How to Lead With Empathy: Claude Silver on Emotional Bravery & People-First Culture

Most leaders think culture is something you measure, but what if it's something you feel? Today you're about to meet the world's first chief heart officer. Someone who leads 2000 odd people not with dashboards, but with humanity. And what she's about to share may change how you lead forever. Welcome back to Chats with Jason, the show where we explore the stories, the strategies and hearts behind extraordinary leadership. And today I'm absolutely thrilled because we're not talking about leadership theories or culture frameworks. We're talking about the heartbeat of leadership. My guest is the world's first chief heart officer at VaynerX, the person Gary Vaynerchek trusted to shape a culture where 2,000 plus people feel seen, heard and supported. She's an award winning leader, a coach, a mentor, and an emotional optimist. And the author of Be Yourself at Work, Claude Silva is with us and her message couldn't be more needed in the world right now. So let's dive in to authentic presence, emotional bravery, and what it really means to lead from the heart. Claude, welcome to the show.

Jason, great to be here. Thanks so much for having me.

I appreciate it. And Claude, your personal journey is filled with incredible turning points. From Outward Bound to rebuilding trust in yourself, to stepping into leadership in your 40s. What's the moment that truly shaped the leader you are right now?

I do have to say two moments. One is Outward Bound. It was an enormous turning point in my life because I always knew in my heart that I wanted to be of service, but I didn't know what that was called. And at that time it was called servant leadership. I call it empathetic leadership now, but same. And so Outward Bound really gave me the nomenclature, I guess the North Star, if you will. That is the kind of leader I want to be. I want to serve people. That is me. And so it's interesting. I waited tables, I bartended, I catered, I did a lot in the service industry. I worked in a grocery store, all of those things. And if you think about it, that is all about being of joyful service, which is actually my North Star being of joyful service. So Outward Bound was very pivotal. And then everything I did after Outward Bound, as jobs, before I went into the corporate world, really gave me more and more of that understanding of how do you want to make someone feel you're serving them food, you're giving them a drink, you're bagging groceries, how do you want them to experience this moment? And that was really powerful for me. The next moment was really, when I did move to London, when I was almost 40, I moved to London not knowing anyone. Left a great life in San Francisco and restarted in many ways. Not that I thought about, I was restarting, but I was transferred there. They asked for me to come there. I put on different shoes, I will say I put on brand new shoes. When I walked in to that whole experience in London, I had a very different skip in my step, I think because everything was new and I got to try different things, techniques, different ways of connecting with people, mentoring, unofficial mentoring, those types of things. So those two big moments for me were really shaped the leader I am today. And then of course my nana, who I speak about in the book, My Nana, My Heart, she would leave every interaction she had, buying groceries, buying flowers, going to the bank and she would literally say to the cashier, would you do me a favor and have a peaceful day? And I thought, wow, here's this 95 year old woman, 98 year old woman, she doesn't have to do that, but she did and that made all the difference. How we make someone feel to me is the end all be all.

So I was just thinking how beautiful that is. It resonates with me because I learned so much from my grandmother as well. And it's amazing to think how they show up despite living in some of the most challenging times.

That's right.

Recent. When I say recent, in the last hundred odd years.

Yeah.

In your work you talk about, say emotional bravery and that the most powerful part of emotional intelligence is emotional bravery. What does that look like in real moments of feedback, in conflict and uncertainty?

Yes, that's really the question because it actually is used in those moments of adversity, feedback, uncertainty, where am I, where do I stand? Emotional bravery is really understanding that you have the agency and the power to take action on anything you want. And so if you received negative feedback from your manager, doesn't feel good, right, you're going to go home, think about it, you're going to feel terrible, all of that stuff. However, tomorrow you're going to wake up and you're going to say, you know what, I'm going to go ask that manager if they'll give me 15 minutes because I'd really like to talk to them about these two points. Taking action even though you're shaking in your boots, even though because you're emotional, you have emotion, but it's doing something with it rather than wallowing in your emotion, rather, oh, woe's me. And being a cynic and then leaving the job. It's actually saying thank you so much for that feedback. It was a hard conversation. I'd actually like to double click into those last two points you made because I disagree. I see things a little bit differently. And that is amazing. You have then shown yourself confidence, courage, bravery, admits amidst a hard conversation. And that's really, I think, what it's all about that is really using all of your eq, emotional intelligence skills and also emotional fluency, the ability to speak human, and sticking up, advocating for yourself.

What's one thing that can help someone step into that bravery? I absolutely agree that it's absolute powerful step to follow up on that feedback that perhaps hurt or cut hard, but what's one step they can take so that they can actually build up that confidence, that bravery to take that step?

Yeah. So the first thing is really to understand why it affected you. So yes, it affected you because they said you, you were not going to get a raise or a promotion. Okay, but what's under that? Why did it affect you? Did it trigger you? Was it like growing up in your household? You have to have self awareness in order to feel your feelings, Right? Otherwise you're feeling feelings that don't really live anywhere. But most of our feelings are rooted somewhere deep inside of us. When I was 3, when I was 7, when I was 20. And so to understand why you feel a certain way, where it's coming from, that is 80% of the challenge. And it's not easy because you have to do some work on that. You have to figure out, gosh, why does it affect me so much when someone interrupts me, hmm, that happened at my dinner table when I grew up. Why does it affect me so much when someone raises their voice, those types of things. And so once you have that self awareness and you know where it comes from and where it lives, then you have the choice to show up as a victim and small or large, and take up space because you own it. The emotion doesn't own you, you own, own yourself. And that's what you need to do. Whether or not it's bad feedback, whether or not someone cuts you off on the freeway, whether or not you just have a bad first date, you have every single right to advocate for yourself. Especially if you're coming from a place of knowledge, self knowledge, and also a place of good intent, positive intent.

I think that makes the difference is the space in which you're coming from. And if it's from a positive place, then it's likely to lead to a positive movement forward. Yes, whatever that might look like in the situation at the top of the show, I introduced you as the world's first chief hard officer. For someone hearing that title for the first time, what do you actually do in the role?

Yeah, I love it. Let me tell you what my boss, Gary Vaynerchuk, Gary Vee, as some people probably know him on social media, told me when we came up with that role together. I asked him, how do we know if I'm successful? Because there is no job description. So this is ten and a half years ago. And he said, you will touch every single human being and infuse the agency with empathy. Okay, we were 400 people then we're 2,000 globally. How am I going to scale that? That's the first thing. How am I going to scale that? I know what empathy is for me. I know how to teach it. Empathy is an emotion. The action is kindness and compassion, which we learn at 1, 2, 3, 4, 5 years old. Right. We're always learning that. So I had to figure out who could scale that for me. That was already in the building that I knew had a similar belief in human beings as Gary and myself did, that saw possibility, that trusted first, that believe that people come at things with a positive intent rather than they're not cynical because they have nothing better to do. They're cynical because they get hurt. So I had to find people to scale it. And then eventually I built a team. And I had never done HR before. I built a team, we call them People and experience, the People and Experience team. And so I could rely on them as well to be HR business partners, as you would call them, most likely. So how I spend my day, every day is I have a lot of one on one meetings. Sometimes people come to me, they might feel a little fragile, they might feel a block, they got bad feedback or they just want some personal high potential coaching. So that might be. Or I'm reaching out to them because I've never met them. I can see that there's some smoke in the distance on the account that they're on. I've heard that this person really isn't showing up well at work or not doing their work or expecting other people, whatever it is. I'm looking for patterns as I listen to people doing a lot of coaching, trying to figure out what their imposter syndrome is so that they can then take authority over that. I'm meeting with teams really trying to figure out like how is the team gelling? Are they not gelling as they're fighting where Is that coming from what Global strategies. I oversee everything that has to do with people. So whether or not it's recruiting or benefits or culture or learning and development, everything that you can imagine. And so I have my finger on the pulse of what's going on in Singapore tomorrow. Okay. I know that they're going to be doing this training. I know to slack them before I go to sleep in the night when I'm in New York and give them some good vibes for tomorrow. Those types of things. When someone is hurting in another office or going through a devastating thing in their home life, I can slap one of these culture champions that I was talking about and say, you know what? I heard that Robert is really going through a hard time with his dad in the hospital. Do you mind checking in on him and maybe taking him for a coffee? Those types of things. So Gary would say, I set the emotional framework for the company. And I would say, yes, that is very true. And I'm also the emotional barometer. Being an empath and intuitive, it allows me to have one conversation with someone and understand the vibe and understand the atmosphere or the environment in which they're around. So I do a lot of listening.

Yeah, yeah, absolutely. I get that. And I'm just thinking about the foresight that Gary had to value a role positioned like it is. It's not something that you would see structured like you are in most Fortune 500, that's for sure. It'd be much more clinical, at least in my experience. The other, perhaps challenge or gift, depending on really which lens you look through.

The.

The founder, the head of the company. Gary Vaynerchuk is no shrinking violet. He's. He's everywhere and anywhere and is somewhat opinionated. You could say he has achieved a lot. I'm not taking any of that away from him. How does that play out day to day in the workspace where you've got all these. Like you said, you're the emotional barometer of the organization. How. How do you keep everything at the right level?

It's not just me. Every single person that is in the agency, in the four walls is responsible for the culture, not just Claude. And together we're all cultivating that culture day in and day out. And I need everyone to take part in it because we are the microcosm of the macrocosm. I need diversity. I need a. A workforce that looks very different than you and I necessarily. Right. And so all day long, I'm listening not only to people and dissecting patterns, if you will, but I'm also listening for the chatter on the floor. I'm watching people get up and collaborate together. I'm really, in literal times, I'm watching who's sitting in a room like this or who's sitting with. Walking into a room like this. Right. Because the experience that we are giving people is noticed by everyone, whether or not you're a leader or not. And so in terms of being the barometer that those are things that I look at all day long, just notice little things. Who, this is ridiculous. But who puts their dishes in the dishwasher or who just leaves them for someone else to clean up. Simple things like that. Who pushes in their chairs or. Or who just leaves them out in the middle of the aisle way there. So Gary and I are on text. I'm talking to all the C suite. I'm figuring out from the department heads, like, how are things going? And not only how are things going internally, what are the clients saying? Do the clients find value in the project management team? Do they find value in having creators that know how to edit video? Do they want to do incremental work with us? Will they sign on for next year? So I'm always trying to figure out not only what's happening behind the scenes and with the people, but what's happening on the floor when they're talking to their clients or trying to pitch an idea and, you know, and dealing with working 17, 18 hours a day for the last week.

Yeah. I really appreciate the sense that culture isn't a department's job or an individual's job. It's not a poster on a wall. It's something that we're all responsible for. It brings me to the question around what do you think the biggest myth leaders believe about people first cultures, and what's the truth that actually drives the performance?

I think the myth is that culture is soft. I think the myth is that anyone that has high EQ doesn't have high iq. The myth is that why do we need, why do we need you? Like, you're not a driver, you're not a, you know, you're not a salesperson, you're not hitting numbers like that's a myth. Because everything I do has a way of feeding the bottom line and the top line. I believe everything everyone does or else we wouldn't have those roles. Right. You know, Gary's way too smart to have a lot of fluff in the company. And so that is the biggest myth, which is it's soft. Top down leadership is where it's at. You do what I say. You speak when I tell you to speak. And you do not, without a doubt. You do not show your emotion in the workplace. Those are all myths. And what we're missing when people set up their companies like that or say those types of things is you're just missing out on the human. And to miss out on the human is you're missing out on all my creativity, all my curiosity, the fact that I am very good on picking up from other people. You know, you're missing out on what actually runs an organization, which is people. And people have hearts. And organizations need those hearts and those minds to push forward. Everyone wants speed. Everyone wants to be faster and faster. Now, yes, AI can do a lot of that. But you still need the human being who's going to create and program it and then go sell it to a.

Client, and the human to put the heart into it.

Oh, yeah. Without the heart, you're getting half of me. And how do you know if that's the right half? You want me to be an emotional creature because we are emotional creatures. You don't want me to spill my emotion and spill my chaos everywhere. No, not at all. That's not what I'm saying. But I would like people to feel like they can show more of themselves, the real selves in the workplace. And they don't have to hide, they don't need to protect themselves, and they don't need to shrink, because shrinking does nothing other than reduce your ability for progress.

Couldn't agree more. So in your book, Be Yourself at Work, you're introducing emotional optimism, emotional bravery, and emotional efficiency. Which pillar tends to transform leaders the fastest? And why do you think that is?

I think there's something to be said obviously about all of them. But the emotional optimism piece is really. That is where you see possibility, that is where you see motion, that is where you see belief. If you can see something as it's not happening to me, okay, so I got bad feedback, and I'm upset and I'm sad. I'm not a sad human being. I'm having a sad experience that really shocked me. But the amount the emotional optimism piece is knowing that the sadness is going to come and it's going to go first and foremost, and that I, whether or not I do it on my own or I get help from my therapist, my support team, my coach, tomorrow's going to be a different day and I can go at it in a different way. And so it's having that ability to see, okay, it might be dark Right now. But it's not going to be dark forever. And I'm not alone. Having the agency to then find that bravery inside of you and say, you know what, boss, I disagree with two of those points. Can we sit down and chat about it? But I do think the ability to see possibility as an entrepreneur will is really where leaders need to hang their hat on. And then of course, they do need to take action. I want them to be able to see what's in front of them and see themselves as I can do this, I can do this. With help. You can do this. I'm going to be here for you. That type of stuff.

Yeah. Appreciate the. What opens up when you consider what's possible versus what's happened and why. Taking that negative lens.

Yeah. Jason, just to say a little bit more on that, the emotional optimism is the same thing as yes and yes, I got you. And I'd like to still talk to you about that feedback. Yes. Client, I see that you just want me to stay in this lane and I would like to talk to you about widening our scope a bit. That's all. Yes.

And I love that. Makes me want to go and do another improv class. But what great framing there. 2000 plus employees. Obviously I'm assuming a multi generational workforce. Remote. Perhaps not at GaryVee, but certainly in other companies. Burnt out and constantly disrupted. Yep. How do we create a sense of belonging and connection in. In these organizations now that aren't all housed in one office that everyone goes to nine to five.

Yeah. That's the biggest question for all of us. And everyone's experiencing whether or not it's burnout or they're getting very crispy. It's just the nature of the speed in which our world goes now. It's this and being always on with our phones. So what I would say is when you're on a screen and when you're in a room zoom or in a room, you want to create psychological safety. You want to create a safe environment. And what that means is that A, I'm paying attention so my phone isn't in my face, B, I'm aware if it's on a zoom that there's an introvert over there in the corner that never says anything. And so I am going to ask him or her to share. Do we want to hear from her or him? What we're trying to do here is psychological safety. Basically says I belong here. And. And it's safe for you to speak up here. It's safe for you to share Your ideas here, no one's going to pounce on you because that's what we're afraid of. Right. And so if we can create that safety, then we can create this kind of connection. I'm going to work with you. Oh, we're partners on this project. Then you develop trust, and then you feel like, I belong here. Human beings are wired to belong. We are wired to be in community with one another. And you have to feel that trust. Someone's not gonna tell you my entire life story if I don't know you. And also if you haven't shared with me, too. And that's the piece with leaders that we cannot expect people to be vulnerable if we are not vulnerable with them. The younger generations are way too smart right now. And Gen Alpha and Gen Zed, they are the ones that are saying, listen, I don't want your burnout culture. I don't care about your speed. I want to be respected and I want to do work that is meaningful in this world. If I can get that here and not burn out, then you have my. Here you go. Let's shake on that. You're hired. And great. But right now we're in this conundrum where there's so much fear in the system, whether or not it's in my country right now with the administration and all of that stuff. AI obviously has created a lot of fear. Technology, the speed in which we go. It's a big responsibility for leaders to try to dispel the fear, and not in a toxic, positive way, but in a real way by talking about it. Hey, guys, gals. I know AI is here, and it's scary. I know that there are people in this room or on this call that feel like their job is going to go away. Let me tell you what our plans are for AI and how we're going to use it at our company in 2026. Cool. Thank you. Oh, I'd love to know. It's just called being transparent and being a great communicator and not leaving things to. Not chance. I mean, listen, we make up a lot of things in our head when we don't know the truth. A lot of things. And now those things are scary.

Not only scary, but they lead to poor outcomes.

Poor outcomes? Anxiety up the wazoo. Yeah, well, performance. And then what? They go out on a medical leave and then you're really in trouble because then you don't have that body.

Yeah. And it starts that ball rolling down the hill, collecting moss. You need to nip it in the bud. I think what we're seeing now, more so, and I'd love your take on this, as our workforces become more diverse in every sense of that word, generationally, ethnically, socioeconomic backgrounds, locations, et cetera, the key for transparent, timely communication is paramount. It is a driving force behind the culture, even of Christmas.

Yeah, absolutely. We are, to your point, working on different time zones. I've mentioned the speed already in different cultures where we don't speak the language, we don't know of their, the ceremonies or their religious events, all of those things. And so the most important thing is to go in, be present, be mindful of this person in front of me has a life that I know nothing about and they started their day in a way that I know nothing about and, you know, have no idea how I started my day with my children, the dog and this and that. So we need to give each other some kind of grace. That how you open your laptop at 9am and when it's 9pm in Singapore, to be very different. You've already worked an entire day. It's dark out, you're exhausted. I'm just having my coffee. Right. You have to be mindful of these things and I don't think it's difficult. You just have to put it here in your head and your heart. Here's a human being who's 15 hours away from me right now. Jason, you're starting your day and I'm ending my day. Very different realities.

Yeah, yeah. So if a CEO or a leader has been listening along with us today and wants to start bridging the gap between operations and humanity, what's one operational decision that they should rethink through the lens of heart led leadership?

Yep. I'm really glad you asked that because things can be overly operational and then you just lose all human touch. So what I would say is, rather than rolling out that next process or that next dashboard, bring people together and talk about it. Talk, don't even show it. Talk about it. This is what we're doing. Get human about it. This is why we created the dashboard, because it's going to save three hours on the project management team. Just get real. Don't let the operational process speak for you. That is what I would call lazy. Use your voice. Use the position that you have to make people feel that they matter and recognize them enough that you're willing to take an hour out of your day to speak to them. And that's what we need to do more of. We need to basically show our stripes, just like we're asking everyone else to show their spots and stripes and whatever. Right. Otherwise, people are going to continue to be in fear, continue to shrink, and then you will not have any kind of retaining of top talent. They're going to bounce and then you're going to have to spend money to hire.

Makes perfect sense to me. So it's been an absolute pleasure, Claude, to be with you today. As we come to close out the time together, what's the one thing that you want every leader listening today to remember about leading with heart, even when it gets messy and uncomfortable and even uncertain at times?

Yeah. What I would say is, as leaders, we are very important in putting our fingerprint and our heart print on this culture. People are looking at us all day long. And so we actually are big parts of the culture. What is it like to work with me? What is the experience I'm giving people? Ask yourself that. How do you know? How do you know? Because you might not realize that you walk into every meeting with your phone in your eyes, in your hands. What is the experience? How do I show up? And is there any possible way I can show up a little bit brighter tomorrow?

Yeah. It's being aware and curious about how I can be better myself. I'll share a quick story before we wrap up. Very early in my leadership career, I was working in an open office environment, and my team was split across multiple rows of desks. And I would walk in and I'd say, hi, team. Hi, team. And then the closer I got to my desk, it would be, hi, Mary. Hi, Bob. Hi. Hi, John. Using their individual names. And I had a team member, one of the leaders that reported to me who I, to use your language, showed emotional bravery and came up to me and said, in a safe space and said, do you realize what you're doing every day when you get to worse? And I'm like saying hello. And she's, you're saying hello to some people and just giving a glance. Or he might as well just wave your hands and keep on moving to the majority of your team. And that I was just like, she's absolutely right. It wasn't my intention. No, she's absolutely, absolutely right. And I'm not saying I got it right every day after that conversation that has always stuck with me, that she had that bravery to have that conversation.

Yes.

And I think it absolutely changed the way that I showed up in front of people because it is so easy just to get in your head and into your habits. So I would definitely encourage anyone listening today, regardless of what level of the organization you're in. Just show up, be curious and show demonstrate that emotional bravery that we've talked about today. If you want to learn more about Claude's work and her latest book, of course there's going to be links to that in the show. Notes. I can't recommend following Claude's work strongly enough. It's fantastic, Claude. It's been great having you on the show too, Jason.

And thank you for sharing that story. That's really impactful. I appreciate it.

Appreciate you, Claude. Thank you for bringing your heart, your wisdom and your presence on the show today. Your work reminds us that the future of leadership isn't more automation, more it's more humanity. And to everyone listening, remember, when you transform the experience, you transform the business and the world around you. I'm Jason S. Bradshaw and this is Chats With Jason. See you next time. Hey, just quickly I wanted to reach out and say thank you for taking the time to listen to this episode of Chats with Jason. I'd really appreciate a five star review on your favorite podcasting app. Or if you're watching along on YouTube, give me a thumbs up and show that you like this video. And be sure to subscribe so that you don't miss out on the awesome content and the great guests that we've got coming up for you.