On this week’s episode, host Conor Bronsdon sits down with Emily Nakashima, VP of Engineering at Honeycomb.io, to discuss how you can prepare to be a VP of Engineering, and how the role differs among companies. Being a VPE varies based on company size, culture, and the existing team's makeup, and Emily provides valuable advice for engineers aspiring to leadership positions.

Emily also discusses using personality tests for better team dynamics and the need for regular self-evaluation as an integral part of career advancement. The conversation closes by talking about the impact of AI on the workforce, the importance of aligning engineering and business goals, and the potential of AI to enhance rather than replace human skills.

“ 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, and fairly quickly I went, oh, this is the wrong way to think about this.

Once I switched and said, ‘this is a team that's trying to solve a problem together,’ that ended up being a much healthier approach.”

Episode Highlights:

Episode Transcript:

(Disclaimer: may contain unintentionally confusing, inaccurate and/or amusing transcription errors)

Conor Bronsdon: 1:06

Hey everyone, welcome back to Dev Interrupted, live from Leading Eng Sf. I'm your co host Conor Bronsdon, 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. Uh, because frankly, so are we here. We, 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. Because 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 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, the type of company. Yet we like to think about VPs of engineering as kind of standard like, okay, you're 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 a difference between VP of engineering across the board?

Emily Nakashima: 2:20

I do think that, and I don't think it's just developer tools, companies, I really think, especially startups, but really, any kind of like scaling company. I think so often the roles are really defined by who's there and what the organization does well. You know, there's this real understanding'cause we've sort of, I think, idolized founders and CTOs that we have sort of become more aware of all the different shapes. Um, but you know, the reality is that the VP of engineering can take on almost as many shapes as the CTO. And I don't want people to miss that.'cause I think like 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 of in their head of what it

Conor Bronsdon: 2:54

could be. Well, let me just say to VPs of engineering who are watching and listening. We think about you too. we we're big fans, uh, and that's why Emily, I'm, I'm really glad you're here to kind of talk, uh, 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?

Emily Nakashima: 3:12

I do think that, you know, some of the kind of, sort of maybe stereotype that people have in their head, there is some truth in that. Like, 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, you know, a portion of the technical teams in a larger company. It rounds to true in most places, I think. I think 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 on the leadership team, too. Probably if you think about the VP and CTO relationship. That kind of like makes more sense naturally to people. Like I work with charity majors who's Honeycomb CTO, um, Charity is very well known to come from, uh, a really strong operational background. She was A DBA at one point, you know, she was like a sys admin back in the day. She understands backend engineering very well. And so when I tell people, Hey, because Charity has that background, I can kind of come from more of a front end background, be more of a specialist in like engineering and product collaboration. That 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 like 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 really, you know, it's both. It's up, down and sideways that all kind of like shape the role. It's not just who's the CTO, which I think people focus on.

Conor Bronsdon: 4:44

That'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?

Emily Nakashima: 5:00

Yeah. I think that, um, people really, like I said, focus on that V-P-N-C-T-O 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.

Conor Bronsdon: 5:17

Usually healthy

Emily Nakashima: 5:18

or, you know, tension of some sort one, one flavor or another. Um, and then sometimes, you know, you have a, 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 know, 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. And to a lesser extent it's true for other roles on the senior leadership team as well.

Conor Bronsdon: 5:49

Yeah, I mean, I'm not an executive, but I imagine that when you're in that executive leadership meeting, The, the strengths and weakness of that team has been my experience. You know, the one time I did found a company and that didn't go well, let's just say listeners, Um, I, I wonder how you've seen that impact you personally in your role.

Emily Nakashima: 6:15

Yeah, you know, 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, you know, and fairly quickly I went, oh, this is, this is the wrong way to think about this. Um, 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, as you know, 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 like, I represent engineering, you represent marketing. It's like. you're the funny one, who's gonna add levity when we're all like arguing with each other, or I'm the person who's gonna remember to like retrospect and look back. Like that kind of stuff often comes more, much more to the forefront. And having that sort of balance and sort of like skillset and perspective, I think is, as important as the kind of functional balance.

Conor Bronsdon: 7:04

I just wanna say it's very kind of you to, to picture me as the funny one. So, so thank you for that. Um, 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 venturing function, depending on company size, makeup, et cetera. What are those different archetypes?

Emily Nakashima: 7:23

I feel like the more I dig, the more I find more ones then okay. I'll say I'm, I'm coming from, I'm more of a startup person. And there, there really is a big difference between being, um, the VP of engineering at a smaller company versus being a VP of engineering at a bigger company. Mm. Um, I, you know, I know a little bit about that divide, but I haven't been that VP of engineering at a bigger company and, um, I think that, you know, it can really change Often at a larger company you have a much bigger scope, you know, 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 know, you can't just go rewrite the travel policy on a whim on a Friday afternoon, you know? So that really can shape the role. I think you get a wider array of archetypes sometimes at smaller companies.

Conor Bronsdon: 8:10


Emily Nakashima: 8:10

And then you get more, there's such a range of, from internal facing to external facing. Oh, trailblaze versus steward is a dynamic I really like. Okay. My COO, Jeff Gray uses that description of the two different possible flavors where the trailblazer is the person who is like out, you know, innovating new technology, like 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. Yes. I'm, I'm gonna make sure it keeps doing that. You know,

Conor Bronsdon: 8:37

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

Emily Nakashima: 9:13

Yeah, absolutely. A lot of times, like where the vision comes from can be the biggest thing that kind of shifts around. And I think often if you have founders in those roles, they can often like, look into the far future forever and tell you like what the product should be and then, you know, 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. Yeah. When you like hired that person into the role. That can be an interesting thing that really kind of forces people to grow or sometimes forces a, a change.

Conor Bronsdon: 9:39

So how do you identify the archetype that your company needs when you come on board or when you're hiring? I suppose.

Emily Nakashima: 9:47

It's a good question. I'll, I'll say when I was sort of a, manager, Director, 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, and 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. You know, that's often the biggest clue that something needs to change, where like, maybe you see an organization where you really think product and engineering need to be tight, or engineering really needs to be, you know, very closely aligned with the revenue goals and shipping certain things that, you know, you know there's revenue behind, and you don't see that happening. Those kinds of things are often the sort of The really concrete warning signs that maybe there's been a misalignment in the shape.

Conor Bronsdon: 10:50

And I imagine the needs, I mean, we know the needs evolve over time, uh, for roles. So I can see how this would really shift as organizations grow in scale.

Emily Nakashima: 11:01

One of the interesting things about being a startup VP versus potentially being in a bigger company is like, the pace at which you need to kind of become an entirely different shape or archetype can be a lot faster. You know, I do think the role is always evolving no matter what company you're at, just because businesses, business conditions are changing. But I think at a startup you can kind of have a completely different, most important problem every maybe six months. Sometimes it's just, I need to think about X and, and now I need to think about Y. But sometimes it's, I need to be someone who's like the planner, who's so organized, who's putting the right systems into place and all of a sudden you need to become like the visionary leader. Yeah. Who's like inspiring people. It can really kind of push you to grow maybe faster than, than not. Everyone's comfortable with the pace.

Conor Bronsdon: 11:44

I mean, for folks who are at startups or have been at startups for a while, and the audience, you're probably gonna 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. You know, I want a little bit of scale. Uh, or maybe I love that Series A seeder. I want, 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.

Emily Nakashima: 12:25

Yeah, I really, honestly, I wish we were better at celebrating when people notice that dynamic and make the call for themselves. Yeah. That the company's no longer the right fit. Uh, at Honeycomb, we, we try to be really positive when people choose to leave. We always frame it as like a graduation and not like, this person quit or like this person's leaving. We always say like, they graduated from the team because we always want to, we want them to feel positively about that chapter. We want them to sort of like close the book at a moment that like 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. You know, I think sometimes people always feel like there's that one more important thing that they can't leave behind. And, you know, when you stay too long, I think it's, it's not good for you, but a lot of times it also holds back growth at the company. Um, so yeah, it can, it can be sometimes hard when you, when you, 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. Yeah. And you can stay in that situation where kind of the day-to-Day isn't working for you for a long time. And I, you know, I think we try to put as much positive framing around that as possible to remind people that it is a choice, right?

Conor Bronsdon: 13:27

Are there particular signs that you've seen of when someone maybe does need to move on?

Emily Nakashima: 13:33

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, put 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?

Conor Bronsdon: 14:06

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? Because if it becomes sustained, that's where you know there's an issue.

Emily Nakashima: 14:26

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 and they kind of can't put them aside, they can't bring them to a resolution, and they look around and feel like their coworkers, they feel alone, right? 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 sort of delta from maybe the people around you is sustained is the thing that kind of helps you go, okay, we have grown in different directions.

Conor Bronsdon: 14:57

Yeah, and I think that alignment is something that is usually felt by others on the team, right? Like, 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, you know, grow and prepare yourself for roles that scale like this. And, you know, Startup VP of Engineering is absolutely a role that will often scale from, you know. Maybe you're hired at the Series A and you scale 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?

Emily Nakashima: 15:36

You know, it's a great question, and I think a lot of people don't realize that they actually can start preparing before they, they get the role, you know?

Conor Bronsdon: 15:43


Emily Nakashima: 15:43

They sort of put the title up on a pedestal and then don't sort of break apart the skills that are, 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 across organization management problem, and then you know, 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. I always felt like I would be stepping on someone's toes. And now, you know, now that I'm on the other side, I'm like, yes, please. Like, please, like 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. Um, and for me, you know, so often my job is a little kind of solo. So when someone wants to kind of 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.

Conor Bronsdon: 16:31

Yeah, I think there are a couple ways to think about this. Like one, like, solve your boss's problems. Don't, don't be one. Like that's an, that's an obvious one, right? Like, let's try to help solve their problems and usually. I mean, people differ. Some, some people are very authoritarian or hierarchical and don't want you to take on problems yourself. And also to differs culture to culture, whether that's, you know, internationally where, 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 start solving. 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. but usually I'm just stoked you're you're doing it.

Emily Nakashima: 17:15

Yeah. And you touched on something really important, which is, you know, sometimes it has 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.

Conor Bronsdon: 17:25

Oh, I love that.

Emily Nakashima: 17:25

Um, you know, I'm so used to it since I sort of grew with the company and so many of the folks on the team are people that like I hired or I worked with directly as a manager back in the day. Like, I can have that sort of 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, like that's my favorite moment.

Conor Bronsdon: 17:43

That 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, and things are changing on the ground. And ICs have not just different frames, but also depth in certain areas that maybe you don't have, and so do managers in different areas. However, I also think there are skills that are really crucial to develop that are not just this problem solving piece. start to develop those manager of manager skills, uh, as you work towards that next stage of your career, if that's what you want.

Emily Nakashima: 18:26

You 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.

Conor Bronsdon: 18:35


Emily Nakashima: 18:36

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? You know, like, you don't,

Conor Bronsdon: 18:51

Someone's gonna be worried about that.

Emily Nakashima: 18:52

Exactly. Exactly. You don't wanna be the problem. Um, but it, it is a totally different skill to build that picture of what's actually happening in the organization and where things are working and, and not, from secondary sources versus from going and talking to people directly. So 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, the end result is paying for their teams. So I think you can practice it, you can try to make sense of what's going on in like an adjacent part of the organization and sort of see what you come away with and try to develop that picture. So I think that like, that, that piece is one you could try anywhere. I also think just sort of building your, 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 gonna be trying to build at the same time. And it's nice to get the jump on that when it's not you know, when you're not already in the hot seat.

Conor Bronsdon: 19:52

Yeah, and I know a lot of folks who listen to this. We, 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, yeah, I do want be the manager of managers. You gave some great insights about how to approach building that skillset. If you were to give like a couple of actionable tips of like, okay, try this, try that. What would you say to those folks listening who are, are trying to build that skillset?

Emily Nakashima: 20:16

Number one is definitely just like literally pick a project or pick a part of the company. And say, I'm gonna develop a really nuanced picture of what's working and not working over there. And then, you know, I'm gonna try to like read the status updates. I'm gonna go try and look at the ship work, look at the change log. I'm gonna, you know, look at the metrics I can see in, in, you know, linear B or whatever engineering metrics tool is, and then go talk to the manager of that team and go, Hey, I'm just trying to understand this better. And see how much like what you have come away with matches their perception.

Conor Bronsdon: 20:44

You know, 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, and helping prepare people. How are you leveraging those?

Emily Nakashima: 20:55

So there, there's a backstory for, for our executive team by how we got into these, um, 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. Um, and that's really nice, but, you know, it takes a while to get the group to gel. Mm-Hmm. So, you know, we had gone through a period where we had brought on a couple of new, um, executives who were new to the company but not new to their jobs. And we were sort of trying to figure out how to gel as a team. And I think it was our, our CEO Christine Yen who decided, you know, we were, we started to do quarterly offsites as an exec team. And she was like, great, we're gonna do a personality test and we're gonna all talk about the results and that's how we're gonna get to know each other. I can't even remember which one it was at this point. It might've 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 then discuss theirselves. A new one. Different time. Yes. Love It was a different one each time.

Conor Bronsdon: 21:58

I love that. That's kind of fun.

Emily Nakashima: 21:59

Yeah. Yeah. So we did, uh, Myers-Briggs, we did Insights Discovery. We did the Working Genius Framework. At one point, I, um, you know, just to be cheeky, I got everyone to do their astrology chart. Oh yeah. And I talked people through what that meant. And 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 there maybe not every quarter, but there's really good moments to play.

Conor Bronsdon: 22:30

It's a great conversation starter. If nothing else. Like yes, it's not always gonna be a hundred percent accurate, but it can help you frame. And I think I've found also when I, when I've done it, and I'm not advocating you spending spend much time on this, I agree, but it is kind of fun. Um, you can say, okay, like. I got, for example, I got EN tj, um, or I got IN tj and I've, I've gotten both on that Myers-Briggs test. Like, do I agree with that right now or is this a reflection of how I'm feeling in the moment? And interrogating that result is really interesting, I find.

Emily Nakashima: 22:58

Yeah. And another reason that I really like them, there's two situations that I'll deploy them in that, uh, I think not every, everyone thinks of when they think about these as tools. Number one is if you have a team that you think is really talented, but there may be lacking a little bit of self-confidence. Mm-Hmm. Like sometimes, you know, those tests are really good at just sort of holding up a mirror. And this is gonna sound silly, but like they just remind you that you are good at some things. Yeah. Or potentially, you know, we have a number of very senior engineers and sometimes people could come into the company and feel this sense of, oh gosh, everyone here knows so much. Like, what can I contribute? And just reminding people, Hey, you're a different shape. You know, no matter how, how much you respect your teammates, there's something you bring that they don't have, can be really powerful and can really remind people that, like as a team you are, you know, bigger than the sum of the parts of the people on the team.

Conor Bronsdon: 23:45

You're stronger together.

Emily Nakashima: 23:46

Yeah, exactly. So that's one case. The other case I think they can be really powerful for, um, underrepresented employees, who may be, you know, because of biases in the workplace, people don't always recognize the sort of leadership skills they might bring.'cause they're sort of expecting them to come in a different package. StrengthsFinder is actually my favorite framework for this. You know, I think certain people, people just, you know, jump to the conclusion that if you're strategic or you're ambitious or you know, you're, achiever, like you might look like something different. And you know, because these tests are just, you know, you fill in the bubbles, you get the score. Yeah. They can identify anyone as those things. You know, there's always like cultural biases and that kind of thing to worry about, but I still think that like they can be a really good tool for helping people see themselves in a way that maybe they haven't been stereotyped in the past. So. I feel like sometimes they can kind of help level the playing field and help people see themselves in a way that they wouldn't.

Conor Bronsdon: 24:35

I also like your point about the mix of personalities and skill sets you need on a team. Because, um, if everyone on a team is, you know, one Myers Briggs category, that team probably has some issues. Like, it's true it's got some strengths, but it's gonna have some weaknesses, too.

Emily Nakashima: 24:48

Yeah, and especially, like, it can be so easy to miss this until you see it, like, on the chart of your exec team. Uh, our CEO Christine Yen and the COO Jeff Gray, when we do the Insights discovery profile, we're all blue, which means you're very analytical. You love to work with data, you know, you love to like solve problems and like make decisions. And when we're all like jamming, the three of us are like jamming on something together. It feels so good'cause we think the same way. But it's so easy for us to miss, uh, you know, to sort of have blind spots and like miss that perspective that a coworker who thinks different way is gonna add.

Conor Bronsdon: 25:22

Well, I have to ask, since she's been a guest in the show before, uh, what's Charity Majors? What's,

Emily Nakashima: 25:28

that's a good question. Charity and I are generally opposites, which is kind of great.'cause it means we, we, we work together well. Chair, there's a, there's a red one, which is sort of like, you just wanna like go, go, go and get it done. You're fiery. Yeah. I think like the tagline for that one. Be brief, be bright, be gone, or something like that. like they wanna get it done. They, you know, they're like, they'll be in awe of your brilliance. They'll encourage you. But they also are just like already moving on to the next thing with their minds Um, totally different than the analytical blue where you just wanna like stew in the data. Yeah.

Conor Bronsdon: 25:58

This is great. I, I'm gonna have to go, listen, we've actually done two episodes with Charity on previous seasons. I'm gonna have to go back and listen to them in this context and be like, okay. You're red, I think. All right. Alright. How's, how do you work with Emily here? How does this work? So this is, this is wonderful. I really appreciate the perspectives you brought to this conversation about the changing role of VPs of engineering and, you know, how that impacts the rest of the executive team. And something else we should also mention is that, uh, there is a lot of change happening generally in the world right now. The role of a VP of engineering is changing. We're being asked more to be business leaders, not just bringing engineering efficiency, at least in many companies, of course, it may vary as we've brought up. What are you thinking about going into 2024, Emily, that you see changing either the VP of Engineering role or the technology space in general?

Emily Nakashima: 26:44

Yeah, I, I think as you said, it certainly is a very interesting time and it can be really hard to kind of, even like at this point put your finger in the air and kind of know where things are going. Yes. And I'll say an interesting conversation that keeps popping up. I did a meetup a few months back that was with other engineering leaders and people who were just sort of, you know, making conversation. It was one of the first in-person meetups a lot of people had been to in a number of years. And, um, the question came out, uh, is your board pressuring you? To lay off 30% of your engineers, ah, or more and replace them with AI Yeah. I have a lot of respect for our board and I think they bring a good sort of measured perspective to things and we are not getting that exact flavor of pressure. But a number of people just put their hands up and some people said, I'm being asked to lay off 50% of my team and replace'em with ai. Um, so that's definitely. Whether you're excited about it or not, and I'm, I'm a little skeptical. It's something that people have to have an answer to.

Conor Bronsdon: 27:36

I, I think that's a really great point. I, I talked to a CEO, uh, just in the last couple days, who told me that he had laid off 80% of his team. And yes, new innovation is down. He's like, Hey, we're keeping the lights on. You know, I'm still retaining the value. And I mean, that's a, you know, three, three rounds, brutally deep cuts. But there's a financial incentive for, for some of this behavior and, because of how most organizations are constructed, that will often happen. So it's important that we think about how we're allocating resources, both, you know, financial and, and human capital. Um, I, I know it's a little demeaning to say it that way, but it's that conversation isn't going away.

Emily Nakashima: 28:17

Yeah. I, I think this is unfortunately like the painful fallback to reality and a lot of teams are moving. Yeah. They're moving back to operating in the mode that they kind of maybe should have been all along, like. We should understand the impact of investments that we've made. We should make sure that we are spending our time and energy on the things that have the most business impact. We should make sure that we can look at our data and observe that that's really true. Those things sound so obvious when I say them out loud, but I think a lot of engineering teams, there was a real moment of pressure to just grow, grow, grow, and people really stopped focusing on those fundamentals.

Conor Bronsdon: 28:51

I mean, ZURP, Zero Interest Rate phenomenon, right? The big dogs, the Microsofts, the Googles, the Apples, the Facebooks of the world do then. And we were just going, oh shoot, we gotta, we gotta get our engineers in here.

Emily Nakashima: 29:07

I'm certainly not someone asking, you know, can we lay off the engineers and replace them with ai? I think that's, in general, I feel like that's quite a horrible approach.

Conor Bronsdon: 29:14


Emily Nakashima: 29:14

But I do think that honestly, engineering is a craft, much more fun and much more engaging when you are trying to respond to business constraints. So, um, there that part. I welcome.

Conor Bronsdon: 29:23

Yeah, it's really interesting. We partnered with Google on their Dora research this year. Uh, that reports recently out. Highly recommend, But one of the interesting things that I heard Nathan Harvey, who's the head of, uh, Dora's team over at Google talk about when he and I broke down the report is, okay, like, we're seeing AI be leveraged in about 50 percent of the companies in our 33, 000 person survey. However, we don't have a clear correlation to efficiency gains at this point. Now, what they did find is a correlation to increased dev happiness. is being leveraged to help developers get rid of annoying tasks. I think there's a ton of opportunities for that. And maybe help devs feel more efficient or feel like they're not having to spend as much time on things that aren't equate to value in their mind. So as someone who's a DevTools nerd myself, that gets me kind of excited. But there is so much pressure that you mentioned from shareholders, from the board, from CEOs and CFOs sometimes, quite often. To say, okay, well we can be more efficient, we think the data's not quite there, that it's for sure bringing efficiency gains, though.

Emily Nakashima: 30:35

Yeah, that's a good call out. There are fundamentally some different philosophies and I do totally, I think people will have to kind of pick which one they align with. Like, for us specifically at Honeycomb, Christine, our CEO, um, says we wanna build like meta suits and not like. Autonomous robots. You know, we wanna build tools that make people feel more awesome at their job and, you know, make the things that they have to do easier, but they're sort of still in control.'cause we think that like there are so many things about human judgment that just, uh, can't, there's just not a good replacement for it. Especially, you know, so much of what we do is engineers is about, making challenging trade-offs and you have so much context that I think is just very hard to translate at this point to a machine. I'm much more optimistic about those use cases that are about empowering humans and making their job better and easier than the ones that are like, how can you replace the people with code?'cause I think it's, it's, the outcomes are quite

Conor Bronsdon: 31:25

different. Yeah. I think you can replace processes with code sometimes. Like, that's where I'm excited. Policy as code is an idea is, is a huge opportunity to cut down some of these process pieces. In the end. I, I agree with you. I think, you know, human decision making, human context is important, and we will perform better if everyone gets a copilot like thing for their job. Whether that's an engineer, whether that's a marketer like. Right. Whether that's someone working in an entirely different role, let, let's give everyone a tool that's tuned to how they need to approach the world to help them. Because yeah, that's gonna see a lot of efficiency gains that's gonna make people happier. It's going to, you know, see these improvements. But there is this conversation happen thing where it's like, oh, well why can't we just completely replace the humans?'cause humans are expensive for a corporation because we have to spend the money. Um, but, but I agree with you. I think it's a little shortsighted at, at least for now, the tech, tech doesn't seem to be there yet in my mind.

Emily Nakashima: 32:20

I agree with that. There is one aspect of this that I'm, I'm welcome and I'm really excited about, and this is something that, that our CTO Charity Majors sort of clued me into, where she pointed out that all of these software teams building with ai, building with llm. They are starting to have to accept the certain realities about production software that actually I think, have been true for a long time. Hmm. Um, you know, there's sort of myths that we tell ourselves about our software that haven't been true for a while. You know, the idea that, you know, our software is perfectly deterministic that if the test pass it works, that, you know, once you ship it to production, what the software does doesn't change until you ship again. All of those things have become sort of like less and less true over time in the cloud era. And, you know, LLMs really sort of put those issues in the forefront. And so I, you know, she's kind of excited and I, and I agree that I think we're gonna have more of a conversation where we, we sort of evolve how we think about supporting software and production and how we ship. And I think that's gonna be really cool and interesting part of this.

Conor Bronsdon: 33:20

Fantastic. Emily, I've, I've really enjoyed this conversation. I appreciate the thoughtfulness with which you've approached, this topic, and I hope everyone who's interested in being a VP of engineering in the audience has listened to this and has found some value, and maybe VPs of engineering in the audience.

Emily Nakashima: 33:39

I think, you know, one of the things I'm really excited about as I look out is just I do think that there's a return to really wanting to make sense of, of the data that you're seeing. Like it is a moment that really calls for that. Yeah. And so I think that like, um, all of a sudden. You know, our tools become so much more important. They become so much more precious to us. And I always wanna encourage people to sort of dream big for their tools. I think it's so, so easy to sort of, um, get used to dealing with your tools in a certain way. And I think like the nice thing about AI is it's, it's forced us to sort of re-envision what those experiences can be like. I think you can do that with everything you use. You don't necessarily have to limit it to, you know, the, the AI that's coming to, you know, replace typing in your text editor. So I think it's a good time to kind of look around and go, what else can we upgrade in our lives to, to make our jobs a little easier?

Conor Bronsdon: 34:24

Yeah. Well it sounds like you think upgrading to linear B is a good call, so I'll, I'll take that, the implied guess on that one. So thank you. Emily, where can our guests follow your work?

Emily Nakashima: 34:33

Oh, that's a good question. The social media landscape is very weird at the moment.

Conor Bronsdon: 34:37

I believe we had David Yee we talked to earlier and he called it the social media hellscape.

Emily Nakashima: 34:42

That feels very accurate. I think a good place to find me if you are on Blue Sky, I'm there at EA Nakashima. I think, you know, I'm also just all over the place at Honeycomb events. So come find me in a booth somewhere and I'd be very happy to talk to you about data and AI and anything else.

Conor Bronsdon: 34:58

Awesome. That sounds great, Emily. Thanks for coming on the show and spending the time with us. I've really enjoyed Emily.

Emily Nakashima: 35:04

Thanks for having me.