223. Laughing Matters: Levity, Leadership, and Lasting Connection

Summary

Think Fast, Talk Smart: Communication Techniques

Episode 223 — "Laughing Matters: Levity, Leadership, and Lasting Connection"

Host: Matt Abrahams
Guests: Alison Wood Brooks & Naomi Bagdonas
Date: August 19, 2025

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Overview

This episode centers on the role of levity and humor in communication, leadership, and building strong relationships, both at work and in life. Host Matt Abrahams welcomes back Alison Wood Brooks, Harvard professor and author of Talk, and Naomi Bagdonas, executive coach and co-author of Humor, Seriously, for a wide-ranging discussion. The trio dives deep into actionable communication tactics, the science behind conversational habits, and how adopting a mindset of levity can enrich leadership, teamwork, and personal satisfaction.

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Key Discussion Points & Insights

1. The Power and Practice of Asking Questions

(03:12–06:43)

• Question-asking as a core skill: Alison shares that across her book tour and teaching, people are consistently drawn to the topic of asking questions—both how to do it effectively and why it's essential.
  • “Just ask more. Go into every conversation with this mindset of I can't leave this conversation not having asked any questions.” — Alison (04:42)
• Follow-up questions as treasure-hunting:
  • Naomi likens each response in a conversation to “gold,” suggesting that good follow-ups uncover deeper meaning and connection.
  • “Even a boring sort of mundane question can become great by asking great follow up questions…” — Alison (05:57)
• Practical tip: Start with any question and listen closely; follow-up is where the magic and connection happen.

2. Leadership Principles and Designing for Serendipity

(07:05–09:17)

• Guiding principles for leaders: Naomi discusses having executives define their personal guiding principles to navigate life and leadership decisions. Hers: “Go where there's light and heat.”
  • “If I today set a goal for five years from now, it will not be anywhere near as good as if I navigate my life palms up and I pay attention to where there is light and heat...” — Naomi (07:33)
• Allowing for serendipity: She purposefully allocates 15% of her time and budget for “serendipity,” giving room to seize unexpected opportunities.
  • “I have a 15% serendipity fund. What that means is that 15% of my time and my budget is allocated to pursuing serendipity.” — Naomi (08:24)

3. What Is Levity? Why Does It Matter?

(09:17–13:06)

• Levity defined:

  • “Levity is navigating your life on the precipice of a smile.” — Naomi (09:35)
  • Not just about humor, but about openness to joy, delight, and connection.
  • Creating and receiving levity are both essential—levity is a collaborative act.

• Levity as a core—not a 'bonus'—part of working and relating:

  • Alison emphasizes levity’s influence on group dynamics, status, influence, and engagement.
    • “It’s a core determinant of the status hierarchy in every group...not just this extra thing.” — Alison (11:24)
  • Naomi cites research showing laughter in teams increases creativity, engagement, and satisfaction—even in romantic relationships, reminiscing about laughter boosts satisfaction by 23%.

4. Permission for Nuance, Risk & Fluidity in Conversation and Levity

(13:06–14:41)

• Navigating discomfort: Matt notes that for many, the fluidity and risk-taking required to practice levity or good conversation feels unsafe or hard.
• Courage in communication:
  • Alison explains that real connection in conversation and humor requires “fleeting moments” of courage and risk.
    • “It's these little fleeting moments that require risk taking and a little bit of courage. ...are you going to be courageous enough to take that risk?” — Alison (13:56)

5. Vulnerabilities & “The Liking Gap”

(16:42–18:30)

• Fears around levity and offending others: Matt shares his personal anxiety about post-conversation worries: “Did I offend someone with my humor?”
  • “I worry about... did something I say offend somebody?... I replay it in my head over and over.” — Matt (17:06)
• Misalignment in perception (“The Liking Gap”):
  • Alison notes research shows people like us much more than we think; we ruminate on the wrong things after conversations.
    • “People like you a lot more than you think. ... We're all overly pessimistic about how we think things have gone.” — Alison (17:50)

6. Creating Spaces for Humor & Humanity

(18:32–20:48)

• Leaders as containers, not providers: Naomi stresses that her job is to create a safe space so others feel comfortable bringing their own levity and “goofy,” rather than performing humor for them.
  • “It's not about me being funny. ... Am I creating the right space, the container for other people to fill it?” — Naomi (18:32)
• Physical cues and breaking formality: Naomi shares a story (19:50) about changing the group dynamic at a formal dinner by sitting on the floor—a strong cue that breaks barriers and invites humanity.
  • “When you give space for people to bring their humanity, their sense of humor will follow.” — Naomi (20:48)

7. Meta-Awareness in Leadership and Levity

(20:59–21:50)

• Matt shares a story about a CEO who delivered bad news by stepping off stage—a signal of presence and reducing formality.
• To support levity and presence, leaders must hold dual awareness: being fully in the moment and observing group dynamics to sense what’s needed next.
  • “...it's holding that duality of—I’m in the moment present, but at the same time, I'm observing and feeling what's going on so I can make the difference.” — Matt (21:00)

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Notable Quotes & Memorable Moments

• “Levity is navigating your life on the precipice of a smile.”
  — Naomi Bagdonas [09:35]
• “Just ask more. Go into every conversation with this mindset of I can't leave this conversation not having asked any questions.”
  — Alison Wood Brooks [04:42]
• “I have a 15% serendipity fund... my time and my budget is allocated to pursuing serendipity.”
  — Naomi Bagdonas [08:24]
• “It’s a core determinant of the status hierarchy in every group...not just this extra thing.”
  — Alison Wood Brooks [11:24]
• “It's not about me being funny. ... Am I creating the right space, the container for other people to fill it?”
  — Naomi Bagdonas [18:32]
• “People like you a lot more than you think. ... We're all overly pessimistic about how we think things have gone.”
  — Alison Wood Brooks [17:50]

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Timestamps for Key Segments

• 03:12 — Alison on what resonates most from her book (Talk): Question-asking and parent-teen communication
• 04:42 — Top advice on asking better questions
• 05:22 — Naomi on follow-up questions as “magic”
• 07:05 — Naomi: Guiding principles for leaders and the “serendipity fund”
• 09:31 — Defining levity and teaching it to students
• 11:24 — Why levity is central, not optional, in conversations and leadership
• 12:14 — Research on laughter, team success, and relationship satisfaction
• 13:56 — Alison: Why risk and courage are needed for great conversation and humor
• 17:06 — Matt on the anxiety of humor and not knowing how it “lands”
• 17:50 — The “liking gap” and why people like us more than we think
• 19:50 — Naomi on visual cues and breaking formality to foster humanity and levity
• 21:00 — Matt’s story of the CEO who shifted dynamics by stepping offstage

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Final Thoughts

This episode intricately weaves actionable communication techniques with deeper reflections on humanity and connection. Levity, far from being a frivolous or optional extra, emerges as a vital tool in our arsenal to foster creativity, collaboration, trust, and satisfaction. The guests encourage listeners—and leaders in particular—to be intentional, risk-taking, and human, emphasizing that laughter and warmth are not just nice-to-haves, but central to real, effective communication.

For deeper dives into these themes, the host recommends checking out earlier episodes with Naomi and Alison, as well as their respective books.

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Transcript

[A]

Hi Matt here. I am super excited to let you know that our August newsletter is now available. In it you'll learn lots of useful tools and advice, we'll introduce our upcoming September Tech Tools miniseries, and there's a whole article on how to speak better when you're speaking in a language that's not your own. Check it out on LinkedIn and subscribe or go to FasterSmarter IO and under Resources Find Our Newsletter.

[B]

One sure way to connect and to build relationships is to bring levity into your communication. My name is Matt Abrahams and I teach strategic Communication at Stanford Graduate School of Business. Welcome to Think Fast Talk Smart, the podcast. I always look forward to interviewing my guests, but today I am super sized excited to be revisited by two guests today. Not only are Naomi and Alison fantastic teachers, authors and communicators, they're amazing people and I'm proud to have them as collaborators and friends. All right, enough gushing. Let me formally introduce you first to Alison Wood Brooks.

[A]

Allison is the o' Brien Associate professor of Business Administration and Hellman Faculty Fellow.

[B]

At Harvard Business School.

[A]

Alison's research focuses on the science of conversation and interaction and she teaches an.

[B]

Award winning course called talk, which also happens to be the name of her.

[A]

New book, the Science of Conversation and the Art of Being Ourselves.

[B]

Alison is also our first three time guest ever. Allison and I today are joined by Naomi Bagdonis. Naomi runs her own consulting company where she helps not only organize high stakes gatherings, but coaches leaders to be more successful. She's coached CEOs and celebrities for media appearances on Saturday Night Live and the Today Show. She trained at the Upright Citizens Brigade Theater and teaches courses about humor at the GSB and the San Francisco County Jail. Along with Jennifer Aker, she wrote the only business book I have ever learned and laughed through called Humor. Why Humor is a Secret Weapon in Business and Life. Thank you both for joining me. This is such a thrill for us to actually be in person together. We talk all the time on Zoom and on email. Wonderful.

[A]

This episode is brought to you by Stanford University. At Think Fast Talk Smart, we strive to bring you tools to help you succeed in business and in life. Like the ideas you heard from my Stanford colleague Tina Selig, who studies how to ask more creative, insightful questions. I'd like to share another way that Stanford research matters. Chronic heart failure is a major cause of death, in large part due to the short supply of suitable hearts for transplant. Stanford bioengineer Mark Schuyler Scott is trying to change that by using 3D bioprinting technology. Mark and his colleagues are working to create new hearts and other organs on demand using cells from a patient's own body. Mark's work is just starting and it looks promising. Groundbreaking research like this happens every day at Stanford and you can learn more at researchmatters Stanford.

[B]

Edu. So Alison, I'm going to start with you. You are on tour for this awesome book Talk. What has surprised you in terms of what's interested people the most? There's so many good things in here. I'm curious what has interested people more than anything else?

[C]

The content of the book is based on my course, also called Talk. And so I've had such a lovely privilege of seeing how a lot of people react to this content over many years and I think the lovely people that I've encountered on my book tour are reacting in ways that are similar to how my students have reacted to the course. A couple things that stand out. One is about question asking. I think that just is an evergreen topic and skill that really resonates with people both on the asking side. They have so many fears about asking or hesitation and on the receiving end of annoyance when people don't ask them enough questions. And one other thing that's really stood out to me on book tour is that it seems like people really want to get this in the hands of teenagers. I know that it's helpful to adults and executives and people who have fully developed their conversational skills, but a lot of parents are co reading the book with their teenagers because there seems to be quite a bit of fear and concern about kids these days not actually developing their conversation skills as much and as well as they could.

[B]

That was something that was surprising to me when my book came out. All the parents saying hey, my kids need this and there's work to be done there. What is the one big bit of advice you give on asking questions?

[C]

Oh, top line advice. So easy. Ask more questions. Obviously much of the advice that you will read in this book or hear about on its surface seems so simple, but when you try and put it into practice it's really hard. So the top line simplicity of this advice is really important. Just ask more. Go into every conversation with this mindset of I can't leave this conversation not having asked any questions. I should be pushing myself to ask on the margin a few more. Once you get past that top line advice of ask more, then you can get into the nitty gritty of what is a good question, in what circumstances and what types of question asking should.

[D]

We avoid I want to add one thing that I loved that changed me in the way that I interact with people is this idea that everything that someone gives you, they are giving you gold. And follow up questions are this magic way to uncover meaning and intention because we all attribute different meaning to what people are saying. And there's so much to be uncovered with really good follow up questions. I'm curious, is there anything related to follow up questions that you in particular love?

[C]

Something that I've realized there's a lot of rhetoric you'll see on LinkedIn or among people that's like, well, don't ask this question, ask this question. And to some extent there is maybe a little bit of a difference between what makes a good question or not. But the better mindset to realize is no matter where you start on a topic, whatever that root question is, what actually matters more is that they're going to give you an answer, you listen to their answer, and then what's the choice that comes next? Because even a boring sort of mundane question can become great by asking great follow up questions. If you're constantly searching people's answers for treasure and then diving in towards that treasure, it's going to take you to great places, even if the original question isn't anything special.

[B]

And not only do follow up questions signal that you're interested in listening, it also allows you to connect better and it can set you up for a better relationship in the future. Naomi, you've been doing a lot of work in leadership and leadership coaching and I'm curious, is there something new that you're looking to do or are doing that helps you help leaders be more effective?

[D]

I teach a class here at Stanford called A New Type of Leader with Jennifer Aker, who's a dear friend of all of ours and an amazing collaborator. We now have all of our executives create guiding principles. And the idea is, what are the principles that when you are living in alignment with these principles or in resonance with them, your life unfolds magically better. And they're different for everyone. So one of mine, I'm going to be curious what yours are. One of mine is go where there's light and heat. And what that means for me is if I today set a goal for five years from now, it will not be anywhere near as good as if I navigate my life palms up and I pay attention to where there is light and heat and I follow those instincts. Now, that's not true for everyone, but for me, I have found that living in alignment with that principle is really Important and makes my life better. Because I'm curious, is there a principle that each of you have?

[C]

Doing that palms up and chasing light and hate means that you also need to leave space for serendipity.

[D]

Yes.

[C]

Even practically speaking, in your schedule, in your calendar, and psychologically in your mind, in order to sort of chase that energy when the opportunity arises. Do you do that very intentionally?

[D]

I do that extremely intentionally. So I have a portfolio career, which means that I have different percentages allocated to the different things I'm doing. And I have a 15% serendipity fund. What that means is that 15% of my time and my budget is allocated to pursuing serendipity. If I'm giving a talk somewhere and I have a conversation with an executive who's in the audience afterwards and they say something about something that they're working on, or perhaps it's an event that they're leading and they say, there's no chance that you're going to be in New York next week, are you? And in my mind, if there's real light and heat, there I go, okay, serendipity fund. Actually, yes, I am in New York next week and part of the work that we do. Matt, to your point, not only what are these guiding principles, but how do you design structures in your life that allows you to live in alignment with them, which is super important.

[B]

I'd love for one of you just to define what is levity and perhaps the other can share why it's important. And I invite you to share with us what your students get when you guys have that discussion in your class. What is levity? Why is it important? And how do you help students understand.

[D]

That levity is a mindset?

[C]

Yeah.

[D]

Levity is navigating your life on the precipice of a smile.

[B]

I love that saying.

[D]

It is looking for reasons to be delighted rather than disappointed. And it is staying open to the possibility that joy and magic are everywhere. If you just look for.

[B]

Seems to me that a key to that definition is being open to it. Many of us feel judged, evaluated, threatened in our work, in our conversations.

[D]

Yeah.

[B]

How do you encourage your students, the people you coach, your friends, your family, to be open to those moments of levity? Because they're very rewarding intrinsically. But how do you encourage people to be open?

[C]

So the whole premise of talk the book and talk the course, one of the really profound things that I hope people come away with is that every interaction is co constructed that includes levity. It's not just happening in your own mind. It's not just happening in their mind. It's something that you are co constructing together. And so there's, it's a two sided challenge. One is about creating moments of levity and the other is about appreciating and receiving moments of levity. And I think to succeed in fulfilling this mission of the mindset and the universal goodness of levity, you need to really be open to both. As when you see opportunities, do you seize them to create levity in conversation? And when someone else offers you this bid for humor or for warmth or connection or levity, do you accept it? Do you accept it with open arms? Or do you judge it and keep it over there in a box and feel threatened by it? That feeling of acceptance and openness is part of the levity mindset. And it's not just openness. It's like a almost a proactive appreciation for it.

[B]

It sounds like presence and being other focused are critical ingredients to being in that place where you can be open.

[C]

When we think of humor or levity, it's easy to think of it as this like extra bonus thing, like some people I know are funny, or like that meeting we had that funny moment of laughter. And that was great, but it was ancillary, it was extra, it was like this bonus thing. And then we got back to work. What we find as behavioral scientists is actually it's not just this extra thing. It's incredibly core to how people are relating to each other. It is a core determinant of the status hierarchy in every group. It's just the correlation between levity and status, power, influence, persuasion and all of the other goals we're trying to achieve is so intrinsic that it's actually not to think of it as this extra thing, but more this is a core goal that we need to engage with to sustain conversational engagement and successful interpersonal exchange.

[D]

And the research around this is so robust that teams, when there's the presence of laughter in team meetings, those teams are more successful and more creative leaders with a sense of humor, not even a good sense of humor, just a sense of humor, are seen as more motivating, more admired. Their teams report being more engaged. And so there are all of these benefits. Even when you ask couples to reminisce about shared moments of happiness versus shared moments of laughter, those couples that reminisce about the shared moments of laughter then afterwards report being 23% more satisfied in their relationships. And so even the act of recalling these moments, they're not just valuable in the moment. For making us more creative, higher status, more successful, more bonded. But they also have incredible benefit down the line of maintaining that relationship satisfaction.

[B]

Many people listening might be afraid that I'm not funny, and I want to direct everybody to Naomi and Jennifer's book Humor Seriously, which helps all of us become more comfortable with and understand how to use humor. When I reflect on what you both have studied and work on, it seems to me that there's a lot of nuance and fluidity that's involved in both conversation and in levity and humor. And that can be something that's very hard for people to pay attention to the nuance or to allow themselves permission to adjust and adapt. Any suggestions or guidance on how to let go so you can do that? A lot of people hold on tightly to what's comfortable and you're asking and saying there's benefit to pushing yourself to be uncomfortable.

[C]

So a lot of what makes people good conversationalists, not just levity, but including levity, but even asking questions or switching topics. It's these little fleeting moments that require risk taking and a little bit of courage. When things start to get boring, it means you need to muster yourself up for that moment and say, I'm going to go take us in another direction. Or I'm going to ask a question that maybe is a little risky and maybe they're not going to want to answer, but I trust that they're going to tell me they're not comfortable answering it if it's too personal. So it's these little bids that require risk taking and a bit of courage and levity for sure requires it. It's like these little fleeting opportunities arise and are you going to be courageous enough to take that risk?

[A]

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[B]

Always ask people three questions. People can listen into your episodes. Allison People can listen to episode 73169 to hear your answers. Naomi in episode 13 so I'm actually going to turn the tables. I've never done this before. What question should I have asked that I haven't asked for us to discuss?

[C]

I would love to hear from both of you what you struggle with when you think about levity, particularly in conversation. You've both spent a lot of time thinking about communication and about levity. In your experience as a human in the world, what sort of keeps you up at night about it or stresses you out or you find tricky still.

[B]

So when I attempt to be funny or when I am funny, if people laugh sometimes, it will happen so quickly that I'm not thinking about it and I worry about I stay up at night thinking about did something I say offend somebody? Is there something that I said in some way because it was in the moment and it just came to me and did it potentially offend somebody? And so I worry about it and I replay it in my head over and over. Thankfully, my wife encourages me one to talk to the people I'm afraid of offended, rather than building it into something bigger in your head. But that's the thing around levity that really, I think the beauty of it is it happens in the moment. And when you have spontaneous levity, it's just amazing and fun. But in my case, sometimes I am afraid that maybe I pushed somebody in the wrong way and that worries me.

[C]

It's an impossible problem to solve because even when people laugh and are having a great time, you really don't know. You can't read someone else's mind. You don't know what sticks with people and what Doesn't. There's a lot of nice evidence suggesting that we ruminate about the wrong moments. Maybe that joke was totally great and they loved it, but there was something else. You didn't even notice that actually they're continuing to ruminate about. We're very misaligned in what we ruminate about after conversation. There's great research by Gus Cooney, Adam Mastroianni, Dan Gilbert about the liking gap. Do you know this work? People like you a lot more than you think. On average, after a conversation, we're all overly pessimistic about how we think things have gone compared to how they actually went.

[B]

Nami, what's your answer to Alison's question?

[D]

I have a body of work and I teach at Stanford about the power of humor and leadership. I worry that sometimes people can feel a bit nervous about bringing levity if that intention is already set right. So if someone starts conversation with me and they're like, oh, gosh, okay, this person is assessing me and my humor and my levity, and that pressure is the most surefire way to kill someone's joy and levity. And so I spend a lot of time thinking about how do I create a really safe space where this person's goofy can come out? It's not about me being funny. It's not about me bringing humor. It's about, am I creating the right space, the container for other people to fill it, rather than people sitting on the wings and thinking, okay, that person is going to fill the humor, which I think is a broader principle around for leaders. How do you create the space for other people to fill it rather than people sitting back and thinking about it?

[C]

Are there specific things you do that you think help make people relieve that pressure and make people feel safe to play? I think people feel the same way. They're like, I'm so nervous to talk to you. I feel like you're evaluating. And it's almost the opposite. It's like, I understand how complicated this thing is that we're doing, and I think I have more grace and forgiveness for flops.

[D]

It's related to this. It also relates to a broader principle, which is what are the cues, the visual and the physical cues that you're giving off? I was at a dinner party a couple weeks ago, and everyone was sitting around. It wasn't actually at a table. It was sitting around couches. And it was a group of people who we were all professional connections, where we should really be getting along. But the conversation was a little dry and stilted and we were also sitting really far away from each other. This room just was really big. And I just could feel like, how do we bring some? And so I. I just moved to the floor. I just sat on the floor. Cause all the food was in the middle. I sat on the floor and I started eating and one person laughed and then one other woman walked to the floor and a guy kicked off his shoes and sat cross legged on the couch. And you could feel the energy start to shift. And so it's. It's not just about levity, it's more about humanity. Because when you give space for people to bring their humanity, their sense of humor will follow.

[B]

Yeah.

[C]

And breaking the formality, breaking the pace. I often like if there's a certain expectation or norm or whatever, if you can break that a little bit, it really grounds people and brings them together.

[D]

Together, yes, totally.

[B]

I coached a very senior leader of a company we all know, and he had some bad news to deliver and he did something on his own, not through my coaching. He came off the stage in a room of about 2,000 people. And just coming off the stage and having the tough conversation changed the whole dynamic. What's required though, to accomplish this is this meta awareness of what's going on and what's needed. And it's holding that duality of I'm in the moment present, but at the same time, I'm observing and feeling what's going on so I can make the difference. And that is a skill that. That's hard to develop. But courses like all of us teach hopefully help our students do that. You both have helped us in so many ways. Not only did we talk about levity, but we had moments of levity. And thank you for that. And thank you for sharing your passions and your research to help all of us get better. It was a true pleasure to have you both here.

[A]

Thank you.

[B]

I know both of you traveled to be here with me today, and I appreciate you doing that. Thank you.

[D]

You are such a beautiful and generous collaborator. And it's a gift to be here. And the work that you're putting into the world is also such gift.

[B]

So thank you.

[A]

I'm blushing. Thank you for joining us for another episode of Think Fast, Talk Smart, the podcast. To learn more about humor and levity, please listen to episode 13 with Naomi and Jennifer Aker. And to learn more about Allison's work, please listen to episodes 73, 89 and 169. This episode was produced by Ryan Campos and me, Matt Ibrahims. Our music is from Floyd Wonder with special thanks to Podium podcast company. Please find us on YouTube and wherever you get your podcasts. Be sure to subscribe and rate us. Also follow us on LinkedIn and Instagram and check out fastersmarterio for deep dive videos, English language learning content and our newsletter. Please consider our premium offering for extended Deep thanks episodes, Ask Matt Anythings and much more at fastersmarter IO Slash Premium. Hi Matt here. As September approaches, many of us are heading back to school and work to help get you back in the groove and hone your communication skills. Check out Daily Back to basic videos we'll be publishing each day in August. We have identified a weekly communication topic and we'll share a short helpful video each day at 7am Pacific on our YouTube, Instagram and TikTok channels. Please check out these practical helpful videos and be sure to follow us to get your daily dose of Think fast, Talk smart. You can see a complete calendar at fastersmarter IO Basics.