The Sinofsky Legacy at Microsoft: Yet to Be Determined

Microsoft's controversial Windows honcho is gone. We can't judge his legacy until it's clearer what people think about Windows 8 and Surface.

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Scott Eells / Bloomberg via Getty Images

Steven Sinofsky, president of the Windows group at Microsoft Corp., speaks during an event in New York on Oct. 25, 2012.

Wow. Steven Sinofsky, the president of Microsoft’s Windows and Windows Live division and a 23-year veteran of the company, is leaving Microsoft, effective immediately. The move comes less than three weeks after the launch of Windows 8 and the Surface tablet, and is eerily reminiscent of iOS honcho Scott Forstall’s recent departure from Apple. Sinofsky’s departure was officially a mutual decision by him and CEO Steve Ballmer, but his reputation within Microsoft as a hard fellow to work with and for may have been a factor.

(For a long look at Sinofsky’s impact on Microsoft and its products, read this excellent CNet piece by Jay Greene — it was published last month, but is now more relevant than ever. And here are the memos from Ballmer and Sinofsky.)

Sinofsky may be controversial, but that doesn’t mean that there’s no consensus about him. Everyone notes that he was good at shipping software that worked acceptably well in a timely manner. (Microsoft’s inability to meet deadlines used to be one of the longest-running in-jokes in technology, but with Sinofsky’s ascendance it became obsolete.) Everyone says that he was territorial and prickly. (In my dealings with him, which weren’t many, I found him to be a brittle personality.)

He spent much of his time near the top of Microsoft working on the Office productivity apps, and was responsible for Office 2007, the version which — in a sort of precursor of Windows 8’s sweeping changes — dumped the suite’s familiar menus and toolbars in favor of the all-new Ribbon interface. Then, after the disaster that was Windows Vista, he took charge of Windows and shipped the robust and largely pleasant Windows 7.

But years from now, when people look back at the Sinofsky years at Microsoft, I think that Office and Windows 7 will be footnotes. What will matter will be Windows 8 and Surface — and the fascinating thing is that it isn’t yet clear whether the two products will make him look good or bad.

So soon after Windows 8 and Surface’s release, it’s simply way too early to tell whether Microsoft’s big attempt to reinvent Windows for the tablet age, and itself as a PC hardware maker, are going to fly. I think it could be half a decade until it’s clear whether the drastic change spearheaded by Sinofsky was a smart move. And now others — including Sinofsky lieutenants Julie Larson-Green and Tami Reller, who are divvying up his Windows responsibility — will have to figure out how to build upon the fresh start he just initiated.

We don’t know whether Microsoft customers — many of whom are so skeptical of change that they cling to eleven-year-old Windows XP — will accept a Windows that looks so little like Windows. It’s tough to say whether Microsoft can make money with Surface without permanently ruining its relationship with HP, Dell and other hardware makers. The jury is still out on whether it’s possible to split the difference between the PC business Microsoft has dominated for so long and the tablet market which is still so iPad-centric.

Whatever happens, Sinofsky deserves credit for shaking things up. For much of its history, Microsoft was addicted to shovelware upgrades — massive software products with every possible feature crammed in. They weren’t coherent or polished; they felt like they were obsessed with protecting and expanding turf; they were often short on originality; in certain cases, they barely worked at all. Sinofsky’s Microsoft is a more disciplined place which makes better, more interesting products. He left both Office and Windows fundamentally different than he found them, in ways which will inspire debate forever — but I’d choose his approach to software over those of his immediate predecessors anytime.