Microsoft never learned how to lead. Always reactive, always predation upon a segment created and defined elsewhere, always attempted one-upsmanship with feature creep that doesn’t play well together. A me-too colossus that made it big on an apparent cheap cost of entry.
Microsoft’s problem is they are your prototypical front runner. They do grea when they are ahead, but when they are behind the curve and have to catch up they flounder... even when their products are superior.
A perfect example was the Zune, a far, far better device than an iPod, but never caught on because they never spent the necessary time or money to market it. The device was wi-fi enable so you could download music and podcasts from home without hooking to a PC or any wi-fi enabled location. You had the ability to instantly share music with other Zune users... it was a pretty amazing device and a good 5-6 years ahead of its time.
Another example... I have both a Surface 2 and an iPad... I barely use my iPad anymore, the Surface is simply a better device, but the Surface is so far behind the iPad and Google tablets in terms of sales base that I’m not sure they can get enough of a grip on the market. It would help if they cut the price on the device substantially.