a major upgrade of its flagship OS that many perceive as a flawed release. Billed as a product of historic importance, Windows 8 represents Microsoft's attempt to improve Windows' anemic participation in tablets and smartphones, where Android and Apple's iOS dominate.
However, Windows 8, which began shipping in October, has been heavily criticized due to its radically redesigned user interface, which is based on tile icons and optimized for tablets and other touchscreen devices.
Windows 8 also has a more traditional Windows desktop interface for running legacy applications, but many consumer and enterprise users have complained that toggling between the two interfaces is clunky and inconvenient. There has also been an outcry about the removal of the Start menu and button.
Microsoft plans to release an update for the OS, called Windows 8.1, in October. It addresses these complaints and several others, but there is a concern that the fixes may be too little, too late to salvage the OS's reputation and that it might end up being a fiasco like Windows Vista.
Some critics maintain that attempting to build a single OS for desktops, laptops and tablets was a strategic mistake because Microsoft has ended up instead with a product that isn't good enough for any of those devices. Apple's strategy, by contrast, has been to have Mac OS for its desktops and laptops, and iOS for the iPad, iPhone, and iPod.
"If Windows 8 had been a huge success and the business was growing by leaps and bounds, and Microsoft was winning share in the tablet market, there'd be a lot less pressure for Ballmer to leave," Gillen said.