From Microsoft's perspective, they were winning.
They had strong YoY gains on Blackberry, and Windows Mobile was set to overtake them eventually. By offering lower cost devices that didn't need to pay an extra per user Blackberry fee to the phone companies, MS was out competing Blackberry on price, while executing on their traditional strategy of having multiple partners flood the market with a variety of devices to fit everyone's needs.
(Where everyone was defined as business users.)
There were groups at MS experimenting with consumer focused designs, and even exploring app store types of business models (though they hadn't yet evolved into what Apple eventually released), people did realize that opportunity was there, but it is hard for successful incumbents to change.
Windows Mobile 7, which never saw the light of day, had just gotten a new kernel, support for higher screen resolution, and was setting out to be a really nice OS to use for business users.
Apple also did something else, it showed that the relationship with carriers could be improved. Microsoft had a very hard time getting past carriers testing requirements, they had a very hard time pushing out patches and updates. Apple showed a way by which carriers could be strong armed into being less customer hostile. The same way Apple showed that the music industry could be dragged into the 21st century.
Apple also dramatically brought down the cost of certain technologies, as they have continued to do. A single manufacturer making a huge order for one part drops the price of that part for everyone else. The OEM model Microsoft used for Windows Mobile, with the myriads of device form factors, was not able to create those types of market efficiencies.