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Brené Brown & Reid Hoffman on the skills every leader needs now

from Masters of Scale ·

22m 59s

Brené Brown & Reid Hoffman on the skills every leader needs now

The conversation between Reid Hoffman and Brene Brown highlights the importance of courageous leadership, rooted in self-awareness, humility, and emotional intelligence. Courageous leadership isn’t about being fearless, but about recognizing one’s vulnerabilities and the "armor" (like perfectionism or over-deciding) that protects against fear. Brene emphasizes that courage is teachable and measurable, built through value alignment, emotional granularity, and vulnerability. She distinguishes between cognitive empathy—essential for leadership and democratic engagement—and affective empathy, which can lead to burnout. A key insight is that leaders must develop emotional vocabulary to understand complex feelings like regret, awe, or grief. The conversation also stresses systems thinking and permeable boundaries as critical for organizational resilience, especially in the face of AI disruptions. Leaders are encouraged to shift from reactive urgency to strategic, thoughtful decision-making—“settling the ball” before acting. This involves creating mental space, anticipating change, and aligning AI integration with long-term business strategy. The overarching message is that human-centered, emotionally intelligent leadership is not a luxury but a necessity in a fast-moving, AI-driven world. The dialogue concludes with a call to action for leaders to build emotional and systemic resilience, using real-world metaphors like football to illustrate strategic patience and foresight.

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Global hiring is such a headache when you're building fast, but companies like Eleven Labs are scaling effortlessly with Deal. They quadrupled their workforce in 2025 without hiring an HR team. Build your global team with Deal. Visit deal.com slash MOS and start expanding your business today. That's D-E-E-L.com slash MOS. AI is full of possibilities. Enterprises run on realities. That's why Pega combines the world's most powerful AI with the governance, transparency, and control enterprises demand so you can move faster, adapt faster, and scale AI with confidence. All the power of AI, none of the uncertainty. Learn more at pega.com slash AI. Hey folks, Jeff Berman here. Today, we are revisiting one of our favorite conversations from the 2025 Masters of Scale Summit, Reid Hoffman in conversation with the iconic author, Brene Brown. It's full of heart and smart. Two things you're sure to get a lot of when you join us at this year's event as well. It's coming up soon, October 20th to 22nd in San Francisco. Go to mastersofscale.com slash summit to learn more. Thank you. Thank you. Clearly, you have some fans here already. I like it. Howdy. You have a new book out. I do. Called Strong Ground, which explores many aspects of what you call and what should be called courageous leadership. So what is courageous leadership? Well, I heard the word humility during the introduction. And to me, courageous leadership is a combination of a deep awareness of who you are, and leading with discipline and accountability and humility. It's about understanding that to lead is to serve others and not be served. And it's, I think it's probably rooted in every, in above everything else, self-awareness about who you are and how you're showing up probably undergirds all of it. And what are some habits, principles, ways that you help people understand? Are they exhibiting it? What kinds of ways to build into it? Because obviously, it's the right aspiration for everyone to get to courageous leadership, but it isn't just a slogan. It's actually a way of being. Yeah, it's interesting. I think the biggest finding possibly of my career has been that courage is teachable, measurable, and observable. It's a skillset that's made up of four things. The ability to be very clear about your values and to assess whether you're behaving in a way that's aligned with them. It's one thing to have values. It's another thing to operate. It's another thing to operationalize them and then hold yourself and your organization accountable for them. The second is the ability to stay in your integrity in vulnerability. Vulnerability is very simply uncertainty, risk, and exposure. So all of us are in it every day, all day. And the ability to know when you're in it and to not reach for armor. I hypothesized early on that the biggest barrier to courageous leadership was fear. And when we went back to some of the leaders we were studying, they literally said some version of this to us. If you're going to make a list of brave leaders who are never afraid, don't put me on the list. I'm afraid every day. And I was like, well, if it's not fear, what gets in the way of courage? Armor. It's how we self-protect when we're afraid that's usually out of our awareness. So one of the things we do with leaders is what's your go-to armor? Mine is terrible. Mine is perfectionism, micromanagement. I also get super decisive. That's my armor. Oh, interesting. I'll be in a meeting. Yeah, I won't get paralyzed. I'll be like, shut it down. No, move the team. Change the money. We're not doing this. And then I'll look up and I'll be like, oh, shit. I don't know that these are good decisions. And literally the last time I did that, my team looked back at me and said, we never write anything down when you're acting like this. I was like, wait, what? And they're like, this is your armor. That is my armor. I get overly decisive. And so, for us to be courageous, we have to know the very human ways that we self-protect when we're afraid. What's some of the ways to kind of discover that armor and learn how to disarmor yourself? So I think most of us know. I mean, if you want to ask someone, I wouldn't ask someone that works for you. Because there's a power differential there that could make it super cringy for that person to describe exactly how you're an asshole. What form of assholeness do I default to when I'm afraid? Because they'll be able to tell you for sure. They could tell you. You're right. But they may sprightly say, I don't know. I've never seen it. It's when you're too perfectionistic. Yeah, oh yeah. Oh, no. Not the perfectionism. Yes. What's your weakness? Perfectionism. Everything I do is very good. Yes. And that's not how it shows up for me. Perfectionism is like, maybe a month ago, I gave the packing parachute speech. We're packing parachutes. 100% matters. Do you want to jump out of a plane with a parachute that was packed at 90% excellence? People die. And I think we were talking about a font choice. A parachute font coming soon to you. A parachute font. Don't get this wrong. People will die. This is all like a founder problem. But I have a therapist and a coach. I'm working on it. But I think you probably know, like raise your hand if you could think about how you self-protect when you're in fear or uncertainty. I think you know. And I don't think you normally have to ask other people. And if you don't have the insight or the courage to think about it, I question the sanity of you leading people. Yeah. Yes. To be honest with you, because who we are is how we lead. And if you're not willing to have the humility to look into, can I get scary when I'm scared? Yeah. And I think a lot of us can. I can. Yeah. No, it's classic. It's classic. Yes. I'm a legend. Yes. So you do intense research. You meet a lot of great CEOs. Probably meet a lot of not great CEOs. I'd say probably over the last decade or two, there was kind of more generally saying, hey, CEOs should be more empathetic. And it seems to be going somewhat the other direction now. Now, sometimes people might describe that accurately as testosterone poisoning, which we have a certain amount of. What are you seeing in this pattern of what kind of environments are CEOs operating in? And what's the way to maintain kind of a true north for themselves, their organizations, their culture? What are the forces that are acting against it? And what are the ways to navigate it? Yeah, I feel really lucky because I actually go to work every day. I spend probably 90% of my time working with C-suite and then level of direct reports under the C-suite. I'm so optimistic in many ways because when you stop scrolling and you turn off the news and you're just sitting with people in a room, you see a lot of great people who wake up every day and are committed to doing the next right thing, regardless of what's in the zeitgeist right now. And I feel like that makes me very optimistic. I think in terms of the cultural push against empathy, I have two thoughts on that. One is just honest. Look, if my leadership plan includes hurting people, especially vulnerable populations, I'm going to be against empathy. I'm going to diminish and devalue empathy if part of my plan is to be hurtful because I don't need your pushback and your resistance. So that's one. The second thing is empathy is very nuanced. And so it's easy to grab the parts of empathy that are actually not very helpful. So there are two types of empathy. There's cognitive empathy and effective empathy. So if you call me and you're like, hey, Renee, I'm really having a hard time. And I say, tell me what's going on. And you tell me what's going on. And I reflect back and say, God, that sounds like incredibly disappointing. And we have a conversation and you feel seen and heard and believed. That empathy, that cognitive empathy is not only the source code for relationships, it's the source code of democracy, period. Affective empathy is you call me, and I say, what's going on? And you describe what's going on. And then I feel it with you. That's not helpful. That leads to burnout. It actually minimizes compassion. So I think we have to get really clear on what's healthy empathy and what is not. But large sweeping statements about empathy as the end of Western civilization by people who don't understand it and are also doing really dangerous shit to groups of people don't mean anything to me personally. 100%. Yeah. Because I get why it would be convenient if I stopped caring. It's not going to happen. Yeah, exactly. And a lot of how you describe cognitive empathy for me is how I think about compassion. So how do you think about the difference in cognitive empathy and compassion? Oh, God, it's so interesting. From a research perspective, compassion is so brave. Compassion is the willingness to walk through the world and accept that there's going to be suffering and that when you see it, you're willing to do something. something about it. That's compassion. That I am going to move through the world. world, and accept that there's suffering, mine and yours, and when I see it, I'll be moved to do something about it. Empathy is a tool of compassion. It's a teachable tool. It's a hard thing to teach. Like, I've taught in a graduate college of social work for two decades, and like, when we teach empathy, it's like role plays, and you're like, oh, Mr. Smith, you must be feeling super betrayed. Right, yeah, and then Mr. Smith inevitably will say, no, I'm not really. Okay. Sad. You know, it's hard because really good empathy requires emotional granularity. It requires the ability to have a pretty robust emotional lexicon, which is hard because our research shows that adults in this country can name and accurately identify about three emotions, happy, sad, and pissed off, and we think there are about 85 to 90 that are important for emotional granularity. I'll say that's sad, but that's okay. Yeah, that's sad. It's pissing me off. Yes, exactly. But imagine. But I'm not happy about it. But you're not happy. Like, you get three buckets, pick one, but imagine like reducing everything that we experience in life to three buckets, and neurolinguistics would tell us that the ability to access language that accurately reflects what we're feeling is so important to the human experience, which is why three buckets are not enough, because it doesn't include awe, wonder, disappointment, grief, anguish, things that really define the human spirit. More from Reed's conversation with Brene Brown in just a minute. When you've built substantial wealth through your business, it's often tied up in a single equity position. The upside is real, but so is the risk, and knowing when to act isn't always obvious. Creative planning works with business owners to build a strategy around concentrated equity. When to diversify, how to manage tax risk, and how to protect business owners. What you've spent years building. Creative planning, where wealth works together. Learn more at creativeplanning.com slash masters of scale. I hope to see you there. Humans will never be more intelligent than AI. There's going to be two types of companies. Those are great at AI and those that went out of business because they weren't. How do we build a future that is human-centered? I'm Rana El-Khayoubi, and on my podcast, Pioneers of AI, we answer that question and so many more. As an AI scientist, entrepreneur, and investor, I know what it takes to build AI that works for everyone. Every week, I sit down with the pioneers shaping our future, and we take you behind the scenes of the AI that's transforming our lives. Find Pioneers of AI wherever you tune in. Welcome back to Masters of Scale. You can find this conversation and more on our YouTube channel. In the classwork and the students, do you actually run through the entire emotional gamut? Because I could see that being stunningly important in leadership education to just say, let's actually expand your experience of emotional vocabulary. Because actually, if you don't have that kind of sensibility, you can't be compassionate, you can't have cognitive empathy, etc. And the ability to understand, like, I have regret. Do you run through the. Ah, awesome. We do, and they pick two or three that they want to learn more about that they think would make them stronger leaders in their organization. And again, I'm usually at the C-suite level, so they're often picking emotions that are preventing their team from getting back on their feet after failure, disappointment, and sadness. And they're often picking emotions that are preventing their team from getting back on their feet after failure, disappointment, and sadness. After failure, disappointment, and sadness. Because one of the things that you see, especially among CEOs today, is, not if, but when there's a failure and a setback and a disappointment, I need everybody on my team to be responsible for their own bounce. I need everybody to get back up on their own, because I cannot both correct what's happening and remind you of your value. I need everybody up on their own. And so in order to get back up, we have to. We have to understand the whole collection of emotions that we're feeling. Yeah, no, exactly. There's this concept within health things of like cognitive reserve and, you know, motion reserve. Emotion reserve actually strikes me as a really interesting thing to be building resilience in. I mean, I hate this because it rhymes, so it makes it seem less important. But there is something that therapists often say, which is if you can't name it, you can't tame it. If you can't accurately name what you're experiencing, it's very difficult to move through it. When we were doing strong ground research, we wanted to come up with what does the future of leadership look like in terms of actionable skill sets? Emotional granularity ended up in the top five. And other four? Self-awareness. One that I cannot believe has fallen to the wayside, that I see less and less in senior leaders today, systems thinking. The ability to think. The ability to think in terms of systems, which is really scary because if you're familiar with systems theory, you know, the prerequisite for a healthy system is permeable boundaries, where good data and feedback can flow in and out pretty freely, especially with AI. What's interesting. Oh, you got the excited face. What I think is interesting is when a team or an organization loses the permeability of the boundaries, they're not bringing in external feedback or internal feedback. They're not bringing in external feedback consistently. Boundaries get closed. Two things happen to a system, whether we're talking about a cell or a tech team. You become a self-referencing system. And so what you end up doing is, are we good? No, we're great. Do we need to know more? No, we know everything. You know, the MIT Sloan research that just came out. Investments in AI, 90% failure, no return on investment. And a lot of that is because of self-referencing systems. Like, you have to have the courage to say, in this environment, I know very little. In times of disruption, people try to persuade themselves all under control. There is an inherent risk. It's like, no, no, we're moving through times of disruption. Right. You need to have a different stance towards it. And not just you as an individual, but you as a leader, you as a team, et cetera. And that's part of the reason why there's resilience, because it'll be bumpy. Oh, it's so bumpy. Yes. It's so bumpy. And how many of you, I can't see y'all, but how many of you have ever watched five-year-olds play football? Soccer, sorry. Soccer. I'm a big Liverpool fan, so I've converted to football. Although, it's not going well for me right now. We have a midfield problem. But when five-year-olds play soccer, and the ball comes in hard and fast, head height, what a five-year-old does is put their foot up head height, and they try to kick the ball. And, of course, it goes off the pitch, into the pitch next door, where someone's sitting crisscross applesauce making daisy chains. You know, it's great. Both my kids played at that young age. As soccer players get more experience, what they end up doing when the ball comes in really high and fast is they take the ball into their chest. The ball drops to the ground. They put their foot on the ball to maintain possession, because the game's all about possession. They look down the pitch. They think about operationally, where is the ball? Not where is the striker right now, but where is the striker going to be? And they kick the ball to where the striker is going to be. And that set of skills is what's missing right now. You have CEOs and C-suite leaders kicking the ball at head height as hard as they can, not bringing the ball into their chest, settling the ball, taking a breath, looking strategically down the pitch. And the CEOs that I'm working with around AI that are settling the ball are coming out of their skin every day. You know, they're saying, I'm trying to settle the ball. I'm trying to take a breath. I'm trying to make sure that my AI strategies align with my business strategy. And I'm trying to make sure that my budget line for bringing the humans along is also substantial. But I'm scared shitless because everyone else is moving so fast that I don't feel like I have time to settle the ball or look down the pitch. What do you say when you're confronted with that? What's the way to help them? Because obviously the game is made up. It's moving very fast. AI is obviously on everyone's minds. Right. How it integrates their lives, their organization's lives, their work's lives, etc. What's some of the work? that you've been doing and lesson to say hey here are some principles to deal with this very chaotic fast-moving game i think the first thing is i so respect a leader who has a self-awareness to say i'm trying to pause and be strategic and thoughtful and i'm coming out of my skin the first thing i would tell you is anyone that has the the self-awareness to say that immediately gains my confidence because so much of what's happening in terms of the world today is happening outside of the awareness of very senior leaders i mean this is a call that i had yesterday about relocating supply chain because of tariffs and the leader just kept saying we need to move fast what we're looking for and this is tricky i'll be curious about what you think about this i want to see urgency i want productive urgency i want to see risk taking i want strategic risk taking it is the job of a leader today in this environment given the political instability technology changing markets i think the number one job outside of self-awareness of a leader today is to create time where none exists yeah create time where none exists and so to understand that better i had to turn to sport um there's so many sports metaphors literally the question i got from the wall street journal is did you feel comfortable putting a chapter around john keats next to a chapter called the tush push and i was like yeah dude why like i'm like do you like poetry and he's like yeah i'm like do you like football and he's like yeah i'm like shut it i'm like yeah like we we're we we can do both but if you turn to sports and you look at really talented athletes it looks like they're slowing down the ball in play yeah but they're actually not creating more time between a serve and a return or a kick what they're doing and i think this is the future of leadership is a very complex skill set of anticipatory awareness temporal awareness and situational awareness mm-hmm so the leaders today are understanding how to read what they can't see and football we'd call it pocket presence like a quarterback gets a snap breaks back he has three seconds to figure out how to move the ball down but it's a very complex group of skills that he has with his team around being able to see to be able to read a field you can't see so the question i have for a lot of senior leaders is where are you on anticipatory awareness where are you in systems thinking these are the deep thinking skills moving forward and i think that's a very important part of the process i completely agree and part of it is to realize that while it's moving very fast and you cannot create more time your fitness function is not response at speed your fitness function is intelligent response at speed right that's the difference between urgency and productive urgency between risk taking and strategic risk taking every ceo saying i need more risk taking that's like a lot of risk taking and i think that's a lot of risk taking and i think that's a lot of risk taking i was interviewing someone the other day and she said no i'm gonna get shit done a g i'm a gsd kind of person and i was like that i don't need what i actually need it's a gssd get strategic shit done yes because what you're seeing right now and i'm curious if you're seeing this you're seeing action over impact depends on the leader it does definitely happen and obviously we've introduced like five to seven questions that we go on for the next 30 minutes oh yeah but the clock it takes me 25 minutes to order a sandwich so we did pretty we did pretty good yes so as you can see amazing thanks brenny thank y'all so much thank you thanks again to brené brown for joining us at the masters of scale summit her new book is strong ground and we'll put a link in the show notes and while i have you just a deep deep thanks to everyone who came to summit not just those who appeared on stage but who were in community in conversation looking for ways to build a better future we're so grateful to all of you and we're excited to see you back in san francisco next year you masters of scale is a wait what original our executive producer is eve tro our senior producer is trisha bobita the production team includes masha makotunina our senior talent executive is stephanie stern mixing and mastering by aaron bassinelli and brian pew original music by ryan holiday our head of podcasts is the tall mullad visit mastersofscale.com to find the translation of the book and the link to the book is in the description below script for this episode and to subscribe to our newsletter

Podcast Summary

Key Points:

  1. Courageous leadership is rooted in self-awareness, humility, and the willingness to serve others rather than be served.
  2. Courage is teachable, measurable, and observable, built on core skills like value alignment, integrity in vulnerability, and self-awareness of personal "armor."
  3. Common leadership armor includes perfectionism, micromanagement, and excessive decisiveness, which can mask fear and lead to poor decision-making.
  4. True empathy has two forms
  5. Emotional granularity—accurately naming and recognizing a wide range of emotions—is critical for compassion, resilience, and effective leadership.
  6. Systems thinking and permeable boundaries are vital for organizational health, as closed systems lead to self-referencing, poor feedback loops, and AI-driven failures.
  7. Leaders must adopt "productive urgency" by pausing, strategizing, and aligning AI initiatives with business goals, rather than reacting impulsively.
  8. The future of leadership requires anticipatory, situational, and temporal awareness to navigate rapid technological and market disruptions.

Summary:

The conversation between Reid Hoffman and Brene Brown highlights the importance of courageous leadership, rooted in self-awareness, humility, and emotional intelligence. Courageous leadership isn’t about being fearless, but about recognizing one’s vulnerabilities and the "armor" (like perfectionism or over-deciding) that protects against fear. Brene emphasizes that courage is teachable and measurable, built through value alignment, emotional granularity, and vulnerability.

She distinguishes between cognitive empathy—essential for leadership and democratic engagement—and affective empathy, which can lead to burnout. A key insight is that leaders must develop emotional vocabulary to understand complex feelings like regret, awe, or grief. The conversation also stresses systems thinking and permeable boundaries as critical for organizational resilience, especially in the face of AI disruptions.

Leaders are encouraged to shift from reactive urgency to strategic, thoughtful decision-making—“settling the ball” before acting. This involves creating mental space, anticipating change, and aligning AI integration with long-term business strategy. The overarching message is that human-centered, emotionally intelligent leadership is not a luxury but a necessity in a fast-moving, AI-driven world.

The dialogue concludes with a call to action for leaders to build emotional and systemic resilience, using real-world metaphors like football to illustrate strategic patience and foresight.

FAQs

Courageous leadership combines self-awareness, humility, and discipline. It involves leading with accountability, serving others, and staying authentic in the face of uncertainty and vulnerability.

Yes, courage in leadership is teachable, measurable, and observable. It consists of four key components: clear values, integrity in vulnerability, self-awareness of emotional reactions, and accountability.

Leadership 'armor' refers to self-protective behaviors people use when afraid or uncertain, such as perfectionism, micromanagement, or being overly decisive. These behaviors can undermine leadership effectiveness.

Leaders can reflect on their own behaviors during times of fear or uncertainty. Asking trusted team members for honest feedback—especially about their reactions in stressful situations—can reveal hidden armor patterns.

Cognitive empathy is understanding someone else’s feelings and perspective, which supports strong relationships and decision-making. Affective empathy is feeling someone’s emotions yourself, which can lead to burnout and emotional exhaustion.

Emotional granularity—the ability to identify and name complex emotions like regret, awe, or disappointment—is essential for self-awareness, compassion, and effective leadership, especially after failure or setbacks.

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