What really bugged me about Clippy and wizards was that they were both condescending and tended to be a posthoc band aid for bad ui design. "I see you are trying to do X" (it's either wrong OR (worse) it correctly identifies what you were trying and struggling to do because the UI to do that thing is awful).

It's like there's a team that identifies problems with your product but they have no influence over the product engineers so their only hope is the Clippy team.