I use two questions.
To myself - when stumped; "what do I want to know about this person?" then ask that; or find a way to ask that.
To others; "What is the most important thing you could be working on right now?" followed by, "What are you doing about that?" and "how can you do that better?" (also "have you tried X")
Traditionally - people would read paper or books and share that information with people they meet. i.e. "did you read the article about X" but people don't read papers any more.
Keeping a list (either written or mentally) of recent interesting things to chat about is good.
I tend to also ask, "what occupies most of your time?" Because it usually is something they are most interested in sharing.
Interestingly; those small-talk topics when you look at them carefully, are actually the important ones. "how are you?" when taken to steelman is practically the most important question I can ever ask someone. Its just too bad we automate to the default answers so often. (I have a theory that the weather actually affects 8% or so of people's moods. which is a small fraction; but big enough to be of significance for everyone. I don't know how to prove this; but its would explain why everyone defaults to the weather)
Often when people do the interview "how old are you, what do you do" type questions they are looking for common ground with which to share things with you. "Oh I also volunteer", "I also own a car that broke down today, how funny". If you try to broadly hit a few areas of your own interest with "hooks" for people to grab on - it will make it easier to connect.
i.e. "I like cooking" is not as good for hooking interest as, "I tried cooking X last week"... (this advice comes as dating profile advice as well)
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I have a theory that the weather actually affects 8% or so of people's moods.
I remember reading somewhere that people who live in places with better weather aren't measurably happier for it. This doesn't disprove your theory, since people's mood could still swing with the weather even if their baseline happiness is invariant.
This thread is for asking the rationalist community for practical advice. It's inspired by the stupid questions series, but with an explicit focus on instrumental rationality.
Questions ranging from easy ("this is probably trivial for half the people on this site") to hard ("maybe someone here has a good answer, but probably not") are welcome. However, please stick to problems that you actually face or anticipate facing soon, not hypotheticals.
As with the stupid questions thread, don't be shy, everyone has holes in their knowledge, though the fewer and the smaller we can make them, the better, and please be respectful of other people's admitting ignorance and don't mock them for it, as they're doing a noble thing.
(See also the Boring Advice Repository)