The Escalating Complexity of the Microsoft Ecosystem (Premium)

We use Microsoft productivity products and services because they are superior to the alternatives. But the creeping complexity of these solutions has suddenly escalated. And this complexity, combined with the erratic and seemingly random way in which Microsoft deploys new features and functionality, threatens to undermine its customer's confidence and its dominance in this space.

I often write about my frustrations with Windows 11 these days, but let's mix it up and talk about Microsoft 365, an even more widespread, complex, and necessary platform. Of course, doing so can be a slog because Microsoft 355 is a sweeping set of software and services with both commercial and consumer variants that are made available as both services and standalone software with free, perpetual, and subscription licensing across Windows, Mac, web, Android, iPhone, and iPad. Indeed, a visualization of the matrix of features provided by Microsoft across these disparate endpoints would be almost impossible to create and would more closely resemble a three-dimensional map of our solar system than a typical features chart. Because of this, it's necessary to whittle down this discussion to a more human level so we can more easily discuss it.

So let's just talk about Microsoft Word, a convenient representative for the whole of Microsoft 365 that's well understood by everyone because it's existed for even longer than Windows. In fact, Microsoft just celebrated Word's 40th anniversary, a milestone that triggered me to write an earlier complaint about the product's complexity in Windows. No worries, I'm not going to rehash anything from that earlier post. This one is much broader, and the problems I outline here apply across the entire Microsoft 365 set of solutions.

And these problems go back to the very beginnings of Microsoft 365, a product line that not coincidentally got its start with Microsoft Word. In fact, you may be surprised to discover that its earliest implementation in 1983, as Multi-Tool Word, was on Xenix, a short-lived Microsoft derivative of Unix, and MS-DOS. It was designed from the beginning to work with a mouse, and later iterations were ported to the Mac (1985), Windows (1989), OS/2 (1989), and SCO Unix (1990). There was even a one-off derivative for the Atari ST called Microsoft Write (with no relation to the Windows app of the same name) in 1988.

Word is perhaps best known to the outside world as a member of the Microsoft Office desktop product suite that debuted on Windows in 1990 with just three apps, the other two being Excel and PowerPoint. This was followed up by the first release on Mac, Office 3.0, in 1992 and Office 4.2 for Windows NT in 1994, which ran on Intel, Alpha, MIPS, and PowerPC-based PCs and workstations. And of course, Office grew in size and complexity over the years, too, adding more apps and many more features as time went on.

It was during these years that the creeping complexity I mentioned earlier started to ...