HOW TO INJECT CREATIVITY INTO YOUR CONVERSATION

How to be a Conversationalist

Conversation Hack: every topic has a ‘who’, ‘what’, ‘when’, ‘where’, ‘why’, ‘how’ that you can address…often ‘why’ leads to a more interesting discussion.

I was so timid when I was young that whenever I spoke, it was such a rare event my family would jokingly make a big deal out of it. Needless to say, I wasn’t encouraged to talk more.

In high school, I remember listening to Howard Stern and being impressed with his ability to talk. His show was interview-style, but he still seemed to make it conversational by making relevant comments and asking unique questions. I learned: There was always a question to be asked.

In my 20s, I decided that being an introvert is boring. So began my lifelong and never-ending quest to be an extrovert. I’ve had to develop strategies for small talk to connecting one-on-one with a girl I’d like to date.

This blog will discuss these strategies.

The Best Conversationalists Listen

Yeah, yeah. You’ve heard this before. You have two ears and one mouth for a reason!

Let me attempt to add some meat to those bones.

It’s more about how someone says something, as there are various ways to convey the same message.

“Success requires are work” links hard work to success.

Compare that with: “Success is mostly the result of luck.” That connects success with luck.

Both are revealing the speaker’s experiences or values.

Someone who says “having a lot of money means you’re successful” is going to think Donald Trump, Elon Musk, George Soros, and Jeff Bezos are successful people.

But what if you were talking to a diehard democrat who wouldn’t cede this point for Donald Trump and Elon Musk?

Or a conservative who dislikes the Soros family?

What an interesting conversational thread that would open up (see the Fourth Strategy).

Let’s do another.

“He’s in poor health, he must really hate himself.” The speaker is equating health and self-hatred, which may or may not be linked in the real world, but they are in the speaker’s mind. How else could you say this?

“He’s in poor health, he must be really stressed.” Poor health = stress.

“He’s in poor health, he must not exercise.” Poor health = lack of exercise.

I’m modifying the generic advice, which says the best conversationalists listen to pay attention to how your conversational partner says things. Their word choices reveal who they are, and will allow you to read them cold (see the Third Strategy).

First Strategy: Clothes Hanger

During a conversation, imagine each sentence as a long horizontal string, like a clothes hanger.

Then imagine there’s a handle hanging down from each major word. You have the option of pulling any handle to start a new conversational thread (or association, as discussed below).

Let’s take an example sentence:

I always wake up at 6 in the morning, drink one liter of water, and brush my teeth with my left hand.

I have bolded the major words and underlined the major phrases. Do you see how you have a lot of information to work with here?

It’s that simple. This is how conversation works.

You can talk about the popular book that just came out, or morning routines, or joke about the last time you saw 6am was after a night in Las Vegas, the adult Disneyland.

Or…

You can talk about a study you read that drinking a liter of water first thing in the morning helps to delay your hunger, or that eating a banana is equivalent in terms of caffeine to one cup of coffee.

Or…

You could comment on the speaker’s excellent oral hygiene habits or the story about the last time you went to the dentist and they accidentally pulled out your tooth.

In general, choose the most interesting and/or deepest conversational thread for richer interactions.

“To be a winning conversationalist, you generally want to grab the least obvious but most interesting hook.” (p. 133, Rules of the Game by Neil Strauss)

Second Strategy: Free Association

Building off strategy one, practice the following exercise for five minutes.

Take a sentence, and choose one hanger word to create a new sentence. Not a story, just a sentence.

1. The universe has existed for billions of years. (you can choose any of the underlined words as your hanger for the next sentence. For added difficulty, make it extra interesting!)
2. There’s a new telescope in space that says the universe is older than we initially thought.
3. I always thought of life expectancy as a hard number—78 or so—but in reality, it varies wildly depending on your sex and wealth, with older and wealthier people often reaching 90+.
4. Monaco is the wealthiest country in the world because of their no-tax system many of the world’s rich become residents.
5. The 7 Flags Theory says that you should be a resident in multiple countries to offset any risk that your home country becomes bankrupt or otherwise no longer valuable.

Ideally, do this while speaking out loud because your brain will have to work faster.

From, The Trial by Avery Hayden.

A warm-up exercise can be the following: write down five words on a piece of paper. Do that now, before reading the next sentence. What was the first word you wrote down? I wrote down ‘Amazons’ becuase I just came from a trip in Letícia, Colombia. The three words I came up with in about 15 seconds were: indigenous tribes, porn addiction (there was a news story where a tribe got internet access and immediately got addicted to porn, which was fake news), worms.

The exercise is best if you start with a common word that is likely to broach many conversations like flying, dating, dessert, etc. and then come up with the associations of words that only barely have a connection becuase that will increase your mental agility and creativity.

Third Strategy: Cold Reading

People love being told about themselves. It’s partly why psychics are so popular. You can assume a few things about the speaker, which can give you future conversation ammunition to better relate to this person:

• They are right-handed.
• They value productivity because they brush with their left hand.
• They’re a morning person due to rising at 6am.
• They value health by drinking water first thing in the morning instead of smoking a cigarette or using a bong like my college roommate.

Plus, there are a few things you immediately notice about someone. You can remember it with the acronym GGNEE:

• Gender
• Generation
• Nationality
• Education
• Emotions

Cold reading is a vast topic that cannot be fully covered in this blog post. Instead, do a quick Google search to understand the basics.

To level up your conversational creativity, you need to broaden your associations (ie, Rich Associations) to any topic (or hooks on our clothes hanger) which gives you more potential directions in the conversation.

The following game can help you broaden your associations. It’s a two-player game.

Fourth Strategy: From The Natural by Richard La Ruina

Anytime your conversational partner says something, think about how it might relate to one of these areas:

• Character traits
• Motivations
• Emotions

Keeping with our example, it shows this person is disciplined (ie, character trait), has healthy habits or is motivated for something (ie, motivations), and maybe you could ask if waking up to early makes them feel more in control of their day or how do they feel if they don’t wake up that early (ie, emotions).

Fifth Strategy: Small Talk

One of the bigger tips I’ve received at this point is in the area of “small talk”. I find there are three levels in life for everything. Poor, middle class, rich. Young, adult, old. Ugly, average, attractive. Etc. La Ruina introduced me to the three levels in conversation in terms of linking ideas. Let me explain with an example. Often, I live in Spanish-speaking areas, and people frequently ask where I’m from. If she tells me she’s from Argentina, that is a piece of information I can build a conversation on.

Level 1 – Not referring to it or being negative on the point.

Level 2 – Relate the point to your own experience. What I usually do is say that my Spanish teacher is from Argentina and say a few words with an Argentinian accent.

Level 3 (the gold standard) – Positively connect the link while talking about her. Put yourself in her shoes, in her reality. That’s a soothing accent. I bet it’s a bit difficult for you to transition to the Spanish accent. I heard they call ‘almuerzo’ comida and ‘cuadra’ manzana. OR, a little more risque…Neat, but you don’t look like it. I heard Argentinian girls aren’t so attractive or are really tall/short (if she’s not).

This section is from my book summary of The Natural by Richard La Ruina.

Sixth Strategy: DEEP Questions

When forming questions, like

“How was your weekend?”

Change them by focusing on:

Dreams

Elevated Experiences

Passions

A better question asking the same thing: “What was the highlight of your weekend?” (elevated experiences)

Turn “Hows working for X company?” into “What’s your favorite thing about your job/wokring for X company?” (passions)

Seventh Strategy: How to be Witty

Question.

Comment.

Joke.

These are the three levels of creative conversation. Don’t just ask questions. Make comments, especially when someone makes a comment to you.

The other day, I was running down the street shirtless in sandals. I’m fit, so the neighbor assumed (keyword) I was jogging, but I wasn’t. I had been in the high-noon sun for over an hour, without sunscreen due to a jet ski rental fumble, so I decided to leave my brother and get out of the sun as quickly as possible. “Running in sandals!” The neighbor exclaimed. I had no quip, no comeback, no comment.

I was ruined. Ok. It wasn’t that bad, but those times are great to practice your conversation creativity. “I’m not running, I’m escaping!” Or I could have said: “Barefoot tomorrow!” Comment for comment. Jab or jab.

Here are some strategies to convert a comment into a witty comeback of your own.

Everything has assumptions. The neighbor assumed I was running. When else do people run? In getaways!

Exaggerate: Take the current thing to the next level. From sandals to barefoot.

Opposite: Didn’t even notice!

Funny: Kenyan’s study my techniques!

Add a number: I’m ranked 7th nationally!

And, remember: fewer words win.

Bonus Strategy: Verbal Tennis

Player One offers a word (noun or verb). Player Two responds immediately with a synonym or antonym. Then, player one responds with their own synonym or antonym. You can also use short stories instead of words.

Example: hoard…donate…deny…save…

Another complimentary strategy is to increase your descriptions when possible from one word to rich images (bird…fat black bird balancing awkwardly on the skinny tree branch).

This makes our imagination more creative.

Additionally, going from ordinary associations to rich associations makes our thinking more vivid.

An ordinary association stays with the familiar (cup…saucer, spoon, tea) while a rich association goes beyond the familiar (cup…World Cup, the Holy Grail, the cup from which Socrates drank hemlock).

Again, having ready access to a diverse set of associations is an important aspect of creative thinking.

To increase your associations, you can literally do anything. Read books (either fiction or non-fiction), watch sports or movies, interact and socialize more. Generally, have more experiences.

Summary: Creative Conversation

For an example of creative conversational ability in action, watch the Joe Rogan Experience with Kanye West. Kanye is able to synthesize many ideas, not directly related, but in a coherent flow.

If you are not naturally talkative, you must emulate what makes those folks more talkative. They are more creative when it comes to conversations. They do this via two paths.

First is to be able to draw associations to all the major words or phrases in each sentence. Don’t just listen. Actively listen.

Second, you must increase the richness of those associations which broadens what you can talk about. Try it.

Try this: next time you post to your Instagram account, think an extra five minutes about the hashtags. Try to come up with ten unique hashtags not directly relevant to the photo, but tangentially relevant. I find this activity alone stretches my brain’s creative power.

Post this Instagram photo in the comments below. I want to see it!

Happy conversing.