17th August 2022 · The Clay Team

Instantly Have Better Conversations

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A simple practice to be more likable

In his groundbreaking book How to Win Friends and Influence People, Dale Carnegie recounts a dinner party where he had one of the most enjoyable conversations he remembered in a long time — with a botanist. Dale didn't know much about botany at all, in fact his only encounter with the subject was his small home garden! At first glance, the conversation was destined to be a dead end, ending after a few surface level questions. Yet Dale and the botanist had a fascinating and enriching conversation! In fact, as the conversation concluded, the botanist told Dale that he was, “...most stimulating…” and a “…most interesting conversationalist.” What a surprise!

Dale didn’t know anything about botany, but he did know the secret to having a good conversation with nearly anyone: listening with great interest to what your conversational partner has to say and capitalizing on opportunities to ask followup questions. With these two tools, Dale could have a great conversation with anyone. And so can you. The best part is that you can start practicing these tools right now, allowing you to have better conversations instantly.

Practicing The Magic Formula

The formula is simple: listen closely to your conversational partner, and then ask followup questions. Implementing this formula is a bit harder however, because it involves concentration and hard work. Choosing to actively listen to a topic in which you have very little immediate interest is difficult! Asking relevant follow up questions is even harder work. But, similar to exercise, you can develop mental muscles that allow you to more easily and effectively employ these skills. Over time, you’ll even come to enjoy using this skill. There are two quick tips that can help you kickstart learning to be an engaged listener:

1. Assume the other person is interesting. Then, find out why.

Conversation is easy when you find the other person intriguing. In fact, time seems to speed up when you are actively engaged in talking to someone you find interesting! You have endless questions, and their insights and experiences are exciting and intriguing to you.

Here’s the first tip: every person is interesting, so assume they are. You can learn something from every person you come into contact with because each person has experiences or interests or opinions that make them unique. The shy colleague from your office may be an accomplished woodworker. You can learn about the merits of black cherry vs. walnut from them. Fascinating! Or, a friend of a friend who you meet at a party may have written a poetry collection. What can they teach you about their process? Your plumber might be an accomplished dulcimer player. Why did they choose to play the dulcimer?

Sometimes someone doesn’t seem interesting on the surface, but they surely are! So, when you are talking to someone, assume that they are interesting. This immediately makes you invested in the conversation. Then, make it your job to find out why they are interesting. Ask them questions: what are their hobbies? Why did they choose those hobbies? What does their ideal Saturday look like? By assuming that they are interesting, you will give them the freedom and space to feel interesting — and then show you that they indeed are.

2. Look for opportunity hooks

After you’ve discovered how your conversation partner is interesting (because, remember, everyone is), look for opportunity hooks — a conversational invitation to expand or contract the conversation.

Each conversation is a choose your own adventure game — you make choices in where you want the conversation to go based on the way you treat your opportunity hooks. By looking for opportunity hooks and then expanding on them, you can continue and deepen the conversation. For example, if your woodworker colleague tells you that they prefer working the black cherrywood instead of walnut, ask why. Or, ask what the general consensus of woodworkers is. Or, under what circumstances they might choose walnut instead. In this example you took their answer as an opportunity hook to expand the conversation — and then you did just that.

With some practice, you’ll learn to quickly identify opportunity hooks (and the kinds of questions that best expand the conversation given the specific opportunity hook). However, there are two easy principles to get you started:

1. Move from the general to the specific, and vice versa

When someone gives you a general example, ask them to drill down to a specific opinion within that topic. For example, if your plumber tells you that they play the dulcimer, ask them where they got their dulcimer from, or who taught them, or if they perform. The opposite is also true: you can move from the specific to the general. You could instead ask your plumber if they like Appalachian music, or if they play any other instruments. This approach should provide many more opportunity hooks, leading to a virtuous cycle!

2. Ask about counterexamples

If someone gives you an opinion or a fact or a story, ask them about the alternative ways of thinking about the subject. Have they changed their mind over time? Do they know other people who think differently? Why do they think the way that they do? This allows you to get to know why the person thinks the way they do, which will provide more opportunity hooks.

Start practicing today

The formula of actively listening to someone and asking engaging followup questions will transform your abilities as a conversationalist. You will indeed have better conversations instantly.

But, to truly master the skill, you’ll need to practice with effort and mindfulness. Thankfully, the two tips we explored above can give you a headstart in pursuing these skills and becoming a better conversationalist.

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