> 2. I have yet to read a flattering portrait of Ballmer and here he almost kills Microsoft going all in on OS/2. Was Microsoft successful in spite of him?
I don't have a lot to back this up on, just years reading books on the subject, but I always got the impression that Gates/Ballmer in the early Microsoft days made a fascinating good cop/bad cop routine. I will continue to wonder how much of what was attributed to either Gates or Ballmer in those early days was simply their assigned good cop/bad cop role (with the weird twistiness to it that I think the roles swapped in internal communications versus external communications; Ballmer was the friend of IBM, the respectable salesman, and Gates the hot shot kid that wouldn't take no for an answer / Gates the founder that loved technology and took everything seriously but Ballmer was the business man trying to reign in freedom) rather than their actual thoughts on the matter.
I certainly got the impression that early Microsoft was successful because of that two-headed dynamic. Microsoft could pet IBM with one hand and stab them in the back with the other, and IBM would let them try that again mostly because they succumbed to that good-cop/bad-cop routine quite effectively.
Some of the mythos internally at Microsoft always seemed to suggest that the dynamic played similarly inside the halls, in building the early culture.
I wonder if in Ballmer's tenure after Gates' retirement the problem was simply that he never quite found that replacement good cop to keep the dynamic alive internally (despite externally didn't really need a bad cop anymore). Satya to all appearances is nothing but "good cop", externally and internally and maybe that's all Microsoft needs now to survive. Early Microsoft probably wouldn't have.
Anyway, just supposition on my part.