Two and a half decades is a long time to lead any segment of the enterprise technology business. Is the clock running out for Microsoft? Unless you’ve been sitting in a windowless data center for the past year, staring at the blinking lights and shunning a Web browser, you’ve probably noticed that not very many people are holding out hope for Windows 8’s success. In fact, many quite knowledgeable people are fairly shocked that the Redmond giant is not wavering in the face of nearly universal disdain for the upcoming release of its flagship product. I mean, when even your friends point out your potentially gargantuan mistake, it’s a good time to listen.Then again, everyone laughed at the iPhone and the iPad, and look what happened there. Of course, it could be that the iPhone and iPad were actually compelling products with extremely well-designed interfaces and an amazingly well-thought-out ecosystem behind them. But this is Microsoft we’re talking about.[ Also on InfoWorld: Windows 8 review: Yes, it’s that bad | The case for Windows 8 | Get expert advice about planning and implementing your BYOD strategy with InfoWorld’s 29-page”Mobile and BYOD Deep Dive” PDF special report. | Keep up on key mobile developments and insights with theMobilize newsletter. ] We might see any of a number of different scenarios play out in the next six to 12 months. One is that Windows 8 will be a roaring success, smashing all kinds of sales records and vanquishing XP, Vista, and Windows 7 to the scrap heap. No, I don’t think so either.A second is that Windows 8 does as well as Windows 7, not burning down the house, but quickly becoming a generally accepted and lauded OS that provides Microsoft with a nice win and its first back-to-back OS successes. This, sadly, is equally unlikely.A third scenario is that Windows 8 follows the path of Vista, which is to say it’s fairly horrible, leading organizations that quickly jump on it to regret the decision later — just as Vista’s early adopters soon realized that they had to do it all over again because Windows 7 showed up and actually worked. Microsoft’s inertia being what it is, this is the most likely scenario. Believe me, those who hopped on Vista won’t be doing the same for Windows 8. They’ll be waiting for the next release. Once bitten, after all. A fourth scenario: Windows 8 ultimately costs Microsoft the farm. I can imagine the meetings that were held in Redmond where executives, designers, and engineers discussed how the next version of Windows should look. I suppose that someone was fervently pushing the idea of bringing a common UI to all devices: tablets, smartphones, and the PC. By getting this common UI philosophy into the brains of consumer and corporation alike, it would be a huge win, and not just along the lines of what Apple has done, but actually a step further in some respects. However, they missed a key element that Apple did not: Make the UI equally usable and elegant for all of those hardware platforms.I expect plenty of people in those meetings argued that the traditional Start button should remain available, and there should be a “classic” mode to allow longtime Windows users to feel at home. Those reasonable people were outvoted, presumably due to the misguided thinking that if Microsoft offered a way back, then too many users would stick with the old and the whole Metro push would fail. Frankly, it’s probably true that most people would cling to a classic desktop, but they’d have Metro available to them as well.Rather than allowing for a gentle transition, Microsoft opted for the baseball bat to the kneecap and even actively removed API elements that would allow third parties to resurrect the Start menu in Windows 8. All this despite having had a recent model of success to learn from: Apple’s complete renovation of its OS and even its processor architecture over a period of several years, while at the same time maintaining concurrent operation, emulation, and a clear path through the woods. That said, I have to believe Microsoft has an unannounced update waiting in the wings that would restore the classic Start menu if the furor over its absence reaches a high enough pitch. I mean, it would be horribly irresponsible if that were not the case. In IT, we live and breathe change and turmoil. We adapt to new APIs, new frameworks, new elements of computing on a daily basis.However, the vast majority of the computer-using business community does not. To them, the computer is nothing more than a tool, not something to be carefully inspected, contemplated, and relearned; it’s stable, familiar, and functional. Give a carpenter a saw without a handle and see how well that works.As if annoying the end-user wasn’t enough, Microsoft chose to throw this mess onto its server operating system as well, forcing administrators into the warped Metro world. Because clearly, nothing is more enticing to a Windows admin than messing around with sexy, flickering Metro panels (click me! click me!) while fighting an emergent problem. This specifically is a hard pill to swallow because what I’ve seen of Windows Server 2012 is good stuff on the back end. Marrying it to a disturbing mobile phone UI is just sad. The culmination of all of these decisions may be like a NASCAR crash during the last few laps where the front runners go down in flames, and the cars in the back of the pack are suddenly viewing the winner’s circle. If Microsoft’s fortunes play out this way, and we have another Vista or worse, it may not be just a bump in the road for Redmond. It may be the beginning of the end for the company that was so successful with the Start menu but couldn’t figure out a way to move forward with new innovation and adapt to changing times. Huh — sounds a lot like a company called Novell back in the ’90s.If Microsoft’s future does bend this way, don’t be surprised to see amazingly unlikely players moving into the corporate data center and desktop. Android? Mac? Cloud? It’s all possible, and if any number of brilliant companies step into that vacuum like a young, lithe Microsoft did 20 years ago, we’ll all be remembering how it used to be when Microsoft ruled the roost.This story, “The Windows 8 doomsday scenario,” was originally published at InfoWorld.com. Read more of Paul Venezia’s The Deep End blog at InfoWorld.com. For the latest business technology news, follow InfoWorld.com on Twitter. Technology IndustrySoftware DevelopmentSmall and Medium Business