Womenflare Presents: Unfiltered

Hey, everyone. I'm Nimisha, a security program manager intern here at Cloudflare this summer, and welcome to this week's Womenflare episode of Unfiltered. Before we get started, I'd like to tell you a little bit about Womenflare and what to expect in the upcoming episodes. Womenflare is an employee-led group here at Cloudflare. Its mission is to inspire and elevate all who identify as women. Our program, Unfiltered, will cover topics such as career journeys, advancement stories, personal development strategies and tips, mentoring lessons learned, and much more. We're super excited to be here and looking forward to having unfiltered conversations with you all. So stay tuned for upcoming episodes on Thursdays at 3 p .m. Pacific, 5 p.m. Central, and 6 p.m. Eastern. So today we have Michelle Zatlyn, co-founder and CEO of Cloudflare, here to chat with us about her experiences with imposter syndrome. Thank you for joining us today. Thanks so much for having me, and I love that we do these series, so I'm really honored to be included. So thanks for having me on as a guest. Yeah, before we dive more into the topic, quick note for our viewers, if you guys have any questions about the segments or for Michelle to answer around this topic, feel free to submit them by emailing us at livestudio at Cloudflare.tv, and you can find the banner right below this video. So today we'll be talking about a topic that touches a lot of us who believe in empowerment but don't feel empowered. Some of us may know this term and have read thick pieces about it, and some of us have actually experienced it but don't know the term, and that term is imposter syndrome, the scariest of thought patterns out there. So I know that a lot of different people have their own definitions of it, so Michelle, what's your definition of imposter syndrome? Well, with the preface of I am not an expert, but of course have experienced it myself, so I guess in my way that I would describe it is when you feel out of place or that you're not ready for an opportunity or that you almost doubt yourself or don't feel like you belong where you are, you almost feel like you got lucky and kind of snuck in versus actually earning it and doubting yourself is my definition of my non-professional, unprofessional definition of imposter syndrome, that feeling of do I deserve to be here or not? Yeah, yeah, for sure. For mine, it's exactly the same. So for me, the unprofessional definition is this cognitive dissonance between what you know other people think about you or what someone might rationally just deduce from looking at your life versus how you actually feel on the inside. So boiling it down to like the industrial definition, it's essentially the feeling that you're an imposter, the feeling or the fear that you'll be found out as undeserving or unworthy or revealed as fraud. So it's like I know rationally X, but I actually feel Y. And if you're doing anything difficult or challenging, it's natural to get pushed out of your comfort zone and have this feeling. And it's not a sign that you're not ready and that you should stop. It's a normal feeling. So speaking of this normal feeling, how do you think, how have you in the past identified if you're feeling this way or that you know that you have imposter syndrome? Yeah, no, it's so sometimes it's just the English language is pretty amazing that you can put terms and it's like once you realize you're like actually that's happened to me so many times throughout my career. And I think it is when you really put yourself in a new situation or challenging situation, I think it is really common. And I think that this is something that recently, and I don't know why I've heard the term a lot more imposter syndrome. And I think when I was maybe earlier in my career, I didn't even know it existed. So I think just having more awareness of it, it's easier to match situations to this. And I even the other day, I saw somebody senior on our team putting it in our team chat room saying, I have imposter syndrome. And it was like an executive on our team. I'm like, wow, like, I can't remember when the last time I'd seen something like that show up in a chat room. So I think more people being aware and understanding what it is, is important. And, you know, I know, if I think about where I came from, I grew up in a small city kind of in Saskatchewan, Canada. Now I'm running this large public company in San Francisco. And I've been kind of really pushed outside of my comfort zone many, many, many times. So as I've reflected on when have I had this, it's happened so many different times throughout my career, because I think I have put myself in these situations that feel uncomfortable, and it's hard to discern. Am I ready for it? Am I not ready for it? I'm the best person for it. And so as I reflect back, I think it's happened many times, and it continues to happen. And actually, you know, I think it's a good thing. I'd rather that than think that I'm so great, almost the opposite of imposter syndrome. So I think it's a good thing. But it's happened to me a lot. And actually having the words around it now is helpful to be able to identify, oh, this is that and that's okay. Yeah. So some questions that kind of helped me in the past to answer if I have imposter syndrome is, do you think all your accomplishments might have been due to luck, or a chance or connections? Or anything else that isn't based on your talent? Do you ever feel like everyone around you is smarter, works harder than you, does a better job than you? Or do you ever find yourself terrified of making mistakes and constantly believing that you're likely to make one, no matter how expert you become in that task or in that job? And the last one that I relate to a lot is, do you ever feel so nervous to a point that you don't even want to try? So those are some of the questions that I like to ask myself if I'm going through, if I'm trying to identify if I have imposter syndrome or not. So speaking of experiences, do you think is it something that you experienced at one part of your life? I know you touched upon it a little bit. But or is it something that has been prominent at a certain stage of your career or an age? You know, I think that when you really, again, I think about where I started and where I am, and that learning curve, it's been really steep. And so you're kind of, the best way I can describe it is, I feel like I've been stretched in so many different ways. And I will never go back to the same size. Again, you know, you kind of you show up in one of these situations, you get stretched out, you almost like get balloon. And then you eventually kind of deflate back, but you kind of are in different shape. And so it certainly wasn't like one point in time or one chapter of my life. Again, and I think part of it is I keep striving for more and finding myself in newer and different situations, which have higher and higher stakes. And so yeah, sometimes it was much easier as a student. As a student, I feel like you get grades, you're kind of, and you're graded on your work, but then in the workforce, it's a little bit more about, well, how'd your project go? It's so much less, it's much more nuanced, I guess. So I guess I miss being a student in some ways, but it's really, it's just been through throughout my career. And I think I've gotten better at dealing with it and almost seeing it as a more of a not a positive than a negative, right? I think some of the questions you asked are good. But once you start to realize, oh, I'm in this new situation, I am being pushed. I mean, there's that really popular saying, surround yourself with people who are smarter than you, right? And that's true. I'm like, of course, I want to surround myself with people smarter than me. But then inherently, you're going to be in awe of all those people, because you feel like they're smarter than you, and they're going to be pushing you, and you're going to be like, wow. And so I think what has changed is it hasn't been, I had it and now I'm over it. I think it's more, I actually can identify it more. I can say I'm at peace with this. And I think it's a natural feeling because I keep putting myself in these different situations. And I see it as a sign of growth. And almost some of the listeners, the way I think about it is don't run away from it, run towards it. Almost put yourself in those situations, because that's how you grow. That's how you stretch yourself. You'll never quite go back to the same size again. I guess that's the thing that's changed over my career is I'm actually more excited about being in those situations than not, because I see it as an opportunity to grow and connect with new people and new opportunities. Yeah, that's a great point. Just pushing yourself into those uncomfortable situations so you can grow from there. So just expanding a little bit about that. So has it ever stopped you or blocked you from achieving something? If so, how did you turn that around into a positive thing rather than a negative thing? Well, I can think of two situations, and so I'll share both. I remember earlier in my career, I had been doing really well in different roles. I graduated with a science degree, and I was working in business, and I really liked it. And at some point, I wanted to go back and do my MBA. And I, like a good student, researched all these programs, and I kind of had my list of programs, and I was getting ready for all my applications, and I was actually at a party. And somebody said to me, oh, what are you up to? I was like, actually, I'm working here, but I'm currently applying to go do my MBA. And this particular person, who I did not know very well, they said, oh, and they're kind of aggressive, direct, and they said, hey, what schools are you applying to? And I thought I was so proud. I was like, oh, my list of schools are, and I kind of had my list of schools. And he looked at me, and I did not know this person very well, and he said, well, Harvard's not on the list. Why aren't you applying to Harvard? And I kind of, I remember kind of, like, I still, it's, this situation is imprinted on my brain. It'll kind of always be imprinted on my brain. And I said, well, you know, it's competitive. I don't know if it's a good use of time. And in my mind, I'm thinking, because it's Harvard, I'm not sure I'll get in. That's why I'm not going to apply. And he looked me straight in the eye, and he said, if you don't put your name in the hat, you for sure will never get it. Like, you've got to put your name in the hat to get it pulled. And, you know, I did not know this person very well. We still are not in touch today. I don't even, you know, our lives have kind of diverged. But the fact that this person said that to me, I went home that night. I looked up the application. I ended up applying. I ended up getting in, and fast forward, that's where I met Matthew, and we started Cloudflare, and this is fast forward to today. We're now at Cloudflare TV talking about this. But this moment of, I didn't, I wasn't even going to apply, because I didn't think it was possible. And I see that happening all the time, where people say, they almost stop themselves, they filter themselves, say, I'm not going to apply, because it's not a good use of time, I will never get in. And I try and pay that forward of, well, if you don't ever try, you for sure won't, you for sure won't get in. And so, I think that's an example, like, in my, you know, earlier in my career, where someone really pushed me to say, put your name in the hat, put your name in the hat. And I just think that's a good metaphor. And I hope that inspires other people to put your name in the hat. Doesn't mean you'll always get pulled. But if it's not in the hat, it certainly won't get pulled. And so that was one example. Fast forward, we were, my second example is related to Cloudflare. So early on, Matthew, Lee, and I were working on Cloudflare. And it was an idea, and it was getting a lot of traction. And we started to raise some venture capital, right. And yeah, I had not done that before. And neither had Matthew, nor Lee. And so it was a new to all of us. And anytime you have to show up to somebody and explain what your idea is, and by the way, will you give me money to do it, that's a really hard thing to do. I know it sounds, I think you read these stories, and it sounds so easy, but actually raising money is a difficult thing to do, especially the first time or second time around, it's hard. And I remember that this was our series B. So we had raised a couple million dollars, and we had good traction. And this was right after we launched Cloudflare. We're actually coming up on our 10th anniversary. So it was right after this was like October of 2010. And we had had really good traction. And so we had been invited to talk to a lot of venture capitalists was going well. And I remember thinking for our series B, we thought we were going to raise about $6 to $8 million. And that seemed like a lot of money to me, like a lot of money. And I remember having to practice in a mirror saying, and we're raising $6 to $8 million, are you interested? Because that just seemed like a lot of money to me. Well, and I really had to practice. It was a very unnatural thing to do, because I just thought, who's going to give us $8 million to go see whether we can make this idea happen. Turns out we ended up raising $20 million that round. So if you had to practice $6 to $8 million, imagine like two days later, or 10 days later, we were practicing $20 million, being like, oh, wow, okay. We really had to practice. I personally had to practice. And I think it's probably fair to say Matthew had to too. Fast forward, a couple years later, we raised that $15 million, and then we raised $300 million, and we just went public where we raised $500 million, and we raised another half a billion in the public markets a few months ago. It's gotten a lot easier. All those times I was like, okay, I've got this. But back to that time, that time where I had to ask for $6 to $8, which turned into $20, that was very hard. And I just thought, who's going to take us seriously? And the way we overcame it is we actually practiced. We practiced in the mirror. And the more we said it out loud, the more normal it became. And next thing I knew, I was saying it to somebody else. And the first time I said it, it did not go very well. But the second and third and fourth time, it got a lot better. So I guess practice makes perfect. Yeah, those are great examples. So you touched on two things. You touched on how you had a support network or someone that you met at the party to push you to apply to Harvard versus also your own efforts that you put in by practicing and practicing until you got it right. So just going back to the first one, so you talked about how that you had a support network to kind of push you to do those things. How has that experience been? And now I'm guessing, because you've succeeded so much in your career, how has your experience been being an ally versus having one? You know, I am so lucky that I have, you're right, that I, in that particular person to me was my older sister's friend. I have two sisters and my parents. And I'm the luckiest person that they, my sisters, their husbands, my parents have always been a huge champion, kind of cheerleader. And I acknowledge how lucky I am to have that. And so it was my older sister's friend who was the one who said, you should apply to Harvard. And to my credit, at least I listened to him. A lot of people would just not listen. And so I'm kind of a sponge a little bit. That's probably both my, one of my greatest superpowers and whatnot. But so I have a great family who's always kind of rooting for me. And that makes it a lot easier when you have someone rooting for you. And even my boyfriend at the time, who is now my husband, as I built Cloudflare, you know, there's a lot of times you're like, should I do this? Oh my God, am I crazy? And he was always like, you have to see where this goes. And I think if you can surround yourself with people in your life, a life partner, friends who aren't saying, why are you doing this? Telling you all the reasons not to do it. But instead of, I don't really understand what you're talking about, but you should go for it. I mean, that's a huge difference, right? And I was really lucky to have that early on and collect more people like that in my life along the way. I was also really lucky to have two amazing co-founders, Matthew Lee and I, where we all really believe in what we're doing. And when you're down having someone up to say, Hey, it's not all so terrible. Here's some good things. And, or when things, when you're like, when everything you're on the top of the world, cause you're part of whatever you're controlling is going really well for them to be like, Oh man, I just had a really hard meeting. Do you have any good news? And you're like, yeah, I do have some good news. Right. So we kind of be that ying and yang. And so I had really great co-founders to be allies with. And I'm, I think that if you're thinking about starting a company and if you can find great founders, co-founders, like that's great. If you can't find great co-founders and doing it by yourself is better because I think bad co-founders is so detrimental to the progress. But so I guess those were some of the places that I was really lucky. I will say that, you know, one of the things that I think gets under underappreciated, which I will say here is, you know, I've been building club for 10 years and there's been, I mean, we've learned so much, we've done so many things and it's not, it's, it's not like I've had formal mentors along the way. Like I've had really supportive boyfriend now husband, like life partner. And I've had supportive family members. I have amazing business partners, but there's been a lot of people who've inspired me along the way. And it might be through what they write. Like I don't even know them. They could be total strangers, but it's kind of like this idea of they wrote something online about their experience and I took something away from it, or I heard them speak. And when they're really vulnerable about something and you're like, wow, here's the lesson I learned. This is what I'm going to take away. I think as I look back, that's actually helped me a lot where it's people sharing their experiences. And then you can kind of identify which pieces you want, and then you feel empowered to go make the decision that's right for you in that moment. And so a lot of my allies over the time have been, again, I've been super lucky, but some of them have been strangers that don't even know that they made a big impact in my life. And I think that that's one of the greatest assets of the Internet. You can find information, people are willing to share things. And again, that doesn't mean everything is great, but if you can find those people that you're like, wow, that's really interesting. It can have big impacts in your life. Just like a book can. And I, I, I used to read a lot every night before bed, I'd read an hour about something. And there's always something going on. I was just trying to follow people who knew and trying to filter out the things that were helpful to me and not helpful. So that's kind of the, the unobvious, non-obvious piece that I think can really help people in their career as they grow. Cause it's like, if you don't know, and you don't know the people, just go find them online. You don't need to know them. And it's almost like a, to me, it was really a level playing field where I didn't have to know the person. I just had to do the work and read up about it. It was kind of like, if you were a good student, if you're a fast learner, it almost, it's almost a much stronger superpower than actually knowing the person. Yeah, that's a great point. Thanks for sharing that with us. So you touched on a lot of things about how you had, you just found random things on the Internet that helped you. So who and what inspires you the most? And is there anyone, you know, or you look up to that has also suffered from imposter syndrome or has there been a story that shocked you? Yes. Well, I mean, I'm inspired by a lot of different, so I, to me, what I love is that I feel like there, I have like a collection of people and stories that inspire me. And so it's, so it makes this a hard question to answer where it's like, not one, I can't say, Hey, go follow this person. If you follow this person, you will find the answers to life. Unfortunately, that's not the case, but I, but I feel like I have a broad range of people who inspire me. And it's, it's everyone from, I think entrepreneurs who have built companies larger than ours, like that are a couple of years ahead. I look up and I think, wow, look what they built. And it's almost like seeing that they've done it means that we can also do it. Like they've shown it's possible. So if they can do it, why can I do it? Right. And I think that that, and, and, and so when there are challenges along the way, you go and look and find out how did you do it? And again, you either go research it or you ask them and whatnot. And I think that's, that's kind of like on the business building side, but you know, I often say we have, you know, over a thousand people that work at Cloudflare and I, I'm, I've, this is something I've said over and over again. It's the best part of my job are the people I work with because I'm inspired by the people I work with. Like, they're so smart and ambitious and they care and they have like a domain expertise that I don't have usually like, right. Like, for example, like you're in security, you know, way more about that than I ever will. And it's like, I get to work with you and we get to come together to solve problems, to go deliver something for our customers. And so I find myself, I remember we were, I was meeting with our cryptography team and we were getting ready. We were doing a, a week of launches for something called crypto week where we're going to launch something every day. And I, I got a pre-briefing of kind of what to expect. And I just remember saying, I remember the end of the meeting saying, this was the highlight of my week because I just learned so much. I'm like inspired by all these things that you're doing. I can't wait to give it to our customers in the world and the researchers around the world to go use it. And I like, I feel really lucky that I get to call you a colleague. Right. And I think so. So I am often inspired by those that I work with as well. And then there's, you know, people that aren't in business or that, but they're just really good at what they do. Right. Like an amazing artist who's like at the top of their game, like, how can you not be inspired by greatness? You know, even I read, I watched the last dance during this pandemic COVID about the bulls in the, in the nineties. And whether you're a sports fan or not, or what you think of like Michael Jordan, I mean, they were the, they won six championships and seeing the inner workings of that. There are so many times during that series where I thought there are so many parallels to entrepreneurship and like inspired me to want to come and win championships at Cloudflare. Not only six, I want to win seven and beat the bulls record, even though we like in a totally different. And so I'm also just inspired by other people who are top of their game as in, in different ways. And, and I love that it's a portfolio and that I can kind of find hook onto different sorts of things. And that works really well for me and that won't work well for everybody, but that definitely works well for me. And, and that makes it fun to learn about different people in different industries and how they approach things. Cause I feel like there are more, we're more similar than different at the end of the day. Yeah, that's, you talked about like how your coworkers inspire you so much. Are there any trends that you've maybe noticed over the years while building Cloudflare around imposter syndrome or maybe like your direct reports came to you? Like, have you, how has that evolved as you've been building Cloudflare for so many years? Oh, I mean, I've told that Harvard story. If you don't put your name in the hat, you'll never get pulled many times in my career. Internally, I'm just like, what do you mean? Like, go for it. Like, put your name, like raise your hands. And I think that that's, I'm sure, I feel like that story is something that a lot of people, I, I tell it on purpose. Cause I think a lot of people acknowledge, wow, that's really made me rethink how I've approached something. And like, I love that. Right. And so that's something where people stop themselves from even thinking that they're the right person for the job and being like, no, no, no. Put your name in the hat. Right. Go. If you want to change roles internally, put your name in the hat. Cause if you're not on the list, then no one's going to come tap you on the shoulder. Right. Like you gotta, you gotta raise your hand that yes, I'm interested. So I, that's, that's something that I see often of cause the opposite of imposter syndrome is thinking, you know, at all and that you're overly confident. Right. And, and in many ways, I would rather have imposter syndrome than that syndrome, but that means you stop yourself from doing things. And so I see that often like as a trend. And so you really pushing yourself to do it, raise your hand and say, Hey, I'll step up to this challenge. I think that that often ends up being a positive, not a negative. So that's, that's one. And the other one is, is, as you said, is someone who's really thinks that they, they really, someone who does a really good job and it's, wow, you did a really good job. And then they say, Hey, I got lucky. Right. And, and sometimes that's kind of a it's a way to deal with that recognition because it feels uncomfortable sometimes to be said, to be put in that spotlight of, wow, you did a really good job. But sometimes I've had to say to people, no, you didn't get lucky. You've made that happen, right? Like it would have been a different outcome if someone else had been running the project or involved. And I'm sure, sure. Luck is some part of it, but it would have been a different outcome if someone else was running it and you did an extremely good job. And even if you're uncomfortable, you should just think what the answer is. Thank you. And think about what you learned from it and just know that you'll always have that. And you should think back as a, as a very proud moment. And I, so I think that, that downplaying the role that people, that as I've seen, especially earlier, her downplaying the role you've had on the outcome of a project. I don't understand why, cause it's kind of humbling and whatnot, but I think that there's a really fine line between kind of being overly confident and humble and just being acknowledging. Okay. Yes. Thank you for saying that. Like, I was really proud to be part of this and I'm really proud of the outcome. And of course it was a team effort, but I'm really proud of the outcome. And I'm proud that I got to play a role in that. I've, that's something that I've seen as well as a trend. And I try and encourage people to kind of correct it the other way. It's like, you know, companies are people, a collection of people doing things. And the best thing you can do is do a lot of things in your career. Cause by doing, you learn, you kind of push yourself. And if you can do things that have good outcomes, it's just like, it becomes this really strong momentum in your career. Right. So getting to kind of like the more unfiltered part of the segment is I know that imposter syndrome can oftentimes, especially the minds of women in tech can create like a vicious circle where they're constantly kind of second guessing themselves when taking on like a new project or a new task, also criticizing themselves during performing or performance reviews, or also doubting their own worth when taking like a new offer or negotiating for that offer. So what do you think are some of the steps that women in tech can take, especially when tackling this feeling? Again, I think acknowledging it, just saying, okay, I feel outside of my comfort zone. But I'm, I'm going to get pushed myself outside of the comfort zone. Cause that's how I get to the next level. I remember Matthew, my business partner wants to use this analogy. So I'll use this. And I think when you're in that situation, what I want you to envision is like being a puffer fish, like kind of like puffing yourself up and be like, okay, I got this. And, and even when you don't really feel like it, you got to kind of just say, okay, I got this practice in the mirror, practice asking for the money practice saying, okay, no, I do this. Like trying to overcome it and just saying, I am going to do it versus letting some of the negatives rise up. I think that that matters. The analogy, the puffer fish is a good one, but the other, the other thing that like, I think of visualization is like one off the side of the cliff, just run off the side of the cliff and don't stop yourself, like run. And like the, the, the, the parachutes got you, the paraglides got you. I think is, I hope you think back to this conversation and think, don't not put your hat in the ring. Don't stop yourself, like run off the cliff. And I think you'll, you'll, you'll learn a lot more than you give yourself credit for. And so I think just acknowledging it and then hopefully thinking back to the puffer fish or the cliff analogy, or putting your hat in the ring. I mean, any of those, and it's just like, okay, I'm going to, I'm in this uncomfortable situation because I'm in a growth. This is a growth opportunity and, and I'm going to learn and do my best foot forward. And, and I'm going to bet on myself. And I think that hopefully will, will come a long way. And, you know, I think that there's lots of tools where you have allies, friends, you can go to someone internally and maybe, Hey, I'm having second thoughts and you kind of need someone to kind of raw, raw you up. Sometimes like you need a cheerleader sometimes and find a cheerleader in your life to say, you've got this. And, and, and just like, go. Yeah. Thank you for sharing that with us. So a standard women's player question that we ask everyone who comes on to this segment is when do you feel empowered as a woman to do your best work? And when do you not? Oh, yes. Uh, I do my best work when I feel like I'm surrounded by people who believe in me. And so, um, I, I, there's some research that sometimes people are in a situation where everyone's given an a and it's your, it's, it's up to you not to lose the a versus starting with an F and having to prove everyone you deserve an A. Like those are very different situations. So I love when it's like, yeah, no, you, you, there was a bar to get in, you're in, and now we're all together and there's not more to prove. It's like, now let's go focus on doing great work. That's when I do my best work where you feel empowered. And it's like, where it's not, was I the mistake? And do I have to prove myself to be here? And so I think those are two very different situations and I do better when I feel like, yep, I'm here. Let's go do work. We're all in this together. We're on the team. Let's, let's go win the championship together. Thank you so much for sharing all your insightful experiences and getting unfiltered with us. It was really helpful. All your, all of your analogies from running towards the cliff and the pufferfish and putting your name in the hat. All of that I think is going to be super helpful for our viewers. So thank you so much for coming on today. Thanks so much for having me and good luck with everyone. Thanks so much for having me in the Michelle. This was awesome. Great. Thanks a lot, everyone.