The Conversation Toolbox: Make interesting conversation by always knowing the right thing to say

What is good conversation worth to you?

Being “the life of the party” is a skill. And like most skills, anyone can work toward it.

And even if you don’t like being the center of attention, the tactics we cover here will help increase your value as a conversationalist.

The very-attainable tactics we’ll talk about today will allow you to:

– Reinvigorate almost any dying conversation (and take the credit for it).

– Recall and retell an apt personal anecdote for almost any conversational situation.

– Pull from a seemingly endless pool of really good jokes.

– Use profound and/or humorous synonyms to enliven the quality of your language.

– Contribute high-quality quotes at appropriate moments.

Thanks to the tricks up your sleeve, you’re able to nail interviews, dates, classroom discussion, and any other situation that involves talking with other people. With practice, it’s almost as effortless as saying “good morning.”

Conversation is a skill. The ability to make high-quality conversation raises your perceived quality as a person (read: “gets people to respect you a lot more”), so it’s a skill worth developing.

I’m about to show you how.

1. Starting off

Before we dive into the really cool stuff, here are some resources (with mnemonics) you can use to get a conversation started out on the right foot:

– Master small talk with the mnemonics: “ARE” (anchor, reveal, encourage) and FORM:

– Be interesting: Check out a great new post on Art of Manliness: Be More Memorable

2. The conversation toolbox

This is where the real quality of the conversation comes in. We’ve learned how to start a dialogue going, but what about the meat of the conversation? How do you really demonstrate that you’re someone who has interesting things to say, and that you really know what you’re talking about?

Simple: A conversation toolbox.

I have to give credit to Ramit Sethi for the idea of a “story toolbox”. Ramit teaches students to build resource of about 10 rehearsed anecdotes, which can be easily told whenever the need arises.

Thanks to Ramit’s idea, I’ve decided to combine this concept with mnemonic tactics, and then to expand the toolbox to include other handy things, such as quotes, jokes, and synonymical phrases.

Objection: “But don’t most people have lots of stories in their heads? Why should I have to organize them systematically?”

You may have a lot of stories in your head, but that does NOT mean you have ready access to them.

For example, how many jokes do you know? Probably several dozen. But if I ask you to start telling jokes, will you actually be able to think of all of them? Almost definitely not.

What we’re going to do is give your mind ready access to everything you may want to pull up in a conversation. The idea is to put all these things in a mental toolbox so that they can be quickly recalled at will.

As always, if you want to be able to remember something, you have to have some sort of trigger. A trigger is something you’ll easily be able to think of that will then cause you to remember what you’re REALLY trying to remember, be that a story, a synonym, or anything else in the conversation.

There are two types of triggers you can use as the basis for your toolbox:

1. A memory palace, with different stories/synonyms/etc. in different stations

2. Number pegs, with different stories/synonyms/etc. attached to different numbers

I tend to prefer number pegs. In a conversation, it’s a lot easier to come up with a number spontaneously than to think of a random location in a memory palace… probably because, as I’ve written elsewhere, memory palaces are concrete and location-based, while number pegs simply float around loosely in brain-space. With number pegs, you can catch them and release them at random, like fish, instead of having to count them off one-by-one, like railway stops.

OK, it’s time to build our toolbox. Let’s start with jokes.

This is a great place to start. Jokes are very easy to learn quickly (because they’re funny, which means they’re memorable), and people love someone who can tell a good joke. We’ll get you there in a matter of minutes.

First of all, you’ll want to list whatever good jokes you can already think of, and then do some browsing for more good jokes.

Biggest problem here: You’ll find very quickly that high-quality jokes actually aren’t that easy to find. However, if you want some ideas for good jokes, just email me, and I’ll help you start building your toolbox. I know some pretty good ones. (The refrigerator-in-the-apartment joke is my absolute favorite to tell; everybody loves it, and I never tell it the same way twice.)

Once you have a list of your first 10 jokes, start pegging. Attach the jokes to your 100 number mnemonics. Rehearse and recall. You can use a set of flashcards, like this Quizlet set (my own), for simple prompts to remember which jokes go with which pegs.

Objection (again): “But I already know lots of jokes! Why do I need pegs?”

Oh sure, I probably know hundreds of jokes, and I have for most of my life… But I could never seem to think of them at the right times, until I pegged them for easy access.

Again, the point is to create triggers that can be activated whenever I want. It’s like the jokes are all sitting on a sheet of paper in front of me, and I can always bring up a new one at a moment’s notice. It’s as easy as thinking of a number.

How about applying the same concept to personal anecdotes? No matter who you are, you’ve  had some interesting things happen to you in your lifetime. People will value you more if you are able to turn those interesting things into good stories, using them at appropriate moments in a conversation.

A toolbox will allow you to think of the right story at the right time. You have all those stories organized and ready for immediate access, so you can just reach into your toolbox and pull one out at will.

You may not be able to think of 100 anecdotes as quickly as you can think of 100 jokes, but start small. Choose stories you’ve told before, then slowly add stories as you remember them.

Synonyms? Funny phrases? Other conversational elements?

Once you have jokes and stories down, there are dozens of other ways to improve your conversation. You can easily own synonyms, compliments, funny phrases, and anything else you want to add to your conversational value, all with just a little memorization work up front.

For example, let’s say you want to have 100 compliments. You’re tired of just telling people “you’re awesome” all the time. Let’s create a toolbox of something more valuable than that!

Now, since each of the 100 characters in your number peg system has a distinctly different personality, you can simply associate a different compliment with each character.

Suppose Elvis Presley is your character for the number 53. Any time you think of the number 53 in association with compliments, you can say, “You’re a rock star!”

Or maybe Maria from “The Sound of Music” is your mnemonic for 14. “You’re a saint.”

Quirky compliments can be associated with quirky cartoon characters. It wouldn’t be hard to associate the Tasmanian Devil with “Talking with you is my favorite part of the day! …Except of course when I’m sleeping. And when I’m eating. …Talking with you is my third-favorite part of the day.”

And if the Tasmanian Devil is your mnemonic for the number 63, instantly thinking of that “compliment” is as easy as pi.