Microsoft 365 for Consumers Could Fix Our Windows 10 Woes (Premium)

It used to be so easy: Microsoft built its empire around Windows, the software that never stopped giving. Thanks to regular PC upgrades, an ever-growing PC market, and a family of codependent products like Office that swelled its coffers for decades, Windows fulfilled Bill Gates’ vision of “the magic of software” and made the company both rich and dominant.

And then it all came crashing down.

Thanks in part to the rise of mobile, the PC market peaked in 2011, just before the release of Windows 8, and it’s been in a tailspin ever since: In 2018, PC sales were lower than at any time in the previous decade, with the market shrinking by 30 percent over that timeframe. Added to this, PCs are more reliable than they’ve ever been, and customers are holding on to them longer. And sensing the weakness, PC competitors both real (Chromebooks) and erstwhile (iPad Pro) have made major pushes to convert dissatisfied Windows users to simpler platforms.

Microsoft hasn’t helped matters by botching its response to these trends.

In addition to its years-long attempts to fix the touch-first disasters in Windows 8, the firm decided to make Windows 10 upgrades free in an attempt at keeping Windows users with Windows. It moved Windows 10 to the “Windows as a Service” forced updating scheme in which our PCs get two major version upgrades a year, and at least one hefty, reboot-triggering cumulative update every month. And it has sought ever-more insidious ways to monetize a Windows 10 user base that won’t be paying for Window every three years with a new PC purchase: It has added advertising, crapware games and apps, and privacy-invading data collection to this once-proud platform.

These efforts have all been unsuccessful. Aside from the sheer terribleness of forced upgrades---“Windows as a disservice” is perhaps the better name---Microsoft’s efforts to further monetize Windows users can’t possibly have turned into a financial windfall. Worse, they simply piss off customers and make them more interested in examining the Chromebook and iPad Pro alternatives. Put simply, this whole plan has backfired.

We’ll see what, if anything, Microsoft does to correct these issues in 2019. But remember that Microsoft serves two core audiences, businesses and consumers. And while both have very different needs in some keys ways, both are likewise similar as well. It may be interesting and instructive to see how Microsoft handles its business customers differently than it does consumers.

For example, WaaS is a disaster for businesses too: They need to manage the rollout of new Windows 10 versions to multiple PCs and support those users and their unique, often in-house, custom applications. To meet this need, the WaaS treadmill isn’t as onerous for businesses as it is for consumers. And Microsoft has now extended the Windows 10 version support timeline for business customers at least twice.

Why treat businesses better? Because M...