See ya later, WinMo: Microsoft's mobile strategy needs a reboot

There are lots of winners in the wireless wars. Microsoft, unfortunately, isn't one of them. Thirteen years after it first introduced Windows CE, its homegrown OS for small devices finds itself perilously close to oblivion. With market share for Windows Mobile OS in freefall, vendors fleeing and its mindshare in meltdown, now is as good a time as any for the company to dive into a full-on re-think of its mobile strategy.

Or an exit from the market until it can figure out what makes the most sense.

While it's unfortunate that the company that dominated the desktop for so long hasn't been able to repeat that success on shrunken-down devices, Microsoft's experience should serve as an example to the players now lining up for their shot of wireless glory.

What's in a name?

Microsoft's first mistake was branding. It never stuck with a name long enough for the public to know what it was buying. Or should buy.

What started life as Windows CE eventually became Pocket PC, and then Windows Mobile. With enough variations and flavors to confuse even the most ardent Microsoft fan (quick, what's the difference between Windows Mobile 2003 SE for Pocket PC Phone Edition and Windows Mobile 2003 SE for Smartphone?) it's no wonder that most consumers long ago dropped Microsoft's mobile products off of their radar. Even now, the company hasn't learned: Its current "Windows phone" branding makes a murky brand identity even murkier.

I admit to having owned two Microsoft-powered devices in my lifetime: a Windows CE 2.0-powered HP 360LX and, later, a Motorola Q smartphone that ran Windows Mobile 5.0. While the old clamshell-style HP was too big to shlep around in my pocket, the Q was lean enough to be my constant companion. Unfortunately, its barely-contained Windows heritage made it something of a dog in day-to-day use. Basic address lookups became tests of patience as I stood on sidewalks and waited for my lithe, almost-sexy-looking phone to churn through my contact list and return the name I asked for.

Not lean. Not mean.

When I traded the Q in for a BlackBerry, I spent an hour in-store scenario-testing updated WinMo machines -- by then, up to the 6.0-standard -- against everything else the store had. And still, I waited for even the most basic of tasks. For all its engineering prowess, Microsoft never integrated the lean-and-mean ethos that has always driven competitors who didn't already own the desktop OS market. Even today, claims on its Web site that, "It's like your PC just grew legs," illustrate the kind of disconnected thinking that continues to fuel the mobile unit's decline. Tech-conservative enterprises may like its security and Windows familiarity, but that's no longer enough.

Which brings us to Microsoft's second mistake: assuming that a great mobile OS was simply a pared down version of its desktop equivalent. Microsoft, which has subscribed to this mantra right down to the Start menu and cascading menus that until recently defined the UI, completely missed the mark on this one. We don't use handsets in the same way that we use laptops. We don't necessarily need to replicate the full-on interface and user experience of the average PC.

First, we don't have the screen real estate. What works on a 23-inch flat screen doesn't simply shrink to the 3-ish-inch panels on most phones today. And if you try to make it shrink (heaven knows, Microsoft has tried), the end result is a jumbled on-screen layout and confusing navigation.

Second, we don't have the time. It may be acceptable to wait a few seconds for our laptops to look up an address. After all, we have dozens of other windows running at the same time, so we're absolutely free to pop into any of them and work on something else until the machine completes the task. We can also heat up our tea, catch up on water cooler gossip, or simply sit back in our seats and relax. When you're in transit, you need that answer now. From an often underpowered, battery-deficient sliver of technology that you're using in the millisecond before an errant taxi mounts the curb and ruins your day.

Others innovate while WinMo stagnates

Apple, which wisely stripped anything remotely desktop-like out of its Mac OS X when adapting it for the iPhone, gets the need for simplicity. Likewise, Research In Motion, whose BlackBerry devices are often pilloried by tech-fashionistas for having an OS whose interface hasn't changed much in a decade, remains a model of stripped down simplicity. My BlackBerry may not incorporate every last feature from the laptop in my office, but when I'm zinging from meeting to meeting, I don't need every last feature. I just need the thing to work. And it does. Fluidly.

The success of Apple's App Store and Google's Android Market illustrate another key Microsoft weakness. Apple's 100,000 apps and Google's 10,000 dwarf Microsoft's Windows Marketplace for Mobile, which launched in October (for 6.5-based machines only) with about 250 titles. Last month, it tacked on a whopping 84 apps to that title, by finally extending the Marketplace back to WinMo 6.0.

While the oft-delayed WinMo 7.0 could have created some much-needed excitement before compelling new alternatives hit the market and shifted vendor attention away from Microsoft, it's becoming increasingly clear that not even a new OS can rescue WinMo.

Microsoft's acquisition last year of Hiptop vendor Danger Inc. shows it's not giving up just yet. Rumors have also swirled that the company's interested in acquiring RIM. Still, the Danger acquisition has already bitten Microsoft after a high-profile data loss in October. A possible RIM buyout would lead to similar grief, as it makes no sense to break the bank before you get your own house in order. On culture alone, a Microsoft-RIM linkup would be an integration nightmare.

After 13 years and countless kicks at the can, it's time for Microsoft to call it a day. Kill Windows Mobile, consolidate resources and skills from the shuttered unit as well as Danger and Zune -- which continues to impress with technically sophisticated offerings that languish on store shelves -- and pick one cohesive strategy. Then stick with it. And whatever the company decides, it has to move fast. By this time next year, the market, dominated by RIM, Apple, and Google, will be even less forgiving than it is now.

Carmi Levy is a Canadian-based independent technology analyst and journalist still trying to live down his past life leading help desks and managing projects for large financial services organizations. He comments extensively in a wide range of media, and works closely with clients to help them leverage technology and social media tools and processes to drive their business.