I went from being a bad conversationalist to a good one after learning about conversational signposts.

Before defining the concept that led me to having more engaging and diverse social interactions, I’d like to first showcase an awkward chat I had recently.

[The topic of music came up]

Her: “Do you play any instruments?”
Me: “Yeah, I’ve been playing piano for 20 years.”
Her: “Hmm, cool.”

[Awkward silence]

Me: “So, uhh, do you play any instruments? Or are there any instruments you wish you could play?”
Her: “Nah, not really.”

[Awkward silence]

It’s possible she wasn’t interested in talking to me. But it’s also possible that she didn’t know how to advance the conversation. She could have been aided by using…

 

Conversational Signposts: distinct bits of information that, when followed, lead to divergent paths in a conversation

 

From the statement “I’ve been playing piano for 20 years,” I can extract out two unique components:

  1. playing piano, and
  2. for 20 years

These are conversational signposts that represent different directions she could have taken our chat.


Her general interest in music could’ve helped guide her to choose which signpost to follow. And if a particular branch of conversation fizzled out, she could’ve always circled back to previous signposts mentioned in the conversation:
 


Putting my awkward conversation about instruments aside, I want to contrast it with a…

A successful example.

While talking to somebody else last week, we seamlessly followed each other’s conversational signposts (which are highlighted in bold).

Me: “Did you get up to anything Friday night?”

Him: “Yeah, I went line dancing at a place called Stony’s.”

Me: [I don’t care about dancing so I opted for a joke.] “Oh cool, does that place double as a weed bar?”

Him: “Huh?”

Me: “Cuz, you know, Stony’s.”

Him: [Groaning]

Me: [Jokingly] “I’ll see myself out” [and fake walked away]. “No, but seriously, is the reason you’re into line dancing because you enjoy the hypnotic effect of dancing in unison? If so, you might be interested in joining a cult—have you ever experimented with that?”

Him: “I think a lot of people experiment in their 20s. Some of the cults I’ve tried were too intense. I remember this one time, I was drinking the blood of a virgin my cult had just sacrificed, and I thought, ‘You know, I think flag football is more my thing.’”

We took turns following the conversational signposts that piqued our interest the most. This leads to the last aspect of the concept which is that they help to…

Direct the flow of conversation.

Last year, I went dragon boating in Arizona and spoke with a beautiful woman for two hours who worked as a consultant for McKinsey.[1] While she never asked me any personal questions all night, it didn’t matter. I still had a great time because I was in full control of our chat. By recognizing the conversational signposts, I got to ask the follow-up questions I was most curious about. (I ended up learning her entire life story—it was a fascinating tale of raw ambition and business networking that left her struggling to connect with people on a personal level).

Like with any new skill, trying something for the first time can be stiff and unnatural. But the longer I practiced noticing and following conversational signposts, the more enjoyable conversing with a variety of people became.

  1. ^

    By now, perhaps you’re recognizing the different conversational signposts in this sentence. The ones I came up with are:
    What is Dragon boating? Beautiful woman—I take it you’re single? What were you doing in Arizona?

New Comment
1 comment, sorted by Click to highlight new comments since:

Conversational signposts are just one technique to improve social interactions. For more advanced techniques, I would recommend checking out: