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Last year, I interviewed for a job and was asked, “What part of the job would you not enjoy doing?” I said, “I could see a world in which X type of cases could be challenging because of A, B, and C.” The interviewer responded, “So you would not enjoy doing X cases?” I replied, “No, I didn’t mean to convey that,” and course corrected.

Questions:

1) How do you even answer the first question — aspects of a prospective job that you’d not enjoy doing?

2) Was this interviewer fair to interpret my answer as he did based on his second question?

I mean I think the only fair answer is, "I can't think of any, I'm excited about all the opportunities the job offers. What part do you not enjoy?" or maybe, "It's not about enjoyment, but whether I think the work is valuable, and when I believe in the work, I'm willing to put in whatever work is necessary." Those are of course both bullshit answers, but that's a question like "What's your greatest weakness?", there's no way to answer it honestly so the point is to show that you know an appropriate bullshit answer.

I do think the employer's follow-up question was "fair" in the sense that you ducked the question and he was trying to pin you down on it. It was a total lawyer move and there's a reason the public hates lawyers so much, but the point of the question is to make you negotiate a difficult topic so he's not likely to just let you slide away from it. (To be clear, I think it's a bad question - there are lots of other ways to get at what I think it wants to get at - but yeah, you didn't answer it.)

I was asked something like this for a lit related position, and my response was something like "In some ways, its disappointing when cases settle after I pour hours of work/thought/creativity into them. I know its often good for the client, but it is sometimes disappointing on a personal level." or something like that and had no issue.

Just say that you don't enjoy expense reports.