A way to carry on a conversation is to skip over the expected response. Instead of: Ron: "How was your flight?" Carlos: "My flight was good." Carlos could be bold and say, "I'd be more intrigued by an airline where your ticket price was based on your IQ."

Leapfrog over the expected response

Ask open-ended questions that invite people to tell stories, rather than one-word answers.
Instead of "How was your day?" try, "What did you do today?" Other open-ended questions to try:
<ul>
<li>"What's your story?"</li>
<li>"What's the strangest thing about where you grew up?"</li>
<li>"What's the most interesting thing that happened at work today?"</li>
<li>"How'd you end up in your line of work?"</li>
<li>"What was the best part of your weekend?"</li>
<li>"What are you looking forward to this week?"</li>
<li>"Who do you think is the luckiest person in this room?"</li>
</ul>

How to get beyond small talk

When small talk dries up, it's often due to "mirroring." In our efforts to be polite, we answer questions directly, repeat their observations, or just agree with whatever they say.
For example, one person would say, "It's a beautiful day," and we might answer, "Yes, it's a beautiful day." Instead, we could practice the art of disruption. To move the dialogue forward, we could reply: "They say that the weather was just like this when ... happened (insert a historical or personal moment)"

Practice the art of disruption

In a situation where people are gathered together, it always involves people trying to talk to each other. In these moments, we often fall short and can't think of anything to say, or worse; we fumble through with the aim of not crashing.
However, we can soar in conversations and learn to turn small talk into big ideas.

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