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Episode 47: Interview with Pooja Brown, VP Platform Engineering at Stitch Fix, Former VP Engineering at DocuSign

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As VP Platform Engineering at Stitch Fix, Former VP Engineering at DocuSign, Pooja Brown talks about how every experience is a learning opportunity, people management, and why it’s important to “keep your listening ears on as a leader.”

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 Pooja Brown, VP Platform Engineering at Stitch Fix, Former VP Engineering at DocuSign.

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** Note: At the time of recording, Pooja was currently employed as the VP Engineering at DocuSign.

CLAIRE: Hi, everyone. I’m Claire Lew and I’m the CEO of Know Your Team, software that helps you avoid becoming a bad boss.

I have one of my favorite bosses actually today here on the podcast. I have with me Pooja Brown who is the VP of Engineering at DocuSign, an app that I feel like I just used the other week. I use it all the time. And if you’ve ever had to sign anything, I’m sure you’ve used it as well. And so, I had the pleasure of interviewing Pooja, though I want to say maybe a month or two ago, she spoke on this panel here in San Francisco for the San Francisco Engineering Leadership Group. And I was blown away honestly by the insights that she shared. So of course, had to have her here on the podcast and excited to ask you Pooja, this one question about leadership.

POOJA: Thank you, Claire. Thank you for such a warm welcome. I’m honored to be a part of this podcast, and I look forward to the next few minutes with you. I’ve been in this profession of tech and tech management for almost about 15, 18 years now. When I look back, I keep lying about it because I’m like, “Oh my God, that makes me sound so old.” I’ve been in this profession for a while, and in the last sort of seven years, I’ve been at DocuSign. I’m glad you got a chance to use DocuSign and I hope that your audience has used DocuSign. I feel DocuSign finds its way in anything meaningful in people’s life events. For me personally, when I decided to work for DocuSign, I’d heard about it because every time something important was going to happen to me, suddenly DocuSign was in the middle of it. My green card and I bought my house when I [crosstalk] sort of like hard things like that. Hard and meaningful things, I always found DocuSign in the middle of. So, I’ve been here for seven years and building teams for DocuSign to do some great work.

CLAIRE: Wonderful. I think from those years, by the way, like I was saying, there’s wisdom and a ton of insight that only time can really buy. So that’s what I’m excited to talk to you more about. So on that note, this one question that I’d love to ask you that I’ve been asking the leaders that I respect and admire is what’s one thing, or it can be several things, that you wish you would’ve learned earlier as a leader?

POOJA: Every experience is a learning opportunity. I keep thinking that that’s all we do every day is we learn a lot. And we apply what we learned to day to day experiences. But when I think about things that I’ve learned as a leader, and things that I wish I’d learned a little earlier, if anything, but when I think about my own career in tech management, I still think fundamentally you have to know your skills, whichever career you’re picking. Whether it’s technology, whether it’s legal, whatever you want to do, you have to be good at what you do to start with. You have to have the skills. And I say skills. Skills can be acquired anyway, it doesn’t mean education. It could be acquired in any form, but you have to really enjoy the profession that you’ve picked. And you have to actually have some sort of real experience with it.

And I’ll tell you why I keep saying that because us, leadership is about managing people or leading people. It’s sort of like keep thinking of this, there’s managers and there’s leaders. And technically, people want to work for leaders, in general, whatever profession you pick. And in technology especially, is like people want to work for leaders who can set a vision forward. And then hopefully, you’ve hired well and they can sort of help execute on that mission.

But going back to what I said was you want to really understand the skill and the discipline that you’re a part of and you want to have real world experience yourself with it. That way, when you’re leading teams, you can actually understand how you can support them. You can’t hand wave your way out of it. At some point in life, you have to have empathy to what they did to be able to really be a few steps ahead to unblock some of the challenges that they’re going to get to. Ultimately, leading or managing people is about people.

You are going to spend a lot of your time with just people. It’s like you want to keep motivating them. You want to keep getting them aligned with why it’s important what they do, the value that they bring. I think those are all important things, period. So don’t be surprised if your calendar looks like a lot of people management. But you need to be able to keep going back to your roots and your discipline, and whatever that takes for you to stay in touch with that. People say, “How do you stay technical while you’re a manager?” You’ll find ways. Even if I talk to people 60% of my day, I’m talking about technology. I’m making technical decisions every day. So, your team has to respect those technical decisions, which means you need to have a way to stay on top of technology. An interesting feeling is that as I grew my career in engineering management, I realized my job was about people. But I realized that no matter what, I have to keep in touch with the real skill set that I bring, which is technology. And so, that’s sort of like one thing and you figure out how you spend time with it and how you make time for it.

CLAIRE: Yes. I think it’s a pretty actually counterintuitive insight in the sense of exactly what you said as sort of most traditionally or widely accepted and true perhaps is that when you manage people, it’s about people. But I love what you said about just not being able to hand wave away problems. So, I think sort of inherent in what you’re describing is just not being fooled by the illusion of your own expertise and making sure that it’s rooted in something real and something that you’ve either experienced or are continuing to hone because it’s — and I don’t want to put words in your mouth. I’ll pose a question here. Is it easy to lose touch of that, in your opinion as a manager, as you get further away from the work?

POOJA: Yeah. And then you can get fooled with it because you’re in the domain, right? And you know the domain really well and you’ve sort of been in that domain for a while and you get more and more comfortable with it. The illusion that you know your stuff continues to follow you, which is fine. But the opportunity cost of being comfortable in that illusion is high for you, for your team, and for the company. As an example, you run a software as a service.

Ultimately, you are running a company. You’re not producing coke, you’re actually building software. So, you need to tell what’s happening in the industry and what is happening on the floor as people build software. And if you don’t take those investments, your gigs going to be up pretty soon. People say, “I’ll do POCs on the side or experiment with the new tech stack. If you make it a priority, you will figure out ways to do it. And that could be going deep diving into an architectural decision, that could be diving and really understanding the pros and cons and challenging the teams to think about those critically, asking the right questions, being involved in the right architectural discussions. That could be taking on a hard incident and being a part of it and driving the outcomes of what happened and making sure that that incident doesn’t happen. I don’t know what it is, but I just feel like if you make it a priority, you will make sure that that part of your skill set doesn’t go obsolete.

CLAIRE: Absolutely. I’m actually really inspired now listening to you sharing this because I’m thinking, personally reflecting, how do I stay in touch with the subject matter around the fact that we are a software tool to begin with. Actually, it’s hilarious. I built my personal website from scratch. I produce small [inaudible] project all the time, they’re not very good, but just enough to keep [inaudible] fresh. And then the way that I’ve always actually thought of our company is even more than a software company, we’re an education company. So, the amount of reading that I do around leadership, the amount of people I talk to, the amount of executive coaches minds I picked, that sort of thing. Making sure that I am fresh on every study, paper written around leadership. I’m thinking, “Okay, I do those things,” and I love this idea that it can be different for every person too. So, I just appreciate very personally that reminder, Pooja. So, thank you. How about for yourself though, in coming to this realization. When in your career did it sort of hit you like, “Oh, I better start making sure I’m finding ways to stay in touch with the work.” Was there something that happened or maybe did you yourself have a boss who wasn’t as in touch with the work as they should have and you thought, “Ooh,” that’s maybe hurting their ability to manage. When did this realization occur?

POOJA: I always feel you kind of treat others the way you want to see yourself treated. You think of it that way. When I look at the people I respect around me and look at the careers that I really want to follow, or I’m curious of how they happen, more and more I interact with those folks, I realize how deep their knowledge is in the sphere that they’re working with. There was no aha moment. It was just a realization of the people that I think are awesome are the ones who were actually really good from a technical point of view. And then there’s another part to this question that I do want to answer, which is how do you work with people and sort of how do you really be true to your own self? But I always found them as a very strong balance between technical and being able to work with people. And that was why I sort of realized that that’s just important. And when I work with my teams and when you do career planning and career building, you have to be able to balance both of those.

If you can identify the next technical challenges folks can take for them to really enjoy or be a part of the next growth in their career, then they’re not going to believe that you are actually invested in their career. It’s sort of be better at your job is not a feedback. You actually have to create opportunities for them to take on or identify a matchmaking. “Given this skill set, this is what you can do and this is a need of the business. And I think this could be the next technical challenge for you to do.” It’s always a symbiotic relationship. Some of it is a challenge. Some of it is, “Is this the right fit for the business?” Because ultimately, they’re putting you in charge of making that decision. So you have to keep balancing the two things. But I think unless you do that, your team’s not going to see your value pretty quickly. And the organization will also stop seeing your value. But ultimately, these jobs that we have is, as a VP engineering, my job is to be able to understand the risk associated with the technical decisions. It’s always about risk when you’re talking to stakeholders. How do you assess risk if you don’t understand the technical choices that are being made? I don’t think it was ever like, “Oh my God, what am I doing?” It’s just sort of like the way I started drifting and following people made me realize this.

CLAIRE: I think that’s amazing in the sense that you really clearly paid very close attention to the people who inspired you, the people who you thought were amazing and sort of extracted, “Okay, well these are the things that they’re doing.” And I think what I find remarkable about that it was this insight that you extracted or discovered is, I don’t know, I think a lot of times when we think about leaders who we admire or who inspire us, we think of sort of the broad characteristics of, “Oh, they seem charismatic, they seem dependable. They sort of were very eloquent.” Sort of being able to back up their expertise should have a real deep rooted knowledge is not sort of an obvious thing one gets inspired by, in my opinion. So, I love that that’s something that you picked up. Would you say that you’ve been more influenced by sort of positive role models that you’ve had in your career or more by negative ones or maybe both equally?

POOJA: Some of it is cultural. I come from India. And culturally, authority is what you look up to. It just is what it is. And then the woman from India, it’s a submissive culture generally and you just look up to authority.

CLAIRE: Very similar to Korean culture. I’m Korean.

POOJA: So when you asked me whether it’s positive or negative, it’s hard for me to go down the negative because my assumption is that if somebody’s authority, it was the right decision and I have to learn. I can’t tell you an example of negative, but I can tell you that the positive role models definitely multiply me, multiply what I can bring. For me, that is always been a positive association of following positive leaders. I’ve worked with someone and I’m going to keep names out of it. But he was one of the strongest technical people at met. It’s just like he knew his stuff. But the fact that he could explain it in more business/sales context was even more attractive to me. But we weren’t talking abstractly about a technology addition or an architectural change. We were talking about that change influencing some major business outcomes for the company. To me, that was so attractive and in my mind, such a hard problem to solve. People say, “Okay, we’re going to make this, rewrite the architecture or we’re going to make these technical investments.” To be able to explain those in a way that people who are nontechnical get actually excited about those investments and want to invest in it is a hard problem. The role models I’ve always had are the ones who are able to do that really well. And it comes with the thoroughness of both domains.

CLAIRE: Exactly.

POOJA: You really need to the technology and to be able to sell it to both sides is not an easy job.

CLAIRE: Speaking of bridging cultures here, I think of it almost like translating one language into another. In order to be an effective translator, you actually have to know both languages extremely well. It requires an immense deep knowledge on both sides, not just one or the other. So, to sort of mirror a comparison here on the engineering side, speaking to the business side, you need both.

POOJA: It’s a really good way to put it. I never thought of it that way. [Crosstalk] the more skilled you get in both domains. And that’s why I seek out opportunities where I can learn either parts of it because ultimately as a leader, you need to be able to speak both languages. What’s funny to me is that a lot of times, engineers are the ones who actually get most motivated by business outcomes. People assume that they want to talk about tech talks. A lot of engineers actually want to see the business outcome they created and they can be excited about that. And just sort of like to be able to even switch dialogues in both sides and to be able to motivate one with the other is part of my job. It’s part of any job as a leader.

CLAIRE: Absolutely. When have you seen this backfire, just to sort of provide like a devil advocate’s point of view. So when have, or if at any time, have you noticed when a leader or a manager will sort of use their technical expertise or domain knowledge as a crutch for dismissing people’s decisions or not delegating things or being a bottleneck? What are your thoughts on that? Do you feel like that’s common? Or something like how do you avoid accidentally leaning on that too much as well?

POOJA: It always happens, the smartest guy or gal in the room. It’s easy to latch onto that technically because to some extent, for a lot of people that is language that a lot of them don’t understand. And if they don’t understand the risk, then you can really freak them out about the risk you’re about to take. I think it’s the power in your hands you need to take not lightly. But I think with it, also humility is a part of it. It’s the humility and humbleness. Sure, you know one thing. You might not know a lot, to be able to ask the right questions. The folks who don’t understand your language can actually even bother to understand the risks that you might be bringing to the table. I’ve always seen these conversations when you’re like this classic, like a business guy talking to an architect. You’re like going nowhere. [Crosstalk] totally happens because the business outcomes aren’t realized. My job is to keep bringing back why we’re doing this. Ultimately, we are responsible to the business we work for. And the more sort of management or the higher in the org that you get, it gets harder and harder. But that is kind of the job you’re paid for is how do you create business outcomes with subject matter experts in completely different disciplines. And how do you get them aligned? You can say, “A lot of meetings.” No, it’s actually not. It’s making people who talk different languages understand the value of the outcome that we’re proposing and why your effort is needed, why their support is needed and how we can get there. It is super critical.

You asked the question of like when has this backfired. And I want to say the reason I brought up humility or humbleness is you also know why you’re brought into the conversation. Like as in at some point, I am engineering. And I can make recommendations. I can inform the business about my recommendations, but I also have to give in at times. It’s all about compromises. And one of these vectors is going to be more important. Don’t know what. Given the situation, one vector is going to be more important. And realizing why your opinion in the space that you are an SME for is important and when to back off is a very important thing.

At some point, you have to realize that business is making a recommendation. Assume that they’re subject matter experts there, just the way they’re assuming you’re the subject matter expert when you’re saying this is the estimation or the risk is high. I think when people don’t honor the expertise in each of the disciplines, that’s when things get anxious. It’s good that I need to be able to talk business and tech. I need to be able to do all of these sides. But ultimately, I’m an engineer. Ultimately, I am in the technology profession. So, I also need to back off when the recommendation from a technology point of view is done. And I feel that a lot of contentious things when people overreach in areas they’re really not subject matter expertise with. They might have an opinion, which is fine. I could have an opinion about what the next feature looks like. But ultimately, that’s not my expertise. We have people hired to do that, and I can help inform and support them, but that is not why I’m included in the conversation.

It’s a personal thing for me when you said when this backfires. I’ve seen it backfire when people forget their expertise and they overreach into other people’s expertise. They may have egos and people challenging each other and then you realize the conversation is not what it started with. It went completely out. And it’s a fight about something else. I’m sure, we’ve all been in meetings like that.

CLAIRE: Oh, yeah. I’m like, “Oh, wow! That’s never happened to me at all, ever. I love the duality that you presented though. So this firm rootedness and curiosity in your own domain, yet a humility to accept that, that’s your domain. And it doesn’t mean you should learn about sales if you’re an engineering or you shouldn’t, you want to learn about support if you’re in design, et cetera. But that when you’re having that conversation, I mean, it sounds like there’s an element of trust in the other person’s expertise. I mean, back to this language as analogy, a common framework for, “Okay, we want to get these things done.” Well, interestingly, I think the more rooted you are in your own domain, it’s very easy to lose sight of that bigger picture. It’s like the more involved and the more in the weeds and, “Oh, if I only knew and understood and saw things exactly how I saw them,” the easier it is to see that bigger picture. So I guess my next question for you, Pooja, is how do you at the same time go really deep and maintain that connection to your domain and expertise? So if I’m a designer, being really up-to-date and understanding design, if I’m an engineer, sales person, et cetera, et cetera, or sales manager. How do you do that without at the same time losing sight of the business vision, understanding broader strategy. I’m essentially trying to figure out how you balance that. Like what are the ways that you think about this or do you have some self checks or things that you do or think about to just make sure that you’re continually connected?

POOJA: I wish I had like a workbook or a playbook of how I do it. I’ll say some things that I —

CLAIRE: It’s fine if you don’t.

POOJA: I’ll give you some things that I do. What I keep telling people is I have two little girls and it’s funny when I’m trying to get my five year old to listen to me. I keep telling her, “You’re going to keep your listening ears on. Listening ears on, listening ears on. Are you listening to me?” That’s one thing I keep reminding myself is keep your listening ears on. People will teach you. You come into the office and you bump into, give and take, 30 people a day. You have 30 opportunities potentially to learn about something. Is it possible for you to maybe deep dive into a couple of those? When I do one-on-ones with people, that’s a great opportunity to learn. One-on-ones, people assume that it’s your manager talking to this about your career or checking in. It is also your opportunity to be humble enough to know that they’re closer to the ground and they will teach you. And approaching those conversations with your listening ears on keeps you close to the day to day.

And I think that’s something that I keep practicing with, whether it’s your managers, your skip levels. Everybody says you have to do skip level check-ins. I actually do it as a way for my own learning exercise. You learn so much. You learn what the code is happening, you learn what their problems are. You understand where the conflicts coming, the teams. There’s tons of opportunities there. So I would say is just sort of like approach any conversation with your listening ears on. And when you don’t know, and everybody will say is ask questions. Everybody tells you that, but it is so hard to ask a question. And you’ll be surprised by just asking a question, once you show humility and so many people want to teach you. And it gives them a chance to feel good about it, too. So, it’s a win-win situation. You just learned and you made this person feel good about it. So, get over the fact that you think you don’t know it and just ask the question.

CLAIRE: I love that sentiment. Yeah.

POOJA: When you do that thinking that way, you’ll find opportunities. Don’t be afraid to get your hands dirty. Actually looking at a pull request and figuring out what happened that could have resulted in this incident and asking questions around it, people welcome it, people welcome it as an interest in what they do. And an understanding versus, “Hey, why did you break this?”

CLAIRE: Exactly.

POOJA: I think if you keep your listening ears on, you’ll keep finding opportunities. Another example I see is people show up to meetings with their laptops and they’re multitasking. I take pride in multitasking. Trust me, as a mother, being able to create multiple lunches and coffee and breakfast for the kids and getting ready and getting out of the house, answering emails. Multitasking is natural to me. But I also think it is a disservice when you walk into a meeting and you decide to multitask because you were losing an opportunity to learn. Either you decide not to go, but if you’re going in there, take the time to learn. Because trust me, there’s a lot of ways that people are actually trying to teach you.

CLAIRE: I’m smiling over here because I’m literally, as you were saying, put your listening ears on, I was imagining like the big Dumbo elephant ears. That was the visual I had on my mind.

POOJA: They teach you at school, right? It’s like little daycare, put your big listening ears on.

CLAIRE: And as hilarious as that sounds, I think it’s so effective because it is like that almost exaggeration of a practice that helps us actually stay in touch as leaders and to make sure that we’re receptive to the things that we need to know of and to make sure that we’re staying in touch. I mean, even as you were talking, I was thinking, “It’s so interesting.” We’ve done so much research and writing on one-on-ones and we have a tool in Know Your Team on one-on-ones. And I was thinking, “Gosh, I wonder if we reframed one-on-ones in companies and teams more as learning sessions.” Or even in the beginning, just sort of have a way for people to think like, “Oh, do you have your listening ears on?” Whether it’s blatant or implicit, but just how much that would change the conversation because everything that you described, Pooja, you’re saying, “Oh Claire, I don’t have a playbook.” It’s not even about that. Because what you described was a mindset. It’s not that you need to be checking things off a box and just doing them because you need to do them. But it’s truly a mindset. It’s like, “Okay, I’m putting these listening ears on and I’m seeing all these opportunities from people I bump into to one-on-one meetings,” truly is a moment for people to teach me something. And I think that’s such a wonderful shift in perspective for so many folks. So, thank you for sharing that.

Pooja, I have one last question here. I could ask you many, many, many more questions. But to be respectful of your time, the question I have is more specific to new managers because we’ve talked a lot about sort of the manager who is supportive, risen through the ranks and maybe spent some time away from their expertise and they need to get back in touch with it. So, what advice would you have for a new manager or an aspiring manager just for them to be successful? Is it along these lines of make sure you really know your domain as you sort of aspire to be a leader? Or is there something else that you feel like new managers and aspiring managers lose sight of or aren’t told very often?

POOJA: I think the keep your listening ears on is something recurring. But I would say one thing, and it is generic, but I still think it’s meaningful, is be yourself. Why I say be yourself? Maybe people say be authentic. You were promoted because you did something well. And that doesn’t mean you’re going to keep doing that. That’s different. But that’s what you know. If you know something, you’re grounded in it and that’s a skill that you bring. And that’s just sort of, I keep reminding myself is that — and I will give you a simple example is even though I’m an engineer and there’s a lot of stereotypes around engineering, it’s like, they’re introverts, whatnot. I like people. I like working with people. I like building partnerships because I know that when the hard times come, these partnerships are the ones that will actually help me move forward, whatever that means. But it’s just sort of like it is, I like working with people. And that to me is an authentic self. And I think when I’m truest to what I actually enjoy doing and it’s true to my core values, my best self comes out. I’m sort of hand-waving this answer, but as a new manager, I keep saying is that what you are is what is most important. And being honest with what you are and what you don’t know is probably what’s going to get you to the next thing. Sort of like, just don’t deny it. [Crosstalk] And you’ve never had promoted anybody? It’s okay. Just be honest with it. And tell people, there’s people who have done it. Get some feedback. Just don’t fake it. [Crosstalk] until you make it. I say don’t do any management. Don’t fake it until you make it. Be honest with what you are. Be honest with what you know and be brutally honest with what you don’t know. And trust me, people will reach out to help.

CLAIRE: Yes. I find that advice so refreshing Pooja, because I think for so many new managers and aspiring managers, the hundreds and hundreds of new managers that we work with time and time up, again comes up this true insecurity around, “Oh, I don’t know enough,” or, “Oh, I’ve never done this before. This is my first time managing people,” et cetera, et cetera. I mean, I felt that before. And I think the sort of language and the tone around how we treat new managers, it’s all about becoming and developing and getting to that next place. And I just love this, like I was saying, very refreshing advice to just accept and sort of be what you are and to admit what you don’t know, but to not feel like that should be sort of any reason for downfall. But that honesty of where you are, where you at is exactly where you’re supposed to be. And you’ll get to that, you’ll learn and grow in the ways that you want to eventually. But to be yourself. I think it’s such a wonderful piece of advice. So, thank you.

POOJA: Absolutely.

CLAIRE: Perfect. Well, thank you so much for sharing all your advice today and I appreciate everything.

POOJA: Thank you for your time, Claire. I hope our paths cross again and I look forward to additional engagements with you.

CLAIRE: Wonderful. Thank you.

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.