It Was the Best of Times, and Then It Was the Worst of Times (Premium)

That the same leadership and teams made both Windows 7 and Windows 8 is an incredible fact of history that’s still hard to fathom. But Windows 7 and Windows 8 are both misunderstood, too, all these years later. For all its accolades, Windows 7 was simply a service pack for Windows Vista, an easily-achieved goal. And Windows 8? Yeah, it was a freaking disaster from a UX perspective, but the underpinnings and desktop advancements were far more impressive than what Microsoft had delivered in its predecessor.

What a world.

I covered the history of these two Windows versions, and a lot more, in my epic Programming Windows series, which I’m now working to turn into an eBook akin to the Windows 11 Field Guide. But the story is important enough for a high-level overview: after biting off more than it could chew with Longhorn, Microsoft was forced to continue updating Windows XP while it plotted a much more modest new release that came to market in 2006 as Windows Vista. Vista … was not loved, to put it bluntly. But it was also widely misunderstood, and its problems were quickly solved via two service packs and other updates. And, it should be noted, by the release of an Intel integrated graphics chipset that could finally render its attractive Aero graphics. Time heals all wounds.

But Windows Vista was also Microsoft’s first major stumble with its still-dominant PC platform: driven by years of non-stop success, the ego-driven software giant didn’t grasp that public perception would sink this system until it was too late, and then it responded slowly. Windows Vista is now understood to be the point in time when Microsoft’s market power peaked and then began its inevitable decline. And by the time Microsoft shipped Windows Vista to consumers, Apple had already announced the iPhone, changing everything.

As bad, the transparency of the Vista regime, led by Jim Allchin, was replaced with a Politburo-style veil of secrecy under new Windows chief Steven Sinofsky, a divider who saw only loyal faithful and enemies of the state inside of his team, elsewhere at Microsoft, and out in the world. You were either with him or you were against him. It was a recipe for disaster.

But at the beginning of his tenure, it was easy---perhaps too easy---to be with him. Sinofsky’s first job was clear, and those inside and outside of Microsoft rallied behind the mission to right the wrongs of Windows Vista. He would use---then rely on, and then overly rely on---telemetry data, automated feedback that came out of the product, to guide the direction Vista’s successor took. He was a fixer, a man with small ideas who was somehow paradoxically also convinced he could be Microsoft’s Steve Jobs, an industry seer with a finger on what would come next. It’s worth pointing out that Jobs never relied on telemetry data to figure out where to go next.

But fixing Vista was easy, and telemetry data did, for this one release, tell the tale: Vista was b...