Nobody Was In Love With Windows
Why did Windows Mobile (CE, ME, etc.) fail? It had something like an eight year head start against the iPhone, yet it never really caught on.
The answer is simple. Hardly anybody’s really in love with Microsoft Windows, nor were they eight years ago. The reason so many people used Windows is because they were afraid that if they didn’t, they would have big headaches interacting, computer-wise, with their friends, relatives, and co-workers.
What Microsoft should have done was create a mobile operating system that interacted heavily with Windows, in a way that was very useful to the user of the mobile device. It didn’t need to look like Windows; in fact it shouldn’t have. And if it wasn’t going to look like Windows, it shouldn’t have been called Windows, either. It just needed to be tied to Windows in ways that were genuinely helpful to the Windows user (i.e. the typical computer user). And mobile phone users who didn’t have a Microsoft mobile phone would be left out of that.
But that’s not what Microsoft did. Instead, they made a mobile OS that wasn’t particularly useful or helpful at all to the Windows user. They made a mobile OS that wasn’t in any special way tied to desktop Windows. But it was called Windows. And the interface (much to the user’s detriment on such a small, and mouse-less device) looked like Windows.
Microsoft, I think, was truly trying to extend the success of Windows into the mobile arena. But they had completely misdiagnosed the reason for Windows’s success. Apparently, they must have thought, “People use Windows because they love it. They love the name Windows. They love using the Windows user interface. So if we make our mobile OS look like Windows, people will naturally gravitate to that. And if we call it Windows, people will think, Oh good, it’s Windows; that’s what I want.”
The ugly truth of the situation — a truth that nobody at Microsoft wanted to see — was that people didn’t like Windows, but they used it anyway. People begrudgingly used Windows because they were afraid of going-it-alone with anything else. They were afraid of being afflicted with crippling compatibility issues that promised to cast them into the exterior darkness if they didn’t use Windows.
But in the mobile arena, there was no such fear. Everybody saw people using Palms, and Nokias, and a bunch of other non-Microsoft devices, and having no troubles for it. And they never saw any special advantage to using Microsoft’s mobile offerings. Even while they used desktop Windows, they didn’t see any issue with owning a Sony Ericsson smartphone. Or a BlackBerry.
Microsoft could have ruled the mobile world with an iron fist long before Apple even tried to enter it. Believing that people actually liked Windows for what it was, not for what it wasn’t, was Microsoft’s mobile downfall.

