How Much Can Microsoft Afford to Change Windows?

Pondering the next Windows 10

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Windows isn’t software. It’s an iconic entity that’s allergic to change. Think of it as a cherished work of art that needs regular upkeep: Everyone is happy with the brighter colors and fresh shine, but no one is pleased with the redrawn contours, painted over a blemish, or poorly recreated visage.

Windows 10 bears little resemblance to the Windows I first encountered in 1991, roughly around the time of Windows 3.1. In the 30 years since, I’ve seen and beta-tested countless iterations, each promising better functionality, performance, and utility. Later came assurances of better security. With notable exceptions, most updates treated the interface like a precious canvas, very slowly moving key elements, introducing new ones, and, occasionally, deprecating others.

In some ways, this process was like watching someone you love gracefully aging. Unless you leave them for a while, you don’t always notice the subtle changes. With Windows, key elements like File Manager, Task Manager, Device Manager, and the Registry Editor have barely changed in decades. I think this is both out of necessity and by design. Even though Microsoft Windows code is arguably completely different than what it was in, say, Windows 2000, these remnants play a crucial role in bridging the present and past.

Microsoft’s record of success with its various updates is uneven. For every Windows 95, there’s a Windows Vista or Windows 8. The more subtle the changes, the better the user reception.

Microsoft Windows Vista didn’t change the OS that much, but it wasn’t as structurally sound as Windows 98, Windows NT, or Windows 2000. The OS nadir is Windows 8: that time where Microsoft tried to cajole millions of Windows fans into giving up the Start button. To be fair, Windows didn’t launch with a Start button but its introduction with Windows 95 marked a key moment in the history of personal computing. It was the “Start” of billions of normals’ relationships with personal computing.

Start became a touchstone for everyday users, something Microsoft recognized right up until it didn’t in 2011. Windows 8 is the last time Microsoft tried reinventing Windows. It was supposed to be a touch-first interface. That intention turned out to be prescient, as virtually all Windows systems now offer touch screens. However, the removal of the Start button and the tile interface (RIP “Metro”) broke the cardinal rule of Windows updates: Slow and steady. A chastened Microsoft eventually brought Start back.

This is what I’m thinking about as Microsoft announces a major June 24 Windows event that promises the biggest changes to Windows in a decade, something during the recent Microsoft Build developers event.

Generally, I’m a big fan of change and innovation and I get that 2021 is not 2011, especially not for the Windows ecosystem. Unlike back then, Microsoft cares little about the screen or interface you use when accessing their services. “Want to produce Microsoft Word docs on an iPad Pro and store them in OneDrive? No problem, as long as we get our $99 a year for access to the Office365 suite.”

That doesn’t change the fact that any significant change to Windows will be felt like a shockwave around the world. Microsoft Windows users embed the platform with their homes, business, and most important work. Turning on a Windows system that asks you to wait patiently and not shut down the system while it moves all your cheese is not anyone’s idea of a good time.

If the new Windows, which likely won't arrive before the end of this year, features the big changes Microsoft is promising, there could be over 1 billion frustrated Windows users.

My advice to Microsoft: Tread lightly and pay close attention to beta-tester feedback.

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Tech expert, journalist, social media commentator, amateur cartoonist and robotics fan.

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