The Windows Mobile Manifesto

A former Microsoft employee has written a lengthy post about the history of Windows Mobile, noting with regret that the software giant should have owned the mobile market. That sounds pleasant. But it was never going to happen.

If you’re a Microsoft or Windows phone fan, you should of course read The war Microsoft should have won. It’s interesting because of its insider perspective. But this post provides no new information about that platform or it history. And its entire premise is incorrect.

Interestingly, my own history with Windows Mobile goes back quite a bit further than that of the author of this post, Christian Hernandez, who joined Microsoft as an intern in 2002: In 1995, I was part of a very limited group of people outside the firm beta-testing Project “Pegasus,” which included an embedded OS that was eventually named Windows CE (for “Consumer Electronics,” despite subsequent denials) as well as early bread-board based hardware that we had to swap out occasionally and then at the end of the testing period to get final NEC hardware. In fact, in 1995, I was plotting a web site called “Pegasus Place” that would have been to Windows CE what the SuperSite for Windows would later be to Windows NT 5.0. (I quickly saw how pointless that would be.)

The initial version of Windows CE was a Windows 95 look-alike, but in gray-scale, and the Handheld PC (HPC) devices of the day that used this system featured clamshell designs with small keyboards and a stylus to replace the mouse. Over time, Microsoft evolved this platform, and renamed it several times, sometimes to avoid legal action from competitors. That’s sort of beside the point, but by the time we get to what was called Windows Mobile, it had evolved into a PDA and phone platform.

As is often the case with the defeated, there is an ongoing fiction that things could have—should have—been different and that, in this case, there was a brief moment in time when Windows Mobile had in fact beaten the competition and was somehow the number one solution in some market. But as Hernandez’s post demonstrates, that fiction—which I too had fallen for, at one point—is incorrect: Windows Mobile beat Palm, yes, but only as the market for PDAs was winding down. And it never controlled or even led the market for smart phones. Those markets were controlled in the pre-iPhone/Android years by RIM (especially in North America) and Nokia (especially in Europe and elsewhere).

The problem with the market(s) that Hernandez describes is that they were so fluid, and Microsoft found itself adapting Windows Mobile (or whatever it was called at the time) to meet these ever-changing needs. It split the platform into separate PDA and smartphone variants at one point, for example, just trying to keep up.

What Hernandez doesn’t describe is the real reason Microsoft failed, and to be clear it was always going to fail. Back in the late 1990s and early 2000s, Microsoft’s biggest success, by far, was Windows, and it’s go-to-market approach had two core pillars: Protect Windows at all costs—that is, everything Microsoft did had to prop up its money machine—and copy the partner-based Windows business model.

So Microsoft created the OS, at did for PCs, and it let hardware partners—some of which were PC makers, too, some of which were not—create the hardware devices—HPCs, first, and then various PDAs and phones—sell the devices to consumers. This seemed to make sense at first—hey, it worked for Windows!—but the system fell apart when phones became the core of the platform, because now a third party—wireless carriers—was added to the mix. And it stretched the model too far, with both hardware makers and carriers competing with each other to differentiate.

Hernandez is right about one thing: Microsoft’s inability to attract its core business market was Windows Mobile’s undoing, and this was even more problematic in the Windows phone era, when Microsoft literally ignored the enterprise in order to market the handsets as a consumer-facing alternative to the Apple iPhone.

Hernandez also doesn’t mention that Microsoft went public about all of its Windows Mobile failings when it launched Windows phone. In fact, Windows phone was explicitly about repeating what worked with Windows Mobile and abandoning what didn’t work. And while closet analysts are always trying to point to the magic strategy that Microsoft could have used to propel Windows phone to success, that was never going to happen either, because the market had changed too much by then. The iPhone and Android were simply inevitable.

But Windows phone, like Windows Mobile before it, was simply a victim of circumstance. That is, like Windows Mobile suffered from Microsoft’s insistence on aping its Windows PC strategy again and again, Windows phone suffered from Microsoft’s fixation on Apple. Instead of playing to its base—the enterprise—Microsoft tried to out-Apple Apple. It created a high-end, expensive platform for consumers at a time when what everyone wanted was the iPhone.

The carriers didn’t help, either, and I’m sure you’re familiar with the story where I warned Joe Belfiore and the rest of the Windows phone team in front of a representative of AT&T Wireless that the carriers would simply f@$k them over as they have always done, and that Microsoft could not ever trust the carriers. That little outburst of honesty earned me one year of silence from that team, but as history has shown, I actually understated the issue.

But let me tell you a story about Windows Mobile that neatly encapsulates the problem.

Back in the Windows Mobile 6 days, I visited the Microsoft campus and spoke with the team about their initial attempts to compete with the iPhone: Microsoft was plotting a spit-shine for Windows Mobile that would add a touch-friendly (and admittedly nice-looking) UI on top of the creaking mobile platform. I was taking notes on whatever laptop I was using at the time, and everyone on the team had a brand-new Palm Treo 800w. This was a very expensive phone because you could basically only buy it outright for, I believe, about $600, an inconceivable price for the day. And Palm clearly wasn’t hugely interested in selling or supporting these Windows-based devices, so it was completely pointless. Worse, I felt like these people were out of touch with what was going on in the world.

“So how are you going to react to the iPhone?” I asked. “It seems like Apple is eating your lunch.”

And then someone from the Windows Mobile team—I really don’t remember who—said the dumbest words I’ve ever heard from a Microsoft employee.

“The success of the iPhone has proven something we’ve thought to be true for a long time, she said, “that consumers would flock to a device that was easy to use.”

As she said this, my typing slowed and then stopped, with my hands sort of hovering over the keyboard as I processed this claim. And then me being me, I blurted out the following.

“Do you even listen to the words coming out of your mouth?”

“You knew this type of thing would be successful,” I continued, “and yet you never made it yourselves? Really?”

And that, folks, is the moment I knew that Windows Mobile was doomed. Which it was. And as I just discussed in A Few Thoughts Ahead of the 2016 iPhone Event, I then proceeded to shun Windows Mobile along with the rest of the world, and I simply stuck with iPhone.

Until, that is, Microsoft announced Windows phone. Like many at that time, I was full of irrational hope. I knew that the rise of Steven Sinofsky in Windows had led to an exodus of great talent from that team, and that many of those who previously worked on “Big” Windows were now working on Windows phone. (In fact, I had heard from a few friends in late 2009 who intimated they were working on something big in Windows Mobile, and I joked more than once that I was curious why they were being punished.) I thought they were going to get it right.

They didn’t, though that is a different story.

But the point remains: Microsoft was never going to win in mobile, and that’s as true of the original Windows Mobile era as it was of the Windows phone era. It was just never going to happen.

But I’d like to discuss something else in the Hernandez post. He recounts how then-Microsoft CEO Steve Ballmer dismissed the iPhone in 2007, and repeats the conventional wisdom that this statement proves how out of touch Ballmer was.

“It would be disingenuous to end this post without a link to the infamous video of Ballmer laughing at the iPhone when it launched … ‘It doesn’t appeal to business customers because it doesn’t have a keyboard…’ ‘Right now we’re selling millions and millions phones a year and Apple is selling zero…’ ‘I like our strategy … I like it a lot!’ A few years and billions spent buying Nokia later not sure it was as funny.”

Sure. But that was never funny.

I don’t know what anyone expected Ballmer to say about the iPhone in 2007, but what he did say sounds about right for the CEO of a company that competed with that product.

And Ballmer was right, the iPhone wasn’t appealing to businesses when it launched. He was correct to make his core customer base part of the conversation. And the part Hernandez leaves out in this laugh-fest is that Ballmer also said the iPhone was too expensive, which it was at the time. Everyone seems to forget this, but one of the big iPhone controversies of 2007 was that the device wasn’t selling well because it was too expensive. So Apple didn’t something it hasn’t done since: It dropped the price by $200 just two months after launch. Sit down, haters. Ballmer was right about the iPhone. It’s just that Apple adapted.

But Microsoft—and by extension, Ballmer—didn’t respond well enough or quickly enough to the iPhone, of course. But that falls as much on the Windows Mobile team’s shoulders as it does on Ballmers. Isn’t that where Hernandez worked at the time? And he’s making fun of Ballmer? Really?

I find that a bit disingenuous. Because as I noted above, the Windows Mobile team of 2007 was just about as clueless as anything I’ve ever seen from Microsoft.

Woulda, coulda, shoulda. Yep. That’s the real story behind Windows Mobile.

One more thing.

Today, Microsoft is of course plotting a new course for Windows 10 Mobile, the successor to Windows Mobile and Windows phone. And if we understand the strategy, the idea is to make a phone that can transform into a PC using Continuum. I find it hard not to root for these guys, still, and there is part of me that actually believes this strategy has merit, that it could work. And that says a lot about me, really, because I’ve fallen for this trick too many times. We’ll see what happens, of course, and history isn’t always a guide for the future. But … You gotta wonder if this isn’t just the latest in a long line of do-overs and strategy shifts that will simply amount to nothing. After all, it’s happened again and again.