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 ne...