I can only tell you what it was like in my experiences; not what it’s like today. For all I know Bill has changed his methods and style in his foundation.
Over the years at Microsoft meetings to review plans and status on products morphed into something that, by the last few years that Bill was still at the company, caused product teams enormous amounts of grief and worry. My experience of Billg meetings were that he would ask the three vital questions that you hadn’t thought of, and that, in hindsight, were obviously critical to your plans. How he managed to do that I don’t know.
He was always late. His schedule was always crammed–it was tough to schedule time on his calendar. You’d be in the room all set and waiting for him to show up. When he did it was all business, no small talk, no fooling around. You’d start the presentation and he’d interrupt with questions; he wouldn’t wait until you were done.
Bill was (and probably still is) super analytical. What you couldn’t do in a meeting with Bill is speak to your intuition or feelings about stuff; what he wanted to know was what facts could you bring to the table. Everybody can argue about their hunches, or intuition, or best guess; nobody can argue with data. So instead of saying “We think we customers will really value extended database capabilities in Excel” you would need to say, “Here are the results of extensive customer feedback, help desk issues, focus groups, and market surveys that tell us that the most common use for Excel is to create non-relational databases, basically flat files.”
A pattern I saw in Bill was that he would challenge an assumption that your team brought to the meeting. I suspected over time that he did this not because he had an opinion about, but rather how you would respond to the challenge. So if you said “70% of accountants plan to switch to QuickBooks in 5 years” he might respond with something like “That’s incorrect. Accountants want a richer product than QuickBooks, something with full integration to their practice management system.” (I’m making this up.) If you responded with something like “Yeah, you’re probably right…” he would immediately assume you didn’t really believe in your assumption about QuickBooks. But if you responded, “No, here is the data we’ve gathered to support our assumption” he would look at the data and move on. See, it was a test. A test of you as a person (is this manager data driven or does this manager work from unfounded hunches?) and a test of the product direction (are we making thoughtful decisions about where we invest resources?).
To say that Bill was blunt is a serious understatement. A friend took a proposal in for approval. His management chain had decided since the proposal which highly controversial inside the company (one big chunk wanted to do it and another big chunk hated it–very typical scenario at Microsoft) that they needed to get Bill to approve it. After it was presented he thought for a minute and then asked, “What bozo came up with this idea?” After a long silence my friend–the junior guy in the room and in his first meeting with the big boss–said, “Uh, that would be me.” Nevertheless the plan was approved.
During my tenure I worked in some arcane areas of the company. Whenever it chanced that I was in a meeting with Bill I was always impressed by the depth of his knowledge and understanding about the area I was involved in. I doubt this was coincidental; I can only expect this was true for all areas of the company. His memory was famously close to photographic, and his breath of knowledge about products, competitors, partners, technology (both hardware and software), industries, large companies (many of which were our customers) was exhaustive and exhausting when you were face to face with him.
My last observation is something you can actually see for yourself, if you look closely. I still see it today so I know it’s still the case. A lot of the time you could see that Bill was kind of quietly chuckling inside; not from anything malicious but rather more like he just found much of life amusing. Watch some videos of him and you’ll see it. I really think for him the world of business is just a big game like Risk, and it’s not to be taken too seriously. That doesn’t mean he didn’t play to win–he was super competitive and wanted to have the #1 product in every category we competed in. But I remember a quote once that kind of sums it up: He said to an interviewer who was complaining about business practices: “We just make these little boxes. It’s not like we hold a gun to anyone’s head to make them buy them.” Or something to that effect.
Now based on the comments to the last Quora post I did on Bill I expect a flood of corrections by people who never even laid eyes on the man, let alone sat in meeting with him. I wish some of my fellow ex-MSFTers would join in and correct me where I’m wrong.