Windows 11 is Not Ready for Business (Premium)

I assume few enthusiasts were impressed with Microsoft’s first Windows 11 event since last summer. But that’s not the biggest problem: Windows 11 wasn’t ready for primetime when Microsoft first shipped it last October after just three months of external testing, and it’s now obvious that it will still not be ready when it reaches its one-year anniversary this fall. And that’s because Microsoft is focusing too much on adding new features and too little on fixing the functional regressions it introduced.

There is so much to unpack here.

But let’s start with the obvious stuff. If you watched yesterday’s Windows 11 hybrid work event, you will have surely noticed that Microsoft tried to make the case that Windows 11, somehow, is ready for businesses to evaluate and deploy. This is an absurd point of view, and if any entity other than Microsoft had made it, I would have assumed it was an April Fools joke of some kind. But because Microsoft is making this claim, as delusional as it seems, we have to take it at face value.

Having charted business adoption of various Windows versions over roughly 15 years at what I’ll call Windows IT Pro (the former Windows NT Magazine), I learned a few things. With every Windows version, in turn, Microsoft worked to broadcast how ready that version was for business, and that businesses would not need to wait for the inevitable Service Pack 1 (SP1) release before even considering it. But with one major exception, that never happened: businesses have always moved very slowly to embrace new technologies of any kind, and migrating to new Windows versions was always disruptive at every level, and expensive in terms of training, software compatibility, and the like.

That one exception was Windows 7, when, for the first time, businesses did move quickly to upgrade. But there were two reasons for this difference, neither of which apply to Windows 11: Windows 7 benefited from the multi-year issues that Microsoft had shipping Longhorn/Windows Vista, causing Windows XP to remain in-market for longer than expected. And Windows Vista was so poorly received that businesses ignored it. So by the time Windows 7 arrived about 8 years after XP, businesses were uncharacteristically ready to upgrade.

Compare this situation to that of Windows 11, which arrived alongside a new version of Windows 11, was installed as if it were a basic Windows 10 feature update, and has functional regressions compared to its predecessor. Unlike XP, Windows 10 is not out of date, and unlike XP, it’s actually more feature-rich and familiar than its successor. Like the best Windows releases, including Windows 7, Windows 10 was basically a superset of its predecessor. But whatever. Businesses are each at whatever point they’re at in various hardware and software upgrade cycles. And if Windows 11 was a true superset of Windows 10, as it should be, businesses would simply just upgrade when the time came. There would be no need for Microsoft to push it.

But here we are, and Microsoft is pushing Windows 11. A new version of Windows that has serious functional regressions when compared to Windows 10. A new version of Windows that has arbitrary new hardware requirements, meaning that businesses won’t just need to train users to workaround the features they’re missing, but will also need to buy new PCs in many cases. Those hardware and software cycles are converging, and when combined with the training issues, that means it’s even more expensive to perform this upgrade in many cases. That businesses might often time hardware and software upgrades for mass migrations is a fair point, but this time it will be required for more.

To be clear, there are useful new features in Windows 11, just as there will be more useful new features coming to Windows 11, based on yesterday’s presentation. But this is one of the few times in the history of Windows where Microsoft required you to deal with missing features that the userbase knew and expected in order to get new functionality. The last time it did so was Windows 8, which, among other things, didn’t even have a Start button or Start menu and forced users to deal with a full-screen PlaySkool interface for reasons that remain unclear to this day. And we all know how that went.

No, Windows 11 is no Windows 8. It’s not that bad. But Windows is also a very mature software product, and if history has shown us anything, it’s that new versions of Windows that are wholly additive—meaning they bring new features but do not punish customers with regressions to well-understand features—are usually successful, while those that are not, are not at all successful. And I’m not just basing that on the Windows 8 experience: Windows RT, Windows 10 S (S Mode), and Windows 10 on ARM have all made this point in recent years: functionally limited new versions of Windows do not succeed.

Look, I understand Microsoft’s desire to simplify Windows. I even applaud it, in a vacuum. I’ve been applying the same type of decluttering in my real (non-digital) life as my wife and I prepare for our next move. But the focus here is all wrong: what Microsoft should be doing is making Windows visually consistent by modernizing all the user interfaces it intends to keep and replacing all the legacy UIs (Control Panel as the obvious example) it does not. It should do this as it moves forward without removing actual functionality. And as it adds new functionality. If that’s what Windows 11 was, we’d all be high-fiving each other in disbelief. Businesses would applaud this.

Put simply, Windows isn’t a new, thin, light system designed for devices, a word Microsoft insists on using these days, it’s a complex, legacy system designed for PCs, a special kind of device that is both complex and full-featured. Windows is what users turn to when they need power. It’s not the right place to impose limits.

Obviously, Microsoft has also tried and failed to make Windows make sense on smaller, lighter, and more modern device types. We all lived through the Windows Phone disaster, and we know that its most recent effort along these lines, Windows 10X, fell apart before it even shipped. But what’s astonishing to me, what should be astonishing to anyone who still cares about Windows, is that Microsoft ignored what it learned from those failures and isn’t just trying again, but is instead foisting the overly-simply Windows 10X user interface on everybody with Windows 11. Guys, we tried this already. In Windows 8. Is this really the model we want to follow now?

We can get into the specifics of yesterday’s announcement, and we will. As I mentioned earlier, there are some useful new features coming to Windows 11, though it’s not clear at all when or how they will arrive. (And seriously, given the overpromising and underdelivering that happened at the initial Windows 11 event last summer, we should all be worried about that, too.) This kind of behavior is what sunk Windows Vista, right? It’s like the Windows team is cherry-picking all of the bad mistakes from the previous 20 years and trying them all again.

Except, of course, they’re not even that self-aware. We’re all familiar with the phrase, “those who cannot remember the past are doomed to repeat it.” Well, I’m steeped in the past now, thanks to my recent experience writing the Programming Windows series. And I am troubled by what I’m seeing from today’s Windows team, which seems to be blissfully unaware of both the past and its own limitations.