Upleveling Your Software Team with Rob Zuber, CTO of CircleCI

(Intro Narrator at 00:00:03) Hello, my friends. Today, Joel is talking to Rob, CTO of CircleCI, and they discuss how to uplevel your software teams, why teaching and mentoring others is beneficial to your own skills, and how the best way to have quality software is to move quickly and deploy often. All of this right here, right now, on the Modern CTO Podcast.

(Rob (CTO of CircleCI) at 00:00:28) Here we go.

(Joel Beasley at 00:00:29) This is the Modern CTO podcast.

(Rob (CTO of CircleCI) at 00:00:38) So 2020 to 2022, it's an interesting part of all of our lives, I would say, since we've last seen each other.

(Joel Beasley at 00:00:45) Oh, yeah. What's been happening over at CircleCI?

(Rob (CTO of CircleCI) at 00:00:48) Oh my goodness. So many things. You know, we continue to grow through that time. Unsurprisingly, people have continued to build software, and so that portion has been good for us. But take that two year slice, all the standard turmoil, all of the, you know, just consternation is maybe a good word. Just everything going on around us to the point of trying to do the right thing at work every day, but then also try to do the right thing for all the people that we work with every day, right? How do we help each other make the most of the good times and kind of get through the bad times on this roller coaster of the last couple years? So it's been, I'd say, from a leadership perspective, probably not what most of us thought we were getting ourselves into. You know, whatever it was that anyone listening joined the ranks of leadership, there's always been hiccups, but a global hiccup all at the same time and then a long series of them, I think, tested a lot of folks. But, you know, those kinds of tests also bring out the great in a lot of folks, so that's nice. It's a nice upside if you can find it.

(Joel Beasley at 00:01:53) Yeah. Well, we've definitely learned how to have difficult conversations because you had the pandemic and then you had a number of social issues come up. It just doesn't seem to stop. It seems like every quarter, there's something really big and really new happening. And, you know, you've got to figure out how to get your team through those things and then make sure that you're focusing, that you don't just ignore it, but that you also focus and get work done. It's a delicate balance.

(Rob (CTO of CircleCI) at 00:02:20) And I think for a lot of leaders, I've started projecting. I'll just speak for myself, I guess. For me, building a better understanding of the connection between creating that space for folks and giving them what they need to then do great work versus "I need this from you right now. We'll talk about the world's problems later," sort of like this doesn't work. Not that I thought that was gonna work, but this has been a good test of those theories, let's say, to say, okay, yeah, I get it. I mean, even now, the macroeconomic cycles, you know, having a pretty big impact just on people's confidence. Just, hey, what's happening in the world? How does this affect us? I mean, that's a series of conversations that we have to have. We feel very good about where we are, but it's hard to wake up and not be hearing about, you know, what's happening in the market, inflation, interest rates, all this kind of stuff. And being able to connect that to, again, the kind of work that we do every day is important for people in making the space to have those conversations and help folks understand. When you start out as a software engineer, on the trajectory that ultimately leads to leadership in engineering, you know, those aren't the things you're thinking about, right? I explicitly did not take economics, psychology, any studies of humanities or whatever when I was in college, right? I was all about engineering, engineering, engineering. That's not most of what I do now.

(Joel Beasley at 00:03:40) No. You just have to figure it out. It's just getting thrown into it.

(Rob (CTO of CircleCI) at 00:03:44) Yeah. And I think on the very topic of podcasts like this or, you know, the community of people that we get a chance to meet or listen to or whatever, I mean, the last couple years for me has been figuring it out. Yes. Figuring out who I am in that, but also finding people who I can relate to or understand or say, oh, I like the way that that person leads. What do I like about that? How can I take that and incorporate it into the way that I think about it? Thinking that you're going to figure all of this out by yourself is probably your first mistake. Finding communities, resources, whatever it might be, you know, great podcasts to listen to and say, oh, wait. No. That makes sense. I think I could do something with that. You know, not everybody's playbook is gonna work for you, but something inspired that idea that will inspire your idea and say, oh, okay. Yeah. No. I see how I could do this in a better way and help my people.

(Joel Beasley at 00:04:32) Yeah. This is a good time to plug is it the Confident Commit? Is that the name of it?

(Rob (CTO of CircleCI) at 00:04:36) The Confident Commit. Yeah. And I will say the thing that I love about doing that, and maybe you can relate, is the amount that I learned. I get the opportunity to say, hey, come hang out with me. And I'm blown away every time, you know, about new ideas that people have or different ways of looking at things. I end up listening to it. It's so weird because people hate listening to their own voice. I don't know if you fall into that camp. But I listen to all the episodes because I know I couldn't keep up, right? I'm busy thinking about where are we gonna go with this conversation? What's next? Okay. Try to make mental notes about the next question or whatever that might be. And when I go back and listen again, I'm like, oh, I didn't even notice that the first time. That's brilliant. So I go through and make even more notes about what people have said and, you know, the possibilities to learn. So, again, I don't know if that's been your experience doing this, but it's such a gift. It's amazing.

(Joel Beasley at 00:05:28) Oh, absolutely. And you're exactly right. I at first hated listening to my voice, but it's just something you get used to after several hundred episodes or however long. It didn't take that long.

(Rob (CTO of CircleCI) at 00:05:40) Mhmm.

(Joel Beasley at 00:05:40) But you just get used to it because at first, I was shy. You know, I'd be in the office and people would be editing clips, and so you just hear my voice constantly. But then it's just what it is. This is just what's going on now. Yeah.

(Rob (CTO of CircleCI) at 00:05:53) Yeah. And listening is also a bit like watching game tapes. It's one of my favorite expressions these days. That's your opportunity to realize, oh, I sort of didn't ask a very sensible question as a follow-on to that. What did I miss? How could I do that better? Or this structure or something was confusing. You know, it's the opportunity to go back and reflect on that. So, yeah, getting over that discomfort, I guess, with hearing yourself and using it as an opportunity to learn and grow and, you know, get better at it. I think it's huge.

(Joel Beasley at 00:06:24) Well, we're actually working on a book on how to host podcasts. So we could clip some of that advice of yours about watching the highlight reel or the game tape back and give you an honorable mention in the podcast and the book.

(Rob (CTO of CircleCI) at 00:06:36) I appreciate that. That'll be my big pro tip. Get over it. Learn to listen to yourself because you'll learn from it.

(Joel Beasley at 00:06:43) Now did you have that podcast last time we talked?

(Rob (CTO of CircleCI) at 00:06:46) No. I think we started it soon after that. Beginning of last year, I think, of 2021, was when we started. So we did one season. Now we're in the second season right now. And seasons are sort of interesting. I mean, it's not like it's on a broadcast, you know, time schedule or something. It's so funny. I think about seasons from when I was young, and you had to get the TV on at exactly the right time to watch something or whatever, listen to the radio. In the first year, we did sort of just a generic who do we wanna talk to about software? And then this year, we picked a theme, and we've sort of been focusing on that around learning from failure, which is, you know, interesting in all forms of leadership. In fact, the most interesting connection there was my mother telling me recently that she's been listening to it, and I was shocked. My mother was not in software, in case that's unclear. And she said, you know, this is not just about software. This is people, right? Learning from failure, dealing with things when they don't go right, and, you know, building a culture around that, all that sort of stuff is more broadly applicable than just the world of software. It's just that I think about software every day.

(Joel Beasley at 00:07:45) Yeah. And I've actually found that it's really cool because there's lots of podcasts out there, and everybody sort of groups together with industries. And, you know, you listen to a CEO when they're having these types of conversations too, but with a slightly different flavor. But it's really great to get to hear about leadership and then also hear about technology, you know, from somebody leading in technology, which is really close to, you know, what people are doing. And so it's just kind of cool to have your tribe and get to hear what's going on out there.

(Rob (CTO of CircleCI) at 00:08:15) Yeah. But I would say from a leadership perspective even, I listened to a bunch of audiobooks with my son this year. We did a lot of road trips, and we listened to a lot of audiobooks. And he doesn't wanna listen to anything about software or leadership. So we listened to outdoor adventures, you know, mountaineering expeditions gone wrong and stuff like that. And both the human factors that lead up to the problem and then the way that sort of leadership comes into play and the ways in which people deal with the problems or search and rescue and how they apply search patterns, I'm constantly taking notes. You know, it has nothing to do with software per se, but the human elements are actually really, really consistent across so many different domains. And it tends to give me new ideas in a way that when they're packaged up with a very software flavor, I might have missed. But somehow, they work for me coming with a different context, plus they're just fun books to listen to.

(Joel Beasley at 00:09:11) And then so do you take these, sort of convert them to analogies, and then write articles? I saw you had an article, Upleveling Software Engineering Teams. Am I saying that right?

(Rob (CTO of CircleCI) at 00:09:22) Yeah. So, yes, sometimes internally, sometimes externally. So it depends on the context. The search and rescue example, I read something really interesting about capturing the expertise of all the people involved and ensuring that it gets exposed at this sort of consensus model. And then thought about how could we apply this in operational incidents in software, right? Is there a model for exposing that understanding for people's estimations of where the problem might be, you know, in the not the ones where it's like, oh, we did a thing and we just need to revert it, but the ones where no one knows what's happening. You know, can you use those same kinds of models? And so less writing an article, more getting a few people together and saying, hey, this is interesting in a very different lens. Can we learn something from this? Can we apply this in some way to the work that we do? So I'm constantly thinking about that. I feel like I wish I had more time to write external articles about that sort of stuff, but we're still exploring a lot of it, right? And so I'm probably on the side of once I've tried it and I know it works and I learned something from it that I can then say, okay, this is how you would take that, then maybe I'd write something. Up until that point, I'm like, maybe this is just some ridiculous concept that I have, and it's not actually gonna work or help us in any way. And at that point, telling everyone else to try it, I don't know if that's the best advice.

(Joel Beasley at 00:10:40) Two pizza teams, Rob. Come on. Need squads. Yeah. Okay.

(Rob (CTO of CircleCI) at 00:10:45) That's right. Dude, this is funny.

(Joel Beasley at 00:10:48) What are some of the things you have learned that have worked out to be true for you?

(Rob (CTO of CircleCI) at 00:10:53) From all the listening. Well, I mean, I'll tell you one of the most interesting. I don't know if I'm gonna be able to to do justice to this. But speaking of human factors coming into play, we listened to a story about the K2 disaster, basically. And there was all of these teams independently had practiced and trained and, you know, we're gonna go take the summit sort of thing, and then there was one day. So they decided to combine their efforts. Otherwise, it would be too congested. But, basically, under the most grueling conditions on the planet, you have all these groups coming together trying to execute without the trust or preparation or understanding that you have of each other. And I won't tell you what book it is, but whatever. I mean, it's a pretty famous day on the mountain. Things go sideways, unsurprisingly, or else there wouldn't be a book. And one of the most interesting things is the language, which is not something that really happens in most of our workplaces. We don't hire different teams that can't speak to each other in the same language. But there's one pivotal character who is the translator between all the different teams, and he gets sick. And now none of them can even talk to each other, and they're in this horrendous condition or whatever. But what's so interesting about that and what really resonated with me was the preparation and the cohesive team. And so a place that we've applied that internally is actually, you know, speaking of learning from failure, focusing on incidents, building a close-knit response team that works together every day versus what typically happens is you have a few different people coming from different parts of the company trying to solve a problem who at our scale, which is very different from what it was, you know, when we last spoke a couple years ago, those people might have never even met, let alone worked together. And so there's a lot of, you know, just natural communication overhead, right? And when I look at highly effective teams, particularly under pressure situations, you see things like hand signals, right? I can just blink and you know that means go do this thing versus now I take five minutes to explain to you, this is the thing we have to go do. This is what I need you to do. You know, whatever. I wanna have practiced and trained that, right? And, again, it was something that sort of clicked or landed from hearing what happens when a whole bunch of different people who don't really know each other are trying to operate under what ends up being, you know, extremely strenuous conditions.

(Joel Beasley at 00:13:11) So what happens now with the incident team? How does that work?

(Rob (CTO of CircleCI) at 00:13:15) Well, it's a whole interesting thing, I guess. I mean, we don't know what the long term is. On the short term, what we wanted to do was pull together a group and really understand how we want to respond and figure out what that would look like if it was great. And it's difficult to collect that insight from a broad distributed group of people who maybe participate in one but not the next. Yes, you can learn from them. But getting a group of people who really trust each other and work together every day and show up and say, did we do it better this time than we did it last time? And we don't, we haven't taken over for people who, you know, build and run services. We're really just trying to learn and optimize and observe that in the moment. And then, again, figure out how could we be great at this?

(Rob (CTO of CircleCI) at 00:13:59) What would that look like? And then what does it look like to build that capability and capacity throughout the organization? And at the scale that we operate from an engineering team perspective, learning new things and distributing them out to even 200 plus engineers is quite challenging. And so finding a—I mean, just like building software—finding a faster feedback loop to say, "Okay, we did it."

(Rob (CTO of CircleCI) at 00:14:23) We did it. We did it. Oh, there's nothing actually happening right now, which is great. Let's go look at some old ones and see if we can go through the tooling and expose how could we have known faster? How could we have gotten to root cause faster?

(Rob (CTO of CircleCI) at 00:14:34) What could we have done to mitigate on behalf of our customers? Like, get customers up and running. Was there an opportunity to do that even before we knew what the exact problem was? Identifying all those things. And then, of course, we feed that back to teams or go build tools to help us do that or whatever.

(Rob (CTO of CircleCI) at 00:14:48) So it's multifaceted, but it's really, again, getting that tight cohesive group that's focused on the problem and building the trust and just going through the iterations has been helpful and created results for us already.

(Joel Beasley at 00:15:02) So how does it look tactically once you have these learnings actually deploying them out to several hundred engineers?

(Rob (CTO of CircleCI) at 00:15:08) That's the part we haven't figured out yet. So we came from—and I think this is probably a common pattern in scaling organizations. Right? You have a bunch of people. You know, if I go back to my first day at CircleCI, I think we were 17.

(Rob (CTO of CircleCI) at 00:15:22) Right? There was 14 people in the company. We got acquired. We added three. That's a really—like, we all participated if something went wrong in production.

(Rob (CTO of CircleCI) at 00:15:29) Literally everyone was there. We all knew each other and worked together every day. Then you get to hundreds of engineers, and that doesn't just naturally grow. Right? Like, that understanding of the system, perspective on how to behave—

(Rob (CTO of CircleCI) at 00:15:43) Like, these are things you need to define and instill. And so I think this is a response to acknowledging, okay, we've drifted a little bit. Right? We have new people coming in constantly. We don't necessarily have a clear program to build them up and get them into place, or start to get them the skills or capabilities that they need or even just define the communication patterns, the model.

(Rob (CTO of CircleCI) at 00:16:06) And we had been trying to extract that and sort of build something and then, you know, write documentation, get people to learn from that. So, again, we're still in the let's make sure we have a tight group that knows how to do this really well approach. And then as I think about what I expect next, I think we'll lean much more on—I'll call it apprenticeship. I think, you know, sort of a pairing or join as a deputy, play this role, but you're helping someone else who's doing it until you're ready to do it. And interestingly, as a counter to that, I recently heard this expression that I think comes from surgical teams, which is see one, do one, teach one.

(Rob (CTO of CircleCI) at 00:16:45) Like, literally, about your third try, you should be explaining to other people how to do it. But I like to think what we do is important. I think surgery is pretty important. Like, if you're just—you watch one person do it and your next time you're doing it, that's amazing, I think. Hopefully, you have a lot of education before you get to that point.

(Rob (CTO of CircleCI) at 00:17:00) But it also instills this, like, you can't just keep reading about it and then get thrown into it and hope for the best. Like, you need to get in there and practice and work with someone and then get to the point where—you know, I truly believe that if you know how to do something really well, you can teach it. Or vice versa, if you can't explain to someone else how to do something, then there's something missing in your own understanding. Right? I actually taught software classes for a brief period in my career, and it's probably the best thing I ever did for my true understanding of software.

(Rob (CTO of CircleCI) at 00:17:36) I would say before that moment, I knew how to get it to work. After that moment, I knew why it worked, and then the world was my oyster, sort of thing. Like, I could choose to get it to work any way that I wanted versus I've seen this pattern before, and I think if I copy it, it'll probably do what I want. And so, you know, you could apply that to anything. Right?

(Rob (CTO of CircleCI) at 00:17:54) To anything that you're trying to learn, trying to teach to other people, and they say, that doesn't make any sense. And you're like, you're right. I don't understand that either. Okay, now I'm going to go learn because I want to be able to teach effectively.

(Rob (CTO of CircleCI) at 00:18:04) Right? And so I think that kind of—I'll call it apprenticeship model. Like, we use pairing a lot in software. Right? That I'm going to sit with you.

(Rob (CTO of CircleCI) at 00:18:11) We're going to work together. I'm going to learn from you, and then I'm going to feel good about sitting with someone else and helping them grow. You know, I think we often think of mentoring as a one way—call it apprenticeship, mentoring, whatever. But as I said, when someone asks really good questions, it forces you to examine your own understanding and maybe get new ideas, or maybe they'll even point something out.

(Rob (CTO of CircleCI) at 00:18:32) Why would you do this when we could do it in half the time this way? Like, oh, great. Let's improve. Right?

(Joel Beasley at 00:18:37) Oh, yeah. I did, I think, two or three years of mentoring on a site called CodeMentor, and it was pretty cool at the time. You could just go on there and say, hey, I'm available. Here's what I know.

(Joel Beasley at 00:18:50) And then people had those problems. You could match and they connected you on a call. They're not a sponsor or anything. But I did that, right, for a couple years. And I noticed I got a trend of getting people that were coming out of code school trying to figure out, you know, how to actually get a portfolio together and get a job and, you know, needing more help than code schools.

(Joel Beasley at 00:19:13) And through the act of helping them understand things on a deeper level, it really forced me to understand because to convert your knowledge to teach it to someone like a three-year-old takes an enormous amount of effort. And so I remember explaining to her, like, post request and some made-up scenario where people would walk into a post office with a letter. So it's definitely hard to boil it down to be really, really, really simple. But those people that have that teaching gene, I noticed them within my company. Like, for example, we have one audio engineer named Jesse, and I noticed that he had that ability.

(Joel Beasley at 00:19:53) And so, you know, typically an engineer will manage three shows, but he's only managing two shows and he spends the other third of his time teaching other producers. So being able to pick up on that, I found, is pretty important. Because if you have teachers and they are not having opportunities to teach, then they're not meeting that need, at least at work.

(Rob (CTO of CircleCI) at 00:20:15) Yeah. It's a great callout. I mean, I think there's kind of two sides to that that are really interesting. One, recognizing that all—you know, not all show producers or audio engineers are the same. Right?

(Rob (CTO of CircleCI) at 00:20:26) They have a technical skill, but they approach it in a very different way. And if I've built a team, then I can think about how does everybody contribute on this. Like, if I just have one audio engineer, it's like, look, I need you to do the audio engineering. Right?

(Rob (CTO of CircleCI) at 00:20:38) But when I have a team that's audio engineers, software engineers, anything else, how can I bring all of their strengths to the table in a way that, you know, the performance of the team is much greater than sort of the sum of the individuals? That's one great way of thinking about it. The other thing that's really interesting to me, though, like you mentioned, the teaching gene, is I think if you don't have it, you should absolutely go try and teach. Right? Just, like, go be terrible at it.

(Rob (CTO of CircleCI) at 00:21:01) Maybe be upfront or transparent about the fact that you're not expecting to be like—don't sign a huge contract and, like, whatever, but try it. Try, you know, mentor. I think, one, it's enriching. Two, you might find that there's something in it that you really appreciate. But three, recognizing your own sort of strengths and blind spots and where you can contribute, building empathy for people who do these things well.

(Rob (CTO of CircleCI) at 00:21:25) Like, I've done a bunch of different jobs in my career, including business development, which—I don't know how that ended up happening. I don't know how, but I was garbage at it. Right? But I learned so much about what goes into that part of our business that, one, as a leader, I know how to show up for people who do BD, like what they need from me. And so I'm better at doing my job because I've tried and failed at doing their job.

(Rob (CTO of CircleCI) at 00:21:51) And I throw the word failure around really lightly because I think it is—like, we should just try things and say, oh, yeah, I'm probably going to be bad at this. Oh, wow, I was really bad at that. Cool.

(Rob (CTO of CircleCI) at 00:22:00) But now I understand it. Right? Like, I could read a book about doing business development, but it's very different than doing the job for a bit and being like, oh, wow, this is really interesting. Like, these are the traits that make someone good at this.

(Rob (CTO of CircleCI) at 00:22:11) This is what I needed in that role, so, you know, someone else can provide that to me. And so I think whatever it might be, whether it's, you know, teaching, going out in the field again as an engineer, talking to customers, learning from the—whatever it might be, the more you get exposed to those things, even if it's not what you specifically want to do, if you can get exposed safely, let's say. Right? You can try it.

(Rob (CTO of CircleCI) at 00:22:32) You've got some backup support. It's not like the most important deal that's ever been signed by your company. They're sending, you know, an IC engineer out to go get it done. Like, it's probably a mistake. But be there.

(Rob (CTO of CircleCI) at 00:22:42) Watch it happen if you can. Right? Understand what customers are looking for, what really matters to them. Understand what your salespeople are looking for, what really matters to them. Like, honestly, I think I was one of those engineers when I was younger. I was like, what does salespeople even do?

(Rob (CTO of CircleCI) at 00:22:55) I mean, we build the product, we do all the work, and then they get paid for it, sort of thing. And then I went and watched it happen. It was like, I could never do that. They do so many amazing things.

(Rob (CTO of CircleCI) at 00:23:04) Right? Like, they understand the customer so much better than me. They're willing to hold the line on things that I would just be like, it's free. You should take all of it. You know?

(Rob (CTO of CircleCI) at 00:23:11) Like, the whole interaction—seeing it, participating in it is just so valuable. So whether again, whether that's just growing people internally in your company or, you know, getting further afield from what you do, I'm a huge fan of it.

(Joel Beasley at 00:23:24) Yeah. I had heard Gary Vaynerchuk, a marketing guy, one of the reasons why I started the podcast. He had just said, be yourself and start with what you know now. Like, don't try to be somebody you're not. So the way that can translate is, you know, if you're an engineer and you're getting paid to be an engineer, you at least understand the concept of installing some sort of language on your system, using an editor, using the terminal, and, you know, doing hello world.

(Joel Beasley at 00:23:50) And to somebody who wants to get into engineering and has none of that experience, they don't know how to do any of those things. So you can start just by helping them because one thing that we haven't yet talked about is how enormously rewarding it is, like, emotionally or as a person to be able to help other people learn. That's a big driver for me.

(Rob (CTO of CircleCI) at 00:24:10) Yeah. I don't know that I'm quite at the point where I would say I'm reflecting on my whole career, but I'm at the point where I look back and think, like, how did I get here? Like, that's interesting to me even. And the number of people who took time out of their day to help me figure out—you know, I was probably very demanding. Right?

(Rob (CTO of CircleCI) at 00:24:28) Oh, what are you doing? Tell me about that. And I imagine that person now. I'm like, oh, man, I wouldn't have time for that. But you have to because that's how we got here. Right? Like, that's how we continue to build. It's how we build organizations, how we build success is spending time with folks. And, you know, again, looking back at—I got into software with zero background in software because someone just took a chance and said, hey.

(Rob (CTO of CircleCI) at 00:24:50) We need someone to do this job. Will you come try to do it? You know, you seem smart. We knew each other from college, whatever. And I was like, sure.

(Rob (CTO of CircleCI) at 00:24:57) That probably put some pressure on me as well. I didn't want to let them down, so I was like, I'm going to learn this as fast as humanly possible. But that meant I turned and looked to everyone around me and said, can you tell me more about this? Can you tell me more? Why does this work this way? Why does this work this way?

(Rob (CTO of CircleCI) at 00:25:09) Like, just I want to know. And I happen to be around people sort of like the audio engineer you're describing who had that. Right? Who were excited and comfortable and capable of breaking down the concepts and saying, okay, like, step one is this.

(Rob (CTO of CircleCI) at 00:25:23) Step two is this. Step—now you understand how enough to understand this. And I'm super thankful for all of that. And so, you know, I'm not teaching software classes anymore, but, you know, the thing that is valuable and rewarding to me, valuable to the company and valuable to the people that I'm working with is typically more about why do we make decisions like this. Right?

(Rob (CTO of CircleCI) at 00:25:45) What is it about the context of our business or the needs of our customers or the overall market, whatever that might be, that's driving us to this stack of decisions that ultimately ends up with me doing this thing on a day-to-day basis? You know what I mean? And so, like, helping people connect that is probably, for me, the rewarding part. It happens to be also valuable to me as a leader in the organization. But I think it's easily lost.

(Rob (CTO of CircleCI) at 00:26:10) Right? And, I don't know, I'm an executive. I don't have time for this, whatever. And I think it's one of the most valuable things that you can do.

(Joel Beasley at 00:26:16) Yeah. It's pretty much one of the highest priorities of an executive. I call it hops. So, like, how many hops away is this thing from customer value? Because if it's too many hops, I should deprioritize it. If it's really close to customer value, I can justify prioritizing it further.

(Rob (CTO of CircleCI) at 00:26:32) Yeah. Makes a lot of sense.

(Joel Beasley at 00:26:34) I wanted to mention when you were talking about, you know, your personality and sort of being hungry or curious and wanting to learn and then people seeing that and then helping you, I think that that is a thing that can build momentum. So, for example, like, let's say some of the listeners, they've never really tried this because maybe they were too shy to ask some questions. But I noticed myself wanting to give more opportunity to the people I see trying. Like, when I see somebody just continuously falling on their face with discipline and they're maybe learning a little bit and trying to get better and I can sort of see them making a huge effort, that makes me want to help them.

(Joel Beasley at 00:27:18) And I think that's what those people were seeing in you. They were seeing you sort of just kind of go at it. You're grabbing at it. You're trying. You're smart. You're connecting dots, but you need some better input. Right? You need some better knowledge. And so they saw that, and then they felt this sort of community obligation to come help you out.

(Rob (CTO of CircleCI) at 00:27:34) Yeah. I think that's probably accurate. Makes a lot of sense. And I would agree. I don't know how to think about this exactly, but I think the—I'll use my kids as a reference. When they say, I don't know. Tell me the answer. I'm like, no. You know what I mean? Like, try.

(Rob (CTO of CircleCI) at 00:27:50) Learn something and then tell me what it is that you don't understand about it or whatever, and I'll totally help you with that. But don't give up and just ask me for the answer. And maybe that aligns with what you're seeing. It's not the "please tell me, please tell me, please tell me," but I'm really motivated. Almost, yeah.

(Rob (CTO of CircleCI) at 00:28:04) I probably fell on my face a few times. I was like, "No, no, I got this. I'm gonna keep trying."

(Rob (CTO of CircleCI) at 00:28:08) I always tell this—I don't know how often actually I tell this—but when I first learned to snowboard, I basically bought a plane ticket to the mountains and went and tried to ride black diamonds, which for people who aren't into snow sports is the hardest. And I would just fall down rock cliffs. I mean, I was much younger than I am now and say, "Well, that didn't work, but I'm sure it'll work if I do it again." You know what I mean? And just kind of keep going and going.

(Rob (CTO of CircleCI) at 00:28:31) And I think there's a point where you kind of want someone to come along and say, "Come on, man, you're gonna hurt yourself. If you just try this, this, and this, you'll be in a much better place." But it is that combination of, yeah, willingness to try, intent, perseverance with, "Oh, now if I sprinkle some knowledge, that's gonna be really valuable to you." I think if I had, you know, maybe stood at the bottom and been like, "Can someone tell me how to do this?" no one would have helped me. So yeah, I think it's seeing that in folks and then being able to kind of work with it is really rewarding. Right? I can see that you're excited about the next step. I can help you get to the next step. And then I see your excitement having achieved that next step. Those things come together to be fulfilling for everybody.

(Joel Beasley at 00:29:12) How much does parenting help you become a better leader?

(Rob (CTO of CircleCI) at 00:29:17) I would say probably in more ways than I understand or recognize. I think one of the things that is really significant is that you recognize—certainly for me, sorry, I can't speak for everybody else—but I have recognized more about the different ways that people think about things because of the way that I see my kids as they've grown approach problems, learn things, and do it in ways that are really, really different from the way that I do. And I think prior to that—this is also probably standard leadership, but it's something that really worked for me in connecting—and I think it was just you kind of have to appreciate the way that your kids look at things. It seems, for some reason, it seems eye-opening versus frustrating when it's your own kids. I don't know why that is.

(Rob (CTO of CircleCI) at 00:30:02) And so prior to that, I would have thought the way that I learn is the way that people should learn. You know what I mean? And I didn't really spend a lot of time connecting with people on how they learn things. So just kind of being forced to walk through things, introduce your kids to concepts, watch them try to introduce themselves to concepts on their own—sometimes succeed, sometimes fail, sometimes point things out to me. This is the most interesting, where they're like, "Well, what about this?" And you're like, "Wow, I don't know. I never thought about that. That's kind of genius." You know? And that freshness of perspective and seeing how much value comes with it and just how different it can be and still be really insightful, I think is something that really helped me think about—you know, I was talking about teams earlier and all these different perspectives that we have on teams and how does that help us all be better.

(Rob (CTO of CircleCI) at 00:30:46) Right? I think also, I'll just say, patience maybe. Or it's not so much that. Maybe it's—I hate to say this about kids, but it's a little bit of a constrained testing ground for ideas. Right? I don't need them to have developed a concept in some period of time. Right? So the freedom to test ways to say, "Oh, maybe this is interesting," or "Have you looked at it this way?" or "I'm gonna let you go off and try something, and then we'll talk about it later or whatever." And then seeing how great those results can be gives you the opportunity to say, "Okay, that's actually a great way to interact with people in general," versus "I need you to understand this in the next hour, so I'm just gonna explain it to you." Right? And maybe you understood it at the end of the hour, but two hours from now, you've actually completely forgotten because the way I explained it didn't make any sense. You needed to go figure it out. Actually, I went to the farmer's market this morning with my son—this has just reminded me of this, so I'll tell you this anyway. And I put a bunch of bags of stone fruit in the trunk, and when we got home, they were all over the trunk. And he was like, "I knew that was gonna happen." I said, "Why didn't you say something?" He's like, "I need you to make these mistakes and learn for yourself." Okay, it's coming full circle. It's great.

(Joel Beasley at 00:31:58) That happens with me all the time. My son, he's got tunnel vision. So that's one of the things looking back, I'm like, "Okay, that's one of the reasons why I had success is because I'll fixate on something and just drive towards it." But I've never had to interact with me while I'm in my tunnel vision. So interacting with him in that state, I'm like, "Oh man, I'm kind of a difficult person." Or my daughter, she's got the stubborn aspect of me.

(Rob (CTO of CircleCI) at 00:32:23) And—

(Joel Beasley at 00:32:24) When I see it come through her, I'm just like, "Oh man." So it's given me a lot of perspective. So I actually openly talk with my team about the different ways I can be difficult and just let them know, "I'm aware of this. This is part of who I am," and I talk it out a little bit, and that brings a little bit more grace to the relationships.

(Rob (CTO of CircleCI) at 00:32:44) Yeah, I think that's an excellent part of it is the kind of the mirror, right? The opportunity to see that because it's close. Right? They're not twins of me or whatever, but I see behaviors that either I notice or my wife will point out, like, "That's from you. You're the one that's like that," sort of thing. And I'm like, "Oh yeah." To your point, that could be a little bit difficult. I could see how people would struggle with that. So it's helpful, yeah, absolutely, in that way as well.

(Joel Beasley at 00:33:10) I like describing it as if they're computers, but from the 1950s where you could walk into the room and you could see the drives, how big they were. You could see the trans—everything was so much easier to understand because you could see all the components. Now everything's buried in an iPhone. But with the kids, you can see all the emotions. They're huge. The decision-making, the learning, everything's a really big event for them, and that, you know, it just gives me a new experience I've never had of watching people learn.

(Rob (CTO of CircleCI) at 00:33:40) Yeah.

(Joel Beasley at 00:33:41) And definitely patience, man. And also, you know, prioritization, because before them, my life was 100% about me. And now it's not 100% about me. And you've got these little monkeys that you're interested to take care of.

(Joel Beasley at 00:33:58) Right on. You wrote an article. I wanted to title the episode "Upleveling Software Engineers" because you had written an article. It had a handful of pieces of great advice. The first thing is about increased rate of deployments. It's been a trend, obviously, if you've paid attention to anybody giving talks or books that, you know, we should deploy a lot. Amazon deploys a billion times a day or whatever it may be. But you're part of a software which is integrated into people's deployment pipeline. Have you seen people deploying more?

(Rob (CTO of CircleCI) at 00:34:30) Absolutely. I mean, I think so we do a couple things. First of all, yes, we look at the stuff. We sit in the pipeline. We publish annually a State of Software Delivery report. What are we seeing? What are the trends we're seeing? And you mentioned books. We can call them out by name. I think Accelerate, the DORA metrics—this kind of stuff has drawn a lot of focus on deployment frequency, for example, along with the co-metrics. If you deploy a lot and you break production every time, that's not actually a great outcome. So let's make sure we have that tied together. I think, actually, on that point, you know, historically, we've talked a lot about—or we used to say things like, you know, you could have speed or quality—pick which one you want, sort of thing. And what we've learned is that the best way to get quality is to move quickly, which feels counterintuitive. But once you're in it, it makes sense because, you know, you're reducing batch sizes, reducing risk. Every increment is much smaller and more likely either it's more likely to be correct or the problem is gonna be small and you can deal with it quickly. Right? So we are seeing people trend towards faster, to higher rates of deployment to use the specific metrics. But we also—we're seeing people realize that there's kind of a limitation or diminishing returns. I think one of the things I was thinking a lot about was S-curves. You know, this notion that nothing is linear. Right? It takes some time to get going, and then you reach—we'll call it diminishing returns. It's typically applied to growth. Right? You can't have a population grow beyond the bounds of the ecosystem that it's existing in or whatever. Right? At some point, you run out of other resources. And at some point, you know, you could deploy so frequently that every deploy is meaningless. Right? There—whatever the theoretical limit is—is going to be that, as an engineer, I could deploy every keystroke, I guess. But would that make any difference? And one of the things that I think we're starting to see now as—for the teams that are really good, that are already—you know, they have the tooling, they know what they're supposed to be building, there's not a lot of friction or waste in the system, so they can deploy frequently and they feel good because what they put out works—is now you have the opportunity to say, "Okay, the machine works. We know how to take an idea and put it in production. Are we getting good feedback? Right? Are we just shipping increments to be small, but we're not actually realizing that we're still shipping the wrong thing? Are we taking the feedback and learning, which is critical? And are we building the right thing?" Right? From the beginning, we can move stuff through, but are we moving things that are the best, the highest-value thing for the business? Right? It might be for our customers. It might be for something we're trying to do for ourselves or whatever. And so I think it's foundational. We're absolutely seeing people get better and better at this, but they're reaching limits where they say, "Are we still optimizing the most valuable thing?" Right? At some point, we're shipping so much that now the question is a different question. Right? Are we learning? Are we building the right thing? Right? Are we maximizing value for the company? And that becomes a different set of questions.

(Joel Beasley at 00:37:35) How does it work at CircleCI when we're talking a lot about connecting the value to the customer and making sure that people are aware of that? How does that express itself? Does the CEO put out an annual letter of "This is the direction we're headed and these are the primary goals"? Or how does that actually work?

(Rob (CTO of CircleCI) at 00:37:51) Yeah, it's a great question. I mean, it's multifaceted for sure. We do actually—it's funny that you mentioned the CEO annual letter. It's not an annual letter, but at least once a year, we'll do a really big—we do all-hands at least once a month, but a sort of state of the world recap of "This is where we're going, this is what we said we were gonna do last year, this is where we are"—really the connecting the big picture for folks. But that changes within the year. Right? I mean, we were talking about macroeconomic conditions. Right? So is our mission gonna change because of macroeconomic conditions? No. But within that, priorities might change. Right? We might decide to do certain—maybe particular customers that we're going after not doing as well right now, and other customers are doing better. So we wanna focus on a different segment. I mean, it could be anything. Right? There's a million things that could change as a result of that. And so what you don't want is for every one of those changes to be coming from your CEO. Right? What you want is an organization that knows how to adapt. And so when I say it's multifaceted, you want that big picture, long time horizon to be reinforced absolutely by the CEO, but also as other members of the executive. Right? We are saying that to our teams on a regular basis. I mean, we have organizations within our organization that are hundreds of people. So, you know, connecting with those leaders and then all the way down to as an individual manager. Right? I wanna know this is the role that we play in that big picture and be able to work with my—you know, as I'm onboarding new engineers to my team or we're making decisions with product about what we're gonna focus on—you know, we need to have the sense of, not me, but as a team. Right? I'll keep calling it a two-pizza team just because you brought that up earlier. So that team, right, needs to have the connection to that picture, which, yes, you could sit at that all-hands or read the annual letter or whatever and try to dissect it. But layers through the management structure are absolutely breaking that down. Right? At a director level, for example, you're saying, "Okay, in our scope, here's what's really important to us. This is how we fit in." And then the managers are saying, "Okay, within that scope, here's how we fit in." So if you can't ladder that up, then you're gonna struggle. Right? Because you're trying to make decisions every day about what it is that you're gonna focus on. So you kinda need to go back to—how, you know, you've got CEO absolutely saying that directly to the company, but then you've got the CEO saying that to execs who are saying it to their directors, who are saying it to their managers, who are saying it to their people, sort of thing—all of those different levels so people can see the roll up, basically.

(Joel Beasley at 00:40:24) Nice. Yeah. And then, of course, there's always—I've never had a lack of things to do. It's really just always a prioritization. And I've noticed that recently, a lot of my time, because we rolled out a new product where we started making podcasts for other companies, has been just improving those processes. You know, talking with the client, are they happy, what could be better, and then figuring out how to put processes in place. So right now, to give you context for where my head's at, is building out a new product line and new processes. And so for me, that is just trying to figure out how do we make the product better, and what do the customers want, and how do we make their experience better. And I'm not sure that that ever really goes away.

(Rob (CTO of CircleCI) at 00:41:09) No, it shouldn't. Right? The other piece coming back to kind of tying those together, I guess, is I want engineers, right, to understand the customer experience, not just hear from the CEO, "This is what our customers want."

(Rob (CTO of CircleCI) at 00:41:22) We work in developer tools. I mean, you're working in podcasts and you're a podcaster, so you're connected, right, with that audience really closely. Our engineers are connected with the audience. They don't represent every kind of engineer, every kind of team trying to deliver software, but they have an emotional connection and a sense, right, to then be able to say, oh, I get it. Yeah.

(Rob (CTO of CircleCI) at 00:41:41) That makes sense. I could see the scenario where that would be useful, or I see maybe why this whole pool of customers is interested in this thing. And that allows them to make better decisions at whatever level, right? Whether it's working with the product manager to define how we're going to do something or day to day, like, should I write this error message or that error message?

(Rob (CTO of CircleCI) at 00:42:02) You know, which one of these is going to be informative to the customer and get them to solve their problem? Or I chose this one, and then I saw these... I don't know. It was 2022. Someone on Twitter complained about my error message. Probably happens, right?

(Rob (CTO of CircleCI) at 00:42:13) So now I'm going to change it because I see how it could be clearer. And so, again, you don't want that trickling down through an entire organization. So the more... We do things like regular research that is kind of call it one-way mirror. It means video recording. But you can watch our customer research as an individual.

(Rob (CTO of CircleCI) at 00:42:31) Right? Everyone's welcome to watch and see, oh, here's what they said. This is what they're struggling with. And that might reflect on something. And maybe it's not a thing that you built, but maybe you're building something that has a parallel to say, oh, if that's the kind of problem people have, how could we solve that where we're working also?

(Rob (CTO of CircleCI) at 00:42:47) And so 100%, especially as an organizational leader, you're going to be spending a lot of time with customers. And, you know, building a model that helps everyone in the organization understand the customer, what their needs are, what they're trying to do, I think makes everything else smoother. Right? You're not having one-off small conversations. They're trying to do this exact thing right now.

(Rob (CTO of CircleCI) at 00:43:09) It's like, this is what our customers need, right? This is their ultimate goal. And then within that, you can see, okay, this is my part. Here's how I can make my part better.

(Joel Beasley at 00:43:18) Yeah. And you do a fantastic job. I've been a customer

(Rob (CTO of CircleCI) at 00:43:21) Thank you.

(Joel Beasley at 00:43:21) for years and years. And, you know, I think about you a lot when I get all my build emails, workflow emails. You know what? One of my favorite things about your product is that I never really have to think about it. There's a lot of products I have in my life that I don't have to think about.

(Joel Beasley at 00:43:39) And they're my favorite products because the ones that are the most difficult are the ones that I try to spend time getting to work that aren't working, right? But we always sort of take for granted the ones that just... You put it in place and it works and it's there when you need it. So, dude, thank you so much for making that product and spending your time making it better.

(Joel Beasley at 00:43:58) I can tell you from my perspective as a customer, there isn't anything that I want it to do that it doesn't do, and it does what I need it to do really well and consistently. So

(Rob (CTO of CircleCI) at 00:44:07) Good. Well, that makes me very happy to hear. I will say on that point of being kind of, I don't need to think about it, it's a really interesting product challenge, right? Which is we want to be out of the way, but we want to make sure we're providing value.

(Rob (CTO of CircleCI) at 00:44:20) Like, where can we add more value, right, to you without... Especially when you think about developer flow, right? We're not trying to interrupt you. Hey, come look at us. We're important.

(Rob (CTO of CircleCI) at 00:44:29) Pay attention to us. You don't want that, right? That you just said you don't want that. But at the same time, building value for you to make all of those things easier, to make sure that you can continue, you know, deploy more often, build faster, get the things out that you want for your customers as you're building them.

(Rob (CTO of CircleCI) at 00:44:43) So it's a cool space to be in. And, you know, as a... Again, you're a podcaster making tools for podcasters. We're developers making tools for developers. Just being in the middle of that universe.

(Rob (CTO of CircleCI) at 00:44:54) Right, being at the center of so much software development and seeing what people are doing and saying, oh, that's really interesting. Can we help others do something that valuable? It's just fun. It's fun to work on stuff that you really like.

(Joel Beasley at 00:45:07) 100%. Rob, we made a podcast. How do you feel?

(Rob (CTO of CircleCI) at 00:45:11) I feel excellent. It's great to see you again.

(Joel Beasley at 00:45:14) Thank you so much for listening. And if you found this episode useful, please share it with a friend or colleague who you think would get value from it. And if you have topics that you'd like to hear discussed on the podcast, either add me on LinkedIn, or send me an email [email protected]. Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.