Below is a transcript of a dialogue that Will and I had with 800 leaders at Conscious Capitalism in Dallas earlier this year. From the very stage pictured above. We are sharing the transcript as well as the full video below in hopes that it gives you access to an awesome icebreaker that goes way, way beyond small talk or surface level conversation. If you have any questions about how to pull this off at your own meetings, events, or retreats, just get in touch with us. We’d be happy to share tips and ideas for you to amplify connection, belonging, and trust.


Chad: Hey stranger, what’s your name?

Will: Will. What’s yours?

Chad: I’m Chad.

Will: Hi, Chad.

Chad: Freeze this moment. So when you go to connect with another human being for the very first time, what questions do we typically ask? What do you do? How are you? Where are you from? Is it your first time here?

[Pause]

Chad: And in a room of 800 really brilliant people we start to slow down after about four questions. Like, what do you do? Where are you from? Whoa. I was recently in Connecticut speaking to a group of 400 people in the same company and I asked them two questions that I want ask you right now. And the first was: knowing that that’s our norm and that’s our comfort zone, how many of you, just show of hands, loves small talk however you identify that? Show of hands. So there’s like two people raising their hands right now, so you all connect. Second question, how many of you, in the last forty-eight hours, have been in at least three conversations that you would identify as small talk? Hands up. Look around real quick. This is the moment. When I saw that gap for the first time, this is the moment that made me almost swear on stage. Nearly all of your hands our in the air right now.

Chad: The conversations that we have don’t always match the conversations that we want to have. So this guy [point to Will Wise] happened to write a book about asking powerful questions and creating conversations that matter, so I’d love for Will to frame up the experience that we’re about to do.

Will: Our intent, thinking about what just Sean Achor was talking about is how can we bring that joy in the room right now and get us all connected and have a conversation that matters? Chad has created a deck of cards that most of you are now touching: We! Connect Cards. It’s there somewhere. And we’re gonna walk you through a process on how to engage in that. Now some of you are going, what did I do with that card? It was here when I showed up.

Chad: The second intention in what we’re about to do is for you, from this point forward, my invitation is that you ruthlessly misinterpret everything I say and do and apply it to your own context. I’m gonna frame up how this is gonna work, so you’re gonna grab your card and in a moment, and so if you’re still looking for your card, it looks like this, probably a little bit smaller [shows giant We! Connect Card]. So you’re gonna grab your card. There’s a question on one side and an action on the other. We’re gonna leave the kinesthetics for another day and stick with the curiosity. And in a moment what I’m gonna invite you to do is pair up with somebody who you feel like you know least in this room and you’re gonna ask them the question on your card. For example, Will, “what is life teaching you right now?”

Will: If you need to think about it, be okay with that. Just sink into it and listen to the question and hopefully they’ll listen when you start sharing. “What is the most beautiful sound in the world, Chad?”

Chad: So then when I answer and tell him right now it’s this weird yawn that my puppy does, Will’s hopefully gonna listen to that answer and then after we have that conversation, you’re going to swap cards and just signaling that you’re looking for somebody new to connect with, toss your hand in the air and go find them. Now I’m gonna predict that one of two things just happened for you. Some of you were like, ooh questions and new people I haven’t met. And some of you were like, oh, new questions and people I haven’t met. That’s me. And so I wanna infuse choice into the types of conversations that you have. So two primary ways we have choice. So the cards you have are color-coded. So green cards tend to have questions that are fun and light. Purple cards tend to have questions that encourage some level of self reflection.

Chad: Those are the types of cards, types of questions, that when asked, we often need a moment to think about our response. And then blue questions tend to be a little bit deeper. So green light, purple encourage some level of self reflection, blue a little bit deeper. The first way of choice is as you’re pairing up with somebody, if you’re not in a blue card kind of mood, you can just duck and cover. All right, so that’s choice number one. Choice number two is a little bit more deeper. A little bit more deeper. A little bit more “deeperest.” And that is questions are a beautiful key that allows us to unlock this lifetime of un-Google-able experience that all of us carry around in here and in here everywhere we go. And when somebody tosses that question or uses that key, you get to choose what door opens up. And so if somebody asks me, what is life teaching me right now? I can answer that life is teaching me that it’s a little bit warm up here with the lights and I should’ve worn a heavier jacket.

Chad: And that would be true for me. And I could also answer that life is teaching me how to take really deliberate intention with each moment that I have because I recently had a death in my family, came really close, and so I’m really paying attention to life right now, and that would also be true. And so part of our job and our invitation up here is to assume the social risk for you. To share what is real for you at a level of depth that might stretch where you’re at right now.

Will: We love experiences, we want you to create this experience. And pretty soon they’ll be four hundred conversations going on here. So what we would like to do, in a moment we’ll say go and you guys will get up out of your seats, start walking around, find somebody you know least and start engaging. And after a few minutes, we’ll pause you by saying, are you present? And your job is to say, yes I’m present. So let’s practice. Are you present?

Audience Member: Yes, I’m present.

Will: And once we do that, we’ll give you another tool to help you go a little bit deeper if you like and then we’ll go into the cards some more. So you’ll get to finish those conversations. And then we’ll rap up. Are we ready?

Chad: That’s it. Pair up with somebody you know least in the room. Once you have that conversation, swap cards and find a new person.

Conference Icebreaker Video

[5-10 minutes of group conversation goes by.]

Will: Are you present? Are you present?

Chad: Are you sure you’re present? All right, if you can hear my voice, go ahead and look this way.

Our Default Way of Listening and a Better Option

Will: One of the greatest joys I have in this job is that once all these conversations start, people just get into it. It’s lovely. So what did you notice about your own listening? Just think about that for a moment. What did you notice about your own listening? I have a default way of listening that shows up for me.

Chad: That is, when I ask somebody a question, it’s a very easy way to go, but Conscious Capitalism didn’t say, hey Chad and Will, can you come and lead a session on subconscious connections? And yet, one of the ways that I go to listen when I ask somebody, when I fall into that default of where are you from and they answer Boston, I say, oh, I had a second cousin that drove through Boston once. And in that moment, who are we talking about? Me. We may be doing this with the most positive intentions possible, but what we say is oh, I got all this un-Google-able experience.Let me bring it out and share it with you in hopes that I can say, hey look, we’re the same. Can I belong with you? And this is the question that we’re asking, and yet often the focus is on this person. So what is the opposite of listening? Waiting for your chance to talk. So that would fall under this category of, okay you’re saying something, you’re saying something. What am I gonna say? What’s your question? And you’re in that moment. So much more conscious and perhaps more difficult way to listen.

Will: Which takes me a little bit of effort is listening to understand. It’s a conscious choice. It’s truly a gift. When we listen from this place of understanding, our job is to get the other person. How is it that they see the world and experience the world? I wanna share a quick story with you. I was working with a company in which the CEO was having problems with one particular woman. And after we did this experience, we had a followup conversation two weeks later. And he said, I have to tell you that I hated that woman. Every problem that was showing up was revolving around her and I was looking for a way to eliminate her from the company. But last time she got eliminated from a company, she sued the company and we couldn’t afford to do that. But then you had us do this we connect thing and you had me really pay attention to listening. You had us do this other exercise, and what happened in that process is I randomly got picked with her multiple times.

Will: And my listening to win showed up so strong, and I began to listen to understand. And what I realized is I love this woman. She was an asset to the company, and as I listened to understand and expanded my listening I realized that she is a gift for the company. And all of the problems were because of the systems that I put into place. Two weeks after that conversation he flies to London, removes those barriers, and that part of the organization, for the first time in a long time, had two quarters in which they were the best quarters ever. So my invite for you here is to really listen to get. What is that person who you’re talking with? You’ll notice that something will change in the room as we do this. Just pay attention to that. Pay attention to the person you’re talking to. You also might notice that you’re natural curiosity shows up. Ask one followup question if you wish and then continue swapping and we’ll get your intention in a few more minutes. Go.

Will: Are you present?

Chad: Are you really present? All right, if you can hear my voice, peel yourself out of that conversation.

Will: The place that Chad and I stand is a place where access to listening to conversations and powerful questions matter.

Chad: So the way we wanna end is with a question. So I’m gonna ask this one question to all of you and I wanna take ten solid seconds of silence for you to think about, what is your answer to this question? What is your answer to this question? And then quickly I’m gonna popcorn a couple out fast. So thinking about the experience you just had, conversations you just had in that round, one, and then with that lens of listening to understand, what struck you about the last ten minutes. What struck you about the last ten minutes?

Audience Member: I have no idea what the people I talked to do for a living.

Chad: I have no idea what the people I talked to do for a living. Yes. What else?

Audience Member: How much easier it is to talk to people.

Chad: How much easier it is to talk to people.

Audience Member: Sincerity.

Chad: Sincerity. That sounds like authenticity. Welcome to conscious capitalism.

Audience Member: There’s more commonness among us.

Chad: Ah, there’s more commonness among us than we might assume.

Audience Member: How quickly you can achieve depth.

Chad: How quickly you can achieve depth.

Audience Member: Other, not self.

Chad: Other, not self. Felt this balance shift.

Will: So you feel it, right? The power of questions to unlock conversations. What we would like you to do is to continue doing that for the next forty-seven hours that you’re together. And if, at any moment that you’re having difficulty, you can pull out your question and ask, “__________.”

Chad: Most of you walked by this really brightly colored wall labeled “Art of Connection” and so if you enjoyed what happened in here and want it to bleed out into the space, if we choose to trust what Sean Achor just said, that the largest predictor of happiness is social connection. And you want that to bleed out into this space, into your practicums, into the rest of these forty-seven hours, this big Art of Connection wall has a bunch of cards and actions that invite us into more conscious connections and we’d invite you to participate in that collaborative mural that will help us also visualize the levels of connection and belonging and trust that we’re creating in this space. Which is part of the most beautiful things about showing up and being with a group of people like this for this time.

Will: And if at any moment, this is your gift to keep. So at any moment you wanna say where are you from? You can pull out your card and say, what is something you know really well? And see what happens. Have a seat.

Chad: Thank you.


If you have any questions about how to pull this powerful “icebreaker” off at your own meetings, events, or retreats, just get in touch with us. We’d be happy to share tips and ideas for you to amplify connection, belonging, and trust.

We-connect-card-question

10+ FREE Icebreaker Activities

Use this “Getting Started" Kit.

You’ll get a downloadable PDF that has:

  12 engaging questions that build trust

  12 creative uses for the questions

  A link to video tutorials for group activities

  ✓ Excerpt from our #1 Amazon BestsellerAsk Powerful Questions by Will Wise

You have successfully joined the movement of people around the globe filling their communities and organizations with conversations that matter! After you confirm your subscription, you'll receive a PDF with 12 powerful questions and some ideas on how to use them. #askpowerfully