Chad Littlefield (00:00.129) the videos. Great. I just wanted to, I thought so, but I just wanted to, yeah. Okay. Utkarsh Narang (00:01.484) Yes, yes. Yes, so it's audio and video. Cool. Utkarsh Narang (00:13.142) Our guest today, Forbes, calls him having a global impact. Sorry, whenever I script something, it's so hard to do it, but I'll bring it up from the top. And it's 5.30, so I'm okay doing a retake. Yes, absolutely. Chad Littlefield (00:25.923) Give yourself some grace, it's all good. Utkarsh Narang (00:33.409) When we welcome guests to the podcast, the idea is that I'm going to, as a host, ask questions. But today I have someone who is a global expert on asking questions. And so I'm thinking as I'm preparing for it, what is it that I'm going to ask Chad that will lead to a deep conversation? But my hypothesis is that today we'll speak about questions, we'll speak about listening, and we'll speak about human connection in this somewhat fragmented world. What do you think, Chad? Welcome to the conversation. Chad Littlefield (00:59.939) I love it. It sounds like you're open to having a conversation, what I would say is redesigning the world for contribution, not just consumption. I think questions are one beautiful tool to do that. Utkarsh Narang (01:12.554) I absolutely agree. And sometimes I also wonder that is the world ready for making that shift because we are so consumed by the content that we're consuming. Chad Littlefield (01:23.311) Yeah, our world, our businesses, our software engineers, our minds are all incentivized to consume. We make more money when people stay on platforms longer. By we, mean the companies that are promoting them. We get more dopamine when we endlessly consume. But I think the world is actually, I think most people, like 10 years ago, Utkarsh Narang (01:39.062) Yeah. Direct. Chad Littlefield (01:52.941) or 13 years ago when the iPhone came out. We were just enamored with this amazing piece of technology and no downsides, all upsides. This is awesome. It's the coolest tool. Have you seen this? Have you seen this? There's an app for that. There's an app for that. And now in 2025, I think most people would acknowledge and perhaps have even spoken about this love hate relationship where they say technology and Utkarsh Narang (02:16.75) Mm. Utkarsh Narang (02:20.206) Hmm. Chad Littlefield (02:20.815) I think it, I wonder if it might actually be a love-hate relationship with consumption. And they're realizing what happens is I get this huge dopamine rush, but then I feel totally empty after it. And I think that as human beings, think we're wired to contribute and to create and to connect with each other, not just taking information like a LLM that feed me more data. Utkarsh Narang (02:46.542) Love it. Love it. Yeah. Yeah. Love it. Let's break it down. And it's 5.37 AM as we're recording this, where I am in Melbourne and you're in the EST time zone. So if I fumble listeners, please excuse me because my coffee is not kicked in yet. But the first question that Chad, we kick off the conversation with. Chad Littlefield (02:48.065) and I get smarter or better. It's like I don't actually think it works just quite like that. Chad Littlefield (03:06.959) you Utkarsh Narang (03:10.274) And want to go back and LinkedIn told me this morning that you completed 12 years at V &Me, which is such a phenomenal journey. I'm sure and I'll learn more about that. But if that eight year old little boy, the eight year old Chad, wherever he was growing up, if that Chad were to come and meet you right now, what kind of a conversation do you think will emerge between the two of you? Chad Littlefield (03:31.161) Hmm. Eight year old, not 18. Utkarsh Narang (03:34.454) it. Chad Littlefield (03:43.245) Hmm. It's funny, probably age nine or 10, I saw the movie Patch Adams with Robin Williams and I had my whole life figured out. I was gonna be a doctor. The movie with Robin Williams, he just had this magical way of healing people through connection. But by eight, I hadn't seen that. I was not on what I now call the conveyor belt of certainty. So when I saw that movie, I was like, cool, I'm gonna be a doctor. And so from the time of age nine or 10, I was sure that I was gonna go to pre-med. Later on, I was like, yeah, I'll major in biology. That all, that conveyor belt of certainty ended very abruptly on Monday when I took a chemistry class my first year at university. It's like, this is not going to work out at all. 10 years of med school, this is, nope. And so my eight-year-old self, I think I'd be so curious to ask my eight-year-old self a whole heap of questions because I hadn't even gotten on step one of that machine that just kind of took me down like, okay, here's the path, of course, here's the path. And so at that point, at eight years old, everything was actually possible. I hadn't shut out any option or opportunity. I wasn't a mentor, actually, when I... had a little mental breakdown my first year of college thinking, my goodness, I don't know what I'm gonna do with my life now, and and I think a lot of people who flake out of med school or pre-med have a similar experience. And I think the... Chad Littlefield (05:24.941) The idea here that I think is compelling or worth hanging on to is... Chad Littlefield (05:34.031) In that first year, I had a mentor say, hey, have you looked at the list of majors at the university you're going to? And my answer was no. I was sure about this one, so I chose this one. I signed up for this one. That was it. But I discovered week one of college, there was 167 other majors other than the one that I was in. So meaning 99.5 % of the world. was not a possibility because I was so certain about this one track. so this is a long way of saying this, but my eight-year-old self, everything was possible. And my nine, 10-year-old self, the world started to close in. And I think this is probably happening in my own life right now, and I don't even know. I'm on a path. I feel committed to that path. And so I think one of the things that questions allow us to do is crack ourselves open to what is possible. My co-author. Utkarsh Narang (06:17.015) Yeah. Chad Littlefield (06:29.327) Co-author Will had an initial subtitle for the book that we wrote together, Ask Powerful Questions. His initial subtitle was something like, Revealing the Unknown Mystery All Around Us. I was like, Will, nobody's gonna buy that book. Use that subtitle, this is not good. And I had people vote on it, no one voted for it. But the essence, right, this might not be good marketing language, but the essence is, Questions are like a teleportation device into all these worlds that we don't know, that we're not currently aware of, and all these doorways we don't know that we can walk through. So bam, would my eight year old self handle all of what I just said? Probably not, I have no idea. Having a five year old, my guess is no. We'd probably throw something at me before we were done with this conversation. Utkarsh Narang (07:12.398) Hmm. Utkarsh Narang (07:15.884) Yeah, yeah, yeah. Yeah, I agree with that. I don't think the five year old has the patience or the eight year old, but there's so many nuggets of thoughtfulness and wisdom that I want to kind of go down on. One is just this idea of certainty versus uncertainty, because what you said is that the eight year old, everything was possible for that eight year old. And then when you turn nine, then it was like that single vision. I want to become a doctor and that's what you were looking at. And so that skews your view of the world based on internal spaces. But you spoke a lot about questions. So if you could ask a question to that eight year old self, what would that question be? Chad Littlefield (07:56.823) Hmm. Ooh. Chad Littlefield (08:04.847) One for fun, I would just be curious what's taking up lots of your brain space right now? What matters most to you right now? just as a way of, like I have no idea what mattered to me when I was eight years old. I just don't remember. And so I'd be curious my answer to that, my eight year old answer to that. And then the other question that I'm on about lately, because I think that it helps move people forward. And I think it would connect the two of us quite a lot is what is a crossroads you are at? And what about that is important? That's like an adult question, right? But I'm so curious what eight-year-old self would say to it. What's the crossroads you're at, and what about that is important? Utkarsh Narang (08:47.342) Yeah. Utkarsh Narang (08:52.974) I'm going to taking a pause. At some points in your audio, there's some noise or like static coming in. some cable loose or something that you might want to check before we keep moving forward. Chad Littlefield (09:03.823) It's electric. Interesting. Chad Littlefield (09:09.775) Let me see. If I turn that down, is that okay? I'm wondering, it's not like the volume maxed out though. That's not the sound that you were hearing. It was something electronic. Utkarsh Narang (09:15.702) I can hear you right. Yeah. The level. Utkarsh Narang (09:21.324) I don't think so. Yeah, something electronic. Chad Littlefield (09:26.415) Let's see if I can recreate it. Is this doing it? No, OK. Utkarsh Narang (09:28.984) No, it's no. No. Anyways, maybe we've reduced the volume. Let's let's see how it goes. Chad Littlefield (09:35.535) Let me also move the mic a little bit away from the speakers. don't have my headphones on me today. So let's see if that helps. Cool. Utkarsh Narang (09:40.502) Okay, perfect. Awesome. And I'll pick it up from those are two powerful questions because you're asking what's taking up your brain space right now. And what is that a crossroads? What what crossroads are you at right now, which is important is what you're saying. I love this question, but I'm playing the devil's advocate here. And when you bring up these questions to adults, how have you seen them respond? Because to me, It takes people a while to open up. Once they open up, then they share. But how do you see people, yeah, just react to these questions and you ask them in your day-to-day work now. Chad Littlefield (10:21.433) Let's try it experientially. What is the crossroads you're at and what about that is important? Utkarsh Narang (10:27.854) I knew that in this podcast episode a question is going to come back to me. Utkarsh Narang (10:35.66) I'm thinking about it. Yeah, it's a business shift that I'm going through right now, which is making me feel that there is a crossroads here. And so... That's what's taking up my brain space also right now, because part of me wants to just deep dive into this podcast and make this the biggest podcast in the world, hopefully soon. So it's a business decision that I'm right now thinking about. And as I'm answering your question, Chad, I'm thinking that there's this space of trust here between you and me. And I feel I'm okay taking that leap where there's nothing stopping me from answering this question. And so it makes it easy for me to respond to this question to you. But does that happen naturally with others as well? Chad Littlefield (11:18.884) Mm-hmm. Chad Littlefield (11:25.647) I think the context and the framing certainly matters. If I walked up to somebody at midnight in a dark alleyway in Melbourne and said, what's a crossroads you're at and what about that is important? Yeah, probably not feeling psychologically safe. So from that, if that's one end of the spectrum and the other end is a long established friendship with somebody I really care about and I ask, sure, there's a different level of comfort. But I think, I think Most of the time, what I find is that even in your question right now, there is the perceived, what's happening is the perceived risk of asking a bigger or important question. The perceived risk is really high. well somebody's like, they're gonna be offended by that, they're not gonna respond to that, they're not gonna take well to that. So the perceived risk is very, very high. The actual risk is, is there, it does exist. It's not zero, but it's way, way lower than the perceived risk generally is. And so as a non-answer to your question, I would say see what happens if you ask 10 people that question at 10 different levels of trust. So ask a spouse, your spouse, ask a kid, ask a stranger at a bus stop. and seven more people and then come back to me and see what you find. Having invited people to do similar experiments, and by the way, this is not a life recommend, I'm not recommending that we ask all strangers deep questions, but what the exercise will illustrate, I'll kind of, you know, like a cooking show, they show you how to make the thing and then they take the fully cooked thing out of the other oven, so let me take the fully cooked meal out of the other oven. Having done and invited people into a, dozens of these experiments and challenges in the past. What happens is they come back and they say, wow, this totally did not build a relationship of trust. It didn't land. But it also didn't really matter. The person didn't care. Nothing exploded. My ego is still relatively intact. The consequence of asking a question and having it land is minimal. Chad Littlefield (13:53.219) The benefit, the potential benefit of asking a question rather than being scared and holding it in, the potential benefit, the upside, is far greater than the downside usually. And so my invite is, if you're pondering about a question and it's rooted in your natural curiosity and you have the other's best interest in mind, so there's a couple check boxes there. So if you're naturally curious, if you have the other person's best interest in mind, take the risk and ask the question. Now, If you're trying to manipulate somebody or get information from them or use somebody, maybe don't ask the question. But if intentions are aligned, you're naturally curious about it. I also think that one of the most disarming things, I'll give you two ways to disarm just about anybody with any question you ask. So let's just take like a. Utkarsh Narang (14:31.022) Hmm. Chad Littlefield (14:49.199) pretty hardcore question, like what's your greatest struggle right now? Not a question I would ask a stranger on a bus usually, right? But if I had to, the way I would do it would be to get really clear about my intention. Why would I be asking the stranger on this bus this question? And how can I frame that intention in a way that actually benefits them or that they care about? So how might the intent, how might my intent for asking that person a question? So. This is a tricky one, right? Because again, not a life recommendation. But if I had to do this, I'd walk onto the bus and I'd say, hey, I know this is a little bit odd because we just sat down on a bus together. But I'm just finding myself pretty fed up with how disconnected we are as a culture. And so I'm wondering if I could ask you kind of a big question, when the chances that it might start an interesting conversation between us. And I would wait for their consent. So I share my intent. and I seek their consent. If they say no to that, conversation over. I respect their no, because as Peter Block, kind of teachers and mentors would say, you can't say no, then your yes doesn't mean anything. So that's the first one. The second one, if I'm in a group setting and I want to break people out in a work context and answer the question, what is the crossroads you're at and what about that is important? break out into groups of three, have that conversation. If I want to do that, I'm going to remind people that I happen to have chosen the question, but you have 100 % choice and autonomy in how you answer that question. And so you could say, ooh, I'm at a crossroads of I woke up at 5.30 as a very kind gesture to Chad to accommodate his Eastern time schedule so that he could have dinner with his family. Chad Littlefield (16:46.841) but I'm at a crossroads right now where maybe I don't do podcasts before coffee because they might be more fun after coffee. Perhaps, right? This could be an answer or response, but you could also say, gosh, I'm at a crossroads either. I'm going to make this podcast the biggest in the world or I'm going to shut it down. And it's like, whoa, these are two. I'm not suggesting you're even thinking about that, but these are two very different levels of response, but the same question. And it's very disarming to remind people of just how much autonomy they have. in the types of answers they give to any question. What's your greatest struggle right now? Sitting down on a bus next to a guy asking me, what's your greatest struggle right now? Utkarsh Narang (17:26.456) Love it. I love both these things because the way they create safety immediately because you're telling the other person that A, you can answer it the way you want to and then you're taking that consent and that makes it makes it makes them feel that it's not just you forcing this question down their throat but you're politely when they say no you're okay walking away as well. Yeah. So when did that eight year old start to shift these gears because these are some big ideas. The curiosity I'm seeing was there, then Patch Adams happened. What happened next? What happened next in Chad's journey? When did questions start to arrive? Chad Littlefield (18:08.494) What happened next going back to the eight year olds or oh gosh. So okay, this will be interesting for us to discuss but also interesting for anybody listening. had a retreat one time and the facilitator said something that I'll never forget which is if you can share a story from a time when you were age 10 or younger. Utkarsh Narang (18:11.244) Yes, to the 8 year old. Chad Littlefield (18:34.835) where you were doing something that kind of represented the ethos of what you do now, it is like an automatic way to build an immense relationship of trust with someone because it just skips right past people's prefrontal cortex where they're like doubting or reasoning or like what's this person's angle or they're skeptical. And they're just like, if you were that as a kid and now you're doing this now, this is what you were put on the planet to do. And people love seeing apple trees selling apples. so for me, Before I ever watched Patch Adams, my mother likes to say she graduated in the top five of her class at Ohio State, a big university in the US. And she likes to she graduated in the top five because there was only five students in her class. She studied medical illustration. So a doctor in a teaching hospital would say, hey, I need an image of this stage of the surgery from this angle of these muscles especially. And they would use that image. And she would draw it by hand, create this image. So when my siblings and I played doctor, I have two younger siblings, when my siblings and I played doctor growing up, my mom would paint these elaborate wounds on our arms. So we'd have like, you know, my brother would have this like totally wide open cut. He's probably bleeding out. He needs serious medical attention. And when I was played doctor, I would feel, I would not run up and say, oh my goodness, I wouldn't focus on the clinical side. I'd make sure he was comfortable. I'd move his head back on the pillow. I'd ask if he wanted some pudding. It was all care. It was all focused on the human part and none of the clinical part. And it just turns out that when I saw the movie Patch Adams, he didn't heal people through scalpels and medications. He healed people through connection. He had this profound ability to reach a terminally ill patient. by empathizing with them in a way that no other really smart doctor or clinician could. And so for me, going back to that journey, I think that even my eight-year-old self had a little bit of wisdom, or the apples that I selling is, hey, we're wired for connection. I didn't know that the iPhone was gonna be invented when I was eight years old, but I see this world now that is quite heavily incentivized and designed for consumption. Chad Littlefield (20:56.397) And I'm very excited to continually work to redesign it for contribution and connection. And it will take my whole life and then some probably. Utkarsh Narang (21:07.982) Such powerful reflection and I'm going to kind of pause on this because and as you're sharing this, I'm thinking for myself and I'm assuming our listeners are also that whatever you're focused on or pursuing when you're a little kid between that less than 10 years and if you're continuing to do that same work or in the similar vein when you're in your 30s or 40s, then that just builds trust. That just builds credibility that that's something that you're put on this planet to. to achieve, you put me in a reflective state. So I don't have an answer to that and I'm going to kind of go back and reflect. But then what you shared next is also amazing that as a little kid, you were all focused on this human side of things and this deep connection. And yes, it can take a lifetime and more, but how do you feel about pursuing this mission? When Chad wakes up on a Monday morning, what is Chad's mindset? Chad Littlefield (22:08.079) Yesterday? We'll take Monday as yesterday. Utkarsh Narang (22:11.448) Uh-huh. Chad Littlefield (22:14.445) Well, to humanize it, ebbs and flows. Sometimes I'm incredibly distracted, not productive. I wind up down some consumption wormhole, learning about some random thing that I probably had no need to know or understand. But thanks to some algorithm serving me up, something on a platter, I let myself be taken. So there's sometimes where it's probably that. And then I think there are other times where when I come back to building a business of great depth rather than just something to maximize profit and afford a lifestyle that I want. When I think about building a business of great depth, I come back to, for me, a central guidepost or mission. I believe that I partly exist on the planet to gently eradicate small talk and create conversations that matter. And so when I think about that, Okay, so today I was arranging and organizing some of the schedule and some speakers for this Connectors Summit that I host every December. So big gathering of some of the smartest and best folks that are leading groups. So whether that's as an independent trainer or facilitator or as an internal facilitator of any kind. And. Super cool gathering and I know that the time I put in now to designing that and choosing the questions in the flow and how things are arranged will create thousands and thousands of conversations that otherwise wouldn't happen. And so for me it's like coming back to and running through the filter of like is what I am about to do going to make a difference? Is it gonna make something happen that wasn't gonna happen anyway? That was my late co-founder's definition of, Lehman's definition of leadership. Making something happen that wasn't gonna happen anyway. Yeah, so that said, I've also, I'll offer one other, just answer like. Chad Littlefield (24:16.089) There's a guy named Brandon Stanton who created a movement called the Humans of New York. So he walks around New York City, takes pictures of people, and then posts that you look familiar with it. Utkarsh Narang (24:25.942) Love is work, love is work. Chad Littlefield (24:27.795) So Brandon Stanton, I saw Brandon Stanton speak 10 years ago. And he said something I'll never forget. said, when a wave comes, go deep. And so there are times where I'm just so on fire, excited to share, record YouTube video, just like really impassioned. And then there are times where I'm learning now that like every exhale, like every inhale, there are times where I need to exhale and actually disappear a little bit. And without some level of solitude, there is no greater or spiritual depth that enters my work, and it starts to become shallow and maybe overly practical or tips or tools, tactics kind of based. And it's like, no, if I want something to be deep, wise, and intriguing, right? taking that space and learning to take that space. And so I'm actually on a cadence right now of really trying to work a whole heap less than I typically have. I don't know if that answered your question, but I said words. Utkarsh Narang (25:35.094) It does. It does. And I love Brandon's work. A few years ago, I was so mesmerized with what he was doing. And just with the idea of being curious and asking questions, I started walking the streets of New Delhi and asking people, what makes you happy or what is happiness to you? And as I'm reflecting on our conversation, there were moments when people were not interested in answering that question. And I respected that and moved on. And I took pictures of that as well. So all of that is somewhere on social media, I know where in the black ether, in the black hole. But I love his work and I love how he's able to, and I've also seen it when he's asking a question, he would sit down with someone say who's homeless because he wants to be at the same level with the other person. He wants to create that safety where the other person wants to answer that question. And such beautiful things come out. So this idea that when a wave comes, go deep is powerful, but some way. When you were sharing this, what was coming to my mind is that you've helped connect and spoken to audiences from 100 to maybe 30,000. When you still go on stage, do you also have a sense of doubt, the imposter things, things that it seems that only mere mortals have? Do you have those as well? And how do challenge them? Chad Littlefield (26:59.149) It's not going to sound like I'm answering your question, but I am. When people get nervous or doubts are starting to show up, my guess would be, and when that happened often for me, my guess would be that they were quite focused on themselves. And so Will used to say, if you're nervous and you don't want to be nervous, just switch your nervous into service. Will was very lyrical in his speaking. And so it's like, this is part of the business that I created is called literally We and Me. And so now I know, I have enough reps in that I know if I am freaking out about something, I'm too focused on what I'm gonna do or say, and I'm not nearly focused enough on the audience, what they need, and maybe more importantly, I've become clear. in the past years that like I use a very, I have a very particular method of designing any gathering, whether it's for 6,000 people or 60. And I call it the contribution method. And it's a very like particular way that I design any gathering. And it's very heavily focuses on what work I'm gonna ask the audience to do and not what I'm gonna say and do. So in fact, I don't really script out much of what I'm gonna say and do anymore. But I do script out what I'm going to ask the audience to say and do. I don't script out what they're going to say, but I script out how I'm going to ask them. So in other words, I script out, know that at this point, I'm going to ask people to break out into groups of three, and I'm going to ask this very specific question. And then when they come back, I'm going to ask them what struck them from those conversations. And I'm going to listen to what they had to say. And then whatever I say is just going to be in response as a dialogue back to what they've said to me. I don't need to script. I don't need to pre-plan what I'm gonna say. How would I do that? Because I don't know what they're gonna say. And so this is also, like for an organizer, this is interesting. Because otherwise, you know, I've had clients in the past, not so much anymore, but I've had clients in the past say, you know, would you send us your PowerPoint deck? Or would you send us your slides? Or would you send us your script even for the keynote? I'm like, no, no, no, no. You do not want a script for the keynote. If I send you a script for the keynote, Chad Littlefield (29:25.015) It'll be the worst keynote you've ever seen. People will fall asleep and you'll look bad. Rather, what I'm gonna do is bring a beautifully facilitated unscripted experience and the whole group is gonna be awake because they're not gonna know what's gonna happen next. But as soon as they see that I'm on a script, that's it. They're done. They're tuning out because I'm competing now in the land of consumption rather than competing in the land of contribution. Utkarsh Narang (29:54.658) Love it. It answers my question 100%. But here's a thought and as a facilitator when I walk into rooms and so there's maybe a different way to look at this, but I love your views on it because what I have sensed is I love the idea that you don't have to be focused on yourself and it is about the other person. So loved how when you're nervous, tend to service. Love what Will shares with us. But then the other idea that I play with is that all I can do in the room is to be my best self. where whether listening is important, helping the other person feel heard is important, whether opening the room, cracking the room open where the question is important. So then I sense that it's important for me to show up as my best self. How does that play with what you're saying? Like, where do you see it overlying with each other or disagreeing with each other? Chad Littlefield (30:49.913) That's an interesting intersection. I would invite the experiment of what if you just flipped totally on its head and you went in the room and said, instead of, want to be the best version of myself for this group. It's a very on the surface is a very service oriented perspective. I wonder if it would be even more of service to the group. If you went in with the mindset, how can I be most irrelevant to this group? How can I be not the feature story of this group? How can I create such an amazing experience where they don't want to leave their small groups and their conversation and they say, I don't want this to end, not because you're entertaining, not because you're really wise or insightful, but because you've created such a good experience that they are participating in, not consuming. And so in other words, Now that said, for sure, I go in and bring my best version of myself, but it's applied toward becoming irrelevant. It's not applied toward looking like my best self or appearing. So in fact, if you actually watch me facilitate, there are times where it's like messy and they're like, not, I don't have this like perfect script polished down. And I'm kind of like, Ooh, I wasn't gonna do this, but actually we're going to switch up and do that. Utkarsh Narang (31:54.414) Hmm. Chad Littlefield (32:16.291) because I'm not working on looking the best, I'm working on creating the best experience for them. And sometimes that means we were gonna do this, but now I think it's a bad idea based on all the data that I have, and so I'm switching. Just everything I said before, erase it. We're doing this now. And we're going in a different direction. Utkarsh Narang (32:29.282) Yeah. Yeah. Yeah, yeah. Love it. I think it makes complete sense. And I think I'm going to push it one level deeper for all of us. And I'd love your views. I think it's also about how, and I'm going to speak about me, how I am as a human being, because the values that I work with are one of the values is love. And so I want to be of value to the room without being the highlight of the room, if that's the right word. And what I'm thinking is that Like there's this phrase and maybe I would have learned it from you somewhere in some of the YouTube videos. But it's all about the collective intelligence, right? Because I cannot solve the world's problems and I cannot solve a room's problems or a group's problems or whatever challenge they're coming into the room with. They have to do that and I can only create the conditions where they get to that outcome. And so the way I am as a human being is what will enter the room. And if I'm okay being irrelevant, I will be okay creating that space for the room. Does that make sense? Chad Littlefield (33:36.367) hundred percent and nothing to contribute further than beautiful your poet my friend Utkarsh Narang (33:44.582) just learning from the best who's sitting right across me. What makes a question powerful? Are there like criteria to that or is every question powerful? Because I hate questions like Chad, how are you? And then I'm waiting for you to end because then I want to tell you something about my life that's fun or how's the weather today? I hate these questions, but we end up asking these questions in the rooms because yeah. So what makes a question powerful? Chad Littlefield (33:46.948) Hahaha! Chad Littlefield (33:53.077) Hmm beautiful question. Yeah, no Chad Littlefield (34:13.465) So let's do this. Let's try to make the question, how are you, or how's the weather powerful. So for me, the reason that we named the book Ask Powerful Questions and not Ask Great Questions or Smart Questions or Wise Questions or anything else, Powerful Questions, is that questions actually give people power they previously didn't have or weren't wielding. Maybe they had it. But what it does is as soon as I ask somebody or a group a question, I now give the power to them to add something and contribute to the conversation or the room. When I am not asking a question to them, I am assuming the power and taking on the power and the focus and et cetera. And so for me, if I'm to ask the question, how are you, and have it be a powerful question, I'm gonna actually care, I'm gonna choose to care ahead of time what that person has to say in response to that question. So let's just do the typical response. So if I pass you on the street or pass you in the hallway and your colleague and it's just a quick little hallway meeting and I said, how are you? You would say. Utkarsh Narang (35:29.88) Good. It's very busy, Chad. Yeah, that's it. Chad Littlefield (35:30.873) Good. Good. It's very busy. Yep. Like quick response, because it's almost more of a greeting than it is a real conversation starter. Now, if I wanted to make it powerful, I would probably tap into the magic of a second question, because I asked you because I cared about it. And so you'd say, I'm good. It's really busy. And I'd say, what's good and what's busy about it? Utkarsh Narang (35:53.71) Hmm. Chad Littlefield (35:54.873) So a mentor, Eric Tyler, who wrote a book called The Best Advice So Far, was famous for practicing this. I met him when I was a teenager. He was kind mentor when I was a teenager. And so every time he asked us how we were, we'd say, Good. Some version of that. And he would always say, isn't it funny we're talking about notifications and consumption and my computer's going ding, ding, ding, ding, ding. Let me shut this off. Chad Littlefield (36:29.763) So he would say, how are you? We would say, fine or good. And he would always say, what's good about it? What's fine about it? And it taught me, in retrospect, I look back, that was the first time I learned the lesson of the magic of a second question. In general, though, I would say what makes a question powerful is, does it put somebody in the position of their own expertise to speak some of their truth? And if it does, that is quite powerful because it, or I should say, it gives them quite a lot of power. It gives them the power to make themselves seen and heard rather than it being my responsibility to see and hear them. It gives them the power to offer up what part of themselves do they want to be seen and heard for, right? It also gives people the power to omit. So if you ask me a question and I'm not ready to share what my greatest struggle is right now, I can say, woo, come back to me on that one. I need a minute to think. And that being an acceptable response. Utkarsh Narang (37:38.062) Yeah. Yeah. How do you train people to do To do this? Because you've spoken about a very... It's almost like an easy fix that you ask and tap into the magic of the second question. And one could possibly use it with partners and relationships at work, with peers, wherever. I can see the application of questions everywhere in the world. But how do you train someone? Because the brain is again wired to just have these... transactional conversations rather than going deep. Chad Littlefield (38:13.487) So even that question, how do we train somebody or how do we teach someone implies the metaphor that you must, like you train a muscle. If you want a muscle to get bigger, if you want your quadriceps to get bigger, you do squats. If you want your bicep to get bigger, you do curls. And I don't actually, that metaphor doesn't apply for questions. For me, it's much more like a light switch. You either. You can just make a choice right now to be naturally genuinely curious about something. So the example would be if I hang up, if I held up a blank sheet of paper and I said, would crush Chad. Your job is to ask as many questions as possible rooted in your natural curiosity about this piece of paper. Go. Right. What makes the color white? I'm going to be asking, where was it created? Utkarsh Narang (39:03.02) What makes this color white? Utkarsh Narang (39:10.092) What is the shape? Chad Littlefield (39:11.683) I wonder what will end up on it. Utkarsh Narang (39:14.018) What company created it? Chad Littlefield (39:15.897) Who will use it? So we can go back and forth on this for a half hour, actually. That's a blank sheet of paper. But if I pair up with somebody and they have 40 years of un-Googleable experience, I'm sure, I'm positive that I could ask them more questions than I could ask a piece of paper. Utkarsh Narang (39:19.052) Yes. Love it. Love it. Yes. Utkarsh Narang (39:38.126) I'm getting goosebumps. I'm getting goosebumps as this is... And I always thought that there's something wrong with my brain because I thought that things can be light bulb shifts. You can just learn a skill and just run with it. You don't want, you don't need anyone's permission. You don't need, you don't need to really nuance this technique. It's asking questions. Chad Littlefield (39:38.253) Yeah. Chad Littlefield (40:02.477) You do not have to train your car to drive, you just turn it on. This is it. Yeah. Yeah, it's also, I think there's something powerful about it of it reframes training as actually experimentation. now, great, in the first 10 minutes of a six hour training, I taught you the thing. Now let's just go do it. Here's the idea. You got it. All you have to do is choose to turn it on. So we're here. We might as well make use of our time now that the learning is all done. Utkarsh Narang (40:09.55) This is it. Utkarsh Narang (40:29.496) Yeah. Chad Littlefield (40:38.157) We might as well make use of our time. Let's just go try it. So what I'll do with a group is typically a science experiment and what happens when we ask questions that we typically don't. And I'll give everybody a card with a question on it and invite them to pair up with somebody they haven't met yet, ask the question on that card, listen to the response, and at the end of that, swap cards and pair up with somebody new. And I say this is not a life recommendation. Don't go out and do this in the wild. We're just doing a science experiment. What happens when you ask questions you typically don't? And then afterward, I say, what struck you? What did you notice about that experience? And you know what people say? Every single time after doing this exercise with well over 100,000 people, every single time they say things like, wow, I was struck how quickly that conversation became a connection. I was struck by how easily I opened up. I was actually surprised by what I said. I didn't know that I was going to offer that to somebody today. All these things really strike and surprise people. And none of the things that come out are, It's almost all surprise and delight. Utkarsh Narang (41:40.012) Yeah. Yeah, and it tells us right that the human being is craving connection. I think the conditions to have that connection are not being created too often. And so it's ultimately our responsibility as individuals, not as a facilitator, not as only Chad, not as any XYZ. It is everyone's responsibility to do that for their self, their own selves. Chad Littlefield (42:05.71) So can I offer just another light bulb switch? So here's the training. For me, the reason I named the Connector Summit the Connector Summit is because I thought to myself after reading James Clear's book, Atomic Habits, and this idea that if you want to run a marathon, don't go looking for a marathon training plan and get yourself on a, just put your running shoes by your bed so that when you wake up in the morning, you step on them and say, right, it's time to go on a run. Utkarsh Narang (42:05.848) Seems like such a simple- Yes, please. Chad Littlefield (42:33.807) That's it. So it's the idea of atomic, tiny, tiny little acts or habits. And one of the things he talks about in the book, a core idea that I think is overlooked in atomic habits, is identity first, identity shift first, and behavior change second. So don't even try to change your behavior. Just right now, identify as a runner. Say the sentence, I am a runner. And so now your choices that follow are, well, what would a runner do? So when I read this, I used to be a swimmer. And then that identity fell out of my brain. And then after reading this book, I said, oh, I am a swimmer. What does a swimmer do? He figures out what pool he can get to, where he can go, and he makes it happen. And so the same idea for the connector, like we need these conditions to happen, we need more connection, blah, blah, blah, blah. The simplest shift that anybody listening could make right now, if you choose to, you can choose not to. So you're right now, I'm bringing you to a crossroads. You can either leave this podcast and say, I am a connector, or I am not, in which case, not malevolently, but in which case I would offer that you will, in some way, shape, form, contribute to further isolating the planet. And so, and it sounds a little harsh, but if you choose to identify as a connector, the next time you see two of your siblings fighting with each other, or you witness, or you're in an argument with somebody at work, if you bring back this identity and say, I am a connector, what would a connector do in this moment? He would figure out, they would figure out some way to turn this conflict or turn this moment into a connection rather than a point of separation. Utkarsh Narang (44:19.118) I it. I it. I hope folks are listening and making notes of these things. I was yesterday working out of a cafe and I was seeing a dad scroll through Instagram for about 27 minutes while his younger children were just sitting around there scampering through the area. And I was thinking to myself that this 27 minutes of consumption is leading to minus 27 of connection that you can have with your children. And what a disservice to not the child. Like I feel like I have two boys who are now 14 and 11 Chad. I feel it's not a disservice to the children, but it's disservice to you as a parent that you are not getting the opportunity to connect with the child. Chad Littlefield (45:02.383) Hmm. Utkarsh Narang (45:03.906) Such a light bulb moment, I love this. Chad Littlefield (45:05.879) And here's the lie, because I've also been that dad. So take all of what we said and then realize, I've been the dad who's like snuck away for a bit because my patience is low and I disappeared into another room and I just zoned out for 10 minutes while I put all the pressure on my wife to deal with whatever chaos was happening downstairs. So I've been that person. the reason, if I'm to take a hard look at myself, I think the reason that I am that person or I've taken that time for consumption is that I have fallen into the lie that I will be feeling better, more refreshed, more patient, etc. If I just zone out and consume for a bit and kind of just disappear or escape. my lived experience is that I usually come back less patient, more frustrated, and more exhausted. Not useful to fatherhood or, yeah, or, you my own health in any sense of the word. Utkarsh Narang (46:05.016) Yeah. I don't want this hour to end. know. I take a peek at the clock as well. What was it working with Will? Because I wasn't able to find anything on that. So what was it like working with Will and how did the two of you bring this to the world together? Chad Littlefield (46:10.498) Yeah. Chad Littlefield (46:19.961) Yeah. Chad Littlefield (46:25.039) So he, I met him, the way that I actually met him is I was a student at university and he was teaching this dialogue facilitation training course. And the first time that I met him, I didn't know anything about Will, I walked in just day one of the course. Thankfully I didn't go to med school, so I wound up in psychology and dialogue facilitation classes. he moved all the desks to the back of the room and he arranged the chairs in a circle. Utkarsh Narang (46:46.638) I'm glad. Chad Littlefield (46:53.065) And when it was time to start class, he dimmed the lights and he sat down in the circle. He didn't say a word. And he just made uncomfortably long eye contact with every single one of the 20 or so students in the class. And when he was done making eye contact with each of them one by one, he said, are you ready? Are you ready for your life to change? Because if you are not, and he got up and he opened the door and he said, because if you are not, there's the door, you will not enjoy this class. If you are not ready for your life to change. So that's like the first meeting. So you're asking me questions like, well, you know, can you ask somebody serious questions on your phone? And I think if you have the conviction that this Is the question meant for this person? And I'm asking it with conviction and intent for the purposes of, and benefit of the other. think you can ask some very intense questions upon first meeting someone. so what was it like working with them like that for 10 years? So he was, he was the kind of, we had this interesting Venn diagram relationship where, we had this. Utkarsh Narang (48:00.206) Standing in two eyes. Chad Littlefield (48:08.815) core overlap in our values, beliefs. And then this like very different set where, you know, give me a group of 5,000 people for an hour. Will wanted five executives in a room for five days and he would expect all of them to cry and two of them to quit. And that was a good retreat. And it was a good retreat for everybody. It was like those two executives actually needed to quit and they were gonna, they were gonna push, the can down the road for another three years, but he just accelerated these conversations that mattered. cut to the heart of what mattered and kind of made stuff happen that definitely wasn't gonna happen anyway in a very good way. yeah, I learned heaps from him. And I guess the way I'll wrap up this bit, because I could talk forever about Will, but where he's in my mind lately is he used to say that efficiency is the enemy of connection. And I've had some awareness in the past year. that I've gotten very efficient at my jobs. As the newsletter list has grown, as the YouTube channel has grown, there's a lot. Like could spend all day just efficiently responding to emails coming in. But efficiency, if efficiency is the enemy of connection, it's caused me enough pause to slow down to figure out, I'm not gonna keep going down the road of becoming more efficient, because at some point that will break. Right now I could respond to all emails in a day, but next year probably not. And that's if I just dedicated eight hours of the day to doing, and so for me, Chad Littlefield (49:52.609) slowing down, rewinding. And Will was always, I was the accelerator and he was the brake. And when he died, I was like, shoot, like a car without a brake is kind of dangerous. But luckily I had just driven in my first Tesla and I realized, actually electric cars regeneratively brake. So that's my new metaphor is I'm an accelerator with a regenerative brake, but I have to choose to take my foot off the gas. And so I'm trying to do that more intentionally. So I take a good chunk of summers off with family, or as much time as possible. I still love my work and dip into it. But I'm not working 40 hour a week kind of situation. Yeah. Utkarsh Narang (50:36.77) the accelerator and the brake. And then somewhere, I think while you were sharing this, said, where is Will right now in my mind? Something like that. Such a powerful question to ask. Such a powerful question to ask. And I think, yeah, this just come naturally to you. To anyone who's still with us at about 50 minutes, if you can take one light bulb out of this is to just go and ask questions. Ask questions to your spouse, to your peers, to your manager, to whoever you can. Chad Littlefield (50:46.617) Yeah. Utkarsh Narang (51:06.69) And I think there's, can think about that and you can challenge me on this, Like I said, Will, sorry about that. I'm right now thinking about him more as you were sharing. We can feel that questions help the other person open up and build this connection. But I think the questions do serve us as well because as I'm asking you these questions or anyone else on the podcast, Chad Littlefield (51:14.863) I'm honored. Utkarsh Narang (51:35.714) They're serving you and me. What do feel about that? Chad Littlefield (51:39.375) this is, so I've had a really big aha lately. So the first time I heard the phrase connection before content was from Peter Block. And in the last several weeks, I've been attending some sessions with him. And he's been making the point that actually connection before content, it's not just about connection before content. Connection is the content. It is the power. What if he's saying, what if we retired the idea of leaders and instead started hiring connectors? whose job was to bring people together to connect over the problems and challenges they want to solve. And the problems and challenges, what if we just saw them as challenges, the reason challenges and problems exist, are just an excuse for people to get together and connect. What I don't mean is you're just like chatting about stuff and not solving the problems. I mean, you're actually coming together to solve the problems, but you're doing it from a collaborative, connective mind space. So what I have to say about that is absolutely. I think connection is the point. And in fact, the things that you said were probably in this podcast or any other conversation are just as, if not more insightful to you than they were to the other person. And I used to think, I'll split people out into breakouts, and they'll get three new perspectives, and they'll all come back smarter. And now what I realize is I could send people into a room with three cardboard cutouts. As long as the person is speaking their truth, that is where the change in the learning is happening because I actually believe, and a bunch of research would point toward, we have the ability to quite literally talk our way into tomorrow, that our conversations do serve as an edit button for what happens next, and there's something very, very compelling to me about that. Utkarsh Narang (53:31.128) Love it, love it. The final question that I have for you and then we'll come to a close. If we go into the future a few decades and you reach your 80 year old self, eight zero. If that 80 year old self were to come to you right now, what is one piece of, let me reframe the question. I typically ask what is one piece of advice that he would have for you, but I'm gonna ask today in the presence of questions, what is one question that he'll come to you with Chad, the 80 year old self? Chad Littlefield (54:10.689) he would ask me a question and then offer advice right after. And here's how it would go. Chad Littlefield (54:23.809) What currently is the list of things that are categorized as noise in your life, not signal? And would you please go eliminate all of those? And that's exactly how you would say it. Utkarsh Narang (54:44.654) I don't know why you said this, but this is the third time this week that I've had a conversation about the signal and noise ratio. And so I think that tells me something that I have to reflect on this, but I love this question and love the 80 year old Chad's advice. For all those who are listening, I hope you found this of value. And if you can do one thing, then that'll give a little bit of joy to Chad and to myself and to Will is to go and ask questions. Start asking questions and they'll become powerful. Chad Littlefield (54:51.567) Mmm. Chad Littlefield (55:14.445) rooted in your natural curiosity, asterisk. Beautiful. Utkarsh Narang (55:17.312) Love it. Love it. If you listen to this on a podcast platform, share it with others, leave a comment. If you're on YouTube, you have to appease the algorithm gods. So subscribe to the channel, like, comment, do whatever you have to do, but go and ask questions. Thank you, Chad, for this one hour that we had. Loved every bit of it. And yeah, maybe someday there'll be an interview. Absolutely. Chad Littlefield (55:35.801) Can I just offer something? So this call to actions, like, subscribe, algorithm gods. I want to just like double down on this because if you've made it to this point in the podcast, you've dedicated an hour of your life, which means that at some point you were like, wow, I'm in. Like, I'm fully, I'm locked into this, which means that probably you're going to get, if you subscribe or like, or jump into this, you will probably. Find yourself in another conversation that is just as valuable, meaningful, and transformative for you. And so actually do yourself a favor and go and do that. Because I think sometimes we say like, subscribe, et cetera, but we don't extend our intention as to why and what it might benefit another. So there you go. Double down. Utkarsh Narang (56:18.478) Thank you. Perfect double click. Thank you for that. Till we meet again, maybe sometime in a personal, in person, in a physical room and looking forward to many such interactions. Thank you for your time today. Chad Littlefield (56:30.959) would be a treat. Cheers.