There’s a fundamental issue with people, which is that it’s difficult to treat masses of people as separate individuals.

After the 20th time you ask someone to take out their laptop, there’s a part of you that’s screaming, “we’ve done this 20 times, you should know this by now!” Of course, “we” haven’t done this 20 times, only one side of the interaction has the repeated experience. But it’s natural to project that onto the other person, and get into a mode of, “I’ve told you before.”

Obviously this can be overcome, I'm not sure TSA hires people with enough self awareness to even see the problem.