Recognise overlooked opportunities to talk

Conversation requires some shared context – something you have in common with a person. There might be a lot of people who already fit this description for you: co-workers, neighbours, people who take the same commute or frequent the same establishments, and so on. Chances are there are people you already see during your day and could stand to feel just a little bit closer to. A neighbour who regularly walks the block, for example, will likely share many of the same day-to-day points of curiosity – nearby shops, public spaces, construction, transit, other neighbours, etc.

Other points of commonality might include shared activities or interests. Are you involved in volunteering, team sports, a class, a choir, cultural events or other such gatherings? Show up early, before the scheduled activity; maybe offer to help with setting up. When you’re there, see if others seem open to conversation: are they unoccupied? Do they make eye contact with you and smile? Or are they instead locked into their phone, or already talking intently to someone else? Likewise, consider whether you might seem open or closed off to others. Put. Down. Your. Phone. Keep your head up. Notice the world around you and the people in it.

Be open to trying and failing

A common hangup for budding conversationalists is waiting for the right moment. Instead, think about lowering your threshold for trying to engage. If you’re unsure how it will go, give yourself a chance to be surprised. Not only will this provide more opportunities to succeed, it will help you practise the skill of conversation. Developing tennis players will hit thousands of balls into the net before their strokes become smooth and natural. You can derive some satisfaction from the process of getting better, without relying on the outcome as your sole measure of success.

Sometimes, your attempts will fall flat, and that is normal. Some people will be distracted, or tired, or in a bad mood. If you were to see them again, the next time could be totally different. You don’t have to make a connection every time you try. It’s true that there might be some small moment of awkwardness in a failed attempt, but in the grand scheme of things, this should not dissuade you. If you fail to spark a chat, you’ll just go back to not talking – the same place you were when you started. The benefits of connection are worth the attempts. Think about it like a portfolio: be eager to offer others a chance, and don’t dwell on the failures or take them personally. A few successes – say, learning something interesting from a co-commuter, discovering that you share a passion with someone at work, or finding out that an acquaintance is also interested in an upcoming concert – can bring enough joy to outweigh the awkwardness of the false starts.

Research suggests that the reason many of us are reluctant to talk to people we don’t know well is not because we’re unsure about our own interest in talking to them. Instead, we are often wrong about others: we underestimate how much they might want to talk to us. Don’t let this bias your decisions. Give someone a chance to talk back. If they aren’t eager to connect, you’ll find out. But if you never try, then you’ll never know.

Seek an initial spark for conversation

Knowing what to talk about in the first place can be challenging with people you don’t know well. Contextual cues often reveal something about who someone is or what they are interested in. If you’re wearing a T-shirt or carrying a tote bag that signals your interests, for example, you give people something to ask you about. Look for these kinds of details in others. Perhaps they are wearing your favourite shade of green, or carrying a novel that you’re curious about, or their baseball cap shows they’ve travelled somewhere you’ve visited (or would like to go). Some of the most fruitful conversations are centred around similar likes and interests, and if you’re not sure whether the perceived similarity is shared, you can ask.

Don’t be afraid of talking about potential differences, too. But make sure this comes from a place of curiosity, not judgment. What makes their difference from you special, or a springboard for learning about them? Don’t start with aspects of a person that are hard to change, which can be fraught (eg, age, gender, ethnicity, physical appearance). Instead, focus on things they chose about themselves – maybe a choice they would have made that day. What brings them here today? Why are they carrying a particular bag, book or other item? These choices reveal something about their goals.

When starting a conversation, keep your comments short and positive. This leaves space for them to reply, and for you to gauge their interest in continuing. But if you think you have a willing chat partner, you can start filling in with a bit more detail. It can be tricky to get past the initial words to something a little more meaningful. It’s hard to provide an exact recipe here, because every conversation is unique. But there are techniques that can help you keep the flow going.

Help search for topics you both care about

Broadly speaking, you want to be both interested and interesting. That is, you want to show that you care what the other person is talking about, but also share things that the other person might like to know. Many people think about these two things as being opposite endpoints along a single dimension. In this perspective, self-focus and other-focus are mutually exclusive, like a see-saw – when one is up, the other is down. But my research suggests that they are much more like independent dimensions. Conversation can focus on just one of us; on none of us (the worst); or on both of us (the best).

It is amazing how long conversations can dwell on topics that neither person truly cares about, simply because they are top of mind (think: the news, the weather, the day of the week). This tends to lead to stagnation, awkwardness, and the end of the conversation. Try to spend as much time in the good quadrant as possible: your mission is to find topics that you both care about. As with searching for people to talk to, this is a numbers game. You can’t know for sure what the other person wants to talk about, so give them some options, and increase your chances of finding something you’re both interested in.

One trick for improving the topic search: when you get a chance to share something, share two things. Add an extra bit of information to be just a little more interesting and to create a fork in the road. For example: ‘I grew up in Toronto, though I lived in Vancouver after that.’ Or: ‘I’m a professor, though I always wanted to be a firefighter.’ Or ‘I live in Notting Hill, which is great because I like to cycle to work.’ Now the other person has two topics they can follow up on, and you don’t have to guess which path they might enjoy more. Don’t overdo it – a five-item menu would feel awkward and self-indulgent. But there’s usually room for two, even if they ask a very specific question. Don’t say too much on each item, either. Imagine a news website: a few headlines up top, but you have to click on the link to read the full article. Your goal here is to offer a couple of headlines, and then leave space for them to decide what to ‘click’ on.

Show interest and ask follow-up questions

Once you find a topic the other person seems interested in talking about, make sure they know that you’re listening and interested, too. People demonstrate listening in many ways, on different timescales. But it can start with things like nodding your head, orienting your eyes and posture toward them, and maybe offering some ‘back-channels’ (eg, ‘yeah’, ‘mm-hmm’, ‘wow’).

An even better strategy for any kind of conversation is to ask questions that go deeper on what the other person was talking about – questions you can ask only because you’ve been listening. Good follow-up questions go deeper on feelings (‘Were you excited?’), goals (‘Why did you leave?’) and processes (‘How did you learn that?’) They can also move the conversation through time (‘What did you do before/after that?’) Ideally, you will provoke answers that provide more items for your topic menu. Asking follow-ups is a skill that takes practice. You can even practise it outside of conversations. When you’re listening to people talk in a movie, on a podcast or next to you in public, play the follow-up game – ask yourself: ‘What follow-up questions could I ask right now?’

When I was first studying follow-up questions, I played this follow-up game in almost every conversation I had in my daily life. People love getting more time to talk about their favourite topics, and our research suggests they will like you more as a result. So, try to generate follow-up questions as you go.

Even if you don’t ask them right away, you can have them at the ready during the next lull in the conversation. At longer timescales, you can get the same benefits from ‘calling back’ to past topics. It doesn’t need to be a question, as long as you refer to something the person brought up earlier in the conversation, which shows you’ve been listening and processing. You also build a shared frame of reference that can be a foundation for closer connection. For example, if someone mentions that they have a dog, and then later on they mention loving Italian food, you might ask if their dog likes Italian food, too (it’s no coincidence that call-backs are a pillar of comedy).

Follow-up questions are especially potent when paired with positive affirmation (eg, ‘That’s pretty cool – how long have you been doing that?’) However, if it’s a tough topic with potential for conflict or misunderstanding, affirming can seem inauthentic. Instead, you can always simply acknowledge (eg, ‘I see what you mean’) or express sympathy (‘That must be so hard’). You can also soften your own contributions with hedging (eg, ‘I think there are sometimes solutions’ vs ‘There are solutions’).

Beware topic starters and ‘boomerasking’

One of the most dreaded aspects of small talk is the ‘interview question’, which includes generic queries like ‘What do you do for work?’ or ‘How was your weekend?’ They might be appropriate at the beginning, but if you’re already mid-conversation, these topic starters reveal no listening or understanding, because they could be asked of anyone at any time.

Once a conversation is going, topic starters should really be a last resort. These are especially bad when you ask a question to start a new topic and then give your own answer instead of listening to and following up on the other person’s answer. We call this the ‘boomerask’, because the topic boomerangs back to you. It’s OK if the other person asks you a mirror question (eg, ‘What about you?’) and you respond. But if you don’t get an explicit invitation, and you quickly give your answer anyway, it makes you look like you never cared about their answer to begin with.

Make mental notes for next time

Listening is demonstrated across conversations, too. After you meet someone or start getting to know them for the first time, reflect on potential call-backs and follow-ups for next time, assuming it seems likely that you’ll meet again. Do it quickly, while the memory is still fresh. And later, at the point when you’re going to see them again, spend a little time thinking about what topics you’d want to discuss (even 60 seconds of thinking about this is enough to help, according to our research). Not only does this help you show interest in them, it also reduces your cognitive work during the conversation – you won’t have to strain to come up with something to say during a pause.

Every relationship can be thought of as a series of conversations. Attentive listening helps to link conversations together and bring people closer over time. Putting in a little effort between meetings can help you turn a chance encounter into a meaningful connection.