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I actually think your example illustrates this: people use their computers for porn. There's nothing wrong with that. If it's so large that he has no space left, I mean that's a pretty actionable thing to tell him. He's not an idiot for not figuring it out himself. That he "hid" the folder from you–I mean, people hide things from professionals all the time. Nobody volunteers to their doctor that they wipe in the wrong direction and thus have chronic UTIs. It's your job to work around the reasonable things people do that make your work harder and bring them to "oh, that makes sense, thanks" perspective.