August 25, 2013, 8:58 AM — Microsoft CEO Steve Ballmer survived the flop that was Windows Vista, but he wasn't able to do the same after the disappointment of Windows 8.
"Last year, Ballmer said Windows 8 would be his defining moment," said Patrick Moorhead of Moor Insights & Strategy. "Now, this has caught up with him. Windows 8 is the primary reason why he's retiring, specifically Windows RT. There's been a lack of progress on Windows Phone, but the forcing function was clearly the write-down of the Surface RT."
From Moorhead's perspective, it was that write-down, a $900 million charge against earnings to account for excess inventory of the company's Surface RT tablet, that precipitated Ballmer's retirement, in large part because the overstock was a blatant indicator of the magnitude of his misjudgment about how customers would react to the newest Windows.
And Windows 8 may be the thing that people remember about Ballmer, said another analyst, whether that's fair or not.
"Any evaluation of Ballmer can't start in 2007 or 2008," argued David Cearley of Gartner Friday. "His legacy is the totality of Microsoft. But inevitably, a CEO is judged by what the company looked like when he left. [And] Microsoft has struggled to reinvent itself."
The problems Ballmer recently faced were greater than just the Surface tablet or the tile-based, touch-first Windows RT operating system that powers it. Windows 8's failure to spark a surge in PC sales also played a big part.
Ballmer weathered Windows Vista, the delayed follow-on to Windows XP that was widely derided as a mess. But it wasn't Windows 8's poor numbers, by some metrics even poorer than Vista's, that brought down Ballmer: It was his unrealistic predictions of its success that did him in.
Ballmer, known as an enthusiastic promoter of Microsoft and an overly-optimistic salesman by trade and inclination, was, to use a phrase he coined multiple times in his career, "all in" on Windows 8.
"I think with the addition of Windows 8, with these incredible new form factors that are tablets and PCs, I think we're going to see a lot of growth and vitality and explosion in the PC market," said Ballmer last October at the company's BUILD developers conference. "I guarantee you, this will be the best opportunity software developers will see as hundreds of millions of new machines go out with the potential of billions and billions of new applications being sold."