Since I moved into the Boston rationalist house, I've found myself having an overwhelming amount of conversation compared to my previous baseline. The conversations at Citadel tend to be fairly intellectual and interesting, but there is a lot of topic drift and tendency for entertainment over depth, which seems to be a fairly common pitfall. How can we optimize conversations and direct them towards areas of usefulness and insight?

There have been some previous discussions on this topic on LW, e.g. on useful ways to avoid low-value conversations or steer out of them. I would like to focus on the complementary skill of stimulating high-value directions in a conversation.

First of all, what makes a conversation high-value? There are several possible metrics:

people learning from each other’s expertise and experience
people getting to know each other better
exchange of advice and feedback
generating ideas and insights

All of these involve increasing the total amount of information available to the participants, either through revealing information that is already there, or through creating new information. This is more likely to happen in a topic area where someone has strong opinions or expertise, or, on the other hand, an area that someone finds challenging where they stand to learn a lot.

One effective way to steer a conversation is through asking purposeful questions. The questions should have sufficient depth to lead to interesting answers, but not be vague or put the other person on the spot. In that sense, a question like “What have you been thinking about lately?” is better than “What do you care about?” or “What are you terminal goals?”. It is better if the question leaves a line of retreat and doesn’t make the person feel low status if they don’t have an answer.

The types of questions that are productive and comfortable are generally different for group and one-on-one conversations. Two-person conversations are more conducive to openness, so one would be able to ask personal questions like

what memes have affected you strongly in the past or shaped your beliefs?
what has been important to you lately?
what has been difficult for you lately?
what eccentric things have you done?

Some questions are likely to lead to interesting topics in an N-person conversation for any N:

what have you learned recently?
what surprised you about experience X?
what have you been reading?
who are your role models?
I have been confused about X, does anyone have advice?

It is generally harder to steer a group conversation in productive directions than a two-person conversation, but the payoff is higher as well, since more people’s time is at stake. Since a single person has less influence in a group conversation, it’s important to use it well. Sometimes the most useful thing to do in a group conversation is to split it into smaller conversations. Asking someone about a subject that only they are likely to be interested in might be considered impolite to the others, but often leads to better separate conversations for everyone involved.

Questions do have limitations as a conversation tactic, and can sometimes result in awkward silence or a string of brief uninformative replies. If this happens, it’s handy to be prepared to answer your own question, which might inspire others to answer it as well. It is generally a good idea to have something that you’d like to talk about, perhaps something you've been working on or a concept that puzzles you, that you can bring up independently of whether and how people respond to your questions. Thinking in advance of topics to discuss with specific people is especially useful, e.g. relating to their past experiences or skill areas.

Do people have advice or good examples of directing conversations? Recalling the best conversations you've ever had, what made them happen?