I worked at MSFT from 87 to 98. I had multiple meetings with Bill, from the days when you had a meeting with him like you would with anybody else to the days when just getting on his schedule was like meeting with POTUS.
Back in the day MSFT was full of really really smart people. For example, Nathan Mhyrvold was an astrophysicist who had done some stuff with Stephen Hawking. And that kind of background wasn’t that uncommon among the people there. Lots of PhDs in lots of fields (not just CS). (I once remarked to a Really Smart Friend that I always felt like the dumb guy in the room; he looked surprised and said that was how he always felt.)
And yet, with all these smart people, who remember specialized in some small aspect of Microsoft, when they would meet with Bill he would almost always pick out very quickly the things they had missed in their product plans and strategies. HE was invariably the smartest guy in a room of brilliance.
Let me give a specific example from the last time I saw him. I was in the marketing department on a product team that was launching our first ever product for ecommerce (Microsoft Commerce Server). It was a very small team on a product that was not expected to make a great deal of money, but was necessary from a strategic standpoint. My point is, it wasn’t exactly on Bill’s radar. We had gotten the product via an acquisition, ported it to NT (remember NT?) and were ready to launch it.
Somehow we managed to get Bill lined up for the launch event, which was super hard to do because every product team wanted Bill at their events–a Bill appearance would guarantee lots of turnout, both by press and customers, as well as press coverage. So it was a major score. We had one very brief planning meeting with Bill several months in advance and, when the PM started telling him about the product, he cut him off saying, “I don’t want to fill up my head with a bunch of stuff that I’ll just have to learn again later.”
A couple of weeks before the launch at the San Jose Convention Center, we had a briefing with Bill on the product and launch, where we went over features, messaging, competition, etc. We had an hour I believe. Two weeks later and Bill gets hustled in back stage, surrounded by his (now ever present) “bubble”–PR flacks, assistants, security people. Bill went out on stage and did a complete in-depth presentation on the product, space, future, etc, all from memory, no notes. Then dashed off to his next meeting.