How do you keep a conversation going with a stranger. In this video, I’m actually…  This is… Doesn’t really count as a stranger so we’re going to set Mr. Buster down and I’m actually going to… Stephen doesn’t know this yet. But Steven, my film master, I’m going to ask him a question and we’re going to live demonstrate how to keep a conversation going with a stranger. I’m Chad Littlefield, co-author of Ask Powerful Questions Create Conversations  

Blog Note: The following is an adapted and edited transcript of one of our daily YouTube tutorials. We know sometimes it is easier to scroll through written content which is why we are publishing here. Because of that, there may be typos or phrases that seem out of context. You’ll definitely be able to get the main idea. To get the full context, visit our YouTube channel hereAnd if you want to watch the video on this topic specifically, you can scroll down to the bottom of this post to access it as well. 

That Matter. And in this video, I hope to show you how to do just that. Let’s get into it.

For this video, I’m going to ask Steven a question and we’re going to have a little mini conversation. And you’re a part of this conversation. You’re kind of the observer  in this. And I’m going to show you one of the techniques that we talk about. One of my actually  my favorite techniques that we talk about in the book. Let me pull up my We! Connect Cards  and ask Steven. Steven, what has been one of your favorite moments in life. -Wow, one of my favorite  moments in life was I actually snuck into Disney World because I was on a band trip and I forgot my  pass and I just snuck in behind somebody in like one of those turnstiles. -Whoa,  what’s one of your favorite memories about the person you were with when you did that?  -My favorite moment about the person I was with there was that they they were kind of  in on it with me. And I was able to sort of just you know, get really small and like go right behind them and we kind of shared that you know heist moment that makes sense. -Cool.  


Listen to what Steven just shared. From that little response, what did we learn about steven?  Now, you couldn’t see him. I was seeing his face glowing as he’s remembering sneaking behind the lines in Disney. But we learned that Steven’s been to Disney. We learned that he was with somebody when he went to Disney. Based on the face as he was answering that, we learned that, I think, he likes bending the rules a little bit perhaps, right? And we can keep going. The further that  we go answering the question what did we learn about Steven based on that response. Or for you, what did you learn about whoever you’re talking to. That’s probably the more relevant conversation to be having here. If you’re trying to unpack how to keep a conversation going with a stranger in your own context, one of the best ways is to ask what did you learn about that person from what  they said? Even if they spoke for 5 seconds or 5 minutes, what did you learn about that person? Because every item that I learned about Steven, I could turn into another question and it would spin off into another tree of conversation. I learned that he went to Disney. I could ask “Steven, when did you go to Disney world?” -This was on a 11th grade band trip. That would have been 2011. -So, now he’s just feeding me information, right? Now, he’s in  band. Right? And we didn’t stage this. But you can see how quickly that conversation actually becomes exponential. When you think about how to keep a conversation going with a stranger, when you ask how are you or where are you from or what do you do, you get really stock responses.  

Even with though those stock responses, you learn things about who they are as a person. And when you turn each of those items into a question, it leaves you with genuinely unlimited possibilities or directions on where you could potentially take that conversation. Disclaimer: As I’m sitting here recording a video about how to keep a conversation going with a stranger, sometimes the best way to keep a conversation going with a stranger is to not. To just not keep the conversation going,  right? I don’t know why you landed on this video exactly. I don’t know what it is that drew  you to want to unpack how to keep a conversation with going with a stranger. I’m assuming  that it’s because maybe you start a conversation and it ends with like [Crickets] [Whistle]

” Right? And that whatever that awkward thing is you want to avoid that.  Now, sometimes you bump into a conversation, you have a quick conversation like you don’t need to  continue every conversation and turn it into this big deep dive into the life of that person. And  it’s just important to know that so that we don’t trap people in conversations that they don’t want  to be in. Because conversations are not just for you. You do learn lots of really cool stuff  through them but they’re not just for you. And if you treat them like that, that’s super selfish and it’s treating the other person as an object and I disapprove. Cool. If you like that, I got a really cool deck of cards. It’ll keep you uh talking with strangers for years and years and years on end. Also wrote a book about how to make  conversations that matter. You can check out the links in the description.

 Have an awesome day.



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