Better Small Talk: Talk to Anyone, Avoid Awkwardness, Generate Deep Conversations, and Make Real Friends

by Patrick King

They might not be giving you much, but you also might be asking them the wrong questions, which is leading them to provide terrible responses. In fact, if you think you are shouldering the burden, you are definitely asking the wrong questions.

The truth about being a good conversationalist is that it’s more like partner dancing than solo dancing—you need to work with your partner, prop them up, give them cues, and help things flow not just on your side, but on theirs too.

Conversation can be much more pleasant for everyone involved if you provide fertile ground for people to work in. Don’t set the other person up to fail and be a poor conversationalist; that will only make you invest and care less and cause the conversation to die out.

when you lead with a few set parameters and cues, you are actually helping the other person out. It’s almost always easier to answer a more detailed, narrow question than it is to think of something to say to, “So, how are things?”

Prompting others for stories instead of simple answers gives them a chance to speak in such a way that they feel emotionally invested. This increases the sense of meaning they derive from the conversation. It also makes them feel you are genuinely interested in hearing their answer because your question doesn’t sound generic.

If all else fails, directly ask “Tell me the story about . . .”

Most people love talking about themselves. Use this fact to your advantage. Once someone takes your cue and starts sharing a story, make sure you are aware of how you’re responding to that person through your facial expressions, gestures, body language, and other nonverbal signals. Listen for little details you can call back to later. Since there is always at least one exciting thing in any story, focus on that high point and don’t be afraid to show that you’re engaged.

One quick tip to show that you’re involved and even willing to add to the conversation is something I call pinning the tail on the donkey. There is probably a better name for it, but it will suffice for the time being. The donkey is the story from someone else, while the tail is your addition to it. It allows you to feel like you’re contributing, it makes other people know you’re listening, and it turns into something you’ve created together. In essence, you are taking the impact that someone wants to convey, and you are amplifying it. You are assisting them in their own storytelling—they want to extract a specific reaction from you, and you are going above and beyond with the tail.

People will actually love you for it because, when you do this, your mindset becomes focused on assisting people’s stories and letting them have the floor.

Stagnation is one of the sneakier causes of poor interactions because it’s something we all default to eventually. It’s the lazy person’s way of conversing—relying on the other person to shoulder the burden of topics and details.

Great conversations are journeys. They never remain in the same place.

That’s where free association comes in. Isn’t conversation just a series of free-association exercises?

the fact that you are ignorant about the topic means nothing—you can still engage in a lively and personable way in the conversation (and invite the other person to speak more about what they know).

Practicing free association is an excellent foundation for good conversation because conversation is about relating unrelated things, making connections, and going with the flow of topics. Next time you're struggling for something to say, take a step back and tap into your previously practiced free-association skills.

HPM stands for History, Philosophy, and Metaphor. This means in response to a question or statement directed at you, you reply with your own statement that evokes history, philosophy, or a metaphor.

SBR stands for Specific, Broad, and Related. To any statement or question directed to you, you can reply with one of these types of statements.

EDR is the last part of the nine frameworks that you can employ to answer just about anything. It straddles HPM and SBR—you can use what’s in front of you, but it’s even better if you draw internally and speak about your own thoughts and opinions. EDR stands for Emotion, Detail, and Restatements.

For maximum impact, compliment people for two things (besides the obvious and superficial). Compliment people on (1) things they have control over and (2) things they have made a conscious choice about. There may be significant overlap between the two.

when you compliment someone on their choices and thoughts, you validate them to the highest degree. You’re telling them that you agree with them, it was all worth it, and they made the right choice!

Make your compliments sincere, appropriate and respectful. Above all else, compliments trigger one of the most fundamental weaknesses humans have: we are starved for attention. We like to be put in the spotlight and given the attention that we feel we deserve.

Silence is an effective communication tool. Use it more frequently than you think you should. If anyone you engage with answers your questions happily but doesn’t pause to ask you how you’re doing, then they need to shut up more. If that’s you, you’re the one who needs to shut up.

When you are listening, you aren’t only waiting for your turn to speak and preparing for that. You are listening with a blank slate and then tailoring your response directly to what was just said, after they’ve said it. You aren’t listening with an aim to respond. You are just listening, and then later, you are responding.

Not everyone is as interested in your life as you are. Even if you think you are listening and shutting up sufficiently, there’s a chance that you still cling to your train of thought subconsciously and are waiting for the opportunity to assert it.

listening is actually one of the most self-interested things you can do, because you are the person who benefits and learns. You learn more about people, you sharpen your conversational skills, you endear yourself to others . . . and you let yourself off the hook of having to come up with interesting things to say all the time! It’s a complete win-win situation.

Make people feel like you care and they matter. Giving people the spotlight is an entirely different thing from making sure people know they have the spotlight. Treat them as though they were the most interesting person in the room, and as if you are really grateful to learn more about them.

“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.”—Dale Carnegie

A question is a powerful tool that brings together many of the concepts we’ve covered so far—a good question sets a great tone, finds common ground, captivates people, keeps things moving and shows others that you’re paying attention.

Good questions help both parties develop deeper communication. Well-constructed inquiries can prompt a respondent to find new ways to think about their situations, which strengthens trust and keeps communication fresh.

Questions are best when they aren’t asking for plain old data, but require the other person to do a bit of analysis, to interpret, to connect two ideas or compare others. Good follow-up questions will make you sound invested in your partner’s response, and actually engaging in the content itself. Yes, it may take a while for you to get to the answers you both need to know. But that’s more time spent communicating.

Become a person with lots of experiences and lots to say. A more succinct way to put it is this that you should become the type of person you would like to get to know.

It’s easy to think about other people in terms of what they bring to the conversational table, but what about you—are you cultivating the kind of personality that makes other people excited and interested in conversing with you?

The more interests you have, the more interesting you become. When you’re engaged, you’re engaging.

not all “hobbies” are equal. Some are passive and about consumption (boring), and others are active and about creation, learning, inspiration, connection, art, skill and so on (not boring).

An opinion shows that you are interested, that you have made some sort of decision based on the facts you have, and that you are active in thinking about the world as a whole.

Good conversationalists know that it’s better to use opinions to drive conversation and connection, rather than shut it down or create division. They are not afraid of disagreement or difference; rather, they explore it with genuine curiosity. In other words, having an opinion per se is not enough—you need to be broad-minded, flexible and able to hear other people’s opinions, too.

Every conversation is a chance to learn something new, if you have the right mindset.

In other words, appearing benign and non-annoying will probably make you a better conversationalist than being someone who is actually interesting but has frustrating interpersonal habits.

even if you completely disagree with someone, or even if they’re flat-out wrong, it doesn’t matter—you can still learn something from them, still create rapport, and still have a great conversation.

If you only see one way of doing things, if you are constantly governed by “should” and “must” and if you typically assume people are “stupid” or “blind” then you, sir or madam, are judgmental.

You might think you’re open-minded, but if you only have criticisms and judgments of others, you’re probably not.

Judgment is the opposite of open curiosity and playfulness. It narrows our perception, shuts down our compassion and gets in the way of our creativity. And more than that, it’s pretty damn boring!

Sadly, some overly combative people really do think that life is about finding the right answer, clinging to it forever, and beating other people over the head when they’re “wrong.”

A Belief Policeman makes it his or her duty to let others know when they are wrong, and make sure they are thinking in the same way as them. A Belief Policeman might be very effective at imposing their beliefs on others, but this habit is going to make you downright obnoxious to talk to. Who wants to spend time with someone who makes them feel judged, attacked, and defensive?

If you feel that someone is doing something wrong, or thinking something wrong, instead of making that assumption, take a step back and wonder if you simply don’t have enough information yourself. If somebody has an opinion, respect that they have a reasonable basis for that opinion. After all, no one thinks their own decisions and thoughts are stupid. Ask questions about how they came up with that idea and what information and assumptions they hold. You might just learn something.

An additional way of preparing before conversations is to get your own information and life in order, and this can be done by following a conversation résumé. The purpose is to draw into your past and find what makes you an interesting person, and make sure that is all at the tip of your tongue for easy usage. We often forget what we can bring to a conversation, and this lack of available topics adds a sense of stress and avoidance.

the 1:1:1: method focuses on the discussion and reaction that occurs after a story. A story can be composed solely of (1) one action, (2) one emotion to be evoked, and (3) a one-sentence summary.