One of my favorite questions is asking people their least favorite and favorite languages then asking people to give one of their favorite features in the least favorite language, and least favorite features in their favorite language. Shows that they've actually spent time thinking about their tools. You get a surprising amount of insight from it, depending on the answer.
This question would throw me for a loop because I don't have anything I think of as my least favorite language.
I could pretend that Python was my favorite language, but that's more that I'm comfortable with it than any sort of actual feeling that I should prefer it over others. That is, I use it out of inertia and familiarity, not out of some sense that I've found something.
See, but that's a reasonable answer. I might take that and pivot to like "if you had to design an ideal language, drawing from the strengths of the ones you've worked with, what would you think most important?". The idea is to get you talking about things you've worked with to show familiarity and critical thought about your tools.
I hate the question -- I do think about my tools, constantly, but whenever I've been faced with that question, I don't have a "best" and "worst" lined up, and have to think about the question for a few minutes to recall all the moments of frustration, and so anything I give on-the-spot will sound stupid.
I hate that one because I think Scala basically gets it right, and so I can't really give a good answer to least favourite feature in it. It's my favourite language precisely because I don't think there's anything massively wrong with it!
