Among Blackberry, Microsoft, Google, and Apple, Microsoft was the earliest player in mobile computing and smart phones, so why have they failed in this area?

With Windows Mobile 7 waiting in the wings, it occurred to me that I just don’t see people using Windows Mobile devices that much any more. In fact, at work, we’ve seen a shift from WinMo to Blackberry and iPhone, with the exodus split about 60/40 in favor of Blackberry. The market share shift has been swift and decisive.

Now I know this isn’t exactly news, but I was trying to figure out why.  Microsoft correctly foresaw the mobile market as being the next big thing for them and the software industry, and they had very early foresight that mobile was going to sweep our eyes away from our desktops in a major way. They had the timing right, but their solution is, and has been, inadequate.

The Value of Ecosystems

One key difference between Microsoft and Apple is that, while they both offer end-to-end ecosystems (Microsoft with XBox, Apple with iTunes/iPhone/AppleTV), they seem to use their ecosystems to different ends.  I believe Apple’s tightly-integrated iTunes ecosystem was primarily driven by the “digital paranoia” of the record industry in the early 2000’s, and it may not have been Apple’s idea to provide such a closed environment. But, in the end, consumers seem to prefer the “just works” ecosystem over the “bring your own interface” approach. For this reason, Microsoft can be seen to have failed at establishing a clear content-to-consumer delivery model based on Windows Mobile.

What’s worse, the Zune, which could have been a great launchpad for a simplified, stylus-free version of Windows Mobile four years ago, exists on yet another Microsoft island, limiting its value to the consumer. Rectifying this problem by bringing the ill-fated Zune line into the limelight of the Windows ecosystem would go a long way towards making Windows Mobile relevant again. Think iPod.

Failure to Recognize Consumer Patterns of Behavior

It was only a matter of time before the average consumer was using personal devices to manage nearly every aspect of his life. Yet Microsoft took the wait and see approach, preferring to believe that the corporate world would drive personal device adoption, where, in reality, we can see that personal, entertainment-oriented device use has driven the entire mobile industry for the last several years.  Two parts gear lust, and one part nerdification of the general populous, this movement is the exact opposite of the strategy Microsoft used for Windows Mobile.

Most People Lose Their Stylus

The user interface options available on Windows Mobile devices, until recently, have been based on resistive touch screen technology, generally used with a small, inkless pen called a stylus.  Blackberry, by contrast, has always offered its trademark “scroll wheel”, and Apple developed a slew of UI technologies, including groundbreaking iPod controls, that culminated in a stylus-free touch-screen control environment for the iPhone. Windows Mobile never employed either approach, so solving this problem (and Microsoft is solving it) will help.

Give Developers a Reason to Develop

The real trick isn’t coming up with the idea. The real trick isn’t coding the program.  The real trick IS getting people to notice.  Apple has more than solved this problem, for better or worse, with the Appstore.  You bring the code, we bring the customers.  While some web sites have served as communities of developers and consumers of WinMo apps, they exist outside the ecosystem and don’t provide turnkey delivery of content.

When Microsoft finally did show up on the scene with an official WinMo store, they stubbed their toe by naming it “Windows Marketplace for Mobile”.  Srsly?

Stop Trying to Look Like Windows

Windows Mobile shouldn’t look like Windows and shouldn’t even be called “Windows”, since a windowing environment on a 3″ screen is a useless idea anyway. Yet when we look back at the releases of Windows Mobile (and its mobile predecessors), we get the idea that Microsoft has always wanted WinMo to look as much like desktop Windows as possible. Only with Windows Mobile 7 has this pattern been broken. (See above screen grab.)

Blackberry never had this problem, as their main objective was to develop a good mobile UI, and they had no ties to an existing desktop environment.  Apple, who does have Mac OS X, decided not to bother bringing the X look and feel to their mobile device. This was a great decision, of course.

It’s clear to me now that Microsoft, one of the “great American companies” I often refer to when talking to my kids about things I admire in business, has switched from advancement to entrenchment as its retention strategy for existing customers.  That is, rather than move their platforms forward and pull global businesses along with them, a more defensive strategy is emerging–one where Microsoft tries not to hemorrhage too much business to Google and even Apple by reminding companies how cheap it is NOT to migrate away from the Microsoft eco-system.

A fantastic example of this dynamic came to light today when it was announced that the next version of Microsoft Office for Mac will replace Redmond’s clunky Entourage e-mail app with an actual Mac OS X version of Outlook, the predominant e-mail application used in medium and large enterprises.  My company alone supports somewhere in the neighborhood of twelve-hundred Outlook nodes at about fifteen different firms.  So a Mac version of Outlook, as the t-shirt saying goes, is “kind of a big deal.”

But what’s an even bigger deal is that Outlook once ran natively on the Mac–on Mac OS 9 anyway–and shared a great deal in common with its Windows cousin.  And, suffice it to say, it was a better product than its redheaded stepchild, Entourage.  It makes me wonder why they ever canned Outlook on the Mac to begin with.

Now I’m beginning to understand that Microsoft is on an all-hands mission to get as many enterprises, large and small, as entrenched as possible before Google and other market players really step to the plate with something that competes with Microsoft, and in particular Outlook and Office.  (Anybody who suggests that Google Apps currently beats Microsoft Office is smoking some pretty harsh crack, sorry guys.)

Entrenchment is the key to damage control: keep the customer believing that it will cost them more in dollars and difficulty to move away from Microsoft, no matter how compelling the alternative, and they’ll stick with Microsoft.  This was how they (soundly) destroyed Lotus Notes, and Redmond’s incredible staying power may allow it to stave off Google Apps for quite a few years to come.

“Windows Marketplace for Mobile”.

OK, does this name strike anybody else as particularly dumb?  On the syllable count alone, the marketing folks at Microsoft should’ve shot this one down before it had a chance to get into the wild.  Now, it seems, it’s going to have to stick.

Compared to Apple’s “Appstore” (2 syllables) or Nokia’s “Ovi” (barely 2 syllables) or even Blackberry’s “App World” (seeing a pattern?), Microsoft’s elephant-sized name for it’s application store clocks in at a whopping 8 syllables. Imagine the water cooler discussions that will never happen as a result:

“Hey man, where’d you get that sweet pinball game?”

“Well, I got it from Windows Marketplace for Mobile!”

Riiiight.  Who seriously is going to call it that?  Microsoft’s history of self-defeating brand names hasn’t been on display this starkly since “Microsoft Windows Server Base Operating Systems Management Pack for Microsoft Operations Manager 2005“.  Srsly, who uses this wordy terminology?

With Apple having already coined the de facto term “Appstore”, why doesn’t Redmond take advantage of the growing strength of the Zune brand and call their wordy app store something like “Zune Store” or “Zune Place” or even just “Mobile World”?  Even HandMarket, a third-party app store for Windows Mobile, beats Microsoft to the punch in succinctness.

If Apple insists on barring developers who overlap the “built-in functionality” of the iPhone, how is a developer to know what types of applications are a safe bet–in the long run? Since Apple recently banished Google Voice from the app store (which is an epic fail on Apple’s part, btw), one has to wonder, since all apps borrow some of Apple’s API functionality, just what they consider built-in and not.

The article, Apple Makes the Case for Web Apps concludes that developers will be more inclined to  create web-based apps geared at the iPhone.  While Apple’s recent actions may give developers pause to consider the web approach, I disagree that many will abandon their native app inclinations because of all that they lose in doing so.  For one, you can’t create home screen shortcuts to web apps (that I know of).  But the best reason not to develop web apps for the iPhone is their lack of support for front-end controls on the phone itself.  That is, in a web app, you don’t have nearly the power to access the GPS location, the GUI controls, the iPod library,  and so on. The new 3.0 iPhone browser is better at hooking into the phone’s local hardware, but is still quite hobbled compare to native apps, so geolocation and photos won’t have the pinache they would on a native app. Those are the content items that have made iPhone apps so much better than previous-generation mobile apps, and with the web approach, they’re more or less off limits.

How is it that YellowPages.com can offer a directory lookup app on the app store when it obviously overlaps Apple’s built-in Contacts and Maps functionality?  Yet instead of picking on YellowPages.com, Apple is seen picking on Google, arguably their biggest and most powerful ally.  Add to that the insult of Apple’s marketing of the iPhone and iPod Touch to developers as a platform for great apps, and it should make us all feel a bit used.

In the heady days of the computer revolution, Microsoft was forced to recognize that Windows (even MS-DOS) was a platform. Rather than stifling upstart competition by barring certain developers from the Windows ecosystem, Microsoft at least realized that it was developer embrace of the platform that would cause it to live or die in the long run.  The result was that, through the early 2000’s, Windows was the go-to platform for the whole world, and everybody from Sun to IBM lost lengthy, futile, billion dollar battles trying to undo Microsoft’s early decision.

Apple is nearly past that point in their new platform’s life cycle.  If it’s an app platform–let it be.  Palm and Blackberry are still waiting in the wings, and Windows Mobile will be the centerpiece of Microsoft’s revenue strategy in the next ten years.  And, like it or not, whatever else Microsoft did that was crummy and evil, they never told a developer he couldn’t distribute an app.

Let’s face it.  If you can support selling 5 GB downloads (which Apple does in the form of movies) through your e-commerce solution, iTunes, then there’s certainly no intrinsic barrier to doing so with applications, or drivers, or other forms of digital content.  If we fail to think of applications as content, we fail in our understanding of content.   Yet here we are thinking it’s a bold new idea to license and sell application software online–fully confining the novelty of such a thing to the mobile space.   Heh, we’re smart.

An old friend, Fleecy Moss, who was among the architects of the independent takeover of Amiga in the early 2000’s, once gave a talk at a tradeshow in the nineties–and his espousal of the content designation to software was, at the time, a revolutionary concept.  As with many ideas that bubbled up from the ill-fated Amiga wellspring, this concept proved true, and was ahead of its time.  It would be another ten years before the idea was accepted by the greater community.

The app store paradigm has brought this idea to the forefront of the way we think about distributing content.  Yet there’s something holding up the adoption of online app stores to distribute software, and I can’t quite thumb it.  Shareware authors have been distributing license credentials through e-commerce sites for a decade already, yet Apple and Microsoft still don’t sell their developers’ software through their flagship web sites.

Perhaps even more silly is the fact that consumers, vis-a-vis bloggers, don’t already demand such a solution.  If I can buy and download a DRM’d episode of Lost, why can’t I download a credentialed, licensed copy of Squeeze, or Microsoft Office for Mac, or my favorite blogging application, Ecto?   Yet nobody complains.  Indeed, it seems that the idea of a desktop app store is some kind of new idea. Technologizer, the “smarter take on tech”, just ran a piece about it today.   Yet I was talking about it a year ago, and longer.

In honor of MyCrosoft.

1 – Microsoft lost big when it walked away empty-handed from Facebook, and Redmond’s been regretting it ever since.

2- Microsoft’s unexciting efforts in the music-business, including the Zune, may now have renewed hope, as MySpace is probably the only real 2.0 music destination on the web (iTunes is hardly a 2.0 destination; nice try Apple fans).

3 – Silverlight sucks and nobody wants it except Redmond.  Those page takeover ads for the next Batman movie that you see on MySpace occur courtesy of Flash, not Silverlight.  Of course, this won’t change that, either.

4 – MySpace is desperate to clean up its image as the red light district of social networking.  Who better than squeaky-clean Microsoft to bring a little much-needed legitimacy to the table?

5 – There are a greater percentage of Mac users on Facebook than on MySpace.  OK, I’m guessing here. But I bet there’s a pretty Mac-favorable ratio on the Facebook side that doesn’t exist on MySpace.

6 – Windows Mobile is late to the social networking party, and not fashionably so.  Hey, wait, what party ISN’T Windows Mobile late to?

7 – Microsoft would consider making an offer for MySpace, if it weren’t for the horrible fact that MySpace is the world’s largest ColdFusion abuser.  Eek, that’ll scare off a .Net dev in a hurry.

8 – MySpace’s Hold ‘Em poker apps are better than Facebook’s.  (It’s true.)

9 – Microsoft holds in very high regard the design ethic of MySpace (which looks like a 1998-era web site and always causes people to wonder where in the hell the link to edit a photo album is).

10 – MySpace still garners some undeniable clout, even if it’s with a segment of consumers that are less likely to have graduated college and more likely to still be rocking a Pentium 3.

It’s that time of year again: tax time.  As we all pay buku to our local CPAs to fill out forms we’re either too incompetent or too uninterested to fill out ourselves, we cringe at the idea of a federal tax audit and dread dealing with IRS agents on the phone: people who won’t give you their first names and only want to be called Mister This or Mizz That.

At the same time, at least in 2009, Microsoft is introducingperpetrating the most ambitious domestic licensing compliance audit in its history, calling any company it suspects may be out of compliance and requiring them to demonstrate that they “own” all the Microsoft software they’re using.  Microsoft’s SAM group is using tersely-worded phone conversations and heavy-handed verbal and written threats about escalation, audits, and legal action in order to ensure compliance. Call it revenue preservation if you want.

I call it lawsuit bait and a huge waste of my clients’ time.  Yet, Microsoft isn’t going to wait until economic conditions have improved to do this. They’re hurting too, and the easiest way to shore up revenue is the horse technique: go back to the same trough and drink some more.  Call existing customers and make sure they’re loaded with all the licenses they could conceivably need.

This technique is a bit of a gamble, as those being audited are mostly volume licensing customers–precisely the type of customers who have been laying employees off the last year or so.  Indeed, these customers’ licensing requirements have in fact gone DOWN, meaning that, for many companies, the amount of Microsoft software that’s actually needed might be less than what the customer has paid for.  Of course, when I asked my SAM agent if Microsoft would compensate me for my time if we were found to be over-licensed, he promptly responded with a proverbial ‘hell naw.’

I then informed him that if he is going to make arbitrary decisions about how my clients’ consulting time is spend (it does take me time to fill out MS’s compliance paperwork properly), he needs to give me or the client more notice.  I can picture lean I.T. staffs whose projects have to be put on hold all because pouty Microsoft is throwing a licensing tantrum. So much for the server upgrade because Ballmer and the gang decided to foist this lofty audit on our I.T. guys. It’s more than a little absurd.

Microsoft, you’re going to piss off a LOT of customers with this behavior.  (Something tells me your biggest customers like NASA and General Motors aren’t getting harassed on the phone by a war-dialing twenty-something with an autographed copy of Introduction to Microsoft Licensing on his book shelf.)

Bottom line, is if you’re going to show up out of the clear blue, and require something of my time, ie. boss me around, you better be either the IRS or my Mom.  Those are the two people for whom I jump through hoops.

It has become obvious in the last several years that Apple is, first and foremost, a device manufacturer, and their flirtation with software (OS X, iLife, Logic, etc.) is borne as an extension of their inventive nature. In other words, Apple doesn’t necessarily want to be a software company, but they need to be.  It just so happens that they’re probably the best software company in the world (in recent years anyway).

So how is it that you come to be the best at something that isn’t your core business, just so you core business can flourish?   Well, you avoid the pattern exhibited by Microsoft–cut into as many markets as possible while clutching onto second-rate products (Live Search) and outmoded business models (XBox Live).  Ultimately this will mean that Apple’s failures over the years–their poor product offerings like .Mac–were things that they wisely dumped instead of clinging stubbornly onto like Redmond always seems to do.

Apple recognizes that–when THEY put out a crap service like .Mac–they have to cut their losses. Hence no more .Mac.  Ultimately, the same will be true of Mobile Me, when Google and its ilk replace every feature of Mobile Me with something better. And then, Apple will likely dump Mobile Me rather than try to compete in an area where they aren’t wanted and can’t do better.

This is why Apple won’t embrace Live Search. If they’re willing to cut their own failed initiatives and recognize that somebody else can do something better (Google Sync, anyone?), then why in the world would they embrace Live Search.

Snow Leopard or not, I don’t expect a Microsoft/Apple search alliance.

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