Cliff Barrett, CPO at Conexiom, shares how meditation became central to his leadership style. We explore how meditation transforms his leadership from the inside-out, helping him maintain perspective, clarity, and calm in the midst of the cacophony of volatility, uncertainty, chaos, and ambiguity.
You can keep up with Cliff Barrett on LinkedIn.
Transcript
Rachel Nelms: Welcome. My name is Rachel Nelms. For over 15 years, I've been working with executives and their teams across industries and continents. Over the years, the leaders I work with have found clarity and courage when they reconnected themselves with an idea, an experience deeper than their business goals and bigger than their professional position. Those ideas and experiences are what I'm here to explore in Trees for the Forest. I spend time and conversation with leaders learning about that unique experience and inspiration that shapes who they are as humans and in time informs how they show up as leaders. Thank you so much for joining us for this meaningful conversation. I have known my next guest for nearly 10 years, and I feel so grateful to have called him colleague and friend. Most importantly, he is a good human who thinks about his impact on his family, his community, and the planet, and everything he does as a leader. He achieves the seemingly impossible every day.
He infuses his strategic and clear-eyed leadership with equal measures of grace and empathy. This alchemy makes him especially impactful: a product executive who has spent nearly two decades at the intersection of product design and the very human work of building things people actually want to use.
In addition to his current role as Chief Product Officer at Conexion, he's held senior leadership roles at Iterable, ChowNow, and Mailchimp, which is where our friendship was forged. In each leadership role, he takes a leader's responsibility to cultivate creative, curious, human work cultures seriously.
I'm excited to talk with him today because he thinks deeply about his humanity and carries that into his point of view as a leader. I'm absolutely thrilled he's sharing his wisdom with us. Welcome, Cliff.
Cliff Barrett: Thank you. What an amazing description, and it's the same for you. It's been a pleasure to get to know you. Thank you so much for the time.
Rachel Nelms: Thank you. Um, so excited to talk with you. Um, I'm not going to ask you to do kind of a whole life story bio. That would take up our whole time, and I'm sure it'll be very worth it. Um, but I do, I'm kind of asking you to just focus on one point, which is who or what was your favorite teacher as a kid?
Cliff Barrett: Oh my gosh, what a great question. I had a student council teacher. It wasn't even my teacher from class, uh, Mrs. Roberts. She really changed the course of my existence. I did. It was really powerful to have her be confident in what I could do and share that confidence with me. It helped me change how I viewed what I could do. You know, it's pretty powerful stuff. Yeah.
Rachel Nelms: How old were you when you learned from her?
Cliff Barrett: I was a junior in high school. Yeah.
Rachel Nelms: Wow.
Cliff Barrett: Yeah.
Rachel Nelms: Wow. That's great. Um, okay. So skipping ahead a bit, um, one thing that you and I have talked a lot about over the years is mindfulness. Um, and our mind, our individual mindfulness practices. Mindfulness's place in the workplace and leadership, and we've talked about its impact on your own personal growth.
So I am curious, I would love to hear, uh, first of all how you kind of came into a mindfulness practice. What's the, what's the story there?
Cliff Barrett: Yeah, for sure. So, um. I'd say there are a couple of key moments that helped me find mindfulness, but probably the moment that I discovered it is I had a really amazing job at CNN, um, and 20 million active users on our, um, mobile app, which we redesigned over the course of 13 months, went down 20 million after users were not happy.
It was a very stressful environment. It was, it was treated, product was treated as any other news. Um, IT department, it was high pressure all the time. What I realized at that point was I was taking that home, I, I had taken stress home from work. I was in the middle of rebuilding a deck, um, at our house, and I had to stop and fly to California because they needed something.
It was that kind of environment. And slowly, um, there was a really amazing mentor named Kathy, uh, Farr. And she was always the calm one. And she was not a mindful person. She was not a mindfulness person. She was just always the calm one, and she would always say, Cliff, it's gonna be okay. It's gonna be okay. But around the course of that time, I realized that it was impacting my entire life. And I slowly, CNN offered a meditation class. And um, the teacher there was brilliant. We'd go after work and it was. It was weird. You'd have quiet time where the lights were off at a work environment, they brought a teacher in and, um, I'd say it was that time that it really transformed my life overall.
And I, and I credit, um, that course, that brief course, which was only like six weeks, and it showed me what it meant to slow down. Especially at work. At work, I was always go, go, go. And it taught me a lot about stepping back and taking pause. Yeah.
Rachel Nelms: Love that intro where you felt like, this is not sustainable the way
Cliff Barrett: No.
Rachel Nelms: up, and there has to be another way and then kind of. Playing with this new tool. So when did it become non-negotiable for you?
Cliff Barrett: Oh, it's a great question. I'd say shortly thereafter, you know, um, by the time I got to Mailchimp, it was already part of, part of the reason I went to Mailchimp is CNN was just super intense. It was nonstop hours. Um, and going to Mailchimp and really realizing that that class taught me so much. I'd say Mailchimp was where I started to, and you might've seen this in some of the ways that I interacted with folks, but I really started to push, um, myself to, on a daily basis, start each day with at least 20 minutes of silence and really think about behavior at work specifically, I'd say. At home, I've always been filled. I teach my kids, I send them texts that loving kindness is the only way to live. But at work it was, you know, it's competitive, it's stressful. You wanna win, you wanna do well, and taking pause and saying, Hey, I need a minute to clear my head, but also to think about why I do this. What am I doing every day, you know, which we talk about a lot.
Rachel Nelms: Mm-hmm. What was that journey like, bringing that kind of personal, the life outside of work, the perspective that you had already embraced outside of work into work where there might be some tension there. How did you, what was that like for you?
Cliff Barrett: Yeah, it's, it's one of the things that's translated across the rest of my career, and I think if you talk to any of my team members or executive team, uh, colleagues, they would say there was a, a calm about me. And so bringing that to work was. It was not easy because, you know, at CNN I had been told that calm demeanor could sometimes come across as not caring and that that stung a little bit because I wasn't one of the more intense folks when it came to crisis.
I could say, okay, we have, we're down. Let's figure this out. Right. That's the whole point. So I'd say that it was not. Um, I'd say that it was more along the lines of just being aware, self-aware at work, and when their tensions rose, being the one who tried to step in and calmly say, what are we trying to solve for? What are we do? Are we, we're doing this together, right? Number one, and we all want the same, right? We wanna bring value to the customer, to the business, and to ourselves. This is, this is not a, you know, nonprofit we wanna, wanna do well. Um, so I'd say there's a mixture of things. One of the books that really, there are a couple of books that really helped me, and I found one later at ChowNow, but there's one called Reboot, and there's another one called Conscious Business. I think there's a bit of, as you're growing as a leader or in any IC role or otherwise, the self-awareness to understand. In Reboot, this is the way they frame it: What developed your relationship with X? What developed your relationship with achievement? What developed your relationship with money? Conscious Business is more along the lines of, Hey, we're all on the same team. We all have the same responsibility. Like, I think, uh, Fred Kofman uses this analogy where you ask someone what's the, what's the job of a goalie versus, uh, on a soccer team? And folks will say, Hey, you know, they all think about it and say to stop someone from getting a goal. And his point, his, uh, punchline is, no, no, no.
The responsibility of a goalie is to win. The responsibility of a forward is to win. How you get there, that's what you shared. That's your shared responsibility. So those two really, I'd say over the course of time. Um, folks know at work that I meditate. It's not something I shy away from. Um, and I think Mailchimp was really transformative in the way that I was able to bring that to work.
Especially through some of what you taught to folks during the course of that time.
Rachel Nelms: So much of what you shared, one thing that's coming up for me is how it is a little bit of a cultural challenge, and it can create at least in the narrative about who you are as a leader.
Cliff Barrett: That's right.
Rachel Nelms: And so kind of going there, and I would love to come back with a couple observations, but kind of going there for a moment, how, how have you kind of reclaimed the narrative about yourself and, and the way you show up?
The calm, intentionality versus what the world says, this is what leadership looks like, or this is what
Cliff Barrett: Yeah.
Rachel Nelms: or whatever. Fill in your,
Cliff Barrett: Those are both really good points, and they're both tropes, and I agree completely because that's, to learn the hard way specifically at CNN, that those are real. And um, you know, I'd say in the most recent leadership role that I had, there's this really, it's, it's being self-aware because perspective, one of the things that Kathy Farr taught me: don't ask yourself, um, if their perspective is true or not, ask yourself why someone has that perspective. Right. And I think that's a really meaningful moment for me that I've taken throughout my career and actually coached my product leaders and design leaders on, I can still have conviction. I can still hold my point of view, but I don't have to have this aggressive, to your point, there's, there's these themes around who you are as a leader and if you come in guns blazing that you're a strong leader. Versus if you come in and listen and pause and calmly recommend, those are not seen as, really, historically not seen as someone who can enter C-suite. I'd say. But for me, what's been a meaningful transition, and I would say this is over the last two roles, which were, a good six years, seven years, is learning to convey conviction. And that translates more for folks than assertive aggressiveness that you're talking about. Right. Um, one of the things that's really telling for me is in the most recent role that I, uh, took on, I had some references and without prompting, one of the folks said, Cliff is calm under pressure, shows empathy during crisis and can lead through that.
And that's, that's helpful to hear, you know, so.
Rachel Nelms: I, I, I do think so much, especially in our work culture, facing so many challenges in the externalities. Conviction is conflated with urgency.
Cliff Barrett: Yes,
Rachel Nelms: not running around with urgency, then maybe you don't care. Like, well, no, I care so much
Cliff Barrett: that's right.
Rachel Nelms: saying
Cliff Barrett: That's right, that's right. Yeah. It's so funny you say that. 'Cause I actually said this in an interview recently, where I promised myself after CNN I wouldn't scramble, and scrambling, it's that false urgency, right? It's the, oh my God, I don't have too much to do. I can't get it all done and I'm gonna do it all and I'm gonna non stop.
And that to me is just, is equal to someone who doesn't care because you're not really thinking about how to focus. How do you bring this into a, a really meaningful point where people have clear expectations and you have set ways to measure those expectations, and that comes from. Managing folks to trying to succeed at a goal for an organization. It, it's just funny that you say that because that scrambled probably not the wrong term, but that is something I committed to with all of my teams and I believe they've all felt it, that this isn't false urgency. This is focus and that's the intention of where we're headed,
Rachel Nelms: Uh, you know, I have young kids and they're learning emotional regulation, and frankly, I'm learning emotional regulation. We're all in this
Cliff Barrett: Oh my God, we all are,
Rachel Nelms: but. When they get, when they encounter a problem, they get really frustrated and angry, and we talk about how you can't solve a problem when you're angry.
Cliff Barrett: No.
Rachel Nelms: Anger is, that doesn't mean anger is bad. Anger has a place, but you have to first calm yourself. So then you can think clearly. But as long as you're in this agitated state, you're not able to think clearly about what's in front of you. And that's a connection I'm also making
Cliff Barrett: I was just gonna add for two seconds that that is something that you are always growing and learning. I don't care what age you are. You know, I, I look at, um, folks of all stages of career and we all get so twisted over that we think is the end of the world.
When in truth, if we pause and just think calmly, what does this mean, how do I address it? That transforms how folks view life in general, not just work. So I agree with you.
Rachel Nelms: That, that brings me to something else that came up when you were talking through this journey, um, which is a leader's role in one of, one, part of leader's role is to establish and hold perspective for the team.
Cliff Barrett: No.
Rachel Nelms: So, you know, thinking about. Going back to the soccer analogy, the coach helps him understand that you're, we're all here to win.
And this is kind of the, the strategic, um, tools in our toolkit to win. But the striker needs to be able to focus on being a
Cliff Barrett: That's right.
Rachel Nelms: need to be able to narrow their focus,
Cliff Barrett: That's right.
Rachel Nelms: that someone's holding the broader perspective. Um, and so that's what I'm hearing when you're saying, well, hold on, let's, you know, rather than focusing on what my individual part is, let's make sure we're taking some time to zoom out and see what's the broader context that we're a part of and what we're trying to get after.
Cliff Barrett: Yeah, and I think that I would add to that and say there's so many variables and complexity to that, right? So there's this notion that the coach knows. We're all trying to beat this team. This is how we're gonna beat this team. This is the broader goal. But then within the team, there are dynamics that maybe the striker wants to come back and get some help from somebody else who's not ready to help them.
Right. And I think when you're looking at any organization, the complexity within the organization as much as the complexity of the market. That's where a strong leader, and listen, I'm not amazing at this always, but I would say that that's the core of a strong leader is to say, look, I understand that engineering feels this way.
I understand that sales feels this way, but I also understand that the market is showing this. And I also understand that our customers need this deeply. That's a lot to pull together. And then if you're scrambling or you're this anger or frustration, you know, one of the other things that they say in Reboot is all of your baggage translates to your team. Right. So if you, if you run hot, your team's gonna feel that and they're gonna feel stressed and they're not gonna feel comfortable making decisions because they know that, at some point they're gonna feel the pain of what they just did. I saw some of that at every organization, and just think that's a really thoughtful thing for someone to think about as a leader, which is, what do I bring to the table?
What do I bring to the table and what does that mean for my team?
Rachel Nelms: Yeah. As a leader, you really are creating the context that your team has to live in every day. And so are you creating a context that's about your own, fear, your own ego reactions, all of that? Or are you creating a context that's expansive enough so they can show up and
Cliff Barrett: Right. That's why I love our conversations. 'Cause you've talked about fear before. I don't think enough people talk about fear. Right. There's a fear of failure. There's a fear of judgment. There's a fear of just, am I living up to this title that I have? Right. There's am I who I say I am, am I who I say that I am Right. And that's a challenge. I've seen that take shape in so many other leaders that, I do think a very meaningful moment to say, what am I bringing to my team? And how is that impacting them on a day-to-day basis,
Rachel Nelms: I mean, fear is about constriction, it's about protection, right? And how do you create and innovate? How do you see possibilities when you're in a constricted and constrained place? But we, uh, I mean it is a. So, such a dominant force. I mean,
Cliff Barrett: A hundred percent.
Rachel Nelms: a dominant force
Cliff Barrett: A hundred percent.
Rachel Nelms: made,
Cliff Barrett: Yeah.
Rachel Nelms: which I, I suppose, makes, might make your point of view as a leader even more, uh, critical and more challenging when you're walking in these spaces and people are like
Cliff Barrett: Yep.
Rachel Nelms: using your.
Cliff Barrett: That's right. And I would say, uh, example is fear of what does AI do to my job specifically and what I do in software development. Like, I try not to use AI all the time, but whatever innovation is most current, however we're gonna call it, whatever we're gonna call in the future, but I think that's a prime example of am I acting in fear of some unknown, or am I being intentional in what I want for my life, for my career, for my family, right? And I think that's, that flips it a little bit instead of the, you know, I'm not sure what, what's happening. This is a really horrible moment for my career. How can I take advantage of this innovation? Be intentional. Maybe I don't wanna take advantage of innovation. Then you switch how you work, where you work, what you do, right? Um, but I, I think to your point, that fear broadly right now, especially, is heightened, no question.
Rachel Nelms: So I'm curious, just in general, what lessons are you learning right now and who or what are your teachers?
Cliff Barrett: Yeah, that's a great question. I'd say the two words that are in my brain right now are conviction and accountability, and my teacher is life, it's what's happening right now, right? Like I, um, I've had mentors in the past, uh, and um, I don't currently, so it's more along the lines of, we talked a little bit about this in the past.
How do I ensure that I'm self-aware enough to understand where my opportunities are where I've landed in these discussions as I switched roles and, had a bit of a reflection is. Listen, no team is gonna feel good if a leader doesn't have a belief, right? A reason to believe it's, it's, you know, and, and no team is gonna feel good about a leader.
No organization is gonna feel good about a leader if there's no accountability, if there's no sense of, listen, hold me to the fire. I said I would do something. I said we would do something. And if it doesn't net out, it's not always the end of the world. But what do we do to learn? How do we adjust? And I think those two for me are sort of centered values for myself right now. And it's, it's, it's also, um, what I said earlier, which is whatever innovation is happening at the moment is where you need to learn, you need to grow. And I think you can avoid it. And that's, that's a fine path, but you just have to be certain in your choice or, I mean, have to be confident in what you choose to do.
That's all.
Rachel Nelms: Yeah. Um, that intentionality piece. It's, well, your description of accountability, I think there's a nugget in there that is very different from what the common conversation about accountability is. Because you seem to be including in how a leader must be held accountable, by their team. This idea that. Hey leader, you said this works, work matters and if we fail at it and we abandon it and we learn nothing, then the work didn't matter. That's what you're telling us is that the work didn't matter. And so it's not so much accountability for direction or results, it's, although it is that, but it's also, you said it mattered enough for us to spend our time and enough for us to learn from it?
Cliff Barrett: That's exactly right. And I was in an executive team meeting with seasoned leaders and there was this debate over the definition of accountability. And all of the leaders were frustrated with the term because they felt like it was. A tool for the teams to use against leadership. It was almost this, this negative intent around accountability. And my pushback to them specifically was, listen, if you don't set milestones, and to your point, ensure that these folks know why this matters. I think that's a great phrase. Why does this matter, right? Because we're all in this, sure, we can care about marketing software, we can care about online ordering and there's purpose driven moments there for sure, but we all have goals for ourselves.
We all wanna learn and grow. We wanna understand that the leadership team sees that. But also understands how to communicate back and articulate this is why this is valuable. Look, it went south. We had a mistake. Totally, totally my fault. I did it. I drove us here. Let's switch lanes. Let's go a different direction. But we learned so much from what we did. Took away. You would never get this outside of this moment in your career to learn this much in this short amount of time. And I think those things really empower teams to think differently about what success means.
Rachel Nelms: Yeah, I love that. I think that is a great thought to move into our final
Cliff Barrett: I love it.
Rachel Nelms: questions. Um, and so this is just a sprint of questions, um, where, I'll ask you the same questions I'm asking all of the guests and you can, your answers can be kind of quick to the point, um, but I'll also be curious to know why,
Cliff Barrett: I love it.
Rachel Nelms: you chose that answer.
Um, and so if it's good with you, we can dive in.
Cliff Barrett: I am ready to go. Let's do this.
Rachel Nelms: All right. First question. What is your favorite word?
Cliff Barrett: Love. That's that one. I can, I can paint a picture for a long time, but I, I do send texts to my kids about loving kindness being the main thing. Loving and kindness to yourself, loving kindness to others. And I think growing up in New Orleans and seeing the love that everyone has for their friends, for their family, and just transcends any problem you're ever facing.
Rachel Nelms: I love that. What's your least favorite word?
Cliff Barrett: Ah, torn on this one. I would say hate is there. Um, and I'd say what I try to convey, which is always successful, is can't, we shouldn't use the word can't. You can always solve a problem and there's always a way to figure something out.
Rachel Nelms: Hmm.
Um, what is the best thing about being you?
Cliff Barrett: Loving kindness. I have amazing family and friends, and my existence is bolstered by every one of them. I have this friend who, since I moved away from Atlanta, sends me voice messages. I mean, they're just hilarious. They're, they're caring, they're checking in. Um. Yeah, I have a really strong family and you know, my kids, thanks to my wife are brilliant, loving, kind kids, so I was all very, very lucky to be me in that way.
Rachel Nelms: That's awesome. So then what's the hardest thing about being you?
Cliff Barrett: I think we talked about it a little bit. I, I, I'd say I'm a very goal-driven, oriented person,
Rachel Nelms: Mm-hmm.
Cliff Barrett: Oh, sorry. These are one word answers. I'm, I'm, I'm trying on,
Rachel Nelms: One word.
Cliff Barrett: Okay. Um,
Rachel Nelms: Go ahead.
Cliff Barrett: It is the kind, empathy, assertive, aggressive conundrum that's, that's a hard, a hard thing for me to, a hard line for me to walk. And it presented itself at work because there are times where it wasn't working out with someone and I really wanted it to work. And it was probably better for me to be more assertive for both of us. And I didn't do it. So I learned from that.
Rachel Nelms: What inspires you?
Cliff Barrett: Uh, I'd say what inspired me throughout my life is art. Art in general. Just, um, I'm all about being outside. I trail run, mountains blow my mind, beaches blow my mind. Since I was in high school, two of my favorite painters, Mark Rothko, um, Cy Twombly, those kind, just for me, it's, inspiring to see that that's still happening in this world.
Those are older painters, but art in general,
Rachel Nelms: What, uh, demotivates you?
Cliff Barrett: Um, selfish people, and they're hard to deal with. Folks that are only focused on themselves. It's a struggle to work and lead those folks. Work with and lead.
Rachel Nelms: Uh, just a, a pause on that. So what kind of, what's your path forward with that? I imagine, especially as you are a leader, you know, you're working with lots of different people, so how do you,
Cliff Barrett: Yeah. So
Rachel Nelms: I.
Cliff Barrett: one of the ones I had to learn the hard way, is to really think about how I react to that versus trying to change it. What I have found is that selfish folks, they're not, they're not all there. Most of the folks I've worked with have been brilliant and self-aware and all that, but those folks, it's more about how do you interact with them in a way that doesn't take your spirit and is empathetic and caring, but at the same time understands that that's just their nature in certain, in certain ways. Always, of course, I always assume positive intent, but I think that's, that's one of my struggles.
Rachel Nelms: I, uh, my own on myself is I realize that selfish behavior my own selfish and self-protective behavior.
Cliff Barrett: Yeah,
Rachel Nelms: And so
Cliff Barrett: So true.
Rachel Nelms: like, you're not taking me into account, I have to protect myself even more. And so that
Cliff Barrett: God, it's such a good call. I know it well. Yeah, for sure.
Rachel Nelms: Why do you do what you do professionally?
Cliff Barrett: Okay, so this is gonna be a longer answer, but I, I'm gonna give it to you anyway. I started off studying fine arts at LSU. It's not known for a fine arts school as a fine arts school. Um, and then I realized that creation or the creation of something from nothing drives me. And then as I grew in product, I learned that, listen, this is a really interesting space to be in for a career. And it requires creativity. It requires empathy, it requires discipline. It requires all the things that I care about. And so each moment that I've grown and leading teams and setting direction, it does feel like the evolution of a creative, I'd say.
Rachel Nelms: That's wonderful. If you could do anything else, what would it be?
Cliff Barrett: Okay, I'm gonna give you two. I guess that's,
Rachel Nelms: Oh,
Cliff Barrett: not, I'm not following the rules. Um, I'd say fine arts painter in galleries or I like public art a lot. Or standup comic. I think it's one of the last standing art forms, which I'm a huge fan of. Yeah.
Rachel Nelms: Really?
Cliff Barrett: Yeah. True art forms. Less than true art forms.
Yeah.
Rachel Nelms: What is attractive to you about standup comedy?
Cliff Barrett: I think it's not about the attention, it's about, you know, I think one of the famous comedians, the fact that it's just you and a microphone and you're trying to elicit laughs, thoughtfulness. You're trying to elicit responses by telling stories, which I think is a core component of what we do as product leaders. All of that combined, it's, I find it really compelling. I took an improv class in Atlanta and fell in love with it, but haven't made the time to, more for sure.
Rachel Nelms: Standup comedy seems like the hardest job.
Cliff Barrett: It does, doesn't it? Yeah. Yeah. I think it's one of the hardest jobs, but also probably one of the more rewarding, it's immediate.
Rachel Nelms: So.
Cliff Barrett: Yeah. I can see you doing standup. I can see that.
Rachel Nelms: That's a, that is very kind. Um, what is one thing you wish every leader knew?
Cliff Barrett: I'd say that. It's all about that
Rachel Nelms: Hmm.
Cliff Barrett: you forget that in this, in search of goals or search of winning, you know. But what I've seen is, uh, um, some leaders can forget what got them there, how they got there, that the humans involved are making their lives better. I think that's one thing that I've seen for sure.
Rachel Nelms: What, final question, what's one thing you wish every team member knew?
Cliff Barrett: You know, I'd say one of the more important things for a team member to know is that they are in control of their career. They forget. What I've seen a lot of team members is kinda put their hands up and say, when am I gonna get this? Or, how do I get this? They should flip that and understand that what drives them, what motivates them is what gives them their intention. And that is the transformational moment for your career, not whether someone else sees you or doesn't.
Rachel Nelms: Thank you so much
Cliff Barrett: Thank you.
Rachel Nelms: conversation and for your, uh, being open and sharing your wisdom with us. I loved, uh, chatting with you today.
Cliff Barrett: Same. Thank you so much, Rachel. It's great to talk to you. A hundred percent.
Rachel Nelms: Thank you.
Cliff Barrett: Bye.
Rachel Nelms: Thank you so much for being present for this conversation on Trees for the Forest. Our website is formationsconsulting.com. There you'll find links to my LinkedIn and my Substack. Do you have comments or thoughts about this episode? How did it impact you? I'd love for you to share at rachel@formationsconsulting.com. Until next time, be well.
