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 it was a big deal when I talked. My family would jokingly make a big deal of it due to its rarity. 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. Of course, his show was interview style, but he still seemed to make it conversational by making relevant comments and asking unique questions. There was always a question to be asked.

Being an introvert is boring. So began my lifelong and never-ending quest to be an extrovert. I’ve had to develop strategies for talking.

This blog will discuss these strategies.

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.


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.


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.

Second Strategy: Cold Reading

People love being told about themselves. It’s partly why psychic’s 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 due to brushing with their left hand.
  • They’re a morning person due to rising at 6am.
  • They value health due to drinking water first thing in the morning instead of hitting a bong or smoking a cigarette.

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 too vast a topic to be 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.

Third 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.

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