Career Journey 6: Your Invitation to the Boardroom

0:00I would just kind of challenge us as a community. Like maybe you ask yourself as a VP of engineering, am I getting invited to the board meeting? How many board meetings have I presented in? And by the way, at my last role, when I was the VP of engineering, I never went to the board meeting. I didn't get invited. I think that's the biggest gap. And I think you get there. You get that seat by practicing what I've been saying on this pod, on the business alignment, come with data, come with allocation, come with project delivery, come with predictability, Talk to your CEO about it. Show that you're like worthy of that business conversation.

0:38The most iconic duos in tech, Steve Jobs and Steve Wozniak, Bill Gates and Paul Allen, and Google's Dora team and Linear B. You heard that right. Linear B and Google Cloud are collaborating to explore the results from this year's 2023 Accelerate State of DevOps report. Gathered from over 33 ,000 global professionals, this annual report is your go-to for independent and view in the groundbreaking software team practices. Join Dora's Steve McGee, Linear B CTO Yashai Berry, and me, Dev Interrupted co-host Connor Brosnan, for a workshop on November 8th as we guide you through the key findings from this year's report.

1:14Learn why teams with faster coder views have an incredible 50 % higher software delivery performance. Gain insight into the latest trends across industries and company size, and see the impact AI is having on team performance. Mark your calendars for November 8th and prepare to elevate your DevOps game. Register now at linearb.io slash events or follow the link in the show notes. The ape doesn't work for you? No sweat. Register and we'll still send you the full recording after the fact. Hey, what's up, everyone? Welcome to Dev Interrupted. This is your host, Dan Lyons, Linear B COO. And today I'm going to be interviewed by my co-host, Connor Bronstein.

1:55Connor, thanks for sitting down with me, man. Man, it's been too long since we did this together. Yeah, absolutely. It's great to be back on the show with you. I'm sad we're not going to get more chances over the next few weeks because you've got this exciting adventure of parenthood round two coming up. I do. I got baby number two on the way any day now. But what you and I were talking about, maybe we do a little like end of year winter solstice type celebration episode. So I think that would be awesome. Let's do it. Let's do it. But today we are here to talk about, I think, some of the lessons that I learned after having some amazing guests on the pod.

2:44And you were going to like at least switch roles for me. You're going to interview me. That's exactly right. We've done this great engineering leadership series. something that we think anyone, whether they're one year into their career or 10 years into their career can benefit from going from, you know, an early stage engineer, senior engineers, up to engineering manager, all the way to VP of engineering, maybe founding. And we want to make sure that folks are listening to the show because we know that folks at all levels, including engineering leaders, but also people who are newer and want to learn.

3:15Over these multiple episodes, we've really looked down and said, okay, like we're going to interview people who are experts in their field. And I know you've talked to a bunch of them, Tiago, Avini, others, but how to put your best foot forward in the interview process, how to succeed your first month in a new role, what it means to lead a product-led organization, all the way to how to think about and hire diversely when you're that founder, that CEO is trying to bring in top talent. We've had these amazing guests, and I know I've learned a lot listening to these episodes. If you're listening right now and you haven't checked them out already, can't recommend it enough, you're going to find something relevant no matter of your career stage, there's definitely an episode or two in there for you.

3:54And yeah, we wanted to wrap it up by talking to you, Dan, and saying, okay, like you've been in these roles. You've grown from a, you know, individual developer to now a co-founder and CPO. What's the advice that you have? And I think it'll be a great way for us to dive in. Yeah, it's awesome. I'm ready to rock. And I think, you know, the cool thing about it is I'm learning too. Like the guests that are coming on, I think like the industry is evolving still super rapidly, especially what it means to be a leader, even since I was really an engineering leader. And so I was just like really happy to keep, you know, my learning going.

4:32So, well, let's start off there then. What are some of the things that you felt like you learned or heard that maybe surprised you during the series? Here's the thing that's happening and I can hear it. And did people say it in different ways when they come on, you know, Bavini, Tiago, like there's this, there's this dual mandate that exists for engineering leaders that was even stronger than when I was an engineering leader many years ago. and I'll explain what this means. It's almost like the responsibility of what it takes to be a great leader has increased. And I think, and just so like everyone knows, when I say dual mandate, it's this responsibility that I have to align with the business.

5:23I have to keep the business up to date on where am I spending like engineering time? How are these projects going? What does it cost me? And then, of course, like all the stuff that I was used to when I was an engineering leader, you know, back in the day, which is like your operational efficiency, your quality, your speed of delivery. And I just I just feel like over the last few years and now I'm hearing in every episode, doing both of those in parallel is almost like the bar to be elite now. And that's what I hear from our guests more and more, which I was actually surprised. I was kind of feeling it as I was talking to the Linear B community.

6:06But to have other people come on and talk about that, I was like, whoa, it is really here. This is crazy. Exciting. This step that's happened where engineering leaders can't just be experts in the operations of the engineering team. They have to be able to translate engineering operations to the resources with being allocated by the business actually making an impact at the feature level all the way down into what's happening with ARR. And that expectation is great for engineering leaders. Huge exposure. We're seeing way more technical founders today than we used to, frankly. It always used to be CEO types, maybe CMO types.

6:41And we're seeing that shift to, maybe I'm a former VP of engineering like yourself who's a founder or a CPO who's a founder. But it does bring with it a lot of challenges around how do you translate those engineering operational pieces to the board? How do you communicate about it? And how do you build that expertise if maybe you started out focused on the operational side of things? It does make me wonder, are you seeing common traits or common backgrounds of the folks who are succeeding in kind of that dual mandate approach of both owning, being a business leader and an excellent engineering operational leader?

7:15Yeah, for sure. I think like one of the characteristics that I'm seeing there, it's, it's almost like the person is checking in with themselves on the balance between the two. And I'll try to describe what this means. it's like this self-awareness kind of on that weekly or bi-weekly basis maybe even monthly basis to say like am I in tune with what the business needs from me and I have I communicated back things like hey business these are the four areas that I'm spending engineering's time on it's 60 % new value it's 20 % feature enhancements it's 10 % keeping the lights on whatever it is and did I get a response back from the business that says like yeah we're cool with that or no we're not but then also checking yourself on the balance side to say like am I still a great technical leader like do I know what's going on am I reviewing PRs do I understand the system architecture?

8:22Can I tell where there's bottlenecks in, you know, my dev pipeline? And I think the great leaders today almost have like either, like I said, a self-awareness or like a checklist that says, where am I strong or weak in these two areas? And like over the next month or two, where do I need to put more emphasis? And you want to be somewhere in the middle. That's what I think the best ones are doing. I'm curious if, because I feel like we hear a lot in the industry about technical challenges, there were particular non-technical challenges that you felt like emerged across your conversations. There's two that stood out to me.

9:03One of the guests, I think it was Tiago, was talking about this concept of like fast decision-making that kind kind of stuck with me a bit. Now, of course, it's usually like, it could be decision-making about a technical problem, like what to do. It could be about people. It could be about what we just talked about, like project delivery allocation, that kind of stuff. But that stuck with me a little bit because when you are a leader, his whole concept was like, making a fast decision is better than waiting, even if the decision's not perfect. That was basically the concept because you can iterate and all of that.

9:43So I thought that was important. The other thing that I'm hearing a lot, people are talking about DevEx, developer experience. And again, they don't always use that terminology over and over again. And I don't think of it exactly like a technical challenge, like, oh, okay, like, how is our database going to scale? Yeah, that's like a technical challenge, something like that. But it's related. It's like, where are developers wasting time? How long are they waiting for a build? How much time are they spending in meetings? What's like the vibe? I hear that kind of over and over again, maybe recently.

10:25And I would classify that oftentimes there's a lot of like non-technical challenges. And maybe it even relates back to the fast decision making. Maybe you can tie them together. there's all these issues that developers are saying hey I'm having a problem I'm not having a good experience I'm waiting okay what are we going to do about it so yeah man those are the two that stood out to me are there takeaways for you that you now want to apply to linear bees engineering or product culture I think that that's a really great question the thing that I think all leaders struggle with. And again, I think it's something new with the industry.

11:08What I'd like to do with Linear B as much as possible is always check myself to see, am I communicating back to the business of what I think we should be doing or where I think we should be improving. Can I relate that back to a business KPI or not? And if I cannot, why? If I can, great. And I even find myself like every day, every week, I'm talking to like my co-founder, our CEO, Ori, and our best, and you know, I'm like right now leading the product organization at Linear B. And our best conversations are always like, okay, we have limited amount of engineering people, that will always be the case, no matter how big you are.

11:58Even if you just, you have a thousand developers, then you have a thousand more things to do. So it's like relative. Is what we're investing in aligned with what we think will move the needle on the business the most? And honestly, anytime I'm making a decision and it's not aligned like that, I'm like, maybe I'm not making the best decision. So yeah, that's the thing with like at Linear B that I want to make sure that I'm always doing, I have to like remind myself. That definitely speaks to that dual mandate challenge that you brought up earlier of, okay, we need to ensure because we have the tools, we have the information now that we are actually aligning our features that we're working on, the bugs we're fixing with what actually delivers value for the company.

12:43And I wonder if that has impacted in any way your perspective on the route to becoming a software engineering leader. You know, there's been a variety of paths that people have taken to leadership. Do you think this is impacting the skill set that is being expected from engineering leaders today? There's like one thing that stands out to me and like a point that I'll try to remake here. I do think if you're, let's say you're an individual contributor, you want to be a manager or you're a manager, you're looking to be a director, director, you're looking to be a VP, whatever it is, like kind of on that side of the leadership track.

13:23I feel like there's nothing better than getting promoted within the company that you were already working in, in that previous role. And the reason being, not only are you going to know like the technical challenges, if you're listening, like, okay, you're listening at the all hands or you're, you know, the business context. And I think it's easier to get that dual mandate of business like allocation, project delivery alignment with operating excellence, cycle time, MTTR, all of that kind of stuff, PR size. Because it might take, let's say that you go to a new company and you're like coming in as a VP there.

14:08You're like a director and now you're a VP. Or if you're like a manager and you're moving to a director, it could take you like a year to like like really understand both sides of it and then make the right impact. So I would just say like, I love, especially like earlier on, like maybe your first team leader role or like director role, like getting promoted from within. I think that's the way to go. I remember a blog that you wrote a couple of years back that I remember reading it when I was applying to work at Linear B and interviewing. You wrote this blog, Dev Methodology Doesn't Matter, So Make It Up.

14:42And the idea behind that was that like, okay, it's a bit of a clickbait title, but the kernel of truths in there are really accurate, which is every company is different. And to your point, like, you know, we just named six metrics that could be great for measuring your business, or some of those may not be exactly right for you, depending on how your team is structured. You know, teams that are doing mob programming versus Kanban versus, you know, classic agile scrum, like there is very different needs for how those teams should measure success. Like, yes, we can connect that back to impact in the end.

15:19We should connect that back to impact. But the operational metrics that make that up and that help you understand the functioning of your team along with conversations and anecdotal pieces, of course, can vary widely. And I hear that thread coming from what you're saying. It's like, there's no one-size-fits-all approach. We can have guidelines and benchmarks, but you need to have the understanding of the cultural context and the needs of the business to actually deliver. I think that, yeah, the title is a little funny, but at the end of the day, it's like everyone, I think by now knows agile methodologies, lean practices, all of that kind of stuff.

15:58Again, the elite leaders are the ones that could go and talk to the CEO and say, hey, for this business, I understand that we have a retention problem. The reason we have a retention problem is I think we have too much investment in new features and not enough investment in feature enhancement. The KPIs that I want to measure are MTTR and CFR. Hey, CEO, how do you feel about that plan? Because this is how I believe we can help with the retention problem. Wow. The reaction you're going to get there is like, OK, now we're talking. now I might as a CEO say I understand why you you're because you know the worst situation is like yeah we're not delivering enough features no I think you're going to get I understand why you want to pull back on features because you think that we we can increase our GRR if we make this allocation adjustment and start you know focusing the business on these two door metrics like that's awesome that I think is that is like that dual mandate like elite impact on the business I'm curious if there are other key themes of like that customization or other other pieces of advice that you wish someone had given you when you were first stepping into leadership roles.

17:15The first thing is it's that balance check that I tried to say in the beginning of the episode of like, hey, you need to stay super technical, stay in the code, review PRs, understand the architecture. but you also need to understand project delivery like what is your predictability is it good is it bad you also need to understand allocation and I wish someone told me like hey there's not like one trick to do all of this it's like monitoring yourself each week to see where you're at and the way that I do it now is I'm setting like every Monday morning or sometimes I'm doing it Sunday night, but every Monday morning, like I set weekly intentions.

18:07So I have a file on my computer. It says intentions, just like a notepad. And I do two things. I set intentions for my family. Number one, so like right family. Here are the things that I want to do, like achieve at home with my family this week and work. Here are the things that I want to achieve at work this week. And the ones on the work usually, and I only do three, three for family, three for work. But you'll see the ones with work have that balance. It's not just like one area. It's like three things that round out to like a more well-balanced like mindset about our business at least. So yeah, man, that's the advice.

18:48I wish someone told me like, try to keep that, that balanced mindset. And that's like the dual mandate thing. Do you feel like that's a challenge that you had in your career where you went too far in one direction or another until you kind of figure out how to take that balance point. Yeah, exactly. It's definitely something I've heard from other engineering leaders too. Because it's like, you know, I think like earlier on in my career, I like went maybe like too far, actually more like on the people and alignment side and like lost some technical chops, right? Wish I stayed like a little more balanced.

19:23Now, oftentimes I see people do the opposite, stay way too technical in the details and don't know anything about how to deliver an amazing product from the engineering side. Let's say you are out of whack. Maybe you get feedback from your team or your leadership, and they're like, hey, Dan, you're a director of engineering. We think you're staying too technical. We want to see more people leadership. What would be the approach you would take, whether or not you got the feedback or you realized yourself it was something you wanted to improve on? I mean, I think first of all, it takes like bravery.

19:59I try to do something like this, like at Linear B, I got some feedback, you know, on the product side. Hey, I want us to be, you know, measuring usage a little bit better. Got that from like my partner CEO. And I say like, I love it. Let me present back to you what I think we should be measuring and how. I'm going to set it up a week from now and you give me feedback. Right. I presented that and it was like, hey, this isn't right yet, but it's a good start. Okay, cool. Give me two more days. I'm going to present it again. And that's like a way that you like echoing back. And then, and by the way, now we got it like perfect.

20:43We have like an unbelievable measurement system now, but it took like a brave step to say, okay, shit, maybe I don't know this. Let me present back to you all where the gaps are and give me feedback. That's the best way I know how to do it. Yeah, I think the buzzword that people hear a lot about this is growth mindset, right? And to me, I almost distill it down more to what you're saying, which is the willingness to put yourself out there, receive feedback and adjust. That iteration is, I think, something that we obviously value highly in software engineering. And it's crucial to apply that same continuous iteration process to your own mindset and career in order to develop as a leader and continue to succeed and deliver what you want to do.

21:30I'm curious if there are other pain points or challenges that you've taken away from either your journey on this or these conversations that maybe resonated with you. I see like in general, maybe 80 % of the time, us as an engineering organization, I'll just talk about the community. I don't think we're as connected to the business as we need to be. I think we've made amazing strides. CICD, automated test coverage, all this stuff about how to deliver fairly efficiently, fairly high quality. I know there's always ways to go, but you look at these companies like Netflix, like Spotify, some of these great companies, and they're doing all of that.

22:15I would just say, like, I want to see more engineering leaders take that CEO role, take that executive chair, but not be like the last one in the board meeting or like not even invited to the board meeting. I would just kind of challenge us as a community. Like maybe you ask yourself as a VP of engineering, am I getting invited to the board meeting? How many board meetings have I presented in? And by the way, at my last role, when I was the VP of engineering, I never went to the board meeting. I didn't get invited. Yeah, I think that's the biggest gap. And I think you get there. You get that seat by practicing what I've been saying on this pod, on the business alignment.

22:58Come with data, come with allocation, come with project delivery, come with predictability, talk to your CEO about it, show that you're like worthy of that business conversation. Because you know any marketing or sales leap or salt will have that data. Yeah, no, they all have that data. They have that data since like day zero, like 50 years ago, they had that data or something. You know, that's like table stakes for us. I think we're all working to make it table stakes. And the last thing, I know it's a little preachy, but I think the best companies in the world are led by CEOs that came from an engineering background because they have the best products and people like love great products.

23:37Right. And so I think if we all start doing that. Yeah. More, more engineering CEOs. So you've really spoken to this idea of we need to make sure we're aligning to business impacts, make sure we're seeing how engineering and product can deliver these larger business metrics that they roll up into and being more clear on how what we're doing operationally and what we're investing time in, you know, those new features or feature improvements, keeping the lights on, whatever it might be, roll up to eventually or, you know, revenue, whatever your key metrics are. and that is obviously crucial, but it's also key that you keep this healthy balance between delivering those results and ensuring the well-being and growth of your team members.

24:22How do you approach that balance of, hey, I still need to develop my people too? You know what? That's like always going to be a challenge. Here's the, I'll just give a trick that worked for me. When you can find the alignment between the two and I'll give an example. The thing is, when you're trying to grow an individual on your team, the best thing that you can do is find a problem that is not solved within engineering and the business cares about it. And you say to that person, hey, nobody's taking this thing on. Why don't you take it? Because if you're, you know, well-being and all of that, we can talk about that next.

25:07But like career growth, giving an individual contributor an opportunity to solve a business problem that no one else is solving basically gives them a shot to not be an individual contributor for one project or like for a few weeks and see how you do in that leadership role. That's kind of the trick. And the coolest thing about it is it's not like you're wasting your business's time or your company's time. You're giving them a problem to solve that the business cares about. You're giving them a challenging opportunity. Yeah, you're giving them a challenging opportunity, but it's not like made up.

25:42It's not like, oh, I don't know, like, let me give you some career advice or something like that. Like I can think about one recently for us at Linear B. You know, I think in our product, we have the best, I would call it like coverage. Like, you know, we support all of the Git providers. We support all of the project management tools. We support all, you know, all these integrations. But there's one integration, for example, that our sales team is really asking for. And no one on my team was communicating back to the business, like, how are we going to solve that integration or like, what's the roadmap?

26:22So I gave it to like an individual contributor to say, hey, why don't you take this and communicate to the business? On the well-being side, because that's the other part of the conversation. The only thing that I know how to do there is like set an example. If you're, if you're a leader, show your people what your health plan is. And I don't mean health plan. Like it has to be like a medical plan. I mean, like, like I tell you, Dan, you got to tell me what's your health insurance? Mine's like blue cross, blue shield or something. No. Like for me, I'm telling them, Hey, every Friday, because this is what I do.

26:59I take time out of my work schedule and I do two things. I do yoga and meditation. I'm doing this from eight to 11 because I go to a class and I got to drive there and it takes some time and all of that. And I'm saying like, hey, that's my plan. That's part of my plan to have like great well-being. What's your plan? So I think you show that like, yeah, you should have a plan. Like that lead from example and encourage others to build a plan. And I'm also curious, you know, we're talking a lot about the good times and how to make sure there are good times, but there are also really challenging decisions you have to make as an engineering leader, whether that's letting someone go or, you know, a variety of other tough decisions that come up in the role.

27:46Is there an anecdote that you could share with our audience, whether something that you heard in our series or from your own career about how to approach those challenging decisions? just being like honest with yourself. Like sometimes with the challenging decision, usually it's also tied to like something that's not very pleasant. Let's put it that way. Could be letting someone go. It could be something more technical. The one that comes to mind for me at my last company, the most fun thing that you could do or the thing that you got the most like accolades for, at least from, you know, CEO and everybody, because it's just natural, is like delivering amazing features.