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 become obvious. Word and the rest of Office obviously matured at whatever pace during these early decades alongside the competition of the time, and it’s hard to pinpoint an exact period or product version in which whatever set of upgrades were more gratuitous than they were necessary. But Microsoft had long struggled to communicate what was new in each release, triggering the “lipstick on a pig” phenomenon in which it was forced to at least subtly change the user interface in each version so that one could easily tell at glance which they were using.

Bringing things a bit closer to this century, Office became Microsoft’s single-biggest product by both revenues and user base in the early 2000s, by which time the software giant had eliminated or rendered impotent its office productivity competitors. And it was then the firm ran into another unique problem: It was competing only with itself. That is, Microsoft Office’s biggest competitors were no longer other software products but were instead previous versions of Office. (This is a problem that would come to dog the PC industry more generally as hardware reliability improved, allowing users to hold onto a PC for much longer than was previously the case.)

But as the decades passed, that creeping complexity came to a head as most of the top customer feature requests each year were for features that already existed in the product. And so Microsoft experimented with a variety of new interfaces, including adaptive menus and toolbars, Smart Tags, and various side panels in an effort to expose features more naturally and simplify the congested Office UIs. And then it finally introduced the ribbon—a sort of tabbed toolbar that could expose functionality as needed—starting in 2007.

By this time, of course, the web and mobile had started shifting personal computing usage away from PCs and desktop computers. And so Microsoft brought Word and Office to new platforms for the first time in many years, following up earlier ports to Windows CE and its successors with the Word Web App and the other Office Web Apps in 2010 after a two-year gestation and then Office Mobile in 2013, first for the iPhone, and then later for iPad and Android. The problem? Each had and still has their own semi-random feature set, with many features available only on some platforms.

This brings us into the modern era in which the Office productivity suite and individual apps like Word are now available on Windows, Mac, web, Android, iPhone, and iPad. But this history also conveniently left out the other half of the story.

Here, I will be brief: Microsoft introduced its first server suite, BackOffice Server, alongside Windows NT 3.5 (the second NT release) in 1994 and the first version of Exchange Server in 1996. And it shifted Exchange and its other productivity servers into an Office Server suite in the early 2000s. But in the same way that web and mobile transformed personal computing, the cloud transformed back-end business and consumer services, with on-premises server installs migrating to datacenters and then hosted online services in the cloud over time. (I’m simplifying this because, again, there’s almost too much here to even remember, let alone discuss.)

In short, the Office Servers were joined and eventually largely replaced by Microsoft 365, but it didn’t happen overnight. Microsoft Online Services arrived in 2004, was replaced by Online Business Productivity Online Suite in 2007, and then that was replaced by Office 365 in 2010. Which was itself replaced by Microsoft 365 in 2017. And Microsoft even tried eliminating the Office brand, arguably its best-known and well-respected brand, in 2022, though that one is still up in the air (and, I think, a mistake).

It is in this modern era that the growing complexity of this platform we now call Microsoft 365 escalated from creeping to explosive. Sticking to just Word—yes, I remember we were discussing Word, the little app that pretty much started it all—we can see the impact that this escalation has wrought, both good and bad. Word and Office were originally updated with new features once every few years with new product editions. But the promise of Office 365, originally, and now Microsoft 365, is that the apps it provides can be updated continuously in a world in which version numbers no longer really matter. And so Word, as part of the Office suite, is not really those five discrete product implementations across Windows, Mac, web, Android, iPhone, and iPad.

No, it’s worse than that, and depending on how you look at it, there are in fact dozens of different versions of Word out in the world today.

Consider the Windows version. Excuse me, versions: Excluding those product versions that are no longer supported, we see today perpetual versions of Word 2016 (standalone or part of Office 2016), Word 2019 (standalone or part of Office 2019), and Word 2021 (standalone or part of Office 2021) plus the continually updated versions you get with the many, many Microsoft 365 commercial subscriptions or Microsoft 365 Family or Personal consumer subscriptions. So that’s at least four different “versions” of Word, or at least configurations of Word, each with its own unique feature sets. But there’s probably more: The Microsoft 365 commercial and consumer subscription tiers differ dramatically in many ways and it’s possible that Word offers some unique features in each. For better or worse, I can make my case without worrying about that.

The Mac versions of Word and Office operate similarly. The web versions have different feature sets based on whether you use them for free (as some functionality is included as part of your Microsoft account) or pay for them via a Microsoft 365 commercial or consumer subscription. As do the mobile versions, though the full features sets you get with a Microsoft 365 commercial or consumer subscription vary between Android phones, Android tablets, iPhone, and iPad. And let’s not forget about the Microsoft 365 app for mobile, which combines Word, Excel, PowerPoint and other Office functionality into a single app, and could itself differ between Android phones, Android tablets, iPhone, and iPad. Again, there are literally dozens of different Word “versions,” for lack of a better term, in use today.

But to be clear, the complexity I’m describing is not really about the number of Word versions. It’s about each of those versions having its own unique feature set.

Here’s a single example that makes the point. In August 2020, Word for the web got a terrific new Transcribe feature that transcribes the speech you dictate or in any uploaded audio or video file. And for years it was the only version of Word to offer this feature: Microsoft didn’t add Transcribe to Word for Windows, the version of Word that must still be Microsoft’s flagship, until January 2023, and that was only in preview for Insiders. It’s generally available in Word for Windows now, but I have questions. Like which version(s) of Word for Windows are supported? It’s obviously not part of Word 2016 or 2019, and never will be. Is it included in Word 2021 when used as a standalone software suite? Or is it a connected experience that requires a Microsoft 365 subscription? And what about the Mac? And the 4 to 8 mobile versions of Word? When will they get this feature, if ever?

It’s possible no one knows or cares. Regardless, this one feature is a microcosm for the complexity issues that dog Microsoft 365 today. It’s just one feature in one app, one star in the galaxy of products, apps, and services that make up the Microsoft 365 galaxy. It’s so small you can’t see if it you move too far away, but it’s so emblematic of the problem that if you pause to consider how this slow and erratic style of feature deployment impacts the millions of features that must exist across the Microsoft 365 matrix of functionality, you might actually lose your mind.

Still with me? Good. Because it just got even worse.

I assume you are aware of the AI hype cycle that Microsoft triggered this year—it was in all the newspapers, but I kid—and that Copilot in Microsoft 365 is just one of the many, many AI-based products and services that the software giant promised and then delivered, albeit to just a small subset of its commercial customers, in 2023. Well, there are some new Word features among the literally hundreds of new features that Copilot in Microsoft 365 provides. Useful features. Features like automatic document summaries in various formats, paragraph rewriting with tone options, prompt-based document refinement (“make this more concise” and so on), automatic table generation, and more. Great, right?

Sure. But these new features heap complexity on top of complexity.

The problem is Copilot in Microsoft 365 adds another tier to that matrix of functionality that already makes Microsoft 365 impossible to understand and nearly impossible to support. It’s an add-on subscription that costs an additional $30 per user per month on top of whatever other Microsoft 365 commercial subscription each user must have (and it only works with the more expensive subscription tiers). Looking again only at Word, I already described the multiple versions of this product across Windows, Mac, web, Android phones, Android tablets, iPhones, and iPads, each with its own feature set. But Copilot in Microsoft 365 grows that matrix of functionality by adding features that are only exposed in Word (and elsewhere) when you pay even more. And only for some customers.

As I write this, I literally don’t know which new Word-specific, AI-based Copilot in Microsoft 365 features work in which versions of Word. But if history is any guide, my guess is that most of them work in some of the web and/or Windows versions of the apps now, and that some current and future new features will come to some of the other versions sporadically and over time, while others never will. And that AI will work as a force multiplier, if you will, by making what is already mind-blowingly complex even worse.

Seriously.

One of the problems I’ve been copying with this past year is that it’s increasingly not possible for me to be definitive when it comes to describing how one might accomplish things using Windows or other Microsoft solutions. Whether it’s for the books or the site, I spend a lot of time using, experimenting with, and documenting how software works. And in an ideal world, I can describe a solution to a problem clearly, write something like “to achieve this, do that.” But this is becoming less common. Previously sacrosanct terms like version, release, and the like have lost their meaning. I can no longer say, “If you are using Windows 11 version 23H2, you will see this.” Now, all I can say is, “You may see this. Or, you may not. You may see something else.”

It’s bad enough with Windows. But with Microsoft 365, this problem is exponentially worse. I feel great sympathy for anyone who supports the people who use these products. This isn’t just about me and whatever compulsive need I have to figure out how things work and describe them clearly. It’s about the people—and there are billions of them—who use Windows, Microsoft 365, and whatever other software that’s developed in similarly scattershot ways. They don’t know what’s happening or why, and they don’t care. They just want to get work done and they need help. And the people who could provide that help are materially harmed by Microsoft’s behavior.

On one level, I don’t understand how an engineering-focused company like Microsoft allows or tolerates this style of feature deployment and product updating. But on a purely human level, I feel that it will drive customers away, push them towards simpler products that perhaps include only a subset of the features that Microsoft provides. And that may be to those customers’ advantage. More isn’t always better. And less isn’t always worse. But erratic complexity is never the answer. And Microsoft needs to wake up to the problem it’s created and fix this before it’s too late.