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

A thread - put simply - is a singular topic of conversation, and any conversation that stretches on for more than a couple minutes will involve the weaving-in of multiple threads, usually as a matter of necessity.

Why Do Conversations Include Multiple Threads?

When you’re meeting a stranger, it’s highly unlikely the two of you have more than a couple minutes of thought to share on any given topic - at least when it comes to ideas that you’ll both know well enough about to understand & appreciate.

The good news is that if you can weave a number of topics & stories into the conversation - leaving many open “loops” (we’ll come back to this), you’ll give the person you’re talking to the (correct) impression that the two of you have a lot to talk about.

It can be easy to stick to one topic that seems to be going well until it wears thin, but as you’ve probably guessed - this is not the best move. You need to keep pulling on threads to keep the conversation fresh.

Why & How To Switch Conversational Threads

The easiest & most reliable way to start a new conversational thread is by grabbing onto one of those “Hooks” from something they said and jumping into it with more excitement & enthusiasm than you had been presenting before.

You might think that it’s rude or unwise to jump from one thread to another without finishing every thought on the matter, but as it turns out, there’s a great reason to leave good topics dangling.

If you can set a good & interesting topic down before it’s fully exhausted, the other person will find themselves wanting to come back to it - and come back to you. This is why loops complete the trifecta.

Loops / Leaving Them Wanting More

Leaving a story or a train of thought intentionally unfinished is what the field of “neuro-linguistic programming” refers to as “creating an open loop”.

When you feel yourself running out of things to say or detect that the other person is - that doesn’t always need to be the end of the conversation. You can often jump to a new topic to keep the conversation alive & engaging by creating one of these loops.

Creating an open loop can be as simple as grabbing one of the “hooks” you’ve identified and using it to excitedly jump into another topic right before the current one starts to run out of steam.

Why Open Loops Are So Compelling

Open loops are a way to describe how people generally want to finish their thoughts & say their piece on a topic before setting it down & forgetting about it. You can use this subconscious desire to keep people engaged with you & the conversation you’re weaving together.

This is - again - done by pulling on multiple hooks and exploring multiple threads over the course of one conversation. Every time you grab a hook and pull a new thread they’re intrigued by into the conversation, you’ve created another topic that they might want to discuss with you in the future.

And creating that desire to keep engaging with you? That’s how you start building deeper connections with fascinating people - even those well above your station in life.

A Word Of Caution About Applying These Lessons

When I first learned about & tried to apply the idea of “structuring” conversations in the manner described above, I started struggling even harder than usual to keep the people I met interested in talking to me.

I was found myself thinking… “This really does seem like a sound concept - one that should be addressing my problems with knowing what to talk about” - so what gives?

I reflected for a bit and realized - I was steering conversations far too forcefully - to the point of being domineering. The exact issue I was trying to solve - being too insistent on talking what I wanted to talk about - was just as present.

These tactics really will help you enjoy & see better results from making conversation - but only when used in moderation. The thing to remember is that engaging in conversation is a multi-player game - and that fact is more important than any of the tactics I’ve described here.

This was a long post, I know - so thanks for sticking with me. I would encourage you to try & apply these ideas over the coming week and see how they work out for you. I suspect you’ll appreciate the results.

Your Friend Fritz
Signing Off