At a high level, I have the same advice as any other instrumental rationality topic: know your purpose. Why do you want to move from small talk to more interesting topics? What anticipated future experiences are driving your choice to be talking with this person at all?
Specific options:
Accept social risk. Often, small talk is used among people who don’t trust each other enough to open up. If you can identify that the actual risk is smaller than the perceived risk, then you can introduce the (somewhat) riskier topics that actually interest you. With luck, it’ll interest them too.
If your goal is social cohesion, as opposed to your own entertainment or information-seeking, steer the small-talk toward the other person. Find topics they’re interested in and guide them in telling stories about themselves.
Change conversational partners. If you can’t identify a strategic goal in continuing a conversation, find an excuse to leave it and do something else. Do be somewhat patient, though: it’s easy to underestimate the value of non-close acquaintances and the time it takes to get enough mutual knowledge to be able to have truly interesting conversations.
At a high level, I have the same advice as any other instrumental rationality topic: know your purpose. Why do you want to move from small talk to more interesting topics? What anticipated future experiences are driving your choice to be talking with this person at all?
Specific options:
Accept social risk. Often, small talk is used among people who don’t trust each other enough to open up. If you can identify that the actual risk is smaller than the perceived risk, then you can introduce the (somewhat) riskier topics that actually interest you. With luck, it’ll interest them too.
If your goal is social cohesion, as opposed to your own entertainment or information-seeking, steer the small-talk toward the other person. Find topics they’re interested in and guide them in telling stories about themselves.
Change conversational partners. If you can’t identify a strategic goal in continuing a conversation, find an excuse to leave it and do something else. Do be somewhat patient, though: it’s easy to underestimate the value of non-close acquaintances and the time it takes to get enough mutual knowledge to be able to have truly interesting conversations.