Leveraging Thought Leadership Live featuring Claude Silver
In this LinkedIn Live interview, host Peter Winick, founder and CEO of Thought Leadership Leverage, sits down with Claude Silver, VaynerX’s inaugural Chief Heart Officer and author of Be Yourself at Work. The conversation traces Claude’s journey from the early days of VaynerMedia, where her office was designed like a therapist’s space, to the development of her book’s core philosophy: embracing one’s “messy self” and showing up authentically at work. They discuss how workplace norms have shifted from the pre‑COVID expectation of “checking emotions at the door” to a new era demanding psychological safety, emotional optimism, and courageous conversations about pronouns, sensitivity, and dealing with jerks. Claude explains the experimental culture at VaynerX that allows her to test heart‑focused initiatives, and she outlines the metrics she uses to gauge success beyond book sales—language adoption (e.g., “emotional optimism”), curriculum rollout, and the ROI of kindness. The interview also delves into the creative process of writing the book, the importance of storytelling, vulnerability, and designing exercises like the “lie exercise.” Finally, they envision a future where employees shed the “armor” they wear to work, become more emotionally fluent, and where both bottom‑up and top‑down efforts reshape organizational culture.
Chapters
And welcome, welcome, welcome. This is Peter Winick. I'm the founder and CEO at Thought Leadership Leverage, and you're joining us on this LinkedIn Live edition of our podcast, which is Leveraging Thought Leadership. And today my guest is an old friend, old like, but an older, an old friend, Claude. I'm going deeper into that hole. Claude Silver. So I'll give you just a quick intro on Claude. She's on a mission to bring more heart and humanity to the way we lead at work and work. And she's the world's first Chief Heart Officer at VaynerX, which is GaryVee's company. She partners with Chairman and CEO Gary Vaynerchuk to build workplaces where people come alive and where they feel safe speaking up, proud to belong, and driven by real connection. And her book is Be Yourself at Work: The Groundbreaking Power of Showing Up, Standing Out, and Leading from the Heart. So there is the book, which is coming in a little flashy. But, um, welcome aboard, Claude. So here, I'll take you down memory lane. So I remember it had— it was pre-COVID, like, yeah, or something.
'17. It was probably '17.
Yeah, it might have been. Yeah, first time you and I met in person, I go to your office at the fancy Vayner offices, which are like in the, in the coolest part of the city. And then you're not the first HR person's office I've been in, so you have a preconceived notion of what this will look like. And I walk in, I'm like, wait, I'm in my shrink's office. It was very, um, you know, Dr. Melfi, if you will. I know that I was Tony Soprano, but it like just a couple chairs, just chill and relax. I'm like, oh, that kind of sets a tone. And we just had an amazing, awesome conversation.
So yeah, that's what it's about. It's literally— I didn't want any desk in my office. I didn't want a separation between me and anyone else, and I wanted people to be able to come in and feel warm and like they could chat about anything. And plus there's that killer view to— yeah, down to, uh, the Hudson.
Yep.
Um, it's very peaceful, very zen, and, and, uh, I would say very me, actually.
Yeah, no, it was, it was totally cool. And then we chatted about you maybe one day possibly maybe thinking about kind of sort of Maybe there's a book, something like that, in me. And then here we are, slow forward, not fast forward, 7, 8 years later.
Oh my gosh.
And, and I, I just finished it, uh, the week before last. It's a great book. So I, I, uh, and I don't say that, um, but this concept of being yourself at work when we're living in a world where, well, that at-work thing needs further definition because that meant something else. pre-COVID, we all know what that meant. And then being yourself is, is not another thing.
What a concept.
Yeah. So tell us about— I mean, where did the concepts come from? And then what's— yeah, how did it come to be?
Well, you know what, I originally, I wanted the book to be called something like Show Up as Your Messy Self. Something like that.
Okay.
Of course, I wasn't going to put the word messy in a title, although I talk about it a lot in the book, as you know.
Yeah.
What I meant by messy was like your real self, the person that has emotions, the person that has good days, bad days. The dog gets sick, the kids throw Cheerios on the floor, you get a flat tire. The real, real. And that's to me, I think, like we all need to— I'd like us all to acknowledge that We're not in— there's no perfect package here. There's no utopia here. Like, you know, we all have a life and our life can be busy, messy, whatever.
Stay there a bit because you and I are both probably the same age, Gen X, whatever. Um, and I mean, I literally remember in the late '80s, early '90s when I was first working that it being said out loud, you know, check your S at the door. Like, we own you for 8 or 10 hours. Yeah, I don't care if your dog died, your mother's got cancer, like, don't care. Check your shit at the door and you do what you do, right? And it was like, and that was the world we live in. Now, there were exceptions to that because you had mentors, yet you found your people, you know?
Of course.
But that was really the vibe. That was really the— oh yeah, is, yeah, we own you for now and Yeah, we don't want to know about—
really don't really want to know about your life. We definitely don't want to know about your problems. And like, we really don't want to know if you have therapy. Like, and now the world has changed, whereas like, I know everyone has a therapist, you know, they're leaving at 3, they're leaving at 2, they're leaving.
Yeah.
Whereas like, God forbid I had to leave the office at 4 o'clock back in 2006 for a dentist appointment, you know, I would pray to get one after hours. I would, you know, you just wouldn't talk about it.
Or they tell you, she must, she must be going on an interview. She's unhappy. Like, exactly.
Or it's like, oh, half day, you know?
Yeah, yeah.
Right. Which is like, so mean to someone now that we know, like, what really happens. Like, people have doctor's appointments, people have— people have— so yeah, you and I grew up in a place where it was literally like, we don't want to know.
Just part of the I would imagine, and I'm just thinking out loud here, that the book resonates easier, or it's easier for the book to resonate with a generation beneath us.
Yes.
And the struggle that we have as leaders and managers at our age is, wait a minute, you're changing the game on me. The boundaries keep changing. And what can I ask? Mental health in the workplace and psychological safety. And can I say this out loud? You want to be helpful, but you don't know where those borders and boundaries are, whether Pronouns, there's so many things, and you want to be good and you want to take care of your people, but you don't know, like, where's the playbook?
Yeah, I mean, that's the thing. Like, I was actually just talking about that today with someone that I want to bring in to do some sensitivity training. I, I, I'll call it something different than sensitivity.
Yeah, yeah, yeah.
But really, like, real talk. Like, yeah, I don't know what to call that person, or what do I do when I overhear someone use that word with that person? Like, yeah. Or someone asked me if I've lost weight and I'm uncomfortable, like, right, the whole gamut. And we haven't even, you know, and I'm not even talking about the color of my skin, the color of the—
Right, right.
Everything. So we're actually— it's like so on my mind because if we don't do something about it and have real talk and real talk, courageous conversations, name it what you will, yeah, we're gonna continue to fumble over ourselves. in our culture, and I'm just talking about the culture at VaynerMedia, will start to erode in a bit because the environment gets so affected when, you know, when there's a chip in the armor, when there's a chip.
Yeah. Yeah. Well, and when you're not, you know, I mean, I think the flip side of being yourself at work is not not being yourself at work. But what if yourself is a jerk?
Well, that's the thing. If you're— that is where the culture has to be able to Police and tissue reject. Yeah, literally it's tissue reject. It's like, is it okay to have a-holes here? Is that like— do you have that gung-ho, like, you know, charge? Or we're lucky, like Gary's an absolute gung-ho charge, but there's no a-holes, right? So what happens if there are jerks is that gets surfaced. And we talk about it. If it's something, if I'm doing that conversation, it's like, hey, I just want you to know that attitude's a real vulnerability for you. You're such a high performer. However, your attitude really stops people from wanting to be with you. What are we going to do with that? That's how I have that conversation or how I would hope leaders have that conversation. Because having jerks and a-holes is not It's not conducive to the environment that I certainly want to be in, and it doesn't make me want to work any harder.
Right. And that's different than, I think, than, you know, and you speak about this a lot in the book, everybody's got bad days.
Everyone's got—
so we're not going to judge somebody on the one day they came in cranky or—
No, it's a consistent— if you consistently are interrupting that You know, constantly in that meeting, every, every single meeting, if you're interrupting, you need to be heard so badly. We need to talk about that. Yeah, that's subtle. But that's, you know, to someone else, that's death by a thousand paper cuts. That's literally, okay, I can't really name it. But when this person's in the room, I know I just feel small. Oh, that's because you're being interrupted every time. Makes a lot of sense to me. Yeah.
So I want to talk a little bit about your journey, and it's early in the process as a thought leader. So you've got a very demanding full-time gig, to say the least, right? Yet you said, I'm still going to do this because writing a book is not easy, promoting a book is not easy, etc. What, you know, what either insanity or passion or some combination of both said, I, I got to do this and I want to do this and here's why?
Yeah, so about 10 years ago, so before you and I met, I had said to Gary, you know, I want to write a book.
Yep.
I told him in particular because there's no one that holds someone more accountable than Gary. And I couldn't just be like telling my best friend because my best friend will let me off the hook, right? So I told him I knew I wanted to write about heart in the workplace. That is what I knew. And why did I know that? Because when he and I were just before we drummed up this role, this title of Chief Heart Officer, I said to him, because I had been working there for about 16 months, like, hey, this is great. I just don't want to do advertising anymore. And he said to me, all right, well, what do you want to do? And I said, I only care about the people here. I care about the heartbeat. So I always knew I was going to write a book about the heart in the workplace, humanity in the workplace. And I knew that even prior to Vayner, I had amassed so many learnings.
Yeah.
And I'm getting old over here. And so it wasn't until COVID hit where I had thinking time, right? I had time to start to think. I hired an agent, and I just like—
Yep.
I just word vomited everywhere, and we started to get to a formation of something. And then, you know, and then I started and stopped and got, you know, insecure. I have nothing new to say, and this and that. And I'm like, well, God, I don't know if there is anything new to say, but the way I say it Is going to be the new part, right? Like, I'm not saying—
The way you say it and then the vulnerability, right? Because a lot of people can get out there as the expert or the academic, or I'm the head of it, you know, like, here's all my accolades and I went to Harvard and blah blah blah blah blah blah blah. But you sort of go the other way, right, and say, here, here's my— here are my warts and all, here's the stuff that I did, the good, the bad, the ugly. And then whether I can relate to those specifics going off into the wilderness or whatever or not isn't really the point. It's like, yeah, we've all got those stories, you know. Why do we— like, those are swept under the rug because now I'm, you know, like a rock star in corporate. I don't talk about that. And I think just setting that tone is pretty cool.
Thank you. I really— I appreciate that. And I mean, you've known me now for a while. It is definitely what you see is what you get. I want people to feel comfortable Yeah. Around me for sure and safe. And when they read that book, I didn't want them to feel preached at. I have nothing to preach. I have nothing to preach and maybe not anything to teach. But what I can say is, listen, it's tough in the workplace right now.
Yeah.
It is tough no matter how you slice it. Most importantly, you want to get yourself right. You want to get to know yourself. You are the CEO of you. It's one of the first chapters. Know that. And then because you know that and you have self-awareness and you're working through your imposter syndrome and the lie exercise, take that into teams. Be your best self in teams. Don't shrivel, don't shrink, don't do the things you used to do. You just did this entire self-awareness journey in the book or through the book. Like, yeah, I want you to show up strong. I want you to show up and be like— and take up space. And that— Looks different for each and every person.
Yeah. And what's one of the things that's interesting about that is, you know, you don't come up as a typical HR head of HR at a, you know, fast-growing whatever, because there's sort of the stereotype of what that might be, right?
I mean, I didn't do HR at all. I stayed away from HR, right? It was a— it would have been a crème de la crème job for someone like me who loves psychology, you know, who studied deep psychology and spirituality, but I stayed away. No thank you. I don't want to do that.
And then I think the other thing that's interesting is having a real organization to, to use and experiment. This isn't just theoretical. And then what, what struck me early on in, in getting to know you is there's this brand of Gary that's just so big, right? And his personality and his drive and his, you know, grind and hustle and all that sort of stuff. And not that I would say he comes across as heartless, but you don't think of heart in that. You just think of like, wow, this guy's a— he's up 24 hours, he's up at 3 in the morning and he's doing this, like, and he's working, working, working. The immigrant story, like, all this stuff. And then you're like, wait a minute, he created this or supported this chief heart officer? Like, did somebody get him on an off day? Like, how did that happen? But it makes perfect sense because I see there's a yin and a yang to you.
Yes.
Yeah.
Yes. And there's a difference between Gary Vee and Gary Vaynerchuk. Yeah, I work with the human, not the brand. And the human couldn't be more empathetic. The human couldn't be more what you see is what you get. This is me, you know, like, and that, and I love that. I wouldn't be able to just, I wouldn't be able to work with someone that didn't acknowledge how important this work is. And he does, and he blesses it. And thus—
Sure.
We do, we do it right. Um, so I'm, I'm extremely lucky, and through that journey I'm able to, you know, find patterns, see what's going on, see like, wow, that person really could use some training or some coaching.
But I think there's also a culture there because it is still startup-y, even though it's not—
there is—
yeah, try new stuff as long as it's not a bet the house, and if it doesn't work, it's an experiment. And we learn and we move on. Where you get to the Fortune 500 and the level of experimentation is close to zero. It's like, if we could be 0.10% better on our retention this year, it's like, oh my God, there's purgatory for me to even think about that.
Yeah. And so what better place, what better fertile ground? It's a playground for me to do this, for me to play, to experiment, to bring different things in. Just like it is for us to go, you know, we're gonna start something with collectibles because Gary really believes in a collectible market. Well, I don't know anywhere else that's doing collectibles. We're gonna give it a shot. If it fails, it fails. We learn. If not, super.
Yeah, very cool. So let's, let's assume it's a year from now, right? So the book's been out, it's, it's a smashing success, blah blah blah blah blah. Um, what's— how would you other than book sales, because that would kind of don't matter.
Yeah.
What are the metrics? What are the things that you're looking at that would say, yeah, that was a success?
So this is, this is so great that you're asking me because without the book, I've seen this happen on LinkedIn. So yeah, phrases that I use. Yep. For example, slides that I share, whatever, that nomenclature has been used. Emotional optimism is something I started saying probably 8 years ago. Um, and it came from a conversation that Gary and I had where I, where I, we put those 2 words together. And I see that used all the time. It's a hashtag that doesn't belong to me anymore. Right. On, on, on—
So stay there a minute, because I think that what's beautiful about that is people, you have to realize as a thought leader, yeah, there's a personality, there's a brand, there's a human that created this, obviously, but the way to get to get it spread is a function of the models, the methods, the frameworks, the language, the definition. We think about words like emotional intelligence. You mentioned imposter syndrome. These are all things that came from different streams of thought leadership. When we start trusted advisor, like, I can give you—
Yes.
Oh, we know what that means. But it's like, wait, where did that come from? Holly Green from 25 years ago.
Yeah, it gets in the zeitgeist. It gets in the water.
Yeah.
If it makes sense to people.
Sure.
Thought leader, advisor, those things make sense if you think about it, if you just break it down to what it is. So, so anyway, back to that, you know, I started seeing that happen probably about 7, 7, 6 years ago, and things were being replicated that I had said and whatnot, which is always a wonderful— It's a great feeling because I know it's sticky and I know I have so much heart and integrity in what I'm saying that I just want it to be used in the same way. Obviously, I have no control over how someone uses it once it's out of my hands. But so for the book, I would love principles of the book, whether or not it's the 3 E's, whether or not it's the lie exercise, whether or not it's the 7 rules of team citizenship, XYZ. I would love to start seeing that more in the zeitgeist.
Right.
More teams talking about it or me seeing it more like living and breathing. And then, um, you know, one of the next things I plan on doing is, um, is rolling out a curriculum, right? And what I'd like to do is roll out a curriculum to both train the trainers, right? Give this to someone.
Yep.
And also, you know, an easy online curriculum if someone just wants to do the lie exercise because they're going through imposter syndrome right now.
Right.
So that, that to me would equal success because Um, then the work is proving itself.
Well, I could see a point in the not too distant future where it's this combination of bottoms up and top down, meaning somebody came from a place like Vayner, right? And when we did things here, it was different. I didn't know that— maybe I was 25 and didn't really know much else, right? But it felt different. And here's why that was great. And then top-down going, all right, we do need to rethink the way we're doing, you know.
Yeah, that's totally— I love that. That's totally, uh, that's exactly what would be great, which is, yeah, in those early ages, it's not that we're sleepwalking. We just want to prove ourselves so badly, right? We really, really do. And you can tell that something might be a little bit different here because your roommate hates her job and her— and, you know, and she complains all day long that her manager is whatever. And that doesn't happen to me. I'm really happy. I go into work and it's like I actually learn something every single day. And then, yeah, to be met with the sandwich of like— and as a leader, I changed too. I changed as a person through this because the book is Be Yourself at Work. You and I both know, and you know me well enough to know, it's be yourself. Yeah. Dot, dot, dot. I just happen to work and I have that as my playground. But what we're talking about in the book is all just emotional fluency. It's just speaking more human. That's all.
Yeah.
What holds us back from it and what propels us forward. We need one another to do that right now. I think that we know that society in the world is in a very different place than it was in Pre-COVID, and certainly when you and I were, you know, getting up there. So, um, there's a lot of anxiety, a lot of fear, a lot of AI is going to take my job, you know.
Sure, especially in the creative profession, a place like you.
Yeah.
So one of the things that, that was interesting to me about the book was some of the stuff that's not in it. And what do I— well, there's lots of stuff that's not like— but what I mean by that, oftentimes sort of people try to put together forensic data to validate their case.
Yeah.
And I, I had thought maybe getting into this book, like, oh, and there's going to be a little— a lot of dropping data around retention, productivity, turnover, blah, blah, you know, the stuff that one would think HR speak, which sort of this faux data metric. Sorry to my HR friends, whatever. But it was kind of interesting to me. There wasn't a lot— wasn't any of that there.
No data.
Really writing to the individual.
Yeah.
not to the C-suite, not to the whatever. So my question is, talk about some of the proof points of this isn't just the right thing to do, or good thing to do. It's actually good for a business, not just the people in there.
Right. And so those are the KPIs that I can— I'm sorry, the KPI, the ROI, whatever I can give at any day. But I didn't want a book. I don't want to open up a book necessarily and get data thrown in my face. I would rather research the data. I would rather, rather ask for it. That's just the kind of person I am. If it was a data book, it would have looked very different.
It would have—
the title would have been different probably too. There are experts out there doing that all day long. Amy Edmondson, she's got a lot of data, right?
Yeah.
Susan David, she's got a lot of data. Simon Sinek, a lot of data. What— I'm not a data junkie. I'm not a researcher. And, you know, yeah, I can pull in data that's already there that's in Gallup and McKinsey, which I have tabs open on my computer. But at the end of the day, the only data that I really care about, which is something that we are getting closer to quantifying, really, is the ROI of being kind at work.
Yeah, that's— I mean, that sounds great. But it also doesn't sound easy. So a couple things.
It's not easy.
react to that is you're eating your own dog food because you're not a data person.
Yep.
Not peppering the book with data because some publisher said, oh, it'll help it sell and, you know, get it into the C-suite, throw in some numbers and blah, blah, blah, blah, blah. Um, so I think that's really, you know, um, aligned with the values of the book because sometimes people write a book and they get into this headspace of, I am author, author means this, I have to be like, um, You know, so being yourself, being an authentic person, you know, and I get to meet lots of these folks. And it's interesting, in some instances, they wrote the book they needed to read. Yeah, it's an outcome of their own personal therapy or overcoming this or whatever. I think in your case, it's just, hey, it kind of open kimono, if you will.
It is. It's literally like, hey, this is who I am. So you need to know, like, who's writing to you. These are the ups and downs I've had in life. This is what I've observed. This is what I've been a part of and observed. And like, this is out of, you know, all of the years I've been in the workplace, I haven't really strayed from these principles.
Yeah. Whether you're using those words or whatever.
Yeah. Like, right. I didn't have the term emotional optimist back in the early 2000s, but I am an optimist. Like, I— and for me, optimism means belief, right? And when I, when I share, like, emotional optimism with someone, or when I share optimism with someone, what I'm saying is I believe in you.
Yeah.
And that's what we need more of, right?
Very.
Like, I got your back. I feel you. Empathy. And I got your back, and I believe in you. Let's, like, let's go. I'm gonna, I'm gonna walk next to you.
So besides people going back to the question I had earlier around using the language, using the models, using whatever, what else do you hope will be different a year from now?
Well, I tell you what, I hope a year from now we are not— we individuals aren't feeling— grand statement— but are aware, at least more aware, of the armor that they put on every single day to walk into that work. Workplace or to get on a Zoom. So whether or not they have to cover themselves up, they have to pretend they're a PhD, they have to XYZ. If we could even get that, if I could get people more aware of what they're actually doing and the cost that has to them, that would be a huge step forward because at least—
Yeah. So I love that. And I was, I was on a call earlier today with someone we're doing a recording. I said, oh, I— he emailed me earlier, um, about, you know, are we going to record this? Do I need to wear a jacket? I'm like, just be you, right? Like, and it's like, you know, the way you and I are dressed now, at the beginning of our careers, somebody would say, oh, this must be 2 pals having a chat on their Saturday. They're not working. These are not seniors.
Exactly.
They're both kind of just chill and whatever.
Just chill. But we're sharing, we're sharing knowledge.
But even, you know, that armor piece, I remember the days having to put on a suit and a tie. Like, I have a Somewhere in the back of my closet, I think there's like 50 ties.
Yeah.
That have been dead for years.
You know, women feeling like they have to wear high heels or whatever, like, you know, the working girl days. And listen, if you want to wear high heels, God bless. But if you feel like you need to because you need to get noticed, or, you know, right, that's a whole nother thing. So if we can bring the awareness, and then of course, what would be amazing is that for people to start recognizing that when they take, when they take stuff off, how do you feel when you, when you unload the weight that you're carrying on your back every day? Because, yeah, I'm hiding at work.
Yeah, not fun.
That's where the magic happens.
So last sort of thread here that I want to touch on is you're on the other side of this now, right? Book is written, you're a published author. Yeah, in that, your obituary, whatever, whatever. Um, what were the What was the most surprising and then what was the most rewarding thing about the process? Forget about book sales and fame and all that stuff, but from, you know, pen to paper or keyboard or whatever to seeing it go land with a thud on your desk.
Yeah, I think the most surprising thing was how much of me I needed to write. So how much of me— I knew I was, and I said this to the publisher, I said this to Janet Goldstein in the beginning, I do not want to come off as a fraud, like I've got it all figured out. So I gotta share some of the, the yuck. I have to.
Yeah.
And I was— I'm fine doing that, you know, uh, I am, because I want to be believable. But I didn't realize all of the stories I would have to go into necessarily to prove a point, right? Because there isn't data, so you do tell stories that you've witnessed, whatnot. So I guess that It was, was a big one for me because it was a real excavation. Like, it really wasn't, you know, and I had to remember, oh, Claude, you walked into this, you chose this.
No, you talk about like real, you know, yeah, real relationships you're in, your, your identity, your like— yeah, there's, there's nothing.
Yeah, I do. So that— what, what I liked about that though, Peter, is like, I I, I, my aim is true. Like, I'm not here to pull the wool over anyone's eyes. I, I've seen a lot in these 50-plus years, as everyone has, and I'm here to share it if people— if I feel as though it will be impactful for someone, or also just like get us on the same playing field. I am no different.
Right.
Right? I am not. So that, I would say, was the most surprising and also very rewarding because it's out there now. Whatever. You don't know all my dirty secrets, right? I'm not gonna go, and you're not gonna do that either. But like, I think you can see me as a human being rather than when I— after I do a keynote or after I do this and people are like, I want to be just like you. And I'm like, no, no, no, no, be you.
Right.
You don't want to be me. I'm me. I got me. Yeah, worry about that. Um, and then I would say one of the things I loved was the creative portion. It was like picking out the colors, designing the font, designing how little things were going to look inside, which I had no idea I actually would have a stamp on, you know. And being able to name things— the lie exercise, you know, the archetypes of leadership— like, those are things that I came up with, which, like, who knew, right?
That's a thing, right?
Yeah, that was— and there was, there was a lot of creativity there. And like, that was very cool for me to be able to like Oh, it's not just stories I'm telling. I'm actually creating an experience of this, of when you open this book.
Right, right. Love it. Well, this has been great. I appreciate it. I appreciate your time. And, uh, appreciate you. You're crushing it. Or is that what—
that's—
yeah.
Can't wait to see your book.
Thank you.
See ya. Bye.
