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Vika comments on How to have high-value conversations - Less Wrong Discussion
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I have tried around half of these questions. I have asked "what have you been thinking about lately?" a couple of times, and found out about a project a friend was working on, for example. Asking what people have been reading led to learning about what people have been reading, which was interesting. Some of the questions were posed to me, like "what memes have affected you?" and "what surprised you?", and I found them to affect the conversation positively (in the former case, we ended up discussing the effect of the diligence meme on my early life).
I agree that a lot of these require some leadup. For example, the question "what eccentric things have you done?" might come naturally after telling people about your skydiving trip last week. Vagueness is partly addressed by the "recently/lately" specification, but I agree that the questions could use some further narrowing down. Do you have any suggestions to that end?
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.