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drethelin comments on How to have high-value conversations - Less Wrong Discussion
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If you need to have form questions for conversation I think having them with built-in blanks to tune them to the existing conversation/people is important. Most of your conversations are probably not going to be with random strangers, but with people you already know a lot about (because they're your friends) or a little (because you meet them in a LW meetup or at school or work).
Even with strangers, people will generally respond a lot better to more specific questions than more vague ones. Consider how complicated the real question behind "How's it going?" is and how lame the answers usually are.
My intention is indeed to improve conversations with people I know well or semi-well. Some good questions with built-in blanks in this context are "How is your project X going?" or "What did you think of book X?". Do you have examples of other such questions? I think the kinds of questions you would use for starting a new topic and for deepening an existing topic are likely to be different, and the latter are much more context-dependent.
It does not seem difficult to avoid being robotic/unfun with these questions, if you ask them with actual caring and curiosity, and if the motivation is not to fill silence but to learn about the other person.