The Power of Connective Leadership with Natasha Vinnik (Podcast & Transcript)

“I think it is important to have a good trust system that people feel comfortable to share when things are not working, having retrospectives and reflections and iterating.” - Natasha Vinnik

Natasha Vinnik is a Senior Engineering Lead for Gmail Client Foundations at Google. With over 20 years in engineering, Natasha has also led engineering teams at Box and Yahoo! She holds three patents in cloud-based technology.

In this episode, we discuss:

• Natasha’s journey from an immigrant who couldn’t afford university to an engineering leader with a master’s degree

• Staying technical as a manager and keeping up with technology trends

• How starting a family changed how she approaches work

• Inheriting teams vs building teams from scratch

• How she manages complex projects

• The value of being curious, trying new things

• Mentorship vs sponsorship
  

Transcript has been edited for clarity.

Karen Ko: Hey there. Welcome to Engineer Your Career, a podcast brought to you by WEST, a learning community, empowering women technologists through mentorship. Join us as we hear from inspiring women tech leaders who are challenging stereotypes and paving the way for future generations. We hope their career journeys inspire you with new ideas to engineer your career. Let's get started.

Heidi Williams: Hello, everybody. Welcome to our latest episode of Engineer Your Career. I'm Heidi.

Karen: And I'm Karen.

Heidi: And we're excited to introduce our guest, Natasha Vinnik, who is a senior engineering lead for Gmail at Google. Welcome to the podcast, Natasha.

Natasha Vinnik: Hello, everybody. It's really nice to be here.

Heidi: Awesome. Well, it's so good to see you. I feel like it's been a blink, but it's been seven years since we last worked together at Box, and I just have to say I really appreciate how close the Box women in tech community was. Everyone's kept in touch. I know you missed the last dinner that we had, but you were quick to say yes to coming on our new podcast, so thank you so much for agreeing to be on this adventure with us.

Natasha: Thank you for inviting me, and I agree with you. It's great to be able to still stay connected. I was bummed about the dinner, but definitely catching up with everyone periodically. So I'm excited to be here and talk about career conversations and things like that.

Karen: So maybe for our first question, can you tell us a little bit about what you're working on these days?

Natasha: Yes, so I am currently at Google, and I lead one of the teams in Gmail. It's a team that's focusing on client platform investments, with a focus on really thinking through how we can improve the developer experience to build features faster.

The product is evolving and it's really exciting phase and then my team is focusing on improving the developer velocity and making code easier to develop in and easier to test kind of working across other different teams and it's covering investments across different platforms, so on Android, iOS, and web because Gmail is a product that's used by a lot of users across different devices and platforms.

Karen: Amazing. I was curious if you'd be open to sharing a few key career moments with us that have led you to where you are now.

Natasha: It's a great question. It's hard to figure out what to start with. Yeah, I've been in the industry for a while. As I mentioned, I've been at Google for about six and a half years, so maybe I can start more from an earlier career phase.

I actually finished high school, and I immigrated to the United States, and I couldn't go to university right away just because it was expensive. So my career is a little bit different, but I think it did play pretty pivotal moments in my life, so I ended up going to work right away. I worked at a startup, and I worked there for, I think, almost four years.

First as an automation engineer and then as a release engineer, but I still really wanted to go back to school. I felt like I wanted to have a depth in my education, so I ended up making a decision, which was actually pretty hard.

It was like post startup boom, and the market wasn't that great, but I was still working and doing well, and I decided to quit my job and go back to school. So this is one pivotal moment, but I think it's really critical. I wanted to make sure that I have the knowledge that will set me up for the future. So even though it was really hard giving up a salary and then starting over, I'm glad I did that. So I quit my job. I went to community college and then transferred to Berkeley and got my education there.

Heidi: That's awesome. What an incredible journey, and I can see how you really persevered through all of that to get your engineering degree, and it looks like it really turned out well for you. That's awesome.

At some point, you became a manager too, so how did that come about for you?

Natasha: After school, I worked through different companies, and I had experience of working in small companies as well as bigger companies, and I worked at a company, Box, where I met Heidi, and I had an opportunity to try management there, and I was debating for a while. I was already a tech lead and leading several projects and really enjoyed working with people and thinking through how to support people and the projects at the same time, but I was really hesitant to make that decision.

I felt that when I go to management, I'll lose all the technical expertise I've built and all of the hard work I did in school and at work. So it was definitely some debates, and I remember I think talking to Heidi and the folks there, do I make this move or not? And then if it doesn't work out, how do I go back?

Is there a way to go back? So this is something I wanted to double-check before making the step.

There's definitely ways to go back if you don't like it, but I'm glad I made this move because at the end of the day, the thing that resonates with me the most is working with people and enabling the teams to be successful and helping people grow. It's exciting when you see someone in the team develop new skills and then get promoted. Had some folks recently get promoted, and so it was so exciting to tell them that news.

So I am glad I made that decision, and I think it's important, I think, in engineering to stay technical in the management role. So I definitely don't feel like that I probably code less now. I do code less, but I think it's still really important to stay technical, and it doesn't go away. In order to do leadership and management role effectively, you need to understand the technology trends and complexity and things like that.

Heidi: You're so right. I think staying technical as a manager is so important, and you have to find different ways to keep up with the industry and what's happening with your team. I'd love to come back to that topic in a minute, but before we do, there was another pivotal career moment that happened while you were at Box. Do you mind sharing a little bit about that one?

Natasha: The next one is more personal than career, but it does affect my career journey. So when I was at Box, we decided to start a family and I had a daughter, so she's now eight, which is also time flies, and I remember making this decision and being really worried about it because I was managing pretty big team and then thinking that I'm going to take time off and how does it going to play and then how I'm going to balance family and my career.

And I think I'm really fortunate that I have a good support system, family and friends, and actually mentors who help make the decision and be okay with that. Something that I learned after I came back after maternity leave is that it does change how you approach work because previously, when I was working, it was main thing of my life. I had friends there, I have work, and then when you have a family, there's another very important thing in your life, so you balance it much more.

So when you are at work, you want to do the best you can, and really, I think it helps me prioritize. If I'm here, I want to work on things that I'm really passionate about and things that I can really bring impact because otherwise I'd rather be at home with my daughter and then spend time there. So it really helped me also find the things that are really important to me and find the better balance between family life and work.

Karen: Well, thank you so much for sharing about your career moments and the ones that really have stuck out to you over the years. I'm curious, as you were starting to build your family and moving down the management track, how was that transition over to such a large company like Google?

Natasha: I moved from Box to Google when my daughter was two years old. I think there was a good moment for me where I wanted to continue growing, and I wanted to learn more, and I decided to try something different, and I was actually debating if I go to a smaller company or if I go to a bigger company, and Google is huge.

It's not just one team, there's so many different teams and just scale of traffic and complexity, but I decided that this is really important for me to continue learning and growing and doing things that I'm passionate about. So I specifically looked for the teams that I can really relate to.

So I joined Google Maps team, also the product I use all the time, so now I switched to Gmail and another product I use all the time, so it's really important for me to work on something that I can really relate to.

And it was definitely a bit intimidating because I felt like, oh, at Box, you have a smaller team and you can work really closely together, and you're building a lot of new things, where at Google, there's a good amount of complexity and a good amount of scale. It takes time to learn different things, but it's also so fascinating. You can do so much, leveraging the system and being able to build the teams there.

So I think it does take time to learn a little bit, but it's also pretty amazing how passionate folks are, or willing to teach and willing explain how things work. I think it was a pretty interesting shift.

Also, it was my first time being hired as a manager because before I was hired more as an engineer and I grew to the management of the leadership role. Here was my first time being hired as a manager. So it was important to understand how company operates and then how the system works and then how to support engineers working on pretty complex projects, but also being able to make progress and I think in some cases it's still the same things: creating good culture, being able to identify the complexities and limitations and identify milestones and really being passionate about what we do and really deliver value to the users for the products.

Karen: Incredible. I've got a funny story to share about Google Maps. Thank you for working on Google Maps, by the way, because that is something that I use every single day. Back before Google Maps existed, for Christmas one year, I got two Tom Toms from my parents and then from my uncle and aunt because I was notoriously bad at directions to the point where that was what they decided to gift me.

So I'm very grateful that the Google maps exist because then I can actually get from point A to point B and not spend five hours trying to figure it out. So thank you for that.

But moving on to the next question, so you were talking about engineering management. I'm very curious about how you've been able to develop your leadership style over the years and how you were able to create that for yourself.

Natasha: Yeah, that's a good question, and now I ask that question a lot too when I'm hiring or when I'm talking to leads about what is your leadership style? I remember when I was just starting out, it was like, how do you know what's your leadership style? Do they research and define specifically? Is there a multiple choice where you choose, okay, this is the style?

So I was really curious in observing the different type of leads and looking into how they work, and then what stands out in them, and also what resonates with me. So I definitely started noticing there's a different type of leads, and also folks adjust based on what the team needs or what the organization needs. It really resonated with me, and this is I think now I build out that this is something I do. I would say my leadership style is bringing flexibility and also being able to be a connector, being able to bring things together, so flexibility in terms of based on the type of the team and the need adjust what role I play.

If there's something that's relatively new, if we're building a new team and there's a lot of technical decisions we need to make at the same time as building a team, I can lean more deeply into more of my technical expertise. If the team has good amount of leads on the technical side and TLs, I can focus more on the vision and empowerment, and then let the team drive all of the technical decisions.

So I do like to adjust, and I think through a career I definitely noticed that different teams needed different things, and also sometimes I had a chance to build a new team, so things that it needed to be then when it was just a few people, like five people is very different when the team grew to 30 people. So you're thinking the scale, you're thinking, how do we make decisions that it doesn't only go to me to make decisions, the team can make decisions themselves.

I think flexibility is really important. Another superpower I think is a connector, and I didn't initially know how to state it, and someone mentioned it to me like, oh, you're very good at connecting. You are a connector in the organization. I was like, oh, that's a cool term. I will add that to my leadership style. But I think this is definitely something that I do a lot and resonates with me.

And there's different type of leads. Some folks really like to go very deep and have expertise in one area, and some leads focusing more on breadth and being able to identify systemic improvement. Systems can connect together or teams connect together, and I definitely do more on the breadth side to identify where are the commonalities between the systems or where are the commonalities between the teams, which teams we can work together with, which teams we can learn from.

It doesn't have to be just working together, but there's a good amount of opportunities to learn. Sometimes it's not like exact thing, this team is doing this feature that we want to use. Sometimes it would be like something the team worked on scales really well, but it's a different project, but they were able to scale it this investment really fast. How do we learn from that and apply to the new investment we're doing that we know we have to rapidly scale. So now I identified this being flexible and being able to be a connector is my leadership style.

Heidi: I can see how both of those would be so critical in the work that you do, both from the complexity perspective, but also, you mentioned observing patterns and seeing commonalities. If you're building a platform, that's exactly what you need to be doing is to figure out what goes in the platform and what doesn't, how to solve multiple problems once as opposed to each problem one at a time and then of course flexibility and the complexity of what you're building and needing to know maybe not just at the team but at the project level, what they need in a certain scenario.

I'm sort of curious. I think you have this theme of moving really complex projects and teams forward. Certainly, at Box, we had a certain amount of scale. I think Google is probably a hundred X scale, but definitely high availability, high reliability systems that are powering how people live their lives and do their work and whatnot. Do you have particular strategies for helping your team stay motivated and on track when you are driving these very important critical complex projects?

Natasha: Yeah, that's a good question. I feel like sometimes projects are very different, but from the other side, there's still good amount of a commonality of how to approach it.

You mentioned the smaller companies, the scale might be different, but it's still, especially if you're driving a long-term investment, it's still good to think through where we're going and then how do we know if we're going to the right way?

If, let's say, things are changing, you might set a goal that in a year we want to have a better reporting system, and then you work on it for a year, and then in a year you're like, oh, actually things changed, or is this a better reporting system now?

So it's really important to set the goal, but also being able to check on it as we go along. This is definitely something that I've learned, and I'm paying closer attention to when it's a very long investment, it's really critical to think through the milestones and the outcomes as we go along through those milestones.

Especially, I think it's really good for the engineering team.

Things do take sometimes time. It depends. If the project is complex, it does take time, and sometimes, if the end goal is really far away, engineers could get demotivated.

They know it's really important at the beginning when they start, but then if it's really far away, they might forget. I'm like, okay, I'm still working on it. So thinking through the milestones and thinking through the outcomes as we go along, and then reminding the teams around it, and actually them understanding it and them coming up with that is actually the ideal, the scenario. Then they know they're not just going to the end, they're going to this milestone and they will see outcome to that milestone. And then we can also assess, is this still the same path, or do we need to adjust?

So something I am passionate about this, thinking through the journey, setting the end goal and thinking through the journey and identifying the same as pivotal moments in the career, but pivotal moments on the project or investments where you can assess if anything needs to be adjusted.

Another thing I think is really important is clarity for the team. And sometimes we'll have projects that need to be launched really fast. I mean, generally, I think it's evolving, right? So we need to be able to move fast. So it's really important to really think through why we're doing this and have clarity, and I think especially scale, and we want to make sure that we deliver fast, but also it's scalable, really understand the goals, and being able to communicate across the teams what the goals are and really get the team on board.

Because the way we do things better is we really buy into it. We are like, know where we're going and why, and we're really passionate about it. We can get things done faster, or we can identify things are blocking us better and things like that. So yeah, so I think clarity for where we're going and why, and then identifying the outcomes as we go along, and then identifying milestones where we can assess and adjust if needed.

Heidi: I remember being really impressed with the milestones you set for a particularly long project at Box, and I think it was on your team—We definitely celebrated each milestone. Even the fun part is writing the code for the new system to be up and running, but you can't forget the long tail of migrating and deprecating the old system. I think, on your team, didn't we celebrate when we finally deleted code and decommissioned old systems? I feel like that was an enormous milestone to prove that we'd actually done it, that the old code was no longer there. Was that your team?

Natasha: Yeah, I still do that on the new teams of being able to think through, okay, this is the launch, and then this is also a cleanup phase. And I think especially for the—right now we're looking at the client platform team, we want to simplify things. So looking into not just what things we launched but also we simplified, we deleted some code, this is great, let's celebrate. It makes the code better, but also it is still a milestone that we spend time on, and so it's good to celebrate.

Heidi: That's fantastic. I love that you still do that.

You'd also mentioned generative AI, and obviously a space that everyone is getting into and Google building their own things as well. How have you kept up with technology trends to support your team? You mentioned that early nervousness of how do you stay technical as you get longer and longer into a career in management. How have you stayed technical? How have you kept up with trends along the way?

Natasha: Yeah, I think gen AI is a very pivotal moment in the industry, and I think we're all learning a lot from that. There's a few techniques I have.

One is being curious and allocating time to learn. There's two different types of learnings. One is when you're working on the project, working with TLs or leads on the team and understanding their...just listening to them, understanding their constraints and limitations. So I might not be coding specifically, but I am in conversations about the trade-offs we're making and then the constraints we're dealing with.

And I think another one is more allocating time to learn breadth. So, not specifically for the project, but what else is happening? I think within Google there's also a good amount of material available and classes available to take. So I do allocate a little bit of time to learn across, and something that again, I'm really interested about it from a connector perspective is when I'm learning, I'm looking into what are the things that are coming up that might be relevant to my team or we can learn from or what technology that we can apply from that side.

And I think another thing is I really like to listen to podcasts. I have a bit of a commute, so when I drive, sometimes also when I run, I listen to podcasts and stay more on the technical trend.

Karen: What are some of your favorite podcasts?

Natasha: The one that I am listening to right now is more on leadership side. So big fan of Brené Brown. She has a bunch of books. She has actually, I think a few podcasts, the one that I'm listening to now is Unlocking Us. She also had the Dare to Lead podcast. It's actually pretty good because she had folks come in talk about different leadership books. So if it resonates with me, then I will get a book and listen to the book.

Another one is called... The Awesome Human Podcast is another podcast I really like. So Nataly Kogan talks a lot about how do we really live a happy life and then enjoy work and life at the same time. She has actually Zoom sessions, and she combines art and also talks through empowering ourselves and believing in ourselves. And she also has a podcast now, she has some folks to come in, and she always starts with asking people to say, 'I'm an awesome human because,' and you have to say, what did you do to feel awesome today? And I really enjoy it to be able to also recognize the things that we've done, and it's like, oh, I did this today. Oh, I did this for myself today. So I really enjoyed that podcast.

Karen: Oh man, I feel like we should have started the podcast with that. 'I'm awesome because blank.'

Switching gears a little bit, I know we talked about management earlier. I'm curious about when it comes to inheriting a team, when you join a new company or you're joining a new part of the org, what are some of the pros and cons when it comes to inheriting a team versus building a new team from scratch?

Natasha: As you said, there's a pros and cons for sure. I think both just different journeys. So when you join the existing team, you coming in and might take time to build relationship and build trust, right? Because you're coming in as a new person to the team, you don't know anyone yet. So I think there could be some challenges around it.

I am usually, then, prioritizing spending time with people on the team and really learning about them and also learning what they're working on and what resonates with what they're passionate about. And I think that the benefits about taking an existing team is that's already a unit that's working together, so they have good amount of knowledge and experience, expertise in the area.

So coming in as a new lead, I think it's important to be curious and learn about it. And usually, also, if you build a good trust relatively soon, they will tell you all the issues that they see, they will tell you all the problems, so then you can kind of look through and prioritize which ones you want to focus on and improve.

But I think it's already a unit that's working, and it's a unit that has a lot of knowledge about the system, about the team, about the product. So I think it's about the existing team.

If you're building a new team, you start from scratch. So the role is a little bit different, too, wearing multiple hats. So it might be making technical decisions as well as building the org. Thinking through who do you bring first, prioritization of the roles. Do you start with getting all the leads or do you start with any engineers first and then get the leads? Thinking through how to grow the team.

You have a chance to build the culture of the team from scratch. So actually, when I was leaving Box, I think Box had a special place in my heart because I built a lot of relationships and it was a really good collaborative culture. When I was leaving, I wanted to make sure that I bring the things that I value in culture with me.

So when I joined Google, I was building a new team and a new investment, and it was pretty exciting to also build it with people who have the same values around the culture. So focusing on bringing the right people onto the team that have expertise but also have the same collaboration culture, and then shifting into that the culture isn't just about what the lead brings, but also the people in the team can sustain that culture and move that forward.

So I think there's definitely differences, but I think both are just the journeys of working with people and figuring out what the most important thing for us to do to bring value to our product, to our users.

Heidi: Is there anything else you would add in terms of a team that's capable of complexity and high quality and rigor? Are there other things? Maybe practices or frameworks or things that you do to set the team up for success for that, or do you think it's really just a question of having the right personalities and making sure that they collaborate well together? I guess, are there things that you do for the team to help set them up for success with complex projects?

Natasha: In addition to the culture and some of the things that I'm mentioning around clarity and thinking through where we're going, I think it's also important to have good trust and being able to have an ability to iterate.

When you're working on something pretty complex, it's not always going to go great, and in some cases, this is how we're going to learn. So I think, a practice I do is about doing retrospectives and then set it as like, Hey, let's try it, and then we'll iterate.

And it could be more on the technical side in terms of investment on the project. It could be more about how we work too, of like, okay, this is the type of meetings we're going to have. Let's try it, and then we'll see if it works or not.

But I think it's a really good practice of being able to start on something, have the point where you can assess as a team. I think it is important to have a good trust system that people feel comfortable to share when things are not working. Having retrospectives and reflections and iterating.

And it also helps when things don't go well—And I did have experiences where we needed to pivot a team or pivot a project—Having that relationship where you assess things together and decide, okay, this is what we're going to do next and this is why, and then pivot. So being able to reflect, retrospect, identify things we can bring and lessons we can bring from one area to the other.

Heidi: I love that sort of encouraging learning and transparency and openness and no blame, but just sort of that constantly thinking about iterating and learning feels really critical to all of that. So thank you for sharing that. It's great.

Karen: It also feels like it's tied to your superpowers of flexibility and connecting, so I love that through line through this conversation.

Natasha: Actually, one more thing I was just thinking about. Curiosity, I think, is also really important. I think it's also connecting to the technical trends, being able to empower the team, not just always do things that were already planned out, but be curious about what else is there, and then bring it into the team from that side. So empowering the team to be curious and then trying new things is really important.

Karen: Along those lines, I think you've shared something about how mentoring your teams to reach their full potential is something that you care very deeply about. And I'm curious if you'd be open to telling us about the role mentorship, sponsorship, and networking have played in your career.

Natasha: It played a big role in my career. I think, as Heidi mentioned, we still have a woman in tech group and then meet together, and I really value that. And I think through actually women in tech community, I was able to find great mentors and great sponsors.

I do admit it's not easy, and I think early in my career I was pretty intimidated of going saying, I need a mentor or I need a sponsor. I remember hearing the talks about mentorship is really important, go find a mentor. And I was like, well, how do I do that? And I'm going to waste their time. What if I don't have a question or why would they spend time with me? Everyone is very busy. So I was really intimidated.

But then, eventually, actually through having a good culture in the teams and in the companies that empowers that, helped me to find mentors and find sponsors. At some point, I think someone just told me, this person's going to be your mentor, and I was like, okay, fine. And then eventually I was like, okay, I see that. So I'm trying to do the same with my teams as well as within Google, I mentor several folks and then outside of Google to make it less intimidating, and just throwing is like, this is learnings, being curious, and we can all learn from each other.

Actually, before Box, I worked at Yahoo, and I had a mentor there actually, I think she ended up being my sponsor. She should start as a mentor, but ended up being my sponsor. And when I decided to leave Yahoo, I was also trying to get advice of what do I want to do next? And it's so valuable to be able to have folks who can talk through how they made a decision, what are the different opportunities, and I think they helped me to identify like, okay, this is what I want to do, and maybe this is what I don't want to do.

Sponsorship. It requires more thought and intention. So I think from mentorship perspective, you don't have to be that prepared. You have some questions you have to ask a mentor. I think you want to have a good conversations for sponsor.

Sponsor is more about they can talk about you when you're not in the room, and it does require more thought of who would be the effective sponsor within the organization.

So thinking through who might not be in my immediate management chain but does have enough visibility to what I do and what I'm good at, and then how do I actually tell them this is what I do, that's what I'm good at and this is where I want to go because there's more information they have as more can help me switching roles within Google. I was also introduced to different leads when I decided I wanted to try something different through the sponsorship program.

Heidi: That's awesome. Thank you for sharing all of that. It definitely resonates, and I agree that finding a mentor, finding a sponsor, can be really intimidating, and I like how you frame the differences in knowing what you want to ask or what you want to get out of it.

Well, I just want to say this has been amazing hearing all of your insights. It's been fantastic. I wanted to ask you one last question. What's one thing that you're excited about this year?

Natasha: I have to choose one? [laughter]

Heidi: Okay. You can have two.

Natasha: Career-wise, I did take a relatively new role this year where I am leading the client platform team and I'm really excited about this role because of the superpower about connecting. I really want to make a difference in terms of how we do development and make systemic changes so that we can enable engineers to go faster, building a lot of new features faster and it brings a lot of experience I have from different companies and then different projects and working in some of the Android stuff and working in some of the web stuff and really looking into this amplified effect of if we fix this or if we make this better, everyone will benefit.

So it's pretty exciting. Improving velocity is something I'm really passionate about, so pretty exciting role. I'm excited about that.

On the personal level, I love being outdoors. We are doing this trip this year where we are hiking and Alps from the point to point across Slovenia and Alps and I'm really excited also to do that and just enjoy the views and have a great time.

Heidi: That sounds phenomenal. I'm so excited for you. I hope you have a fabulous time. Well, I just wanted to say thank you so much. It's been such a pleasure, and I really look forward to everyone being able to hear your story and your insights. It was fantastic. Thank you.

Karen: Thank you so much, Natasha.

Natasha: Thank you. I really enjoyed the conversation.

Karen: And that wraps up another great episode of Engineer Your Career, brought to you by WEST.

Are you ready to take control of your career? WEST can help. The WEST Career Accelerator is a six-month learning program that combines one-on-one mentorship and group-based career coaching to help women gain clarity, save time, and define success on their own terms. We're here to help you create a path towards the career you'll love. Check out how WEST can help you succeed at joinwest.org.

Special thanks to our production team, Scott Williams and Alona Matokhina. If you have questions or nominations for future speakers, please email podcast@joinwest.org. Thanks for tuning in.