143. How Leaders Increase Trust and Connection with Chad Littlefield

Transcript – Episode 143: How Leaders Increase Trust and Connection with Chad Littlefield

Joe: In my opinion, really phenomenal bosses and really phenomenal leaders are masters of designing the room for contribution, not consumption.

Joe: Welcome back, friends, to the show that is food for the boss’s soul. Here on Boss Better Now, we talk with leaders, experts, and change makers about their experiences in the workplace — all in the name of helping you understand how to create the conditions at work for people to thrive. It brings me great joy to introduce my guest this week, Chad Littlefield, co-founder of We and Me. Forbes calls Chad a global expert on asking questions that build trust and connection. He is a TEDx speaker, a best-selling author, and the creator of the We Connect Cards, a tool that is now being used in over 80 countries to create conversations that matter. Chad has brought his workshops, ideas, and interactive keynotes on trust and connection to companies like Crayola, JetBlue Airways, Johnson and Johnson, Starbucks, and even the CIA. If you want to learn more, if you want to get better at fostering connection, then you need to find him on YouTube, where he has amassed millions of views across his impressive array of helpful and interesting videos. Friends, I cannot adequately summarize all the insight and wisdom that Chad shared in this interview. I’m going to invite you to listen for his advice on how you can nurture real connection on teams in ways that don’t actually take much time. And please listen for the incredible strategies he shares to engineer your meetings for contribution over consumption and then benefit from all the ways that can increase the buy-in that people bring to their work. And now, our conversation.

Joe: Chad, I’m going to confess to you, my friend, that when it occurred to me that I was interviewing an expert in asking thoughtful, intentional questions, it makes you pay even more attention to asking thoughtful, intentional questions. So I am not going to start our conversation today with “How are you?” I’m going to start with: Where are you? I want you to tell us about where you’re broadcasting from today and how you ended up there.

Chad: Coming to you live from the booming metropolis of Erie, Pennsylvania. I somewhat funny enough wound up here because of a series of questions, actually. Our finance guy asked me, “What if you were in the last six years of your life — what would you regret not doing?” And I thought about it for a while and I said I would really, really regret not having lived right by the water. My wife’s parents grew up in Erie. I had hesitated to move there because the airport was small, it was a smaller town, blah blah blah. But this guy’s question made it clear to me that yeah, this is actually the move for us.

Joe: And you are known in so many corners of the world as kind of the “questions guy,” right? And that’s such a falsely reductive way to describe what you do. We’re going to get into some of that. But as you know, here on our show we talk a little bit about our past work experiences and we use them to shine a light on what works and what doesn’t in the workplace and around leadership. So I want to start with your origin story. What was your first real job? And what do you remember most vividly about it? When the movie of that job plays in your mind, what do you see?

Chad: The first real job was probably working for the Commonwealth of Massachusetts as a prestigious lifeguard. [Laughter] I worked at a beach lifeguarding in summers of high school and the first summer of college. And my most vivid memory — which I think will maybe be a familiar experience to anybody who’s had a real job — was when the bosses, the big bosses who weren’t lifeguards, they were like the head of the park, administrators, when we heard their truck rolling up and we were in the guard place, we would immediately grab a broom and pretend to be sweeping. Pretend to be busy. Which is just — this happens at work. Maybe a lot of people, especially in big companies, could probably do their jobs fully in like 20 hours a week. But if the boss comes around, you’re so busy, you’re strapped, you can’t possibly take on another project.

Joe: Did you ever save anybody? Did you ever have to run into the water?

Chad: I did. Yeah. [Laughter] Pretending to sweep was my biggest memory, but we also did actually have to run in the water and save a few lives. The first time I ever had to run in and save someone, they were legitimately drowning — ocean beach, high surf — and they were really far away. So I was running like 250 yards and right as I was entering the water, I tripped over the very first wave in three inches of water and went flat on my face. I did end up getting to them. It was fine. Pulled them in. All is well. But that was like — that should have been the opening sequence to Baywatch. Not perfect supermodel people running in slow motion. It’s tripping and falling and scrambling to do the rescue. The next one, I was running full throttle in and I stepped really badly on a shell and came out with a massive laceration on my foot that took me out of lifeguarding for six weeks.

Joe: So it wasn’t the part of rescuing people that you needed the most practice around. It was running into the water, it sounds like.

Chad: Yeah. Once I’m in the water, fine. Everything went fine after that.

Joe: Well, I noticed some things about some of the other stops that you’ve made in your career. I know that early on you worked in a group home with teenagers with psychiatric disabilities. I know that after that you were counseling juvenile inmates in solitary confinement in an adult prison. And then I know that years later you were leading conversations about race and conflict between military cadets and civilians in places like Pakistan, Iran, and Gaza. The pattern I notice is that you just seem to chase easy work, low-stakes, not at all uncomfortable. [Laughter] These are all intense settings with people or situations that a lot of people would not choose to step into. What draws you to this kind of work?

Chad: First of all, can I just compliment your curiosity? That question is beautiful. What drew me to those settings? There’s something that underneath all of the skills, the teachable things, whatever you majored or studied — underneath that is who you are being. And even the most logical, rational-minded people experience this every day. You’ve ordered a coffee and the barista doesn’t have to say any words and you can feel whether they’re having a spectacular day or a horrible one. There’s a lot that’s transferred without words.

Chad: At some part of my being, I’m drawn to see connection happen where it feels most impossible. When I was half the height I am now and a third of the age, I saw the movie Patch Adams with Robin Williams. In that movie, Robin Williams goes to become a doctor to promote the quality of life over quantity. I think I was most struck by the way that he was able to heal people through human connection. He wasn’t the smartest clinician, he wasn’t the top of his class technically, but he got the terminally ill patient to eat that nobody else could get to eat, because he walked into that room with such deep empathy. So I think whether it was the group home or the prison — and by the way, in hindsight, part of it was probably that I was studying psychology and the easiest job to get when you hadn’t graduated was at a group home — there was that Patch Adams element of: if connection can happen here, it can happen anywhere. And if connection can actually create some level of healing here, it can happen anywhere else.

Chad: I remember my senior year of college I was invited to give a TEDx talk. I was on this cold bus in Boston going to the airport — a particularly unfriendly, notoriously unfriendly city, no one talking to each other, everybody totally isolated. And the thought popped in my brain: if I could start a conversation here that felt comfortable and natural and not cringy and not forced, then you could definitely start one at work. I looked down, the guy next to me was wearing a hat that said The Jason Project. I was like, “Hey, man, this is kind of odd, but I’m curious — what’s the Jason Project all about?” And it was like I flipped a light switch on in his brain. He turned on, looked up at me — he worked with Robert Ballard, the guy who discovered the Titanic. And for me, that’s when I realized: you can transform how someone is in a moment by really taking 10 seconds to see them.

Joe: Was there a moment when you realized this is what you wanted to do with the rest of your life — this idea of helping others make connections, nurture trust, and access each other’s humanity?

Chad: The time I first thought “Oh, maybe there’s something here” — I was in between summers in grad school, leading adventure trips for teenagers. Weeklong trips, taking them mountain biking, caving, rock climbing. And the first half-day of that week was quote “team building.” I could not tolerate watching two teenagers try to connect with each other. It was so awkward. I just thought: I’m in grad school — what could I just stick in between those people to help that go better? And that was what I created: the first prototype of the We Connect Cards, which have now gone off and are being used in 80 countries by hundreds of thousands of leaders all over. What nudged me into “oh, this could be a thing” was: somebody saw them and said, “These are really cool. Can I have a deck?” And I thought — maybe a lot more people have this same problem that I was solving for myself. Maybe I should buy a pallet of these and see if more people want them. And so on and so forth.

Joe: For folks who are listening — I have been in a room and watched Chad lead an experience where you create instant connection and substantial dialogue between people who have known each other for years. It is really something to see. Chad, if people want more information about the We Connect Cards, where can they go to find them?

Chad: You could Google that exact phrase, or Google “Chad Littlefield” and it will find you whatever your platform of choice. Or Claude it, or Perplexity it — I don’t know what we’re searching on now. [Laughter] My website is weand.me — the company’s name is We and Me and all the stuff is there. I’ve also got a YouTube channel with 600 videos teaching people how to design rooms.

Chad: What you experienced and described — in my language, my behind-the-scenes language — really phenomenal bosses and really phenomenal leaders are masters of designing the room for contribution, not consumption. We’re not doing report-outs. You’re not coming in and blabbing for 30 minutes about this quarter’s strategy or what needs to get done this week. You’re walking into the room and saying: “Hey everybody, this quarter’s strategy is sitting on your desk. Everybody take five minutes to read it, circle the things you actually like, underline the ones you have questions about, and we’re going to spend the rest of this meeting discussing your circles and your underlines.” That meeting is totally different from a boss trying to convince someone that this is what we need to prioritize and care about. The psychological shift is literally just designing a room for contribution, not consumption.

Joe: I look at a lot of things through the lens of some of the innate personality differences that show themselves in the workplace. For example, I’m your textbook introvert. I like to take in information and then retreat into my mental cave and sort through what’s in it. So many meetings and leadership experiences are designed for people who process externally. I’ve coached introverts over the years to sometimes stop and say, “Do you want an answer right now, or do you want one I can support?” What you just described is such a perfect way of reaching everyone’s depth and expertise in the room by designing for the time and space they need to process as well as contribute.

Chad: The silent five to ten minutes of reading whatever content you’re about to work through — that example wasn’t by accident. Let’s say you have a hundred words of dense scientific content on a PowerPoint slide. You can talk it out to people, say all the words that are already on the slides. Or you can assume that people have a job in part because they can read and say: “You have 30 seconds — read the slide and tell me the most boring thing on it and the most useful thing to your specific job. Then I’m going to have you split off with a partner and exchange both of those.” It’s like the energy in a meeting is completely different.

Chad: People complain that their people aren’t engaged. My question back is: in what ways and when have you invited them to engage? Because if I look at the agenda of all your meetings and highlight all the places where you’re going to actually ask people to meaningfully contribute — not a “Hey everybody, what ideas do you have?” which is not a good way to invite contribution — if there are no highlights, I can tell you your team will be disengaged. If the invitation isn’t there, there’s nothing to accept.

Joe: We gain interest and credibility by the quality of the questions that we ask. There is such a difference between “What are your thoughts?” and “What’s the most relevant information on the page for you right now?” Just the language and phrasing around that invites people to participate in such a different way. Why do we forget about that? Why do so many get this wrong?

Chad: Emotions, in part. Amy Edmondson, who kind of popularized the phrase “psychological safety” and did the work with Harvard and Google to show that the number one characteristic of high-performing teams is the degree of psychological safety — one of the examples she gave was in a hospital setting. If an error happened, let’s say a patient actually died, and the hospital administrator walked in onto the med-surg floor and said, “Who screwed up?” — you don’t want to share. If you screwed up, you’re totally scared. If somebody else screwed up, you don’t want to rat them out because you have to work with those people. Amy Edmondson’s example was: instead, build into the regular ritual or cadence of a med-surg floor asking the question, as people check out at the end of a shift: “Was this week as safe as you would like it to be?” Those are two totally different worlds getting at the same problem. One is likely to magnify the number of errors because people will not share. The other makes it totally normal and psychologically safe to on a regular basis surface the things that might be undermining the quality of care.

Joe: It’s such a showcase for the difference between winging it and designing it — just taking that little bit of time to be thoughtful and intentional about what is the very specific language I’m going to use. How do I honor the time and effort people put into getting into the room and the depth of expertise they bring? I like to de-effort that — to make it really not daunting. What’s your take on that?

Chad: Questions are one of the cheapest — because they’re free — and most transformational tools that take less than three seconds to prepare. In the time it takes you to click to a meeting, you can pause and ask yourself: Who is this group? Why are we meeting? What’s the purpose? Your brain is really fast. Convert that into one question that can invite the group’s perspective, tied to the purpose of why you’re meeting, that also allows people to connect with each other. While all questions are not created equal, just asking a question that is intended to create connection — whether it’s well-structured or not — will put you ahead of 99% of leaders in my opinion. Most leaders start off by saying a bunch of stuff instead of asking one thing and letting the group do the work. And by the way, this is a great way as a leader to reduce your effort by about 80% in every gathering.

Chad: There’s a study done in the UK: kids ask 300 to 400 questions per day. Adults tend to ask 6 to 12 on average. And if the adults in that study’s lives are anything like mine, half those questions are “What should we eat tonight?” or “Where are you?” — they’re not questions that build trust or rapport. Literally just by asking one question that is intended to create some connection and tie the group to the purpose of why you’re meeting — you’ll already be better than 99% of leaders.

Joe: I laugh because we try to do this at the dinner table with our family. I’ve got a high school freshman, a seventh grader, and a third grader. Years ago when my middle child Miles was in kindergarten or first grade, I asked him at dinner, “How was school today, buddy?” He said, “Good.” I said, “Can you give me a longer answer?” And he said, “Good.” [Laughter] He literally interpreted my question. That gave me a moment of pause — no, no, no, that’s on you, man. You’ve got to ask a better question. So now my wife and I try to ask things like, “Tell us about something today that made you laugh,” or “Tell us about something unexpected that happened.”

Chad: Two things. One — on the “good” answer — I had a mentor, Eric Tyler, who wrote a book called The Best Advice So Far. He would ask “How are you?” and when someone said “Good” he would just say, “What’s good about it?” This has solidified for me as a really easy habit: the magic of a second question. When you ask the first question, no matter how little they tell you, you learn something. Then just ask a second question based on what you learned. You don’t have to interrogate anyone. You don’t have to ask 15 questions in a row. It’s just the magic of a second question.

Chad: Because adults ask 6 to 12 questions on average per day — pay attention, after you listen to this, to how often someone asks even one question. I’ll bet you five bucks you won’t hear anybody ask a second question following up on the answer after that. It happens, but it’s so rare. And so again — another way to stand out as a leader is to just tap into that second level of curiosity. It’s a signal of caring. And listening is maybe one of the best signals of caring, and inquiry and curiosity right alongside it.

Joe: I want to ask you specifically about remote work. We spend a lot of time in our Boss Hero School leadership master class talking about how important it is to build people-centered relationships as leaders. One of the questions I get most is about the challenge of building connection and relationships in remote work environments — not just from the leader to the people on the team, but even across the team itself. A lot of people listening to this have teams who are in hybrid or full-time virtual workplaces. Is there a piece of advice or a best practice you can share to make connection and relationship-building just a little bit easier in these virtual settings?

Chad: Yeah, totally. Firstly: pixelated people are people too. It’s the exact same person. They have the same fears, doubts, backgrounds, aspirations, inspiration. Everything a human being in person has, so does a pixelated person. Remembering that — just because you only see the top third of them — they still have the exact same depth as someone standing in front of you. That realization alone causes people to ask different questions.

Chad: Second: I realized this over COVID. In remote work, you can rely on organic connection in person — you bump into somebody, there’s a spontaneous moment, they take a phone call and you find out it’s from their mom who’s in the hospital and now you can ask about that for months. In remote, we live in the vacuum of mute. Efficiency is very much the enemy of connection. While it’s very convenient to click to meetings, there’s no “before” and there’s no “after.” So you must genetically modify remote meetings to put connection before content. It doesn’t need to take a long time.

Chad: Here are a few examples. If you’re meeting with 12 people, use pretty much every video platform’s ability to split into breakouts — groups of three, one question, five minutes. Ideally something related to the purpose of your meeting but it doesn’t have to be super on-task. When you come back, just simply ask, “What struck you about those conversations?” and you’ll get the important bits popcorned back. That’s if you’ve got seven to ten minutes at the beginning of the meeting.

Chad: Many people don’t have that. So do something you can do virtually that you cannot do in person: in a remote meeting, everyone can speak at the exact same time without interrupting each other via the chat. I call the exercise collaborative journaling. Instead of asking people to type one quick word — which is how we typically use chat, for little sips and bites of connection — I invite people: “I’m going to ask you a question. I’m going to give you a full minute to journal out your response publicly in the chat, all at the same time. Then I’m going to give you three minutes to go read through everybody’s responses.” In four minutes, you’ve exchanged more information in a work meeting than most people will exchange in a work month.

Joe: I love it. Super simple. Amazing. And I wrote this down as the bumper sticker: efficiency is the enemy of connection. Can we tag on to that? Efficiency is the enemy of connection — however, connection does not slow things down. It speeds them up.

Chad: Yes. When George Clooney in Ocean’s Eleven is pulling off a heist, in Ocean’s Twelve he can just turn to a counterpart and say, “Let’s do what we did in Panama.” And they’re like, “Okay, cool.” They just saved four and a half hours of prep meetings. You just have to use the power for good, not to steal things. [Laughter]

Joe: We’ve had AI tools come up a couple times in our conversation and we’re all navigating this moment where it seems that there’s a bigger trust deficit than ever because of the way some of these AI tools are influencing communication. I get emails that I know weren’t written by the person whose name appears next to it. Comments on LinkedIn posts that I know they didn’t actually write. And it all feels like these incredible tools are pushing us all further and further apart. How do we protect and honor the need for authentic human connection in a world that keeps insisting we use tools that seem to devalue it?

Chad: This is like a whole separate podcast that would be six hours long. [Laughter] Here is my most optimistic answer. Right before ChatGPT really exploded, I somehow wound up on this interview — I can’t even find it anymore, I think it was removed from the internet — where Reed Hoffman, one of the founders of LinkedIn, was interviewing Sam Altman, one of the founders of OpenAI and ChatGPT. Reed asked: “When we’re at ChatGPT 15 and AI is doing most of the work that white collar workers are doing now, what are we left with?” And Sam, who had clearly lost many nights of sleep over that question, immediately answered: connection and recreation.

Chad: Now, history would say: we invented email, this is going to make us so much more efficient, we’ll have so much more free time. No — now we just work at dinner while we’re with our families. [Laughter] I do think AI will replace a good chunk of what many of us are doing. But here’s a very personal example. I use a tool called Whisper Flow that lets you press a key, speak into it, and it uses AI to dictate your natural language into any platform — it’s all my words, not changing them, just formatting and doing the detailed work. I was on a call with my assistant Taylor, walking through some emails that needed my input. And I found myself getting frustrated because Taylor wasn’t as good as this robot I’ve been using. And here’s what I realized: I’m never going to fire Taylor, because Taylor cares. Whisper Flow obeys.

Chad: If you don’t care, if you’re at work and you don’t care, you are at high risk of being replaced forever. Use the tool to demonstrate the caring through the quality of the work that you leverage the tool to produce. That’s the difference between somebody using a tool to write something very thoughtful versus pumping out AI slop in 10 seconds and sharing it with the world.

Joe: All right, we’ve got a couple of quick questions I love to ask during these interviews. First question: what was the most absurd or unnecessary rule you’ve ever encountered at work?

Chad: The first one that comes to mind isn’t technically at work, but I think it’s very relevant for work. I was at a playground with my kids and there was a creek flowing right by it with a sign that said: Do not step in the creek. And that immediately made me want to step in the creek. [Laughter]

Chad: From a boss perspective: if that sign had said, “Please do not step in the creek — this is a nuclear dump site,” I would not have stepped in the creek. The best bosses I’ve ever encountered are fluent in a second language, and it’s not Mandarin or Spanish or anything that takes a year or two to learn. It’s the language of intent. It is only two words: “so that.” Please don’t step in the creek so that all the critters in here can stay alive for decades to come. When an intention is present that ends with “so that” and includes the currency of what somebody else might actually care about, I believe it roots out manipulation. Manipulation cannot exist when a really clear intent is present.

Joe: It reminds me of a study I saw once where in a park there was a sign that said “Clean up pet waste.” They kept getting violations. So they replaced it with “Clean up pet waste. Kids play here.” Just those three words at the bottom caused a dramatic decrease in waste.

Chad: Which is something we don’t give enough credit for to people — actually caring. The vast majority of people want to do good. They aspire to do good. There are a select few deviants who aspire to do bad, but that’s not most of us. And so if you give people the clarity of how to do good, oftentimes they’ll step into that.

Joe: I actually wrote about this in my book Employalty — how for years we see leaders creating systems and engineering processes designed to address or root out the rare bad apple, and then impose them on a workforce of largely ethical people. It sends signals of mistrust. And when we believe that we are not trusted, we do not show up with commitment. If we orient ourselves to the understanding that most people have integrity and we work with that in mind, it changes how we show up and how they show up.

Joe: My second question: if you could ban one workplace phrase forever, what would it be?

Chad: Don’t bring me problems, bring me solutions.

Joe: I have never gotten that answer to this question. Please go on.

Chad: I just emceed a local TEDx event this weekend and one of the speakers was an Eagle Scout master. He told me an amazing story about a camping trip where the kids were just asking so many questions — “Where’s the firewood? Where are the marshmallows? Where is this?” And he and the other scout masters agreed to do a little social experiment: we’re just going to verbatim repeat back their question straight to them. Somebody would come up and say, “Where’s the firewood? We can’t find the firewood.” And the response was, “I don’t know — where is the firewood?” And guess what? They went off and found the firewood and made a fire.

Chad: That’s all it is. Replace “don’t bring me problems, bring me solutions” with the perspective that you are a facilitator and a connector — not just a leader commanding people around. When people come to you with a question or a problem, you just say: “Wow, that’s a really interesting problem. I actually don’t know exactly how to solve that. Are there any roadblocks I can move out of the way to help you solve it? How do you think we should solve it? Who do you think needs to be in the room to figure this out?” Just ask a couple more sophisticated questions. I’ve had leaders say this phrase in workshops — “Don’t bring me problems, bring me solutions” — and I’ve had to tell them, point blank: congratulations, you will never know what’s actually happening, and you will never get to coach people.

Joe: Last question: what is one piece of professional advice or wisdom that you got early in your career that has stayed with you throughout?

Chad: This is advice that almost certainly whoever is listening has heard and has not practiced. Because I’m about to say it, you may file it under “Oh, I’ve heard this before” — and then it will have no impact on your life whatsoever. I think this is especially important in the age of AI.

Chad: We must at work follow our curiosity, because it’s the only stepping stone that leads us to what’s next. If you rewind your whole career, I bet you could trace how you got to where you are through a series of conversations — a bumping into somebody at an event who had a job opening, a meeting with someone that sparked a connection. Follow your curiosity. And I don’t mean just search it on the internet in isolation. People are the most productive search engine on the planet and they’re becoming increasingly underused because we have a computer in our pockets. When you ask a person — a boss, a coworker — you will discover things that aren’t on the internet that will actually make a difference in your career.

Joe: I am going to end there because it’s such sage advice and it sort of captures the themes of everything we’ve talked about today. Chad, where can people listening follow you, learn more about you, get in touch, and stay connected to the work you’re doing?

Chad: You can probably Google “Chad Littlefield” and I’ve got a YouTube channel teaching this stuff for free — hundreds of videos answering questions all related to some of the things we talked about on this podcast. And my website is weand.me. The internet’s a big place; if you want to find me, you’ll find me.

Joe: Well, there you have it, folks. My sincerest thanks to Chad for spending this time with us. If you like this conversation, be sure to hit that subscribe button so that you don’t miss an episode of our show. And of course, I am always grateful for your reviews, your shares, and your feedback. Tell me what you thought of this conversation by dropping a comment in the box below our episode here on YouTube, or you can email me anytime for any reason at bossbetter@gmail.com. In the meantime, don’t forget: commitment comes from better bosses. Visit joemull.com for more information. See you next time.

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