If you're running or attending meetups a lot, it's helpful to have a short list of conversation starters ready. Conversation starters, sometimes called icebreaker questions, are questions that everyone can answer. They aren't deeply personal, but you do learn something new about the person. Ideally, they're short questions that lead into longer conversations. "How did you find this community" is one example of a decent conversation starter.
You have now read the basic point of this post. If you want to read on, cool, lets talk about implementation details for a bit.
I've found the really good conversation starters tend to fall into one of two categories. Either the question encourages someone to go on a bit of a monologue, or the question leads to answers that are full of jumping off points for further conversation. "What's your most recent obsession?" is a good example of the former. Their resulting oration may not be a back-and-forth conversation, but I like to hear what people find interesting. "Where did you grow up?" is a good example of the latter. I can almost always go from there to something like "Oh, neat! Why did you move away?" or "Cool! What's something you love about the place?" Those questions lead to more questions; if they loved the mountains because they love to hike, ask them about the best hiking trails or about fun hiking stories.
Conversation starters need to have answers. "What did you major in at college?" is a somewhat risky starter in a random group, since not everyone went to college. Likewise, "what do you do for work?" I've been using "what do you spend most of your time on?" since everyone has time. If you know your group, you can use more specific conversation starters: at a LessWrong meetup "what's your favourite LessWrong article?" would be a fine conversation starter, since people have probably read at least one.
I would like to emphasize part of the above. Questions that rely on domain expertise to understand should not be used as conversation starters unless you have good reason to expect people have that domain expertise. "So, what do you think about the latest paper on LLM architecture?" is a terrible conversation starter unless you are at an academic conference on AI. No, a LessWrong meetup is not an academic conference on AI.
Questions that naturally lead to yes or no answers aren't good for this, though once in a while you can make it work with followup questions as a two-parter. "Have you ever gone skateboarding?" "No." doesn't give you much to work with. "Have you ever thought about writing a novel?" "No." "If you were going to write a novel, what would it be about?" isn't horrible, though it is a bit awkward and if I were doing it I'd just skip the first question.
The best conversation starters are just a little bit anti-inductive. If everyone always started with "where did you grow up?" then people wind up retelling the same stories a lot. Wildly unpredictable and unexpected questions can throw people off their stride in a way that can be interesting, but that I would consider an advanced move. "What deep secret have you never told anyone?" sure is an interesting question, but people aren't likely to want to answer that one at a casual meetup.
I used to write my current favourite three conversation starters down on index cards and flash card them on my way to a meetup, so they were fresh in my head. That also let me look at the different questions I've used over time.
"What's the best icebreaker or conversation starter someone's asked you lately?" actually is decent! It's a bit meta, which is usually fine in the kind of meetups I go to. If you are reading LessWrong articles about how to do meetups, I suspect it'll work okay for you too.
I get asked for conversation starters by new organizers interested in running their first ACX Everywhere meetup. For that context, here's a list I use:
- Talk about a recent ACX article you liked and ask what other people liked
- Talk about one of the books from the Book Review you liked
- Ask what their biggest disagreement with something Scott's written is
- Ask how long they've been reading ACX
- Ask how they found the blog
- Ask what they do for work
- Ask what other blogs they read
- Ask if they write anything, and if so ask about what they write
- Ask what they've been really interested or obsessed with lately
If you use conversation starter or icebreaker questions, I'm curious which ones you've had the most success with. ("Success" here is defined however you like; but anything that reliably results in a good conversation is worth considering.) If you're willing to share, please comment with one or two of your favourites! This will create a nice repository of good conversation starters for everyone to dip into.