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How to Become a Better Conversationalist: The Tiniest Choicest Game

We all acknowledge the importance of being better listeners, but how exactly do we achieve that? You can’t listen harder, you have to change what you are listening for.

I conduct Legacy Interviews with individuals and couples that want to record their life stories so that future generations can know their family history.  Often, these interviews are arranged by the guest’s adult child, which can sometimes leave the guest feeling uncertain about sharing their stories.

As the conversation guide, my role is to find a way to quickly put people at ease so that they will be willing to open up and share their most important stories. One of the most valuable things I can do is demonstrate that I am a good listener.. This article aims to highlight how you can become a better listener and, in turn, create more engaging conversations.

How to Become a Better Listener so that People Want to Talk with You

A great listener isn’t just passively sitting nodding their head and saying uh-hm. A great listener finds a way to participate without accidentally making the conversation about themselves.

Two major pitfalls of poor listening are “fast matching” and getting lost in one’s thoughts.

Consider the following example:

“I was in a rush last week when I was dropping my parents off at the train station so that they could go on their cruise to the Bahamas.”

Fast matching: We are taught from an early age that if you can relate with someone by having common interests, that they will like you more.  Unfortunately, thinking that you need to relate to others as fast as possible often causes us to listen to what they are saying and relate to it, but that almost always happens on a surface level.

The person that makes the “fast match” mistake will listen to that statement and say, “oh I went to the Bahamas last year, where did they go?” Or they might inquire, “what cruise line did your parents take?”

What the fast match misses, is that by asking these questions you are no longer talking about the person who is telling you the story, you are focused on their parents or about yourself because now you are talking about your trip.

Lost in our own thoughts: Some people are trying so hard to listen, that they instead get lost in their own mind, “what was his name?” “What should I ask him?” Or “I wonder if he knows I’ve never been on a trip like that?”

You may get so caught up in trying to think about the next question that you aren’t listening at all to the person telling the story.

Choices We Make When Telling Stories: What Details to Leave In and What to Take Out

In order to become a better listener, you should understand how people tell stories, particularly if it is a story they’ve not told before. When you begin the story, you have to place your minds eye in your first-person perspective, you have to imagine you are experiencing it all again.

This is why people fill their stories with tiny choices they made about details to include in their story. The details likely add nothing at all to what you need to know about the story but the person telling the story didn’t choose to prune those details because they are re-living it.

The Trick That Keeps You Present in a Conversation: The Tiniest Choices Game

It is critical to keep yourself present in the conversation and not turn the conversation to be about you. The trick that I use is to try and observe those tiny choices they made about the details in their stories.  By asking about those details you will uncover rich and important information that the storyteller didn’t even realize they were signaling to you.

In our earlier example, the tiniest choice I would use would be, “Why were you dropping your parents at the TRAIN station when they were going on a cruise?”

By asking this question, I show that I am clearly listening. The person telling the story will likely expand and say, “oh my parents never fly anymore because of XYZ” or, “oh because we had a bunch of people at our house and I couldn’t take the time to get them to the airport…”

Suddenly more of the conversation is opened up for you to ask more questions and probe deeply.

When to Use This Tiniest Choices Game

You have to use this game in moderation, asking people about too many of their tiny details will annoy them, making them feel like you are badgering them and make it uncomfortable to keep the conversation going.

A good example of when to use this technique:

I was once talking to a woman that told me she had been in a torrid love affair with an artist for four years.

She said, “I loved him so much that I would go to the studio at his house and watch him paint. He would get sick of me, so he would send me and his dog out to the couch to watch movies while he worked. After several years, I realized it wasn’t working and we broke up.”

I could have asked about the breakup, or talked about a similar heartbreaking situation I was in. But because I was playing the tiniest choice game, I asked, “tell me more about the dog, did you get along?”

The woman lit up like a firework, “I LOVED that dog, Wainright! How did you know to ask? You know, we cuddled, I got him new food, we went for walks, I spent more time with him than my boyfriend. In fact, the dog is how I realized that he didn’t really love me.

I once asked what would he do if the dog ran off, he just shrugged and said, ‘probably just get another dog.’

When I heard that I knew the only reason I was around was because I hadn’t run off, so, with his permission I took Wainright and moved on down the road, and never spoke to him again.”

Why Does the Tiniest Choices Game Help You to Become a Great Conversationalist? 

By asking about the dog, I demonstrated my attentive listening. It was clear that this particular detail was very impactful to her, but she needed the context to explain the rest of her story. This connection seemed to resonate with her, leading her to share additional details that lent depth and impact to her story.


There is no such thing as “listening harder”. If you want to be a better conversationalist, you have to get better at listening by focusing your attention on the details the storyteller gives you.

Avoid fast matching, which makes the story about you or about details that don’t matter, and get out of your head by having something to focus on in what the other person is saying.

The journey to becoming a skilled conversationalist starts with a shift in perspective, a commitment to understanding, and a genuine interest in the stories others have to share.

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