How To Weave A Great Conversation

Making conversation is something that I’ve always found pretty difficult.

What are you even supposed to talk about with strangers? How do you avoid making the conversation all about your own interests? How can you keep a conversation going when you run out of things to say?

It’s not a particularly easy question to answer. As a general rule, people struggle when trying to teach someone else how to make conversation.

The people who are best at conversation rarely have to think about how they actually go about doing it - and the people who are bad at it don’t know how it’s done either.

Even so - it is a skill that can be learned.

One way to think about how is to remember… almost anything you might want to become skilled at involves some mix of art & science. Programming computers is mostly science. Painting with oil on canvas is mostly art (and so on and so forth).

Sometimes, though, the line between art & science is further in one direction or the other than you might expect - and making conversation is a great example of this.

It feels almost strictly like performance art - just you & your conversation partner making things up as you go.

However, if you get really autistic (heh) about it and take a hard look into how great conversations play out in practice, there are a number of specific patterns you can consistently identify and then use yourself.

There are three of these patterns in particular that can be used to reliably weave a fascinating & engaging discussion with almost anyone - Hooks, Threads, & Loops.

I first picked up these ideas in Neil Strauss’ excellent book, “Rules Of The Game”, and I’ve found them to be an incredibly powerful tool for putting together a fun conversation with the help of whoever I’m talking to.

Learning these patterns will serve you whether you’re on a date, at a party, or standing by the office water cooler - and I’m sure you’ll think of some examples of them in your own life as we talk through each one.

Let’s start with finding things to talk about by listening for conversational “hooks”.

Hooks / Picking Out Details You Can Explore Together

When you’re talking with someone you’ve just met, imagine each and every sentence they say as a long string that’s hanging horizontally. Each major word in the sentence is a sort of hook hanging from that string - one you can pull on to start a new conversational “thread”.

This comes across as pretty abstract, I know - so let me give you an example.

Consider the sentence: “I recently moved into town to work at Google”. Not particularly detailed or interesting on its own, right? Even so, we can pull on its “hooks” to find new topics to explore & discuss.

It might prompt questions like:

• What kind of work do you do there? (Because they shared where they work)

• How are you adjusting to things here so far? (Because they’re new in town)

• Have you tried one of the self-driving cars? (Because they work at Google)

And this list goes on & on - limited only by your creativity. More-specific questions that they probably don’t hear very often tend to be a solid bet - but be cautious about going too deep and asking too many personal questions of someone you just met.

Why Use Hooks To Pick Conversation Topics?

The key idea behind hooks is that you’re tying the new topic you want to discuss into something you’ve learned about that person, thus implicitly talking about something they would likely find interesting.

The more you can relate the conversation to the interests of the person you’re talking to, the more likely they'll be engaged & interested in continuing the conversation.

As a general rule, if someone brings a fact about themselves up unprompted, they’ll probably be happy to talk more about that fact, so oblige them - by pulling on a new “thread” of conversation.

Threads / Finding Topics & Keeping Things Fresh