The problem, I suppose, is that it reflects Ballmer's obsession with Windows. He's so loyal to it that he'd rather disrupt his basketball's team existing system than let the staff use whatever they think works best.
It reminds me of the overall contrast between Apple and Microsoft execs in how they approach other companies' gadgets. You know that Apple developed the iPhone because its leaders (particularly Jobs) had first-hand experience of why BlackBerry/Palm/Nokia phones sucked. I suspect they kept using these gadgets afterward, too, if much less often. Meanwhile, Ballmer, Gates and other Microsofties almost prided themselves on how isolated they were from other companies' products. iPod? Nope -- they weren't going to use any MP3 player until the Zune was ready.
There are times when I think this willful ignorance played a large part in why Apple and Google steamrolled Microsoft in mobile. Microsoft's leaders didn't realize how far ahead the iPhone, iPad and Android were in terms of interface technology, and it was only when the company took a market share bruising that it reacted.