There's an aspect to the struggle that suggests that big organizations anywhere share certain traits, whether their product is "national security" (the Pentagon), a "harmonious society" (the Chinese Communist Party), or "great software" (Microsoft). One such trait is the effort of people up and down a bureaucratic hierarchy to guess at what the boss would "really" like, and do that -- even if the boss has never said so, and even if it's might not be what the boss actually has in mind.
Very few people I ran into at Microsoft thought that Clippy was such a great idea. As my Building 17 friend Chris Pratley -- who rose to further greatness as head of Microsoft's OneNote program and who recently took a job at Microsof'ts Office Labs -- pointed out several years ago, Clippy suffered the dreaded "optimization for first time use" problem. That is, the very first time you were composing a letter with Word, you might possibly be grateful for advice about how to use various letter-formatting features. The next billion times you typed "Dear ..." and saw Clippy pop up, you wanted to scream.
The people at Microsoft are very smart, and they knew this. But they also knew something else: that Clippy was a holdover from Microsoft's "Bob" project, an ill-starred attempt to make computers "friendly" and easy to use. Two years ago, PC World magazine named Bob the 7th-worst technology product of all time. (If you're wondering, the original AOL was #1.) For a while the head of the Bob project was one Melinda French, who by the time I was on campus had become Melinda French Gates, first lady of the corporation.
I have only admiration -- I'm not being ironic -- for how Bill and Melinda Gates have conducted their philanthropic lives over this past decade. And I bet that if anyone had actually taken the issue to Bill Gates back when he was actively making software decisions and said: "Look, we know that your wife ran Bob, but we think this Clippy feature is really stupid, and we'd like to dump it" he would have been, as always, lucid and company-minded enough to agree. But this was a conversation with the boss many people were happy to postpone -- much as troops on a military base might postpone complaining about some new project dreamed up by the commanding general's wife.
I don't want to overstate this -- the fact that Clippy had been the brainchild of the boss's wife was mentioned as a little joke, not a seriously decisive factor. But it was a joke everybody knew.