Almost daily, a technology company CEO takes to the stage trumpeting the wonders of tablet computing, their newest slate-style device in hand, and superlative-laced talk of the amazing and innovative technology housed inside. While this is now old hat, one technology company beat them to the party by nearly a decade.

In November of 2001, Bill Gates took the wraps off the first iteration of the company’s Tablet PC operating system, and showing himself to be either a prescient futurist or the world’s worst marketer (depending on your interpretation), predicted that Microsoft’s Tablet PCs would be the most popular PC form factor within five years. Fast-forward to late 2011, and Gates’ latter prediction seems about right, with tablet-format computers flying off the shelves as stalwarts like HP leave the PC business for dead.

Obviously, Gates prediction about what software would be running on those devices was horribly wrong, the shiny silver Apple logo having kicked Windows to the curb to such an extent that your average technology buyer isn’t even aware that Microsoft has had a tablet offering for the better part of a decade. I can only imagine the stares of disbelief in Redmond as they watch Apple gobble up the spoils in a market segment they pioneered, all in a matter of months rather than the years Microsoft put into the platform.

So, the question is: Will Microsoft ever regain a foothold in the tablet space? Despite being a big fan of Microsoft’s products, I see the answer as a resounding “no” if Microsoft continues on its current track. Here are three reasons why.

1. Vertical markets

Take a peek at Microsoft’s literature advertising its Tablet platform, and you’ll surely see mention of terms like vertical markets, manageability, and other meaningless corporate-speak. Based on the resulting sales, as best as I can tell, these translate to “designed by committee” to appeal to a market of about a dozen.

If you look at the disjointed approach to hardware, software, and marketing that Microsoft has taken with the Tablet PC, it’s clear that there’s no compelling vision behind it. Apple shows you how you can make a movie of your Little League game on the iPad and send it to grandma, while Microsoft places ads in the tech rags that feature painfully staged photos of “generic professionals” and talk of “feature porn” rather than what you might actually do with the thing.

Apple’s liberation under Steve Jobs came from the company designing a product Mr. Jobs wanted to use, and the cohesiveness of visions shows through from execution to marketing. While Mr. Gates had clear passion about the Tablet when it came out, the haphazard execution resulted in disjointed products that check most of the “features requested” boxes put forth by hundreds of focus groups rather than forming a compelling finished product that anyone in a real market actually wants to use.

2. Do as we do, not as we say

Those elusive vertical markets keep telling Microsoft they want to run regular Windows applications on their tablets, and I’ve also been guilty of that same assumption. Conceptually, it would be great to have a device with an iPad form factor that I could connect a keyboard to and work on like a regular laptop, while also maintaining iPad simplicity and speed. Unfortunately, this takes you into a world of compromises. I loved some of Microsoft’s Tablet features, like the handwriting recognition and “paper notebook on a dump truck full of steroids” power of OneNote, but the compromises were too great. In a critical client meeting, I couldn’t wait two minutes to boot up my note-taking device or worry that my battery would die in that 2:00 PM meeting.

I replaced my old Tablet PC with an iPad with a great deal of trepidation, and while that device is also not without a raft of compromises, its core seems to have been designed with usability as the first priority. I know almost without fail that I can get into my note-taking application in about six seconds and that there will be plenty of battery — simple but critical features that make or break a highly personal device like a tablet.

In addition, there aren’t constant updates, mysterious hangs, or crashes. Sure, IT can’t manage my iPad to the extent they might desire, but they also can’t load it up with crap to the point that it takes 12 minutes to boot to ensure appropriate “manageability.” Despite the cerebral arguments in favor of an IT-centric approach, running “heavy” applications, and universal compatibility, usability is ruling the day in this form factor.

3. The end of the enterprise

Microsoft is beholden to “enterprise users,” the mammoth corporations that can generate millions in revenue with the stroke of a pen. I’m sure it’s much nicer to cash one huge check than a bunch of smaller ones, but I believe a focus on the enterprise is actually holding Microsoft back.

If you look at all the recent big technical innovations, most are targeted squarely at consumers, save perhaps for virtualization. The technological “cool stuff” that used to happen in the server room is now happening at your local electronics store, and this boat is sailing without Microsoft on the tablet front. Technology has become so personal that even the staid ranks of the Fortune 500 are allowing employees to bring their own devices into the enterprise — a trend that is only likely to accelerate as the newest members of the workforce see their laptop and tablet as just as personal a choice as what shoes to wear to the office.

Similarly, iPads are cheap compared to “enterprise” tablets, and in some ways, they’re more user friendly and effectively “disposable” than a tablet that must be managed, secured, updated, and maintained. $400 looks like a bargain for field service or marketing, especially when you consider training and deployment costs.

The pressure on Microsoft’s Tablet-related divisions must be immense, as expectations for the next iteration have gone beyond “grand slam” to the equivalent of a sweep of the World Series. It’s perhaps too easy to armchair quarterback Microsoft’s failings to win much traction with its Tablet PC, and hindsight always offers a clarity that’s unavailable in the heat of battle. So, in my next post, I’ll offer some brief points as to what I would do if I were running Microsoft’s tablet show.