Preparing for Your First VP of Engineering Role | Honeycomb VPE, Emily Nakashima

0:00I think that this is actually a mistake I made when I first took on an executive role where I really expected to show up representing my function. And fairly quickly, I went, oh, this is the wrong way to think about this. Once I sort of switched and said, hey, this is a team that's trying to solve a problem together. And most of the time, we actually can kind of like set aside the hat that we wear when we're out in the rest of the company and just sort of work together. You know, five people who have different expertise, but we're trying to solve the same problem. And that ended up being a much healthier approach.

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1:03I hope to see you there. Hey, everyone. Welcome back to Dev Interrupted, live from Leading Eng SF. I'm your co-host, Connor Bronson, and I'm joined today by Emily Nakashima. Emily is the VP of Engineering at Honeycomb.io, also known as Honeycomb. Emily, thanks for coming on the show. Really happy to be here. It's my pleasure because you have a background in product engineering, performance optimization, client-side monitoring, design. And I love that you kind of describe yourself as this dev tools nerd, because frankly, so are we here. We love talking to folks like yourself. And I understand that you have identified a misconception that you're seeing in how we all apply not just dev tools, but dev organizations.

1:47Because we talk a lot about how CTO roles can vary company to company. Some CTOs sit over multiple VPs of engineering and they're running the whole engineering org. Others have a kind of special ops group. Or maybe some other roles here where they're focused on security. There's a variety of ways you can look about it, depending on the size of the company, type of company. Yet we like to think about VPs of engineering as kind of standard. Like, okay, you're a VP of engineering. Yeah, your size of the company may be different. You don't think that's the case. You think there's a difference between VP of engineering across the board.

2:20I do think that. And I don't think it's just developer tools companies. I really think, especially startups, but really any kind of scaling company, I think so often the roles are really defined by who's there and what the organization does well. There's this real understanding, because we've idolized founders and CTOs, that we have become more aware of all the different shapes. But the reality is that the VP of engineering could take on almost as many shapes as the CTO. And I don't want people to miss that because I think people can either be drawn to the opportunity for the wrong reasons or they can sort of think it's not for them because they have the wrong picture in their head of what it could be.

2:55Well, let me just say to VPs of engineering who are watching and listening, we think about you too. We're big fans. And that's why, Emily, I'm really glad you're here to kind of talk to us about some of this almost antiquated views of the role that we have. How do you think about the VP of engineering role? How does it break down for you? I do think that some of the stereotype that people have in their head, there is some truth in that. I think in general this idea that the VP of engineering is the lead manager for either engineering as a whole in a smaller company or a portion of the technical teams in a larger company, it rounds to true most places, I think.

3:32I think that the thing that people miss is how much the actual role is shaped by other people on the leadership team. and sometimes other people who aren't in the leadership team too. Probably if you think about the VP and CTO relationship, that kind of makes more sense naturally to people. I work with Charity Majors, who's Honeycomb's CTO. Charity is very well known to come from a really strong operational background. She was a DBA at one point. She was a sysadmin back in the day. She understands backend engineering very well. And so when I tell people, hey, because Charity has that background, I can come from more of a frontend background, be more of a specialist in engineering and product collaboration.

4:12That makes a lot of sense. But a thing that people miss that I think is really important is that I can also have my role because we had some early employees at the company who were relatively senior, who also had really strong operational chops, who made sure that the platform was running reliably, who made sure that we didn't have major architectural challenges. And because those weren't the top concerns, when they went to go pick a VP of engineering, I had a profile that made sense. So I think it's up, down, and sideways that all kind of shape the role. It's not just who's the CTO, which I think people focus on.

4:45That's a really great point, that there are all these different dimensions we don't necessarily think about. And you also mentioned the interactions with other organizations, other business units, and how that impacts how the role of VP of engineering functions. Can you talk a bit about that? Yeah, I think that people really, like I said, focus on that VP and CTO relationship. I see that same sort of reciprocal shaping happening with the VP of product as well. Sometimes you have a really strong VP of product and then there's sort of a healthy tension between the two roles and they're sort of shaped in opposition to each other.

5:17Usually healthy. Or, you know, tension of some sort, one flavor or another. And then sometimes, you know, you have a product function that, you know, maybe engineering has been at the company for longer. The product function is a little less mature. And then the VP of engineering is almost senior to the VP of product. and there's a little bit more of a you're sort of under my umbrella kind of relationship. But it can be really different and no matter what the shape of the VP of product is, it always shapes that VP of engineering role in turn. To a lesser extent, it's true for other roles on the senior leadership team as well.

5:49Yeah, I mean, I'm not an executive, but I imagine that when you're in that executive leadership meeting, you are reacting differently depending on the strengths and weaknesses of that whole team. and you're asked to do different things depending on the strengths and weaknesses of that team. That's been my experience the one time I did found a company and that didn't go well, let's just say listeners. I wonder how you've seen that impact you personally in your role. Yeah, I think that this was actually a mistake I made when I first took on an executive role where I really expected to show up representing my function.

6:24And fairly quickly I went, oh, this is the wrong way to think about this. Once I sort of switched and said, hey, this is a team that's trying to solve a problem together, And most of the time, we actually can kind of set aside the hat that we wear when we're out in the rest of the company and just sort of work together as five people who have different expertise but are trying to solve the same problem. That ended up being a much healthier approach. And then it's not about, I represent engineering, you represent marketing. It's like, you're the funny one who's going to add levity when we're all arguing with each other.

6:52Or I'm the person who's going to remember to retrospect and look back. That kind of stuff often comes much more to the forefront. and having that sort of balance and sort of like skill set and perspective, I think is as important as the kind of functional balance. I just want to say it's very kind of you to picture me as the funny one. So thank you for that. I don't know if it's deserved, but it sounds like you have a few different archetypes in mind as far as how VPs of engineering function depending on company size, makeup, etc. What are those different archetypes? I feel like the more I dig, the more I find more ones.

7:26I'll say I'm coming from, I'm more of a startup person. And there really is a big difference between being the VP of engineering at a smaller company versus being a VP of engineering at a bigger company. I know a little bit about that divide, but I haven't been that VP of engineering at a bigger company. And I think that it can really change. Often at a larger company, you have a much bigger scope. You have more people under you, and you are managing a lot more complexity. Cross-functional relationships are often more complex. But in some ways, you also have less autonomy. You can't just go rewrite the travel policy on a whim on a Friday afternoon.

8:04So that really can shape the role. I think you get a wider array of archetypes sometimes at smaller companies. Totally. And then you get more. There's such a range of from internal facing to external facing. Trailblaze versus steward is a dynamic I really like. My COO, Jeff Gray, uses that description of the two different possible flavors where the trailblazer is the person who is out innovating new technology, coming up with new product lines, and then someone needs to be in that steward position where they're like, this is the product that makes us money today. I'm going to make sure it keeps doing that.

8:37And I imagine there's this, I mean, use this phrase, healthy tension with the role when there's technical co-founders too. So I'll say like Linear B, we have a VP of engineering. We also have a CEO as a former VP of engineering. We have a CPO as a former VP of engineering. So this creates different dynamics than I'm sure other companies where maybe it's a more business-minded co-founder. Not to say that our co-founders aren't business-minded, but maybe they came from sales and have hired a VP of engineering to build out the product of that. That absolutely will create a different dynamic in product and engineering organizations.

9:13Yeah, absolutely. A lot of times where the vision comes from can be the biggest thing that shifts around. And I think often if you have founders in those roles, They can often look into the far future forever and tell you what the product should be. And then if you get to a certain point where all of a sudden that's a hat that needs to be assigned to a specific executive and that wasn't what you were hiring for, you hired that person into the role, that can be an interesting thing that really kind of forces people to grow or sometimes forces a change. So how do you identify the archetype that your company needs when you come on board?

9:45Or when you're hiring, I suppose? It's a good question. I'll say when I was sort of a manager, a director, a senior IC, I was not tuned in to the, you know, even to the idea that I could ask my VP of engineering to be different or that I could evaluate whether the organization had picked the right shape. And only now I look back and I see, you know, moments where we really had the right shape of person for the job and moments when we didn't. And it made a big difference to the health of the company. It's hard to do when people have such a narrow understanding of the job. The big thing I would look for if I were trying to understand that is really those cross-functional relationships and how they're working.

10:19And especially which ones seem to be strong and which ones seem to be like there's not connective tissue there or they're fraying a little bit. That's often the biggest clue that something needs to change. Maybe you see an organization where you really think product and engineering need to be tight or engineering really needs to be very closely aligned with the revenue goals and shipping certain things that you know there's revenue behind and you don't see that happening. Those kinds of things are often the really concrete warning signs that maybe there's been a misalignment in the shape. And I imagine the needs, I mean, we know the needs of all of our time for roles.

10:55So I can see how this would really shift as organizations grow and scale. One of the interesting things about being a startup VP versus potentially being in a bigger company is the pace at which you need to become an entirely different shape or archetype can be a lot faster. I do think the role is always evolving no matter what company you're at, just because business conditions are changing. But I think at a startup, you can have a completely different, most important problem every maybe six months. Sometimes it's just, I need to think about X and now I need to think about Y. But sometimes it's, I need to be someone who's the planner, who's so organized, who's putting the right systems into place.

11:34And all of a sudden you need to become the visionary leader who's inspiring people. it can really kind of push you to grow maybe faster than not everyone's comfortable with the pace. I mean, for folks who are at startups or have been at startups for a while in the audience, you're probably going to resonate with this. So often people join a seed company or a series A or series B, and they find around later the company looks very different. Some people want to grow with that company, and some people want to have all this change and really keep growing with it. But some folks are really like, hey, I love a series B startup.

12:06You know, I want a little bit of scale. or maybe I love that Series A seeder. I want to build. And once we get to Series B, Series C, I'm like, ah, there's too much red tape. It's not what I want anymore. And we see that happen at IC levels, but we also see it happen at management levels where some folks will scale with the company and others will move forward on different areas. Yeah, I really honestly, I wish we were better at celebrating when people notice that dynamic and make the call for themselves that the company's no longer the right fit. At Honeycomb, we try to be really positive when people choose to leave, we always frame it as a graduation and not like, this person quit or this person's leaving.

12:42We always say they graduated from the team because we want them to feel positively about that chapter. We want them to close the book at a moment that feels good and feels like they can celebrate it. And we want to make it clear that we don't expect anyone to stay forever. I think sometimes people always feel like there's that one more important thing that they can't leave behind. And when you stay too long, I think it's not good for you. But a lot of times it also holds back growth at the company. So yeah, it can be sometimes hard when you've really grown attached. When you've grown with the company, a lot of times you get really attached to the team, you get attached to the product, and you can stay in that situation where kind of the day-to-day isn't working for you for a long time.

13:22And I think we try to put as much positive framing around that as possible to remind people that it is a choice, right? Are there particular signs that you've seen of when someone maybe does need to move on? You know, it's hard to say. I think it manifests differently for each person. I got some advice from a coach at one point, which was, you feel this way now. Maybe you feel really strongly that something isn't working. And it can be hard to tell if that's just a momentary thing that's really bothering you, or if something has really changed about the company. And she said, go to your calendar right now.

13:52Put a calendar reminder 30 and 90 days out. Write down how you feel. And then when that calendar reminder pops back up, ask yourself, am I still in the exact same place? Or did I have a moment where I was frustrated with this one problem, and it's actually pointed in the right direction? That's a great perspective to kind of gather that qualitative data from yourself and say, you know, where am I here? Because it is easy to get frustrated in a moment. And, you know, sometimes other things in life are happening that are affecting how you're viewing your work. It's very common. How does that continue?

14:22Because if it becomes sustained, that's where you know there's an issue. Yeah, exactly. When I've seen people realize that it's time, they realize that they have been upset about the same problems over and over. They kind of can't put them aside. They can't bring them to a resolution. They look around and feel like their coworkers, they feel alone. They feel like their coworkers don't see this big problem I see. But the reality is everyone else has a different perspective on it. And so I do think checking back in with yourself to make sure that that perspective is sustained and that delta from maybe the people around you is sustained is the thing that helps you go, okay, we have grown in different directions.

14:58I think that alignment is something that is usually felt by others on the team. Your manager probably sees that if you're feeling that way. And it is better to find the right spot for you instead of struggling to make it fit if this is a sustained issue. That said, there are ways that you can grow and prepare yourself for roles that scale like this. Startup VP of engineering is absolutely a role that will often scale from maybe you're hired at the Series A and you scale at the Series B and you keep growing the team. It's an exciting time. how should people prepare to become a VP of engineering, whether at a startup or an enterprise?

15:37It's a great question, and I think a lot of people don't realize that they actually can start preparing before they get the role. They sort of put the title up on a pedestal and don't sort of break apart the skills that are involved. And I actually think, even as a senior IC or engineering manager, or certainly as an engineering director, you can take on a lot of efforts that will help you be ready. The biggest one is generally just sort of identifying a cross-organization management problem, and then going to your VP or going to your director and saying, hey, can I work on this? I didn't realize I could do that for so long.

16:08I always felt like I would be stepping on someone's toes. And now that I'm on the other side, I'm like, yes, please. You want to solve a big, important problem and you just want some authority and support in doing it? Great, I'm here for you. And for me, so often my job is a little solo. So when someone wants to partner and solve a big problem for the organization, it can be a lot of fun. you get to work together, and then hopefully they get a little taste of what it's like to be in that role too. Yeah, I think there are a couple ways to think about this. One, solve your boss's problems, don't be one.

16:36That's an obvious one, right? Let's try to help solve our problems. And usually, people differ. Some people are very authoritarian or hierarchical and don't want you to take on problems yourself. And also it differs culture to culture, whether that's internationally where you're working or company to company. but in startups, people want you to solve problems. That's what they hired you for. They're really excited for you to solve it. It's like, you identified this problem, you saw a problem that maybe I saw too, maybe I didn't, and you're going to go solve it. Awesome. Now maybe I'll give you some feedback and I'll solve it a different way slightly because I think there's this thing you're missing, this piece of context.

17:12But you just have to stoke you're doing it. Yeah, and you touched on something really important, which is sometimes it is solve your boss's problems, but even more exciting than that is like, hey, I see this big problem that maybe you don't see from your vantage point. I'm so used to it, since I grew with the company and so many of the folks on the team are people that I hired or I worked with directly as a manager back in the day. I can have that false sense that I still know how everything works in the organization. And it's actually changed a lot since I was up close with it. And when someone comes to me and they surprise me with a problem, that's my favorite moment.

17:43That is an awesome call-out. And I think it's something we underrate because we think, oh, we have so much context. We're exposed to leadership. we also have been here for a while. We've scaled the company and things are changing on the ground. And ICs have not just different frames, but also like depth in certain areas that maybe you don't have. And so do managers in different areas. So it's a wonderful call out. However, I also think there are skills that are really crucial to develop that are not just this problem solving piece. There's also the management skills. How can you start to develop those manager of manager skills as you work towards that next stage of your career, if that's what you want.

18:26You know, for me, one of the hardest things was figuring out how to build the same degree of visibility of the organization as a manager of managers. It's tough. Yeah. Like, you know, you're used to being able to kind of go verify directly. You know, you can look at pull requests. You can go talk to the engineer. The more you move up the ladder, the more it becomes really disruptive to do those things or the more you create chaos by like, hey, I saw this on this PR. What does it mean? Someone's going to be worried about that. Exactly. You don't want to be the problem. But it is a totally different skill to build that picture of what's actually happening in the organization and where things are working and not from secondary sources versus from going and talking to people directly.

19:05So sometimes it means, you know, it's a lot of reading status updates. It's trying to make sense of them. It's trying to verify that based on what you hear from other managers. But it can be a really different way of collecting information. And I do see some managers and managers who have never figured out how to make that leap. And I always feel like the end result is pain for their teams. So I think you can practice it. You can try to make sense of what's going on in the adjacent part of the organization and see what you come away with and try to develop that picture. So I think that piece is one you can try anywhere.

19:34I also think just building your context about the business, even though it may not be directly related to the specifics of managing people who are managing people, it is one of those skills you're going to be trying to build at the same time. and it's nice to get the jump on that when you're not already in the hot seat. Yeah, and I know a lot of folks who listen to this, I mean, we have plenty of founders and CTOs, VPs of engineering. We also have a lot of folks who are maybe engineering managers and looking to kind of scale that senior engineering manager director level and say, I do want to be that manager of managers.

20:04You gave some great insights about how to approach building that skill set. If you were to give a couple of actionable tips of like, okay, try this, try that, what would you say to those folks listening who are trying to build that skill set? Number one is definitely just literally pick a project or pick a part of the company and say, I'm going to develop a really nuanced picture of what's working and not working over there. And then I'm going to try to read the status updates. I'm going to go try and look at the shipwork, look at the change log. I'm going to look at the metrics I can see in linear B or whatever our engineering metrics tool is.

20:37And then go talk to the manager of that team and go, hey, I'm just trying to understand this better. And see how much what you have come away with matches their perception. I hear you talk about archetypes. I've also heard that you like using personality tests in how you think about your organizational design and helping prepare people. How are you leveraging those? So there's a backstory for our executive team about how we got into these. And, you know, there was a period where we had sort of hired, our exec team has a nice balance of sort of folks who grew into the role internally. And then we've hired a number of seasoned folks from outside of the company who have been VPs or C-levels before.

21:12And that's really nice. But, you know, it takes a while to get the group to gel. So we had gone through a period where we had brought on a couple of new executives who were new to the company but not new to their jobs. We were sort of trying to figure out how to gel as a team. And I think it was our CEO, Christine Yen, who decided, we started to do quarterly offsides as an exec team. And she was like, great, we're going to do a personality test and we're going to all talk about the results and that's how we're going to get to know each other. I can't even remember which one it was at this point.

21:41It might have been Myers-Briggs. But somehow that started to become a recurring thing that we did almost every offsite. So there was like maybe a year and a half where every quarter when we got together, the thing we would do before we saw each other in person was take a personality test and discuss the results. Was it a new one, a different time? Yes, it was a different one each time. That's kind of fun. Yeah, so we did Myers-Briggs. We did Insights at Discovery. We did the Working Genius Framework. At one point, just to be cheeky, I got everyone to do their astrology chart. And I talked people through what that meant.

22:13And the funny thing is you get about as much value out of that as you do the other ones. At first I was a little skeptical, but I really see judiciously deployed that there's real power for certain teams, especially for management teams in those tools. And so I have come around to, I think maybe not every quarter, but there's really good moments to deploy. It's a great conversation starter, if nothing else. Like, yes, it's not always going to be 100 % accurate, but it can help you frame. And I think I've found also when I've done it, I'm not a advocate who's spent a lot of time on that, I agree, but it is kind of fun.