Thoughts On How To Make Conversation

Most of the advice on making conversation I've come across focuses on what to say and how to say it. You know: Make eye contact, ask open-ended questions, be a good listener, be up-to-date on current news and events, avoid controversial topics, etc. I'm going to pull back and look at some assorted 'bigger picture' factors that can affect how easy it is to talk to others.

There are factors that help or hinder a conversation before it starts

When it comes to social interactions I think a saying that applies is "The outcome of a battle is decided before it even starts". When you chat to a co-worker or a friend of a friend at a party, many of the factors that determine how well the conversation will go are already in place. Some of them are:

Conversation flows out of who you are as a person

You're your own conversation generator. Someone who is sociable, knowledgeable, witty, and interested in a lot of things will naturally have better conversations than someone who's defensive, doesn't like many people, and who has narrow interests. If you think of good conversations you've had, you never really had to think of what to say, it all just popped into your head from your reservoir of personality, knowledge, and past experiences.

It's hard to prepare and plan for conversations ahead of time

People sometimes try to prepare for conversations beforehand by coming up with lists of topics they could talk about. The same people may also try to learn the core rules and structure behind certain types of conversation, so they can have a template that will hopefully allow them to think of things to say and make the discussion mutually enjoyable.

In my experience these things can help, but all our careful planning often goes completely out the window once we're standing in front of someone and have to think on our feet. We don't have a lot of time to recall our pre-planned topics or think of how to apply certain rules. We have to react in the moment, and tend to fall back on our instincts. Again, this isn't to say coming up with things to say ahead of time, or having an idea of a structure to follow never helps. It's just these concepts are tricky to apply in the moment.

How you present something is as important as what you talk about

Someone who's naturally funny, insightful, or a good story teller can take the same basic material as someone else and, as if they're running it through a filter, make it more interesting. It's not always about having the right, magic topics to bring up. Someone who's a good conversationalist can work with all kinds of material.

Conversations don't have to have any goals or proper progression

Reading some other advice on making conversation, you can get the impression you always have to try to move things along to a specific end goal. Like first you must make small talk, then you have to maneuver the discussion into the deeper territory. The goal might be to get to know someone on a core level and connect with them as a human.

That approach definitely has its place, but conversations can take all kinds of forms. Sometimes we're happy making nothing but light small talk. Sometimes we want to just joke around with people on a fluffy, superficial level, or talk about impersonal subjects like movies. Many people have friends or acquaintances they've never 'connected' with that all deeply, but still enjoy their company on occasion.

Having something in common you both want to talk about is a big key to conversing easily

The key phrase is 'that you both want to talk about', so if possible try to find a common interest and then start chatting about that. Most people can talk freely and easily about something that interests them because they have a lot of knowledge/opinions/questions about it floating around in their minds. They don't have to think about what to say; for most possible tangents they already have a couple of things ready to go.

This is a very pragmatic piece of advice, but I find it never hurts to be at least somewhat familiar with the things other people tend to be interested in and are likely to bring up. Even if you can't have an in-depth conversation about a certain area, being able to chat about it for a minute or two can earn you points. Like you may not know everything about a certain popular TV show, but having a factoid or two about it to bring up may help a conversation go more smoothly.

Another key is being comfortable with the other person

You'll have trouble thinking of things to say if you're not comfortable with someone, or the type of person they are. When you're at ease with someone the words flow much more easily. Sometimes we're not comfortable with other people because we don't understand them, or are a bit intimidated by them. At other times there may be this strange lack of rapport because you feel like you have different values from the person you're talking to.

If certain types of people make you uncomfortable, and you want to be able to chat to them, then you can aim to understand and get used to them. You can do this by hanging around them or by digesting the types of experiences that they've had (e.g., if you want to get along better with the people at your job who are in Sales, you may read a few books on selling and marketing to get a better idea of how they see things).

It's not unusual to feel a little nervous and on the spot when you first start talking to someone new. If you hang in there and don't expect too much of yourself in the first minute or two, you'll usually start to relax.

It helps to know about a range of topics

This is a pretty classic observation. The more random stuff you have floating around in your head, the easier it is to chat with people. If you have enough stuff stored away in your brain then pretty much anything someone says will remind you of something you can contribute. It's sometimes eerie how you can be reading about some seemingly obscure new topic earlier in the day, and then it will come up in conversation that very evening. So read new books and articles. Have interesting experiences in your life. Learn about the kinds of experiences people often go through so you can relate better.

Take the attitude that you will have to pull most of the weight in the conversation

If you're half-decent at talking to people this is often true. Many people are awkward at making conversation to one degree or another. It also puts the onus on you to develop your conversational skills and become more engaging.

Don't worry too much about the technical details

If the bigger picture factors are solid then you can get away with a lot when it comes to the little technical details. As long as everyone involved is happy with the interaction there aren't many hard-and-fast little rules you always have to follow. For example, all else being equal it's better to make good eye contact with people while you're talking to them. But if the other aspects of your conversation skills are solid, making so-so eye contact isn't going to totally ruin things.

Making artful segues are another thing you can often ignore. Just going ..."Oh yeah..." or "...Oh, I just remembered..." is usually fine as long as they don't come totally out of left field.

Even lulls and long silences are no biggie:

Not every conversation can go perfectly

I've read my share of advice on making conversation and in a lot of it is this implicit message that the ideal is to be able to talk to anyone at any time. I think if you're a good conversationalist you can get along with a lot people, but realistically you can't win them all. Sometimes you're going to talk to someone and it's just going to be awkward and stilted, or you won't have much to say to each other. Maybe it's your fault, maybe theirs, maybe the circumstances, or some combination of the three. There's no need to be hard on yourself if you can't have a sparkling conversation with every last person you meet. This is especially true if you just want to be somewhat better at talking to people than you are now, but don't feel any need to be a social kung-fu master.