3 Ways to Rescue a Conversation That’s Going Nowhere

Don’t ask, ‘So, how’s work?’

HHave you ever been in a conversation with someone who’s just… bad at having a conversation? You try to keep things going by asking them question after question, but you eventually get tired of doing all the work. So you put on your best fake smile, give some excuse about having just received an urgent text, and flee.

For much of my life, I was that conversationally challenged person. Going to parties, networking events, and business gatherings terrified me. I’d survive the introductions, and then crumble under the weight of basic questions like: “What do you do for a living?”

Finally, one day, a mentor of mine noticed my struggle. When he asked what was going on, I explained that I was shy and didn’t like talking about myself. He told me that he was the same way. I didn’t believe him at first — I mean, nobody could guide a conversation like this guy. He made everyone he talked to feel energized and heard. What was his secret?

He taught me his tricks for rescuing a stalled conversation, and even turning it into a great one. To do so, you don’t need to be charismatic or funny or outgoing — in fact, you don’t need to say much at all. You simply need to listen and ask the right questions. Here’s how.

Keep your questions open-ended

Nothing will kill a conversation like a blanket inquiry, a question that lacks focus and elicits no useful information: How’s it going? How’s work these days? What’s new?

Questions like these put pressure on the other person to think of something interesting to say and offer them no starting point. That’s why you’ll usually get lazy, one-word answers like “fine,” “okay,” or “not much.”

To keep conversations going, use open-ended questions that encourage detailed answers. For instance, instead of asking “How was your lunch meeting?” try, “What happened at your lunch meeting?” You’ll gather enough details to build momentum and keep the conversation going.

Add constraints

The reason the person you’re talking to might get stuck on a question like “What’s new?” is because you’re giving their mind free rein. You need to help them narrow their focus. If you say, Tell me something that happened to you today,” the breadth of possibility makes it difficult to settle on a single event. But if you revised the statement to, “Tell me something unusual that happened to you on your date,” you force the other person to narrow their thinking into a limited space.

This may sound restrictive, but it does your conversation partner a favor. You’re no longer saying, “Go out and find a four-leaf clover,” but rather “Pick a nice flower from the backyard garden.”

Try reversals

Picture a game of Ping-Pong. One player smashes the ball while the other player does just enough to block it and extend the rally. Reversals are similar: They keep the conversation moving by gently bouncing back answers so your counterpart can take the big swings. It gives them a feeling of control, which makes them more comfortable and more likely to open up to you.

The most common reversals include:

  • How so?
  • Really? Tell me more.
  • How did that make you feel?
  • Then what?
  • Why is that?
  • And?
  • What else?
  • Can you elaborate?
  • And that means?
  • Can you share more details?
  • Go on.
  • Because?

Just know that by themselves, reversals can seem a bit harsh, like you’re holding an interrogation, so you might want to use buffering phrases to soften the impact. When paired with the reversals above, they might sound like this:

  • How so? I didn’t see that coming.
  • Really? Tell me more… if you’re comfortable.
  • Curious, how did that make you feel?
  • That’s interesting, and then what?
  • Why is that? If you don’t mind me asking.
  • And? Don’t stop now. I need to hear the rest.
  • That makes sense. What else?
  • Not sure I understand. Can you elaborate?
  • I see. And that means?
  • Intriguing. Can you share more details? If you’re cool with that.
  • Go on — I’m so interested in this.
  • And that’s because? If you don’t mind sharing why.

More natural, right?

For the conversationally challenged, these tools will help you converse with ease. Instead of searching for the nearest exit, you and the person you’re talking to will only wish there was more time.

Experimenter in life, productivity, and creativity. Work in Forge | Elemental | Business Insider | GMP | Contact: barry@barry-davret dot com.

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