If you’re like me and really dislike small talk, you may find these ideas useful.

(1) If you end up talking about their work, ask what they (i) most like about it and (ii) find most challenging about it.

(2) If they end up asking about your work, try to explain what you do in a way you’ve never experimented with before.

Example: if you’re a programmer, maybe you’ll say your job is to convert ambiguous human goals to instructions that are so precise a computer can follow them.

(3) Pay close attention to the other person’s vibe and make a positive (and genuine) observation about their personality or manner. For instance, if they have a really pleasant-sounding voice, tell them that. If they give off a lot of confidence, compliment them on it.

(4) Assume the other person is worth knowing. Give them the benefit of the doubt. Now your job in the conversation is to explore what’s interesting about this person.

(5) When the conversation lulls, say, “This is random, but I’ve been thinking a lot about something lately, and I’m curious what your take on it would be.” Then ask a question you’ve been pondering (e.g., “How do you decide how much time to spend making new friends?”)

(6) Assign yourself the goal of figuring out what they would enjoy talking about (but without directly asking – since “what would you like to talk about?” puts uncomfortable pressure on them). Ask questions about their thoughts and interests to discover the right topic.

(7) If there’s something interesting in the environment, remark on it and ask what their reaction to it is or open the door for them to comment on it too.

Example: “I just noticed that house has a different style of architecture from the others. Do you like its style better or worse?”

(8) Ask the person what sort of things they are interested in. This can be a slightly awkward question, but I think it’s often worth it. In my experience, it tends to have a good payoff in that it helps you jump to talking about something the other person cares about. Sometimes people will talk about work (when they enjoy it), but other times, they will bring up an idea they are interested in or a hobby they are passionate about, etc. From there, I find it’s typically much faster to get to mutually interesting conversations than if we started with small talk.

The thing about small talk is that it’s designed to be low-risk.

Deviating from small talk increases the chance that a conversation ends up being awkward.

And, of course, it’s possible the other person just doesn’t want to engage with you on a deeper level than small talk. It’s important to stay attuned to how the other person is feeling and not push them beyond the level of engagement that they feel comfortable with.

But when done skillfully, strategies like these often make the conversation much more interesting for everyone involved.

This was first written on December 3, 2022, and first appeared on this site on June 4, 2023.