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Could Microsoft’s Foggy Windows 10 Plan Be Any Smarter?

The most important and daring move that Microsoft made Wednesday is far and away making the upgrade to Windows 10 free. Seems dirt-simple and intuitive on the surface, but it represents a startling and abrupt shift in both how users will relate to Microsoft and how Microsoft innovates with Windows going forward.

As long-time readers know, I’m an unabashed Apple fan — but I can appreciate a smart move when I see one, and no doubt about it, making Windows a free upgrade is a smart move.

So what is Microsoft doing, exactly? Well, that’s a funny question, because Microsoft managed to make a cool announcement that left so many questions unanswered that hardcore Microsoft tech enthusiasts like Paul Thurott and his commenting followers were leftscratching their heads.

On one hand, Microsoft said that Windows 10 will be a free upgrade from Windows 7 and 8.1, and Windows Phone 8.1. So far so good. That alone is pretty big news. Then Microsoft said that Windows 10 would be delivered “as a service” for the supported lifetime of the device. Uh, what’s that mean, exactly?

The Devil Is in the Details

Microsoft, unfortunately, didn’t reveal what that sort of “service” idea it has in mind. Nor did the company mention how it might work or what it might cost. It raises all sorts of questions, including how to manage clean installs, whether you can transfer a license to (or within) an enthusiast-built PC, or whether Microsoft will push updates to your Windows 10 device automatically — even if you don’t want the enhancements.

I suspect Microsoft doesn’t know the answer to these questions right now, and not saying anything is a way to buy some time. Alternatively, they could have a pretty good idea, but they’ll let a flurry of interest and speculation lead them to refine the details before they announce the terms publicly.

I find the sheer lack of clarity amusing — accidentally vague or purposely opaque, I have a hard time imagining that it builds confidence in consumers and enterprise customers.

A Very Big Deal

Microsoft’s problems have been due in part to a fractured Windows user base. First, it leads developers to create apps that serve the least common denominator — an older version of the OS — or work much harder to enable features that can be taken advantage of in newer versions but not break in older versions. Over time, this makes building and maintaining apps expensive, as well as a pain in the butt. And customer support? Difficult.

A large chunk of Windows users are running Windows 7, while another 20 percent or so still could be using Windows XP, and some smaller segment is running Windows 8 or 8.1. Assuming that the PCs running Windows XP are lost causes — old hardware with owners disinterested or unable to upgrade — Microsoft is left with a challenge. Even if Windows 10 is awesome, it will still have a fractured user base running at least three different versions of Windows, 7, 8, and 10.

That doesn’t help developers, it’s confusing for everyday consumers, and it leads enterprises to put on the brakes and just standardize on one version for a couple of years or more.

Apple, on the other hand, made the shift to a free Mac OS X years ago, and now a large portion of Mac users are on the latest versions of Mac OS X. The numbers are even better for iOS.

More importantly, making the OS free creates a different level of customer engagement. Instead of figuring out if a release is worth buying, the customer just needs to download and install it.

Before, Microsoft had to build a major new release of Windows that was capable of inspiring its customer base to buy an upgrade. Plus, it added weird consumer questions to the mix, like, “Should I pay (US)$119 to upgrade from Windows 7 to go to Windows 8.1… or should I not bother now at all and maybe upgrade to a new laptop that already has Windows 8.1 on it?”

Basically, free makes the barrier to upgrade much easier to step over, and that alone will help get millions of Windows users up to Windows 10 much faster — and boom, Microsoft will suddenly have a more compelling user base to attract third-party innovation.

Where Did the Money Go?

The key reason this takes guts is that Microsoft is essentially writing off a traditional stream of revenue, which is something public companies are generally terrified of doing. It goes deeper than filling budget slots, though; changing how Windows is delivered will change the whole tenor of how Windows is created.

Instead of forcing gobs of new features into a Windows release in order to create the most compelling OS — in order to spark customer adoption through their wallets — Microsoft can take a more measured approach to how it innovates with Windows.

Instead of being hampered by trying to do too much, too quickly, with shoddy integration and unrealized vision, Microsoft CEO Satya Nadella has changed the game. All at the same time, the pressure to build something cool for the sake of cool is reduced, consumer expectations for each release are lowered, and focus shifts toward the overall consumer experience within the Microsoft ecosystem.

There’s a whole new world of potential wins here.

Apple’s Method of Pushing, Dragging, and Training

One of Apple’s smartest — and sometimes most annoying — tactics is to offer free upgrades to both Mac OS X and iOS, in addition to security patches and bug fixes along the way. So what’s annoying? It’s super easy to upgrade and update — but it’s damn hard to go back. If you don’t like the new version, it’s very difficult to roll back to a previous release. It’s not impossible, but for the vast majority of consumers, it might as well be.

The result?

Customers move forward. When Apple does a good job, they’re happy. If Apple makes a mistake — such as introducing WiFi issues with Yosemite — customers get mad, but they’re still running Yosemite, the latest version of the OS! As maddening as it can be if you’re the one caught in something you don’t like, it’s a powerful business tactic.

Now Microsoft seems to be getting ready to add it to its arsenal.

But wait, there’s so much more.

As a consequence of stepping through a door only to have it lock behind you, Apple users — and soon Microsoft users, most likely — will have no choice but look over their new world and figure out how to use it. For the most part, it will be using cool new features, which is great and all, but from a business standpoint, gradually forcing your own customers to train themselves incrementally is a lot easier than springing a major OS leap on them every couple of years.

Basically, with this new model, Microsoft’s customers will begin to evolve and learn the very latest Microsoft has to offer in a much faster and more straightforward way. The days of Microsoft launching an OS and then watching it struggle to lift off will be gone.

Incidentally, while it seems like Microsoft is following Apple here, this method of doing business with an OS isn’t exactly a secret. Microsoft has been pushing no-going-back updates to Xbox customers for years — and Xbox might even be Microsoft’s most-loved product line.

Changing the Innovation Model

By turning Windows into a “service” that runs on multiple devices — Windows that runs on phones or tablets or hologram-casting goggles — Microsoft is fundamentally shifting how it internally builds and rolls out new features. The company can deliver a hot new feature or service without needing to attach it to a special OS release “event” that’s tied to direct retail and enterprise sales models. This service model represents another huge shift.

Better yet, the first time Microsoft rolls out an awesome new update, customer loyalty and satisfaction will spike.

All in all, the free Windows 10 update and transition to a service-oriented mindset — assuming Microsoft doesn’t shoot itself in the foot with some sort of expensive service fee schedule — both have the potential to radically shift how Windows customers interact with and appreciate Microsoft, all the while building loyalty and increasing their engagement in Microsoft’s new one-Windows-on-everything ecosystem.

If the change helps Microsoft deliver iterative improvements to create a more seamless computing experience across all of its devices and services — rather than dropping big bang product release bombs — that’s a bonus that can only help Microsoft return to a position of greater strength and influence.

Chris Maxcer

TechNewsWorld columnist Chris Maxcer has been writing about the tech industry since the birth of the email newsletter, and he still remembers the clacking Mac keyboards from high school -- Apple's seed-planting strategy at work. While he enjoys elegant gear and sublime tech, there's something to be said for turning it all off -- or most of it -- to go outside. To catch him, take a "firstnamelastname" guess at You can also connect with him on Google+.

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