Episode Transcript
[00:00:04] Speaker A: Hello, good evening.
[00:00:07] Speaker B: Excited about our first episode of what we're currently calling Hallway comp.
[00:00:11] Speaker A: Yay. Let's get into. Introductions are probably a good way to start.
[00:00:16] Speaker B: You want to tell folks a little bit about you?
[00:00:18] Speaker A: I probably should have looked up some of the basic information, but I'm Julian Ramirez, currently an engineering manager over at Dropbox and I've been managing for maybe 10 to 15 years somewhere around there. Mostly working with startups, going from super small teams and then up to around 70. But then kind of after doing that a few times, I wanted to see how you scale that and started joining some larger companies leading me here. Been living in San Francisco for probably also about like 15 years. Love it.
[00:00:52] Speaker B: What do you like to do when you're not working?
[00:00:54] Speaker A: When not working? Coding on little pet projects. Lately been really enjoying using AI to help debugging things. That's been a really cool way where when on like weekends you're kind of already burned out and tired and so it's really nice to not have to hit your head against the wall so much. Solving obscure compiler errors, playing around with 3D printing, eating, drinking, going out, all of that other good stuff. How's that? You cool?
[00:01:22] Speaker B: Yeah. I have also been doing this, managing various kinds of teams for about a decade, maybe a little over a decade. My name is Anna Naisberg. I am a. It's the first episode folks, so we're just rolling with it. I am an engineering manager also at Dropbox. Before Dropbox, I was at a consultancy for about seven years called Carbon five. Learned a lot, it was amazing. And also was looking. I had worked with everything from very early stage zero to one ideas through growth enterprise companies, but was really curious about what it looks like to be in house house at a larger company. And I'd heard good things about Dropbox, so that is why I'm there when I'm not working. Also spending some time on side projects that are AI related, which is fun. Climbing, salsa dancing, cooking lots of soups right now because it's cold and I hate that it's dark outside so early. Yes.
[00:02:10] Speaker A: What's your favorite soup of the moment?
[00:02:11] Speaker B: At the moment I'm actually gonna go home and make a lentil soup.
[00:02:13] Speaker A: That sounds nice.
[00:02:14] Speaker B: That I'm very excited about with like a bone broth and some kale.
[00:02:17] Speaker A: That sounds really perfect for this already being dark and cold.
[00:02:22] Speaker B: It's depressing.
[00:02:22] Speaker A: A frigid November evening. Frigid for Bay area, which means 15 minutes.
[00:02:27] Speaker B: We're weaklings, but it's okay. I take it as frigid. How did you get into management?
[00:02:33] Speaker A: Shane I got into management. I was at TaskRabbit and I had worked with one of your peer companies, Fiddle Labs, and we were working to build out the first version of the mobile app iOS at the time. And I had pestered R CEO Leah a bunch, or Leah and Brian. I pestered both of them a lot. RVP was just always like, when are we going to do mobile? When are we going to do mobile? I had kind of played around with mobile before at like a gaming company that I was at and was just kind of like, this is fun. It was kind of like the iOS like 3 was out and so it was still pretty new and I was asking them to do mobile. And then eventually the stars aligned and they shipped me off to Pivotal for a few months to work with one of their pivots and to learn mobile development. Then I came back, which was a very fun, very interesting experience of disappearing over in Pivotal Labs for like a few months. It may have been like 4 months or so. Different commute, not really doing one on ones with my boss anymore, learning completely new technology, but having a pair that you're working with. So that was like really nice. They were also very strict, like 9 to 5 I think it was, which was very early for me at the time. I think we changed offices as well. When I did come back in front of the office person, they were like, who are you?
I've been here before. Thank you. But I came back, continued working on the mobile app and it started getting some traction and so we started adding more people to the project. I had a little team, I think it was like two other guys, two or three. And we basically had our little section of the community table that all the engineers were at. At that stage of getting two or three people all coding, that's where we started running into problems of who's doing what, who is spending the time to work with product and design to figure out what to do. Initially we just do whatever we were told, basically. But then it became clear that we needed someone to look further ahead than just grabbing the immediate next story. And the team basically just nominated me because I had been working on the product for the longest time. Then it kind of went from there. They were just like, we're fine just coding. We would rather just code. I thought it was really cool how through spending some time to get those things set up, they would be able to code a lot more and be a lot more efficient and be happier doing the work that they Enjoy doing. So I just kind of leaned into it and that took off. TaskRabbit was able to continue to grow. Mobile continued growing, and eventually we added on Android doing a similar thing for learning how to do and build that. Eventually the lines crossed, as I think of it, where, like, we had more tasks coming in from mobile than from the web. That was like, a really fun time. Eventually I felt that it was time for me to move on from TaskRabbit. I kind of wanted to try that again because a friend told me, anyone can kind of go into a leadership role once, but to do it again, to do it a second time, shows that it wasn't a fluke, shows that it was you. And so I was kind of like, okay, challenge accepted. So I went to Imgur Internet Culture meme company and did the same thing of like, joined with just one other mobile engineer. And he and I were cranking on it. And then the product launched, the team grew, helped do that. Similar kind of treaty was struck of like, he just wanted to focus on coding. And I was like, I'm cool with that. Let me help clear the path for you and the other engineers. And it took off from there and pretty much just kind of like, I really enjoy being able to help others align their interests with what the company needs to do. And I feel like it helps them get more satisfaction from their job. It helps the company do cool things. I'm just kind of happy trying to keep that alignment with everything cool. What about yourself?
[00:06:34] Speaker B: I was in consulting for seven years. Six and a half, seven years, something like that. And part of being a good consultant is a lot of the same skill set. And so a lot of it is you're running a team. I led many projects. And so partway through my career there, it was like a matrix organization. So I was managing people that I wasn't necessarily directly working with. But then I also had to manage teams, including not just my team, but the client and the stakeholders for the project. Because the way the carbon tax worked is like, we would form actually one team with the client and our team. And we were together. So it'd be like engineers on our side, project on our side, engineering on our side, and then whoever was on their side, plus stakeholders. So I realized I really enjoyed that part of similarly being able to look ahead and figure out how we're going to get from point A to point B and what needs to happen. And the stakeholder management was really interesting. So I started doing more and more of that. And I led many projects of Varying sizes. So I got exposure to a lot of different ways of working with different types of teams and how to work in different types of organizational settings. Zero to one early stage is very different from growth, which is very different from enterprise. So that was really interesting. I really enjoyed the forward looking aspect, the strategic thinking and the people aspect. Honestly, I was like, I want to keep doing this, but I want to do it in house at a bigger company. Mm. Which is how I found Dropbox. We're getting into some other stuff, but I'm really curious before we get into some of the things that maybe we find interesting or why we stay because management can be hard, I feel like we should maybe share with folks why we want to do this podcast.
[00:08:03] Speaker A: That's a very good question.
You've touched on a lot of things about the consulting world, and I feel like that is a whole vein. Like, I would love to ask a lot of questions about that because it feels like an interesting pocket where I've only gotten to like, peak, like stand out the window and look at it. But hearing the variety of people that you've worked with through consulting and the different size companies and the different cultures that you interact with and all of that would be really fun to just grill you on. And I feel like it's something I've always wanted to ask you about. So I made a note about that as to why this podcast. You and I have worked together twice on the EM Summit at Dropbox, a management summit where we bring together all of the other engineering managers in our org. It's basically two days of talking about best practices, challenges, and all of those things. And then outside of just that summit, once a month we host kind of a engineer manager social knitting circle, which one of our good former colleagues got started. Shout out to Suzanne Kaufman if you ever listen to this. And I think through that we've been able to understand a lot of the value in having a community of engineering managers, both for essentially therapy sometimes as well as for actually, like sharing best practices and all that stuff. Dropbox is a fully virtual company, and so I think that sometimes that also means we have to be more intentional about how we do things and it's a little bit more difficult to share ideas. I think that this is also just generally true of the industry and of our little segment in it. In management. I feel like I haven't been able to find many podcasts or communities of just engineering management. There are some really good communities out there for like, iOS developers or Android or this or that. But for Management in particular, it feels kind of underserved, which I think is kind of ironic because so much of our job is about connecting and providing mentorship to others and everything. I think it's this classic, the cobbler's children have no shoes. So I think us starting and putting out some of this content that I wish was out, just to know that sometimes I'm not working through these things alone and that someone else has tread this ground before, which I know they have, like we all do performance reviews. But getting other people's ideas, even if they're not mine, even if they're not necessarily even correct, I think can get you thinking about new and hopefully better ways of doing your work and getting reinvigorated for it as well. What about you? What are you looking to get out of this?
[00:10:53] Speaker B: A lot of the things that you said totally resonate, I think community. I agree with you that when you're in a leadership role, it is different than being an individual contributor. And finding community can sometimes be more challenging because your peers are not on the same team as you. And so it's not always possible to engage with them in the same way. The other thing that I'm really curious about digging into is I see management, I think, is more of an art than a science. Not all, but most technical problems, eventually you can come to a solution when you're navigating people. I find it really interesting because I think it's more complicated and I really would love to dig into some of the nuances that really differentiate folks that are incredible leaders from folks that are totally decent leaders. There seems to be this gray area between following the practices, following the frameworks, being totally decent and being incredible. And I'm very interested in discussing more about, like, how do we help more people kind of make that leap. How do we dig into the nuances of the job? We can talk about Agile and we can talk about management frameworks, and we will. But I think what is it that really allows somebody to be an excellent leader? And I want to know because I'm similarly constantly curious. Trying to improve yourself, trying to improve how you work so you can better support your team. And I'm really curious how we can dig into some of those nuances that make it more of an art.
[00:12:14] Speaker A: Kind of like having some intentional time and discussion on the major things that we have to do. Spending the intentional study for it as well, hopefully.
[00:12:23] Speaker B: Yeah. And bringing in, like you said, new perspectives and thinking about. Everyone has different styles, right? So it's like, what is it makes Somebody exceptional and what are those pieces? And they will probably fit differently for everyone. But I'm really curious to dig into, like, not just, again, the basics of the things you do as an engineering manager, but what really helps you enhance your skill to better serve your team. So I'm really curious about that.
[00:12:43] Speaker A: Definitely. I'm very excited to also, like, hopefully bring in some guests that are experts with spreadsheets and jira kung fu experts and all of this stuff. I think that there are things that I think as managers, we know we're sometimes good at or sometimes soft at, and it'll be very cool to corner people that we think are experts at this and just really grill them on how do you do this, how do you do that? Every manager probably has a set of, like, three spreadsheets that they think are really crucial for how they do their job. And I'm curious of, like, what everyone's top three are, for sure.
[00:13:15] Speaker B: Specific skills. And I also think I'm especially curious about the things that are harder to encapsulate, like people who really know how to inspire and lead teams, people who really can get folks fired up when things are hard and keep moving through things. So I think a combination of those things, for sure. And I think, to me, that's part of building community is being able to share our experiences, other people's experiences, and hopefully not only make people feel less alone, but provide a little bit of a sounding board of how you might be able to think about a problem differently. I think that is part of what I find really interesting, the human piece. I mean, the structure and the process and all that's very important. And we will get into that as well at some point. Because I think as much as I'm somebody who always jokes like, I just want enough process to keep the thing working. And I am very serious about that. Process is very important, but I'm very interested in. And what kind of keeps me going is this human aspect, right? How do you ensure that folks feel? You kind of have to meet everybody, every person on your team where they are, right? And then your peers in the org where they are, and then leadership where they are. And so you're constantly operating all these different contexts, all these different humans. And humans are far more complex, as we know, than any machine. And so the thing that really I enjoy is figuring out how to better engage, how to better problem solve and help folks come to a shared understanding to go from, like, zero to building something, right? How do we continue to do that better? How do you continue to support and help folks feel inspired and grow. And so it's the human piece that I think is what keeps me going more so than any of the, I think tactical pieces.
[00:14:49] Speaker A: No one loves first written planning.
You're starting to get into the next topic there of kind of like, why do you stay in management?
[00:14:57] Speaker B: Yeah, I think that's basically what I find the human problems more compelling and interesting than the technical ones. Not that I don't find technical problems interesting, I very much do. I just think that the human ones are often more ambiguous and have a different complexity. I wouldn't say they're harder, but they are of a different complexity that I really enjoy. That's the main reason the basics of the job are things I really enjoy, like high context switching, lots of strategic thinking. All of that I really enjoy. And then the piece about really having to work with humans. Thinking about how you can best set yourself and your team up for success, how you can best problem solve, how you can best figure out how to understand and be understood by many different people is I think a continually interesting piece of the job.
[00:15:47] Speaker A: Yeah, 100% agree with that. I think for me, I definitely love the working with people side of it. And sometimes it feels like I am just supposed to be like the professional adult in the room. When you have different teams going at each other's throats or something like that. It's kind of amazing how often I think my job is to just tell everyone to take a breather and then like go have some conversations to try and just understand where are we out of alignment. And then just kind of like a chiropractor, like doing an adjustment to get everyone back in. I really love when I see a conflict and then like doing the digging to it and realizing like, oh, actually like if we just do this one small change, which team A doesn't care about, but team B would really love done, it will resolve how they've been fighting for the last month. And you're just like, this is amazing, this is cool. Everyone's happy now, we're all moving forward. And I think that kind of levels up to the main thing that I really enjoy of getting that alignment between individuals and the organization and the company. I think it's really fun when you're able to take a lot of people who are all kind of going with their own little goals. They might be trying to improve their career, they might be trying to play with some new technology, they might be trying to get a feature built in release to their customer because they really believe in it or something like that. And I think it's really cool to try and stitch all of those things together into a cohesive business strategy. And then seeing that play out and be like, oh my gosh, so and so was able to like build this project out that massively changed the numbers and they just wanted to fix this tiny little corner of the code base. So kind of like coming up with that symphony of getting the teams going towards a goal and seeing how you can maintain that and then kind of like the gardening approach to it as well. Of like, I really do enjoy tending to a team where some people are looking to grow in leading culture, others through developing more technical skills or they want to partner with a QA group or something like that. And how do you just like keep all of that in alignment and help the team move together? And also, it's never my favorite thing, but it is a rewarding thing when someone kind of quote unquote, like graduates is how I think of it. Where they're kind of like, I love this team, I love this company and all of this. But, like, I think it's time for me to go. I always tell people that I try and manage for the long term. And I think it's really cool though, when someone from my team tells me way before maybe they've even started interviewing, they're just kind of like, I think it's going to be time for me. Because I think that's a sign of so much trust. And I know they also say people, they don't leave jobs, they leave managers. But I do choose to think that sometimes people are just looking for a change of scenery or to develop new skills that I can't help them with. I think it's cool when you're able to recognize. I feel like I've done a good job of coaching someone when they realize that their future that they want is not in alignment with what the company or the team wants or needs. And then they kind of proactively make the decision of, this is my stop here. They're going to move on rather than staying and like kind of spoiling or things going sideways.
[00:19:03] Speaker B: Oh, for sure. And I think that it speaks to your skill when somebody's leaving not because they're upset with you, but because you have grown. Right. I think people do. Your manager has such an impact on your day to day at any company. The managers that I think about that were great. I really enjoyed working them. I didn't want to leave. Right. And the places where it was really toxic. I Was like, I need to get out of here. And so when you can get people to the point where they're leaving not because of you, but because they're like really ready to do the next thing, I think that's really awesome.
[00:19:30] Speaker A: Yeah.
[00:19:30] Speaker B: And commendable. And honestly, again, that continuation of. It's kind of like a two pronged question of like, why is it interesting? And then why do you stay? Because it can be really hard. Right. We'll talk about all of the pieces of managing out or, you know, but we'll talk, we'll get to all that stuff. But I think it's the same reason. What makes it interesting is the reason I stay is there's continually. Again, humans are complex and there's constantly new humans and there are new challenges and new ways of understanding how to work with people and new ways of thinking about how to bring a team together. And again, all of that in service of ultimately trying to build a product. Right. And so you mentioned a symphony, which I think is interesting because a lot of different pieces have to come together. And to me, I have this thing that I tell my teams that I think is very true. Like the small things are the big things in many different ways. Right. Because if bad things build up, that becomes a problem and good things build up. That also builds trust with the team, builds cohesion. Either way, the small things are the big things. And again, there are continually new things because the pieces are continually moving. Yeah. And so that, at least for me, is what not only I find interesting, but why I continue to stay in these roles. What about for you?
[00:20:45] Speaker A: I think that's a great point of it is the small things. We've both done software, writing code as well. It's like the main hallmark of Engineer is their ability to take a big thing and break it down to these small things. And so for management, it's absolutely of building it up again as well. I think for me, I very much agree, like with a lot of what we've said already, especially around building up the symphony, doing the gardening. I generally have like a low touch for management and I think it's very fun for me when I'm able to set up just enough, process just enough systems so that my teams are able to go do their thing. And like you're able to set up the trust with the teams, with the people, then kind of like the machine runs itself. I think that's a really beautiful thing. Kind of like, you know, when you have like a computer system, like when AWS like first came out in rightscale was like one of the tools to like manage deployments there. I think it's really cool when you are able to come up with like the management side of that, like with the people and there's like a few templates that I've been using for running team check ins and stuff like that. And I think it's really fun how you're able to regularly get the right information at the right time. Then like you can let your teams focus and ideally do some of the best work of their careers and you don't have to do much. You can just like let the thing run itself and then you find new things to occupy yourself.
[00:22:11] Speaker B: Yeah. It's a good sign when you effectively put yourself out of a job.
[00:22:14] Speaker A: Yeah. Although like that never seems to happen. It just seems that you just get more things to then go work on.
[00:22:20] Speaker B: This is true.
[00:22:21] Speaker A: Yeah. That's kind of like what keeps me in the game of just constantly trying to do the perfect game. When I was managing it team individually, I read about like one time the perfect sprint where like you don't have to pull anything in. The team completes everything, all of the tickets and everything is just pointed correctly and all of that stuff like it never really happens but it's the strive towards it. And I don't even know if like all those things should happen but I think it's still kind of like a fun thing to pursue of as managers. Maybe we would have like the perfect quarter or the perfect year or stuff like that. Never going to happen. But it's a fun thing to strive for.
[00:22:55] Speaker B: Good goals.
[00:22:55] Speaker A: Yeah.
[00:22:56] Speaker B: Well, plenty more to come as we navigate all of the topics across management. I'm curious to kind of send us out really quick. What is your kind of craziest comes to mind management story?
[00:23:10] Speaker A: Probably working at a company that was doing Iot we were building a manufactured product. It was like a digital canvas for artwork. This is my first time in IOT and doing that. There was a lot of learning on the job and working with our head of manufacturing who was just like we need to come up with a test device. And I was like what is the test device? And he would explain it and like learning about the different parts of prototyping and building out the different kinds of verifications and stuff like that was a wild process. Also it didn't help that our product was like a 50 inch digital display as well. And so that thing was freaking heavy. It was also encased in like a proper wooden frame. So it weighed so much. Having to lug those things around. And of course there's always something broken, having to flash it and that means like pulling it from the wall and unscrewing and all this stuff. Like, very fun, very like tactical kind of like engineering thing. But when the head of manufacturing was like, we need to come up with a test device, we don't want to send them our source code, then sending them these like Raspberry PIs that had all of the test software in there and was able to be installed on a manufacturing line. I thought that was really cool to be thinking through of like what is the physical state of the product at any given moment. But then the devices started going offline and disappearing and that was like a mystery of like what is going on here. Eventually just finding out that they were getting stolen and I had fleet management software installed on it eventually and was able to see like where they would reappear.
[00:24:46] Speaker B: Did you find them ever?
[00:24:47] Speaker A: Yes, they were with some competitors.
[00:24:50] Speaker B: Oh.
[00:24:51] Speaker A: Basically.
And I think that they were trying to get the source code for the mobile apps because they're really big on like, we want that.
[00:25:00] Speaker B: Oh, interesting.
[00:25:01] Speaker A: So now we're like very happy that the source code wasn't on there. That it was basically just like a super simple webpage for it. Something like I coded up like on the flight over there. That was definitely like a fun like problem of working in the real world and also having to think through a lot of different factors.
[00:25:20] Speaker B: Always so many.
[00:25:22] Speaker A: Yes. What about yourself? What was the craziest situation you've had?
[00:25:25] Speaker B: I think we were building. We had a client. It was crypto. I was leading a large team. They wanted to build an institutional trading platform, institutional investment. And so it was complicated. The day after it launched, they had to shut it down. So that was a different kind of crazy of like managing the team and how folks were doing and feeling.
[00:25:44] Speaker A: What did you tell the team?
[00:25:45] Speaker B: This is a long time ago. I think everybody was upset because we've done a lot of work for a long time.
[00:25:49] Speaker A: How long have they been working on it?
[00:25:51] Speaker B: I don't remember. It was a long project. And then the woman leading the project from the product side, I was attack leading this project. She basically was just like, we're taking the day off, we're going to the beach, we're gonna have coffee and we're gonna have brunch. I love that. And we are going to reconvene. And it was just a different type of like, interesting when you work so hard on something and there's something that unexpected that happens and then you have to manage the outcomes. There are more wild stories and crazy clients that we'll get into. More to come.
[00:26:17] Speaker A: Oh, lovely.
[00:26:18] Speaker B: Yeah. Thanks, everybody, for listening.
[00:26:20] Speaker A: Thanks for listening.
[00:26:21] Speaker B: Be back soon.
