Windows Mobile 7: Should Microsoft even bother?

This past weekend in Orlando, Fla., I ran the Disney World Half Marathon. I did it in sleet, snow, and icy rain combined with unbearable temperatures. But I finished. During the course of the race, just as my body was numbing up and pleading with me to stop, I read a T-shirt in front of me that made me chuckle. It said, “DLF>DNF>>DNS.” Its meaning: Dead Last Finish is greater than Did Not Finish is much greater than Did Not Start. I found that interesting because it isn’t true of all circumstances and certainly not true when put up against the battle for the ultimate smartphone.

When looking at all the competitors for smartphone supremacy, you might say the Windows Mobile is DLF in the rankings (although a recent report places it at third place). Some would even contend that Microsoft would have been better off never entering this race if it weren’t going to put up a good fight. That may shock the 7.2 million users of the Microsoft smartphone OS, especially those in the enterprise who don’t see the iPhone as a serious contender at all (due in part to Apple’s history of ignoring the needs of the enterprise in favor of the individual user).

[ Check out David Coursey’s “The case for Windows Mobile” to see his defense for the “third most popular mobile OS.” | See why InfoWorld rates the BlackBerry and iPhone as best business mobile devices. ]

Even I, a noted Microsoft loyalist of the highest order, finally chose my first smartphone — and it didn’t run Windows Mobile. The one that excited me, that made me finally make the move? An Android device: Motorola’s Droid. It gave me Exchange connectivity, all the collaboration features I needed (e-mail, Internet, news feeds, weather), and thousands of cool apps (mostly free) to download from the Android Market.

But, hey, don’t start cursing my name just yet — I wasn’t the first person in my position to make the move! Mark Minasi, a globally famous tech speaker and technical author of over 25 books, held an iPhone high in the air at a Windows conference last year and heaped it with accolades. He said in WindowsITPro that he had “grown tired of begging Windows Mobile to do the stuff” that he paid for. Most of my friends use BlackBerrys or iPhones. I thought I was at least being somewhat rebellious and going against the tide to go with the Droid.

Glimmers of hope for Windows Mobile 6.5 Despite the seeming abandonment by the Microsoft faithful, there may be hope. There is talk that Microsoft is making a comeback with its Windows Mobile product line. It has slurped down a GU packet (an energy gel for those who aren’t sports enthusiasts), got up off the pavement, and is back on track. Where’s that talk? In Paul Thurrott’s SuperSite for Windows and his article “Microsoft’s plan to save Windows Mobile,” in which he explains a few important pieces of the plan.

The Windows Mobile group went through a realignment that pushed Windows Mobile 6.5 out the door in 2009 so that Microsoft could compete with Apple, as well as RIM, Palm, and Google. The product was only half-baked — easy to see if you play with one and note the frustrations of using a resistive touchscreen (which requires more pressure and can often cause accidental selections) as opposed to the iPhone, WebOS, and Android phones that use the much more responsive capacitive touchscreens. To be honest, I often hit the wrong keys on my Droid too. Sometimes my fingers are simply too big and I’m still learning to hit a flat-screen keyboard properly. Other times, it isn’t me — it’s the phone (I swear!). Microsoft has been working on this issue (and releasing updates to assuage the criticism), so we’re supposed to see Windows Mobile 6.5 devices in 2010 that have the capacitive screen, the first one being the HTC HD2 smartphone due out this spring.

A second issue Thurrott notes is that while the 6.5 flavor of Windows Mobile starts off with some nice user interfaces and easy-to-tap UIs, once you get below the surface, you are faced with UI designs that go back to the days of the stylus. Thurrott says, “These UIs actually predate Windows Mobile and were originally designed for the PocketPC and Windows CE devices of the 1990s.” Unbelievable — is there any wonder why Microsoft is losing this battle? Starting with the 6.5.3 release, however, this will change and Microsoft will be able to stand on equal footing with the iPhone, Android, BlackBerry, and so on. And then Microsoft has a chance to wow us with Windows Mobile 7.

Bad news/good news for Windows Mobile The bad news is that the fight for 2010 is already over and Windows Mobile 6.5 just isn’t going to rally the world. I have my phone, and others have theirs. I just don’t see how a capacitive screen or a new set of UIs (which should have been in place with the release of Windows Mobile 6.5) will turn the tide. Perhaps it may simply stop current Windows Mobile users from going to another vendor.

But in a world where a smartphone is not just a device but a statement — a coolness factor among all age groups — it isn’t good business to be the handset people are ashamed of. When people boast about their new iPhone or Droid mobile, Windows Mobile users slowly extricate themselves from those conversations and hide their phones in their pocket.

The good news? Every year is a new event. When it finally ships this year or next, Windows Mobile 7 might blow away the competition and take the lead. Unlike the OS world where it may be years before you see turnover, the smartphone world moves forward, with people upgrading their devices or switching from one to the next as often as every six months.

Plus, in the enterprise, smartphones aren’t replaced as frequently as they are in the consumer market. Much like other IT infrastructure changes (your desktop OS, the network infrastructure, servers, server software), it takes time to upgrade all these techologies, and smartphones have to wait their turn in line. That buys Microsoft a little time to keep businesses from switching over to another competitor.

Of course, the competition isn’t standing still. But I’ve always believed that if Microsoft puts its mind to something and places a project in the right hands, it can triumph — not only finish this race but finish first.

My colleague David Coursey seems to feel the same way: “If Windows Mobile were a consumer product, I’d put it on the ‘guarded’ list, but as a corporate purchase its condition — again in medical terminology — rises to ‘serious.’ And that is a quite a distance from life support. Lots of ‘serious’ patients recover, as Windows Mobile may prosper in the future.”

That is my challenge back to the Microsoft Windows Mobile team. I have a Droid that I like — but if you can convince me to pick up Windows Mobile in the future, I’ll tell the world.

This article, “Windows Mobile 7: Should Microsoft even bother?,” was originally published at InfoWorld.com. Follow the latest developments in mobile computing and Windows Mobile at InfoWorld.com.