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Episode 39: Interview with Katica Roy, CEO and Founder of Pipeline

As the CEO and Founder of Pipeline, Katica Roy talks about knowing your own values as a leader, the delineation between worthiness and confidence, and being intentional about the type of leader that you want to be.

Every few weeks as part of The Heartbeat, I ask one question to a founder, CEO, or business owner I respect about their biggest leadership lesson learned. This week, I interview Katica Roy, the CEO and founder of Pipeline.

CLAIRE: Hi, everyone. It’s Claire Lew here, CEO of Know Your Team. And I am honored today to have a really special guest on The Heartbeat. I have Katica Roy who is the CEO and founder of Pipeline, this super, super incredible software company that helps companies achieve financial performance through closing the gender parity app. I was first introduced to Katica, I think, in Austin. We both spoke at this great conference called Culturati. Your presentation, I think, was only like five minutes and I was floored. I think everyone was like, “Oh, my God!” On the verge of tears. It was that good. But Katica, in addition to running and founding this company, she was the global VP for SAP. She does a ton of speaking worldwide. Most recently was just giving a keynote at, I think, Watermark here in San Francisco.


CLAIRE: So when I saw her on the stage, I was like, “Oh yeah, she’s an old pro at this.” But we were not here to talk about your public speaking skills, Katica. We’re here to talk about your tremendous experience in leadership. And so, I’m excited to ask you this one question that I’ve been asking leaders who I respect.


CLAIRE: All right. So the question is, what’s something you wish you would’ve learned earlier as a leader?

KATICA: I think that there’s actually two things that I would say. One is knowing my own values. When I started out, I started leading teams really early in my career. My very first job out of college was as a litigation paralegal and as a litigation paralegal in big law firms, you’re overseeing a lot of temp workers, a lot of contingent staff. I’ve led those teams and then more formally started leading teams later in my career. But one would be that I’m worth it today. I don’t need 20 or 25 years of experience which I now have. But I don’t need that in order to be worthy. I’m worthy today and I have value today. And often when we started after we graduated from college and you get your first job out of college and you’re sort of trying to figure out what you actually really want to do with your your career, we feel like we need a lot of experience. And experience is valuable, don’t get me wrong. It’s just not a mark of our worthiness. And so that would be one thing that if I was to tell my 22-year old self or 21-year old self, that would be one thing. The second piece about leadership that I learned over time was what could be called the ripple effect. But essentially that when you lead people, when you impact their lives, you impact the lives of two to three other people at least, whether that’s their family or that’s their colleagues that they work with, whatever that is. And so to be conscious about what are you sending out into the world, my guess would be that many people had the experience we have had to be worthy of.

CLAIRE: I know what you’re talking about.

KATICA: One of my old coaches said to me, “So you realize you’re the boss when you’re the topic of dinner conversation at somebody else’s house.”

CLAIRE: I love that.

KATICA: People talk about you. They tell your family or you meet their family and they feel good so much about you. So it doesn’t mean that you don’t make difficult leadership calls or you don’t make those decisions, it’s just a very conscious and intentional perspective on the fact that whatever you are doing, you are sending that ripple out into the world and what do you want that to be.

CLAIRE: Oh, man. I overhear nodding, laughing along because both are all too relatable. Let’s dig in for a little bit on the first part that you discussed which is this idea that when you are younger, starting out in your career, I can totally relate to this. I started running Know Your Team when I was 24 years old and I started my first company when I was 21 or 22. And all I wanted was experience and to be “taken seriously” or how am I going to be helping all these leaders if I don’t have 10, 15, 20 years of being a CEO at some big company. And so, this idea that while that’s undoubtedly helpful experience, my God, like I’m so much smarter now hopefully than when I was 22 or 24. But to your point this idea of worthiness, tell me a little bit about what 22-year old Katica was struggling with then at that time. Was it sort of this confidence of feeling like, “Am I worthy to be managing these people because I don’t have the experience?” Or what was sort of the tension there?

KATICA: I would actually delineate too between worthiness and confidence because I can feel worthy and still not all as be confident.

CLAIRE: They are distinct. You’re so right. They are completely distinct. Yep.

KATICA: And so from a worthiness perspective, it was my experience when I graduated from college. I started to plan for college when I was a freshman probably even before that, but a freshman in high school. And so you sort of have this entire path laid out for you. You’re going to take these classes in high school and you need to get these grades and then you’re going to go to college and it is a consistent set of a path of accomplishments, essentially. And you get your next accomplishment and then go to the next thing and the next thing. And then there’s way more talk about it now than there ever was in the mid 90’s. But essentially, the worthiness is somewhere out there once you accomplish something. So it’s not today when you’re 22 and just starting out. It’s somewhere and it’s always a little bit evasive, like, “If I was just…” And it certainly wasn’t just to the people that I was leading but it was also proving myself to the people I worked for because I was as a paralegal answering to fairly highly powered lawyers who were working on really important litigation cases. And so, it was also about proving myself to them that I could do this job effectively.

But I think that sense of worthiness was about arrival, essentially. Once I arrive at some place in the future, like I’m a vice president or I’m a director or something like that, I will feel it’s almost like magic. I will feel worthy. And somewhere along that journey, in that leadership journey, I realized that it’s not out there, like it’s here. But it took me a lot of experience to realize that.

Actually I remember talking to a friend of mine and there was a woman who was a director and at the time I just wanted to be a director. So this is a long time ago. And she said, “Do you really think that she believes, like she feels like she’s got it altogether and she’s confident?” I just sort of made up a bunch of stories that she did. And then I kind of sat back and thought, “Oh! Maybe she has all those doubts too.” And then it started to solidify to the fact that you could have that today regardless of whatever was happening inside you.

CLAIRE: I want to, for everyone who’s listening and watching, really emphasize this point about self value and worthiness because it’s almost like a disease I think in our society where we tie that sense of self-worth so much to external opinions of what other people think of us, how much money we have in our bank accounts, to what that title is on that business card. And that’s not what makes a person’s life valuable. It’s not what makes a human being interesting or worthy to be around. And I think as a leader, it’s easy when you have a lot of people depending on you or where there’s, like you were saying, this almost addiction to achievement to say, “Oh, but that is my worth.” Or, “All I am seeking is for others to sort of show and share that validation.” So, I think it’s such an important point. It’s a hard one to learn unless I think you get burned kind of badly. That’s how it happened for me — really, what’s the turning point for you? Was it you sort of seeing that mentor or was there something that clicked one day where you’re like, “You know what? I am worthy of being in this position regardless of how many years of experience I’ve had.”

KATICA: You know, I don’t think it was a moment because I don’t. If it was, I don’t remember that moment.

It was more about a journey to figure out how to be useful and to essentially be of service and be useful to other people. And that was and still is honestly an ever evolving learning journey about that. And so I think for me, it was — and so much of that too probably was ingrained to me because I’m the daughter of an immigrant and a refugee and always do your best and never give up. But there was that sense of always continuing to, like how can I be more useful? What can I do to be of service? And if you don’t feel worthy, you can’t be useful to other people, not in a conscious way because you can’t transmit that. So you have to start with yourself and emanate this out.

I have two kids. That’s true with my two kids. My kids will do what I do. They will not do what I say. They’re 8 and 12, but whenever I would think about that, I would think about, “What am I doing? Am I doing the things I’m telling them to do,” because if I’m not, then that’s not authentic. And then also like I said to you, you’re human. That is something I often say to the people who report to me like, “We’re all human. We all make mistakes.” And that is just part of the human condition and being fallible. It has nothing to do with our worth. That’s just part of our humanness. And so, we’re just allowing ourselves that grace.

CLAIRE: It’s beautiful to hear honesty, refreshing. So important, I think. I often wonder if women feel this more. I’d be curious to get your take on that.

KATICA: If women feel what? More about being of service?

CLAIRE: More about feeling like worth is a question. I don’t know. In your experience?

KATICA: My experience is actually that women are more apt to talk about it, that it is not a gender specific. Men feel it too.

CLAIRE: I agree.

KATICA: It’s just that from a very young age, men are taught not to share feelings overall and in particular, nothing about not feeling enough or not feeling worthy because that’s like you’re not going to be safe if you do that. So that women are more apt to talk about those things because we’re more socialized to talk about those things where men are not. And honestly, I mean this is a little bit of a sense but it is true which you can just see that in the suicide rates in the United States that is men and boys account for 79% of all suicides in the United States. They’re four times more likely to die from suicide and that’s a mental health issue which comes from that fact. I’m not a psychologist or a mental health expert but it does come from the fact of not feeling worthy, of not feeling good enough, of not feeling like I have value here. That in fact the opposite, it would be better if I was not here. So, I don’t actually think it’s a gender issue, it’s just that it’s more often that women talk about it.

And honestly, I mean this is a little bit of a sense but it is true which you can just see that in the suicide rates in the United States that is men and boys account for 79% of all suicides in the United States. They’re four times more likely to die from suicide and that’s a mental health issue which comes from that fact. I’m not a psychologist or a mental health expert but it does come from the fact of not feeling worthy, of not feeling good enough, of not feeling like I have value here. That in fact the opposite, it would be better if I was not here. So, I don’t actually think it’s a gender issue, it’s just that it’s more often that women talk about it.

CLAIRE: I think I would agree. I tend to agree with you too, just amongst conversations that I’ve had with leaders of all sort of gender identification. I think to your point, all the more reason to talk about it and to normalize the conversation about questioning what value do I bring. And then to the main point that you are bringing up, which I thought is so wonderful, is how you reverse that narrative as you ask that question, “Well, how can I be useful?” Peter Drucker, [seminal] scholar on management talks about the question ‘what is my highest use as a leader’. And that is a very centering and grounding question. But I love even the question of how can I be of service, how can I be useful because if you try to answer that then you realize and you have to believe in your worth to be in that position. So, thank you for that important reminder.


CLAIRE: And then the other thing that you mentioned about the second biggest lesson that you’ve learned in your years as a leader was this idea of the ripple effect which I thought you were gonna go in one direction with it and then you actually shared something that I don’t think a lot of people talk about which is that you’re affecting not just the person who reports to you but their family and their friends. When did your realization of that happen in your career?

KATICA: I think it happened maybe four or five years ago, something like that. And it was just a thought. I managed really big teams, so I would think a lot about that.

It was a sense of being intentional about the leader that I wanted to be. Who did I want to be? And also the other thing too which was probably why it didn’t come up for a little while is I actually had people who came with me or followed me from company to company. I had this over three companies where I would take a new role and they would come with me. And I thought, “Well, that’s really interesting.” And so, I must be sending something good into their world.

CLAIRE: Yes, you’re doing some good stuff.

KATICA: But it’s more like you’re just not always aware. We’re not always self-aware. So it’s not like I don’t think I send the good things in the world, I do. For instance like today just also happens to be Bring Your Daughter to Work Day. I didn’t bring my daughter because I’m like, “No, we’re not gonna watch the iPad all day.” But my head of operations brought her niece who is my son’s age and so we had a conversation and what I was remembering was — so I was thinking about the impact I might have on her life by the fact that she met me and she’d see my story and her aunt works for me. And also what I was thinking about, my father was an entrepreneur and he had a lead investor who was the first investor and almost always on most of his businesses. And that gentleman had a profound impact on my life because he encouraged me to always do my best. I had a very specific experience where he really encouraged me. I was a freshman in high school and we had to create a historical ornament for world history. And the child who got the highest grade on the historical ornament would get an automatic A on the final. And I was feeling a little defeated. I’d just gotten back from private school to the public school and was like, “I just think I’ll go for a B.” And he said, “No, you should always go for the A.” And I was like, “All right.” So, I did it and I won. I got the best grade and I got the automatic A on the final. And so, those are the things that maybe we don’t always think about but we have this impact directly in leadership.

One of the things that I have often done with people that I lead, because you’re responsible for giving them feedback and coaching them, is to separate intent with impact. That is, most people have good intentions. Most people have good intentions. Their impact just might not be what they intended. And so, when I did that, it didn’t become about the person and their worth, it came out, “I believe your intent is good. Here’s what I believe it to be. And here’s the impact that behavior or action or whatever is having. So let’s figure out how to align those two.” I had someone once say to me, “Thank you so much.” I’ve had it more than once but in one particular — I don’t know that they’d ever gotten feedback that way. And he said to me, “I so appreciate the fact that you separated that so that I didn’t feel bad about myself. And I felt like I could actually change and do this better in the future.”

I’ve had it more than once but in one particular — I don’t know that they’d ever gotten feedback that way. And he said to me, “I so appreciate the fact that you separated that so that I didn’t feel bad about myself. And I felt like I could actually change and do this better in the future.”

CLAIRE: I’m nodding my head over here vigorously because I think that’s such an underlooked part of feedback. And what makes it so difficult is because most folks get defensive because they’re misconstruing intent. And most of the time if you’ve done a decent job hiring, you haven’t hired anyone who’s evil and who has that poor intent. And so it’s a matter of figuring out if the outcome isn’t exactly, whether it’s my outcomes or your outcomes, then how do we get on the same page.

I want to go back really quickly though to this story that you shared about the investor with your dad because it made me think a lot about my dad and how I actually unintentionally have been deeply affected by every single one of his employers across his entire career because we moved, I’ve lived in Atlanta, Georgia, Washington State, Ohio, Minnesota all because of my dad’s job. And it was because he didn’t like his boss or he disagreed with his boss or whatever it was. But there were some dynamic there between the person who he was working for that caused me to change schools, meet new people. I mean, drastically changed not just my life experiences but honestly sort of my temperament of today that I carry with. I think so many of us as leaders now and I’m thinking of our team and I’m like, “Oh wow, yeah. They’re going home and talking to their partner or their kids,” and we don’t realize that deep ripple effect.

And so given that to your point, communicating not just intent but figuring out how to influence outcomes, I think is a huge part of it to your point. But the other thing that you’d also earlier touched on was just this whole idea of just being a lot more deliberate and just asking that question of ‘how do I actually want to be’. I’m curious, is that something you do often? Are there other things that you do to sort of center yourself and making sure that that ripple effect is positive versus not so positive.

KATICA: Not so positive. And especially as a leader, you have positional — in this instance because leaders don’t always have positional power. But in this instance, in my role right now, I have a lot of power. And so, you have to be aware of the impact of, not that you can’t be authentic, but you have to be aware of the impact that your behavior has on other people. And it is magnified because of who you are. And so, that piece is particularly important. And I think when you think about people’s families and the impact that you can have, or indirectly you have on them — I remember another woman who worked for me many, many years ago and she was in leadership development. That was her passion.

One of the conversations I would often have with people is, “Look, what do you want to do and please don’t tell me that you want to work for me for the rest of your life because you’re not going to. I mean, that’s just unrealistic. So, let’s talk about what you actually want to do and then let’s figure out how we get you there because you may be with me for a long time. You may be with me for a short time, but you’re probably not going to be with me forever. So let’s have an honest conversation.”

And so, she was really into leadership and it wasn’t what we were doing as a team. I said, “Well, if you’re really interested in that, then perhaps the best way to do that is like, here are companies that actually invest a lot in leadership and that might be a really good place for you to go. And I am more than happy to open those doors for you, whatever I can do, to help you move there. You’re great on this team and if that’s really what you want to do, that’s what you should do.” And if you think about the possibilities, she had two children, the possibilities of what her kids think are possible. The mindset of what you think is possible that it’s okay to have a passion about something and it’s okay to go towards something that I want to do. I might make mistakes and I might fail and all of that’s OK. That is all part of the journey. But that doesn’t mean that I should not have those things because I might fail. And so, I think that piece of it is particularly important.

CLAIRE: Yes. I couldn’t agree more and I think we forget about that responsibility as leaders. I think we can be so or — I’m not gonna put words in your mouth. I can speak for myself here in the sense of like it’s so easy to become focused on my personal vision for the organization, the people that we want to help, the market and what we’re building and getting really excited about that that you also don’t realize the very close and immediate impact of even ‘how are my actions setting example’, not just for my team but in turn how is that trickling down onto to their families and into their friends.

Katica, thank you so much for all this wisdom. I know I’m leaving this conversation with so many great takeaways. I mean, everything from just being more human and realizing how human I am and mispronouncing your name for the first 10 minutes of the podcast.

KATICA: It’s okay.

CLAIRE: But that too, this reassessment of what is real worth and to ask the question of how could I be more helpful and to consider the ripple effect as leaders. So, thank you so much. I appreciate it.

KATICA: You’re very welcome.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.