It’s weird being an “Apple guy” and attempting to write objectively about Microsoft.

For as long as I can remember in the software world (being 26, that would be from the early 1990s onward), Microsoft was The Dark Side, the Evil Empire…in other words, the Bad Guy. Microsoft was always threatening to condemn my beloved Macintosh to the digital dust heap of history as Amiga and leave us stranded in a Windows World.

Then, by the mid-2000s, when Apple began its growth streak, Microsoft somehow went from being seen as a malignant force of evil to simply being manifestly incompetent. Apple was cranking out hit after hit, while Microsoft seemed to careen from one bad move to another–be it stillborn initiatives (remember Mira?),  market failures (remember PlaysForSure, or the Zune?) to simply bad software (remember when the Windows XP security crisis was followed on by…Vista?).

The worst part of all this was that Microsoft’s leadership didn’t seem to get it. The PR statements coming from the company sounded completely detached from the reality of the world changing and Microsoft’s empire unraveling from below. Microsoft, as one prominent blogger suggested, was fast-becoming the Soviet Union of software companies.

Green shoots / The Reformists

And then, somewhere along the way, some good things started coming out of Microsoft: The Xbox ecosystem blossomed (sales are at an all-time high) while Sony’s PlayStation empire got bogged down in an unwinnable war with hackers. Windows 7 was a well-done OS that helped wash the bad taste from Vista and had some great UI features that I ultimately found myself duplicating with 3rd-party add-ons on my Mac. Kinect was an innovative hit that leapfrogged the Wii’s motion-controllers, and will soon make its way to products beyond Xbox. Microsoft even had the courage to start from scratch in the smartphone space, throwing out the hopeless Windows Mobile and creating Windows Phone, with its unique and beautiful Metro interface that will now be making its way to Xbox and even the next version of Windows itself. As someone who still uses and loves Apple products, I can for the first time say that Microsoft is making some innovative and well-designed things. And I’m not the only “Apple guy” who has nice things to say about Windows Phone–even Mossberg’s AllThingsD and David Pogue say Windows Phone is “a mix of elegance and whimsy that’s a treat to use,” and  “gorgeous, classy, satisfying, fast and coherent.”

Nothing illustrates the divide between the two Microsofts like Windows Mobile vs Windows Phone

These products show that somewhere at Microsoft, there are some people who have seen that Microsoft has a problem, who have identified that problem as one of their products–they weren’t good enough. These “Young Turks” of Redmond concluded that products need to be redone, along with the processes that created them. Perhaps most impressively of all, they actually managed to push these changes through. Most of the people I’ve met personally who work at Microsoft fall into this category.

The Sultans of the Status Quo

Of course, these green shoots still exist in a company that is more known for its cringe-worthiness than for its creativity. For every sign that Microsoft finally “gets it,” there is another to suggest they still don’t. For every promising demo of a Win8 Metro tablet, there is a boisterous official claim that Microsoft’s middling Tablet PCs are the same type of product as an iPad. For every Courier concept, there is…well, a cancelled Courier project. For every move Microsoft makes towards a “post-PC era”, Steve Ballmer vaingloriously proclaims “Windows Forever” in a matter that would make Nikita Khrushchev blush.

These are the people who think the problem (to the extent they acknowledge there is one) is not one of the products, but just the business around them. They just need more advertising. These are the people who brought us the Mojave Experiment, the “I’m a PC” campaign, astroturfing, the Seinfeld ads, the “buy PCs because they’re way cheaper” campaign, and other manifestations of the idea that Microsoft’s pigs just needed a bit more lipstick. This video, asking “what would happen if Microsoft designed the iPod packaging” sums it up nicely (interestingly, the video was made internally within Microsoft, likely by one of the Reformers trying to illustrate just how screwed up Microsoft was becoming):

Right now both of these factions exist within Microsoft, and I don’t think it’s easy to pinpoint who exists where. I would guess this is something that would cut across Microsoft divisions, rather than neatly between them and affording us the luxury of saying “well the Office division has the ‘old’ thinking and the Xbox division has the ‘new’ thinking.” No, these divisions run through departments and perhaps even through the minds individual people within them.

The most recent example of this painful contrast between Old-and-Busted Microsoft and New-Hotness Microsoft was a Microsoft exec saying the difference between WP7’s TellMe and Apple’s Siri was primarily one of marketing and not the actual differences in the abilities of the products:

People are infatuated with Apple announcing it. It’s good marketing, but at least as the technological capability you could argue that Microsoft has had a similar capability in Windows Phones for more than a year, since Windows Phone 7 was introduced.

Microsoft, why do you do things like this when it just ensures that videos ridiculing your boastful claims become one of the top tech stories of the day? How can the same company that made such a brilliant mobile OS say such decidedly non-brilliant things about it?

Microsoft, why couldn’t you say something like this:

“Apple has done great work in raising the public’s awareness of the power of voice recognition technology to make our lives better. We have a great voice recognition technology of our own called TellMe. Right now Siri is ahead of TellMe in some areas of functionality, while TellMe is ahead of Siri in others. We are devoting enormous resources to rapidly improving TellMe functionality–and every other aspect of Windows Phone.”

One of Microsoft’s greatest assets is its staying power. Even if their first attempt is usually a bust, Microsoft will keep at it relentlessly, patiently iterating, improving, and spending money until they succeed (just look at the Xbox, which took a decade to be profitable, and their online services division, which still doesn’t make Microsoft any money). But to what end will this power be used?

Who will win the battle for Microsoft’s soul–Soviet Microsoft, or Metro Microsoft?

For the sake of giving the Apple and Google duopoly a real third-party challenger, I certainly hope the Metro-ification of Microsoft continues–and that it goes more than skin-deep.