I spent last week at the Effective Altruism Summit in San Francisco - a conference bringing together over 100 people with one aim: figure out the best way to improve the world. I spent a lot of time meeting new people, and repeatedly having similar “who-are-you-and-what-brings-you-here?” introductory conversations. These conversations are often a useful starting point, but it can be hard to get beyond the small talk and connect with someone on a more personal level. So I’ve been thinking a bit about how to have more interesting conversations and really connect with people.
Here are a few things I find useful for getting beyond that initial “small talk” barrier.
Begin with slight variations on standard questions
One very simple thing I find effective is to ask slight variations on the standard “How are you?” questions, in ways that encourage less automated responses. A very simple example of this would be to ask someone “How is your day going?” rather than simply “How are you?”. The latter question often provokes automatic, meaningless responses: “I’m good thanks”, “Yeah, not bad” etc. The phrase “how are you?” is so overused that it’s often not clear the person asking the question really wants to know the answer.
Asking slightly different questions helps to break out of standard conversation scripts. If someone asks me how my day is going, it feels a lot more likely that they’re actually interested in the answer than if they simply ask me how I am. It also gives people the choice of answering in as much depth as they feel comfortable: both “pretty good, thanks” and “well, there’s this thing that’s been bothering me actually, can I talk to you about it?” are perfectly reasonable answers.
Only ask about things you’re generally curious about
One of my favourite parts of the past week was playing a game called “The Curiosity Game”. The idea is very simple: you go up to someone you’re curious about, and ask them anything you want. The only rule is that you can only ask questions you genuinely want to know the answer to. I found doing this resulted in me having some of the most interesting conversations I’d had all week, and made me feel way closer to the people I was talking to.
A massive problem with falling back on standard conversation scripts is that we can end up asking questions that we don’t even really want to know the answers to. How on earth can we expect to have interesting conversations this way?! Adopting a principle of only asking questions that you actually want to know the answer to seems really useful, and something I’m going to try and do in the future. Being curious in general seems to be a really good way to bond with people: most people like talking about themselves, and it feels good to get the impression someone is interested in you.
Share something personal or vulnerable about yourself
Asking someone else more personal questions is one way to try to shift the conversation from surface level to something deeper. However, I think sometimes you need to be careful here, especially with people you don’t know that well: some people may not respond well to being asked personal questions. They may not feel totally comfortable sharing personal information, and shifting the social norms beyond standard small talk can throw people off. If you want to try and connect with someone on a more personal level but are worried about making them uncomfortable, a really good way to do this is not by asking them questions but by offering up something personal or vulnerable about yourself.
Think about a time when you’ve been talking to someone you don’t know that well and they’ve expressed something a bit personal or vulnerable: perhaps they told you about something difficult going on in their personal life, or expressed that they’re upset about something. How did it make you feel about that person and your relationship with them? My experience is that this kind of thing almost always makes me feel (a) more affectionate towards that person, (b) closer to them, and (c) like I want to share more of myself with them too.
One small caveat here is that there is such a thing as oversharing. Going up to a total stranger and saying things that are hugely personal or vulnerable can very easily seem weird. Perhaps because it’s massively breaking social norms, or because it makes someone feel like they should reciprocate, but oversharing can make people highly uncomfortable. One strategy for avoiding this might be to start by sharing something relatively small, see how the person responds, and then go into more depth or share something more personal if they seem to be responding positively.
Other useful questions
There are a few other questions that also seem useful for breaking out of unconnected conversation: some of these are questions I’ve used and found useful myself, some have been suggested to me by others. Some of my favourites:
What’s something that’s been on your mind a lot recently?
What’s something that’s been bothering you recently?
What are you confused or curious about at the moment?
What’s something you’ve been working on recently that you’re excited about?
Like “How’s your day going?” these questions generally have the advantage of allowing the person to respond in a variety of different ways, and make their response as intimate as they feel comfortable. Some of these questions might come off as a bit artificial or deliberate, though. One way to get around this I’ve found is simply to preface them with something like “I’m going to ask some slightly different questions, but I think they’ll make for more interesting conversation, is that ok?”.
Getting past the small talk to have more interesting conversations and actually connect with people can be difficult. Breaking out of automated conversation scripts by asking slightly different questions can be a good starting point, as well as sticking to only asking questions you’re genuinely curious about. If you want to have more personal or intimate conversations, it can help to shift the conversation that way by sharing something vulnerable yourself.
This certainly isn’t a complete guide to having deeper, more meaningful conversations - I’d be interested in things others find useful. There are also some great resources on having better conversations here, including how to have more deep, substantial conversations (tip number one: seek out other people who like having such conversations!)