Windows 8: Still Crazy After All These Years (Premium)

Some seem surprised that it took so long for Windows 10 usage to surpass that of Windows 7. But this belated milestone doesn’t say that much about Windows 10, or about Windows 7. Instead, it says a lot about Windows 8.

Which was, of course, terrible.

The ways in which Windows has evolved over the years are many, but it’s rarely happened on a steady schedule. The one exception is the trio of releases that included Windows 7, Windows 8, and Windows 10, each of which shipped three years after its predecessor. That release cadence was so regular that many probably forget that Microsoft had never previously used such a schedule. Or kept to any schedule at all, really.

Instead, that steady three-year release cycle was a reaction to the Longhorn delays and the subsequent poor reception to Windows Vista. Longhorn was supposed to be a major release, the biggest ever, and it was envisioned as a complete rethinking of the platform. But it was also too much to take on at once, and the project collapsed under its own weight, taking Jim Allchin and his career with it. Windows Vista, which was hastily cobbled together in the wake of Longhorn’s demise, provided only shallow hints at the Longhorn promise, with features like virtual folders, hardware-accelerated graphics, and a widget-filled Sidebar.

Windows Vista shipped in just a year and it did so with major compatibility and performance problems, forever ensuring that it would be remembered as one of the most disappointing Windows versions of all time. But fixing Vista was simple, and I’ve often described Windows 7 as being nothing more than another Vista service pack. But despite its easily-attained goals, Windows 7 has gone on to be, perhaps, the most well-respected version of Windows, ever.

And the reason for that, of course, is Windows 8. Which, again, was terrible.

Actually, “terrible” isn’t the right word because it doesn’t do anything to explain how thoroughly and perhaps permanently that release undermined Windows as a platform and set up a coming decade of client defeats for Microsoft. Compared to Windows 8, Vista was just a minor setback, one that was easily and quickly fixed. But Windows 8? We’ll never stop dealing with the blowback from this perfect combination of terrible feature set and bad timing.

Windows 8 only happened because of Windows 7’s perceived successes. Microsoft’s leadership team gave an insane madman, Steven Sinofsky, free reign to make any changes he wanted to drag Windows quickly into the then-nascent era of mobile, touch-based computing. Sinofsky was no visionary, but he was dictatorial. So he was basically everything that was wrong about Steve Jobs, but lacking in what made Steve Jobs special.

The result was a disaster, a product that borrowed heavily from Microsoft’s Windows Phone platform without ever stopping to wonder whether being able to do so made any sense at all for the PC market. Worse, after stealing ideas from Windows Phone, Sinofsky’s Windows team turned its back on what was then perceived as the “B-team” in Microsoft’s client platforms. And so Windows 8 was spat out of Redmond separately from Windows Phone, with absolutely no integration at any level. Imagine how things might have been different, for example, had Windows 8 run Windows Phone 8 apps and shared a common store.

And that, ultimately, was Sinofsky’s biggest error: He perceived everyone outside of his inner circle, even those within Microsoft, as the enemy. And his secretive, insular, and tunnel-visioned approach ended up alienating virtually the entire company.

Microsoft belated realized the error of appointing this dictator in such a position of power—the fact that he was bald-facedly angling for Steve Ballmer’s job as CEO probably helped—and fired Sinofsky on the eve of Windows 8’s launch. To save face, the firm allowed the evil little twerp to appear at the launch event, and then he was railroaded out of town.

But it was too late. Microsoft launched Windows 8 knowing full well that it was a disaster and that the Sinofsky-led Surface PCs it was also launching would alienate the PC maker partners it would need to sell Windows 8 to consumers and businesses. They reacted predictably by mostly ignoring the “touch-first” aspects of Windows 8 and shipped a largely familiar collection of traditional PC form factors alongside the system instead. The message was clear: F$%k you, Microsoft. F$%k you for Windows 8. And f$%k you for Surface.

Windows 8, like Windows Vista, was a major Windows version that never successfully replaced its predecessor in the market. Windows Vista’s defeats—which included the Longhorn delays, of course—breathed new life into Windows XP, and that aging platform ended up being supported well past its official lifecycle as a result. This was costly to Microsoft, both literally and from a reputation standpoint, and the software giant resolved that it would never succumb to this problem again.

But that’s the thing. Windows 7, if anything, is even more popular than was Windows XP. And that is particularly true today, just one year from its official end of support: There are about twice as many Windows 7-based PCs out in the world now as there were Windows XP PCs at a similar point in time in that product’s life cycle.

This reality, of course, has impacted Windows 10 as well.

We can view Windows 10 in many ways. But the fairest, perhaps, is as a continuation of Windows 8. In the wake of Sinofsky’s exit, Microsoft quickly moved to begin fixing the problems with Windows 8, most especially its inability to work well on the traditional PCs that approximately 100 percent of the user base was actually using. The Start button and Start menu were brought back in subsequent updates, and then Windows 10 completely closed the loop by decidedly embracing traditional PC form factors and usage again, while retaining most of the touch-first user experiences that had dragged down Windows 8. As it turns out, a lot of people liked using Windows on tablets and 2-in-1s, and those products—from both Surface and other PC makers—improved and formally created a new PC product category.

To say that Windows 10 is what Windows 8 should have been sounds unfair as I write this. But it is entirely fair: The real problem with Windows 8 wasn’t that Microsoft had embraced touch-first user experiences, it was that it had done so to the detriment of all of the platform’s users at the time. These interfaces should have been added to Windows, but over time. And not to the exclusion of the past. As I’ve argued in the past, the ability to run all Windows applications is what makes Windows, Windows, if you will. Windows 8’s inability to work like previous Windows versions and force customers to use non-discoverable (and inefficient) new user experiences was one of its greatest sins, and it made the release an anomaly compared to other Windows versions. This is the Sinofsky effect. And we saw this with the Office ribbon too, another Sinofsky one-way, dead-end street that is only now being reversed.

Microsoft couldn’t have shipped Windows 10 in 2012. But the product that did ship that year, Windows 8, was so hastily cobbled together that Microsoft should have decided to wait to release it until it was right. That it didn’t do so is indicative of one thing and one thing only: It didn’t want another Windows Vista. It got one anyway. Actually, it’s worse.

What Microsoft should have done with Windows 8 is ship it with the flat, new look and feel to differentiate it from Windows 7, but retain the Start button, Start menu, and desktop. And shipped it with a Windows Phone apps platform and Store to begin that integration with mobile. You know, like Apple just did with macOS Mojave and iPad apps.

That didn’t happen, of course. Instead, Microsoft had to deal with years of delays and false starts, and, ultimately, with the failure of its native apps platform, which was renamed to Universal Windows Platform (UWP) in Windows 10. But everything bad that’s happened on the client since Windows 8 can be tied directly to that release, from the failure of Windows Phone, which couldn’t leverage Microsoft’s PC success, to the failure of UWP, the Windows Store, and even tertiary products like Groove Music. This could have been a big, integrated platform. Instead, it’s a mess.

Windows 8 was too much, too fast, and it was wrong, the perfect storm of ineptitude and hubris. And I still feel that we’re never really going to exit its shadow. That every time some Microsoft consumer product or service fails, you can find some connection back to Windows 8. That Microsoft is still making some of the same mistakes—with ill-conceived ideas like Windows 10 S/S mode, in particular—is disheartening. It’s also goofy, when you consider that Terry Myerson’s Windows team was set up specifically to tear down and reverse Sinofsky’s bad decisions and ideas.

Anyway, Windows 10 usage has finally surpassed that of Windows 7. But Windows 8 is still a hangover that we’re dealing with over six years later. I don’t think we’re ever going to escape it.