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 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.’”

By recognizing and following each other's conversational signposts, we had a great time exploring the topics that piqued our interest the most.

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.

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

Could you summarize a few? :)

Sure! Here are two of my favorites.

(1) From Leil Lowndes' book:

Don't ask what they do. In the US in my experience, the most common question upon meeting someone is "what do you do?" But the problem with this is that while 65% of Americans are satisfied with their jobs, only 20% of Americans are passionate about their work. From Lowndes:

If you instead ask, "How do you enjoy spending most of your time?" It allows people to mention their job or their hobbies. And homemakers are no longer embarrassed to say, "I'm just a mom" to the question of "what do you do?" 

(2) From Dale Carnegie's book:

Never disagree and say "you're wrong". I am a naturally disagreeable person. Learning about this technique hasn't made me more agreeable, I just express my disagreement differently now. From Carnegie:

Never announce, "I am going to prove so-and-so to you." That's bad. That's tantamount to saying: "I am smarter than you are and am going to make you change your mind."

"We sometimes find ourselves changing our minds without any resistance; but if we are told we are wrong, we resent the imputation and harden our hearts. We are heedless in the formation of our beliefs, but find ourselves filled with a passion for them when anyone proposes to rob us of their companionship. It is obviously not the ideas themselves that are dear to us, but our self-esteem which is threatened."—James Harvey Robinson

I've adopted a more indirect way of challenging people's beliefs. Rather than stating my disagreement, I tend to ask questions (à la the Socratic Method) to get to the root of somebody's belief. Sometimes they'll notice contradictions in their own arguments without me having to point them out.

How can you avoid that a conversation degrades into an interview? Where you are the person asking questions and the other is just answering and isn't asking anything back. (This can sometimes work, as you note in your McKinsey example, but is mostly awkward.)

I think "notice signposts" is just one of many unknown tips for good conversations, and perhaps not the most important one. Of course, people with healthy amounts of social intelligence won't need those tips anyway.

To avoid the interview-style conversation, I don't have to wait for someone to ask me a question. I can just open up and share relatable things (via conversational signposts) about my life. And if they're not biting, like at all, it's possible we may not have much in common. At that point, it's okay to make a polite excuse to exit the conversation.

The other consideration is that some people feel awkward asking personal questions. To those more introverted people, I praise any questions they ask me. Here's an example:

Them: "How's work going?"
Me: "Thanks for asking! It's going well, though, I'm a bit frustrated at the moment with my boss."
Them: "Frustrated in what way?"
Me: "Hmm, good question...[thinking] I guess it's because he doesn't listen to my input."

^I'm demonstrating that I value their input and encouraging them to ask more questions. (See: Don't Shoot the Dog).

 

(Also, I removed the McKinsey example. I don't think it was adding much to the concept of conversational signposts).

Ah. So I guess you should neither ask just questions, nor just always talk about yourself, but rather balance both.

Praising questions is an interesting tip to ease-in more introverted people. This reminds me of another strategy a sociable colleague of mine used on shy people: He made playful jokes about his conversation partner ("teasing"), encouraging them to be bold and "hit back" with something, and then laugh about their joke. Which instantly empowered them. This probably works best when both are men. Making self-deprecating jokes is a safer option, though not as effective.