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Episode 16: Management as a true calling and the three pillars of being a director with Dan Na

    Guest Biography

    Dan Na is the Engineering Director of the Market Expansion organization at Squarespace in NYC. Previously he was a Staff Engineer at Squarespace and an Engineering Manager at Etsy. He loves learning and teaching in a collaborative environment and solving both the technical and people problems of shipping software. He’s a weather-agnostic iced coffee drinker, a mediocre golfer, an NBA basketball fan and loves spending time with his family.

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    Patrick Kua:

    Hi everyone. Welcome to the Managing Managers podcast and I’m delighted to be joined today by Dan Na. Dan Na is the engineering director of the market expansion organisation at Squarespace in New York City. Previously he was a staff engineer at Squarespace and an engineering manager at Etsy. He loves learning and teaching in a collaborative environment and solving both the technical and people problems of shipping software. He’s a weather agnostic iced coffee drinker, a mediocre golfer, probably much better than me, an NBA basketball fan and loves spending time with his family. Welcome to the podcast Dan.

    Dan Na: Thanks Pat. Thanks for having me.

    Patrick Kua: It’s great to connect with you. We’ve maybe exchanged paths a little bit over the internet but it’s nice to speak to you at last. I’d love to hear a little bit about how you got first into the management track.

    Dan Na: So my path to management started at Etsy. I worked at Etsy from 2013 to 2017 and by sheer dumb luck, the manager who hired me at Etsy was Lara Hogan, who’s somewhat famous now. She’s a very well-known engineering management thinker. She’s literally written a book about engineering management called Resilient Management, which I consider one of the best books about the human-centred nature of the management job.

    So when I was at Etsy, I was on the IC track for most of my tenure, mostly working on front-end platform type things. But then one of the last roles I took there was the engineering manager of the accessibility engineering team. So that was cool. I bootstrapped that team as an IC and then I moved into a management role and I worked under Lara this entire time. It was just really valuable for me to learn from her example. I left Etsy in 2017. I came to Squarespace. I actually returned back to the IC track. But eventually I became a staff engineer and eventually I moved back to the management track.

    I think I always knew the manager track was my career calling. It’s just the track that’s much more resonant for me personally and I think more consistent with my skills. But the timing wasn’t right until the opportunity came up and I’ve just been on the manager track ever since then.

    Patrick Kua: Fantastic. So I think it’s great that you’ve had a great supportive environment as you transitioned into the management track. As you said Lara Hogan is very well known and make sure her book also appears in the show notes there. It’s a great book. Nice, short and digestible. As you mentioned it’s a really good focus on the human side as you mentioned management. And yeah, it’s great to have that support when you’re actually growing because I think a lot of people get thrown into any type of management track and probably not really having that supportive environment. As you went back to being an IC what were the areas you were working in?

    Dan Na: I was a staff engineer at Squarespace. That was just kind of an evolution of my IC role when I joined. I joined as pretty senior and then I became a staff engineer. I think if you were to ask internally at Squarespace what I’m known for, I was one of the two engineers to bootstrap the international engineering effort which started formally around 2018. In terms of the scope… So the other thing about Squarespace at that time, I think like many tech companies around that time, we were really growing a lot. I think our engineering team had, I think they had, recently added titles shortly before I joined. So it was a pretty flat organisation. Then we had this really big growth push where we doubled engineering in two years and then we doubled it again or something. So a lot of things were up in the air. When you grow that much, they’re just some side effects. Everyone’s just trying to figure out exactly what the processes are: what the management structure will look like, what the titles will look like.

    So if I had to explain my scope it would probably be pretty imprecise. It was just like, “Hey, we want to do international. We’re going to do a small team, so you and this one other person go on this team. Can you just figure it out?” I was like, “Yeah, let’s figure it out.” So the role wasn’t very well defined other than: I was a senior person. I was shipping a lot of code at the time. The team was really small. We were just tasked with setting some foundations and kind of getting our own bearings and figuring it out and so that’s just how it happened.

    Patrick Kua: Great. And what I’m hearing there is even though there wasn’t a strict, perhaps, definition of the scope, I understand it that you had perhaps a clear remit of: Grow or start the international organisation. Lead the technical infrastructure and work out some of those key technical decisions that probably need to be made in those early days. Is that right?

    Dan Na: Yeah. I think it was just: be the senior person in the room. So at the time, when international was in its infancy, the cross-functional team was like 4 people. It was me, as the engineering representative and three people for marketing. And now it’s literally 50 plus people. The cross-functional org is much bigger. The initiative. There’s a ton of cross-functional work that goes behind it. A really big marketing and strategy component. So when it was very nascent, it was just, we were all kind of just flying by the seat of our pants a little bit. We were starting from scratch more or less and we’re like, “Ookay what’s the first thing we should do? Let’s align on that.” And so my responsibility was translating a lot of that into engineering requirements, which was a thing that I was used to. I had managed before. So yeah, it was to ship a lot of the code but also do as much of the technical leadership responsibilities necessary to keep this going, given that it was a very small team.

    Patrick Kua: Great. I’d like to maybe backtrack a little bit and go back to one of the things I heard you say. Which was, I heard you say, the management track as your true calling. What does that mean to you?

    Dan Na: Yeah. That’s a really good question. This is actually a thing that I talk about with a number of people. I’ve had people email me, being like, hey I’ve thought about going to the management track. The best thing I can explain about the… I have tactical reasons why I think the management track is better suited for me personally. I think it aligns a little bit better to some of my skills. Some of my differentiating skills. So, for example, I really don’t struggle to put my thoughts to paper. Which sounds really weird, right? But I do think in the management function when I talk to people who… There’s this trope, “Oh I tried management and it was horrible. I was in meetings all day and I had to write docs all day.” That’s kind of true. I think it’s kind of a very uncharitable take on it. But it’s also, inevitably, a lot of your artefacts are communication. Either written, in person, or presenting. And if you hate that, maybe this isn’t a job for you. I don’t mind that. I actually have never struggled with any of those parts. So that part is not even a thing that I consider a blocker.

    The other thing about calling, though, that I can’t really explain really well, is the analogy I actually give people is…

    So growing up I owned a bunch of guitars. I owned maybe five. And I knew a lot about guitars. I can see a guitar from my desk right now. But the reality is I suck at guitar. And the reason is when I pick up a guitar, I just don’t care that much. As much as I appreciate a good guitarist and I understand a lot about it: I can probably identify what guitar they’re playing and I like music. When I sit down to put in the reps of building the callouses and doing the scales and learning the music theory, I just don’t. I just didn’t. I never did. It’s just not resonant.

    Whereas when I’m in the work of day-to-day management, I really find this intrinsic value in understanding incentives, putting forth… living out the cultural beliefs that I want to be true in a team. I find a lot of satisfaction in… I don’t really mind the long feedback loop. A lot of the pitfalls that I think people don’t like and the main differences between an IC track and a management track are things that I don’t really find that problematic. It’s just ever since I stepped into the function. I like planning. I like making a strategic decision. I like taking a diverse set of inputs. I don’t mind the meetings required to do it. I like understanding the incentives of non-engineering people to help dictate our roadmap. I really like the mentorship aspect. So in that way, it’s really hard to explain resonance, but it just feels better. That isn’t to say I don’t code. I was a staff engineer. I did write a lot of the code. It’s just if I had to choose, it’s the management track.

    Patrick Kua: That’s a really great answer. If I was to reflect back on some of the things that I’m hearing here is that when I hear that term resonance. There’s a lot of activities associated with management and it feels like those activities are interesting for you. Which, if I compare it to other engineers who step into management roles, sometimes it’s a bit of a struggle for them to want to do that. I think you gave a really good example as well of writing your thoughts down clearly. I’ve enjoyed a lot of your writing. It’s one of the reasons I’ve included a number of your articles in the past in my newsletter at some points. As you said, it’s an activity that you’ll be doing as a manager and if you don’t enjoy that, then it’s going to be very difficult. So I can see a lot of that resonance around if you’re good at these things, if it’s needed, and you find interest in them, it’s going to be a lot easier in that area of staying in that management role. So I appreciate that. Let’s talk about your current role then. So if I understand it right, you started off as that staff engineer, working with a small group of people. Today you’re an engineering director so tell us about that journey.

    Dan Na: Sure. So it was pretty organic. As the international business evolved, as the demands on the international engineering team evolved, as the cross-functional team evolved, we just needed more headcount to fulfil our mandate. And as we needed more headcount… So when I started it was me and one other engineer that I still work with, Karim Baaba. And he reports to me today as a staff engineer. So we had a ton of shared context. He’s a really strong engineer. We didn’t need a lot of ceremony because we just sat next to each other and we’re, like, hey, we need to do this. But then as we started to grow the team and add people from outside the organisation or internal transfer or whatever, we were like, okay, this process where we read each other’s minds doesn’t work anymore. We need to double down on something more formal. We need some onboarding.

    Our reach was expanding so we needed a lot more documentation and empowering other teams to use the tooling that we were building. And I was like, “There’s a lot of overhead here where the opportunity cost of me spending time on coding is just too high where someone else can probably do the coding work. Someone needs to step into this more managerial function.” Also, when you add people you need career growth for these people. You need to manage the levels and the tasks and the priority. Somewhat organically as the team grew, I moved back to the management track which is the thing that I think I always knew I was going to do. Then it grew more. The international business is one of our biggest drivers, even today. So as the company has doubled down on that investment, our team has grown accordingly. So eventually we needed to split into two teams. One of the ICs on one of the teams wanted to try the manager track, and so they turned into the engineering manager for one of the teams. That’s been really successful. He’s great. He reports to me today.

    So international is kind of like… It existed and I was the senior manager over that team. Then late last year the company was talking tactically about really starting to invest in the enterprise business. Meaning enterprise customers using Squarespace. Building lots of sites. They have some bespoke needs around security and access and workflows that an individual customer doesn’t have. There are a lot of parallels between the needs and challenges of enterprise to what some of the challenges that international faced in its early days in terms of, “How do you build this abstraction on top of this product that wasn’t necessarily built for this customer?” So when they were thinking about what to do with this org, if they really wanted to invest more in enterprise, they were, hey, we’re thinking of creating this market expansion organisation. Enterprise international. While, at face value, they are very different, they actually have a lot of thematic overlap. So do you want to step into this director role and lead both and that was a great opportunity. So that’s how I became the engineering director. There was a spot they wanted to really invest in. I have a product and design counterpart so there was a sufficient product engineering design triad to work with. That’s how I stepped into my role at the end of last year.

    Patrick Kua: Great. As you were asked, would you like to step into the director role, at that point if I understand right, that level had been defined and that title had been defined, so that there was an idea about the general high level scope about what a director meant. Is that correct? Or is that still fuzzy?

    Dan Na: I feel it’s unavoidably fuzzy to some degree. I think it’s mostly just, you are more accountable for the outcomes here and you have a bunch of disparate workstreams under your remit and the managers that are accountable to those outcomes. I’m somewhat more accountable to the cross-functional stakeholders and that there is ultimately a group of executives that both initiatives roll into that are not engineering. Like C-suite level executives. Thus, by being in that director role I’m invited to those meetings to explain the engineering component to what we’re doing. I wouldn’t say it’s a checklist of, here’s what the job is now. I just knew that it was a heightened sense of you are more accountable to the outcomes here. Especially as the engineering outcomes relate to a business outcome.

    Patrick Kua: Great. Yeah I can see that. Which is the broadened accountability. That sense of more scope and also to more stakeholders. I guess what I was trying to get at is that, is there, or was there, is there a director in the career growth ladder of your organisation?

    Dan Na: Oh yeah, definitely. Like many companies, we have a career matrix. It defines the responsibilities of everybody. I think what I mean is, even if you read a lot of those rungs on that ladder it’s mostly just a scale of scope and accountability as opposed to a punch list of discrete responsibilities. You know what I mean? I think within the director responsibility, it is you have a wider remit over the strategic direction of your team. But you also have much more input and accountability on the business function of your team, which I think is kind of unique… I didn’t feel that as much as a senior manager as I do as a director, I guess I’ll put it that way.

    Patrick Kua: Great, Yeah, no, you’re absolutely right. Which is, as you talk about, it gets more generic perhaps. Or more vague. But there’s that sense of more responsibility or accountability associated with that title. And that’s an interesting dynamic because at some point, there’s expectations. So if you’re thinking about your manager, how do you think about, are you meeting their expectations around your job as a director in your role?

    Dan Na: Yeah, that’s a really good question. I think a lot of this is ultimately self-directed. What do I believe? Given my experience being a frontline manager or even a senior manager, and given my experience being managed by other people across my career, what are the things that I felt other people did well and what are the things that could have been improved? And am I acting on both of those inputs in a way that is consistent with my values?

    I do have some feedback mechanisms. We have twice a year annual feedback. And I make it very clear to my managers, I feel sometimes feedback can be weird because you don’t necessarily have an incentive to say anything bad about your manager who has a say in your compensation. But I make it very clear to my managers – I thank them for the feedback they give me because it’s increasingly difficult for me to get feedback as my level increases, for exactly the power dynamics that I’m talking about. Especially from ICs. So in terms of how I’m doing, I think it’s probably a better question to ask them, but in terms of what I care about I think, I’m driven by three goals when I think about what I want my managers to get from me? The first goal is: I want to demonstrate excellence in my function. I want to be unquestionably good at what I do. I don’t want them to ever question my competence as someone who is accountable to the business outcomes and the strategic outcomes. Managing up. Managing across. So there’s the technical stuff. Am I accurately representing our wins and our challenges and our context to the company leadership? Am I taking the appropriate inputs? Am I approaching them with the appropriate strategic context and the data that’s coming in from marketing and strategy and the business side to help drive our roadmaps? When I have the opportunity to speak or to create a written artefact, is that artefact good? So I think that’s a big thing. Do I demonstrate competence and, thus, serve as an exemplar for them, in terms of what does a strong manager look like. But the other side is also of course… The two sides to the management coin are not only are you good at the technical stuff but are you good at the human stuff, which is critical? Do I manifest the values that I say I care about? Do we have the culture? Does our management sync and the wider syncs demonstrate the psychological safety that I think that I proclaim is critical for the success of a team? So I think that’s a big thing. Am I good at my job?

    So that’s one way that I think I try to lead my management team. But the other thing is… so there are three components. The first goal is am I good? The second goal is am I in the work with them? Am I actively coaching them through problems? I recently listened to this podcast by Scott Galloway, who’s this famous person. He was a CEO and he’s a podcast host. He’s an NYU Stern professor. Anyway, he talks a lot about business and social stuff. And he talked about how he thinks the two frameworks to think about leaders are the inspirational leader and the player coach. The inspirational leader gets up in front of people and is, here’s the reasons why you should work here and why this is a good use of your time. And thus when the inspirational leader gets on stage, everyone is very excited to work for this company. The player coach, conversely, the player coach is not really about that. The player coach is more, hey, you’re making a presentation. I’m really good at presentations. Let’s work together and let me walk you through how to make a really effective presentation. So for me, I think the inspirational part is kind of embedded in the first component. I want to be good at my job. But the second component, player coach is really important too. I have a lot of experience. I’ve gotten a lot of reps. I want to make sure that when my managers are trying things, I’m able to lend my experience in reps to them to make them better and grow their capability to create a roadmap, or to define a strategy, or even make a presentation.

    Then the third component to this is I really want to make sure that I’m sponsoring their career growth. I heard the saying once, where it’s one of these cliche management sayings where it’s like, “Work for someone who will mention your name in a room of opportunity that you’re not in.” So I think that’s really important. I think the notion of understanding the career goals of my reports and then when I hear an opportunity where someone in engineering leadership is like, “We need someone to streamline onboarding” or “We need someone to streamline incident command,” I can put their name in the hat, if that’s something that’s consistent with their goals. With my management team this year we actually went through the book, Good Strategy, Bad Strategy – I really like that book.

    Patrick Kua: It’s a great book.

    Dan Na: I really like the framework. I think it’s so universal. The whole kernel of good strategy. So I challenge them. Not only did we read it but I challenged them. Okay, what’s your biggest problem that your team is facing? Apply the kernel to it and let’s talk about it and let’s grow together. So that’s kind of interesting because I find that not everyone will look to external sources to grow in their job function. Sometimes people will rely just on the reps or they’re too busy or it’s too much of an emotional investment, so they won’t go out and listen to podcasts or read books or read articles or whatever. But sometimes when I find one that’s very resonant, I feel like there’s an opportunity to bring that to the team and then be like, “Hey, let’s work through this together.” Because you’ve already allotted the time for this meeting, so why not spend it thinking about some new ideas?

    Patrick Kua: Yeah. I mean I think that’s a great way of, as you mentioned, learning together and also making time for that as part of work. I think one challenge for a lot of managers, as you said, they’re just busy doing things, and probably lots of meetings. And they feel guilty and are actually taking time out to invest in that learning. And what I’m hearing is that when you ask them to read the book and then to talk through that you’re creating those opportunities in that context as part of their daily work, rather than thinking of this as a, “I have to do this somehow in my busy schedule.”

    Dan Na: Yeah. I mean I want to be pragmatic about it. So we’re talking one chapter a week.

    Patrick Kua: Oh great. Yeah, and I think those three pillars that you talked about were really good in terms of setting the example, actively coaching/working with your team and then also what I heard there with a third part of connecting people to opportunities is what I would probably describe as late sponsorship. And I think that’s a really good three pillar strategy. We’ve talked a little bit about your team but maybe concretely, what does your current team look like or what does your current org look like? So can you describe the shape of that?

    Dan Na: Sure. So I’m the engineering director of the market expansion organisation. So that includes the enterprise and international engineering teams. That’s ultimately about, I think, about 18 engineering headcount roll into me. Or roll up through me. So my directs include 3 staff engineers and then the 2 engineering managers of both engineering teams. So I mentioned this before. Each engineering manager operates within a product engineering design triad. I also have a product engineering design triad, at my level which is a product director and a design director. That’s the basic topology of how our team works.

    Patrick Kua: Great, excellent. Then do you have just managers reporting to you or do you also have some, say, staff engineers or ICs.

    Dan Na: Yeah, so I have 2 engineering managers right now and I have three staff engineers.

    Patrick Kua: Great. Then in terms of how you run, your direct team perhaps, what are some rituals or activities that you do with them?

    Dan Na: Sure. With regard to my directs, I think it depends on their function. So with all my directs I meet for a weekly one on one. I still think that is the fundamental unit of management is to meet on a weekly one on one with people. But I also have a weekly meeting with the managers only, where I use that time to disseminate information. So I also have my own version of these meetings. I meet with my manager one on one. I have a meeting with my peers and my manager’s directs. So I’ll use my weekly meeting to disseminate information through the management chain. Then also discuss any relevant topics impacting any teams.

    I make it a point to stay out of a lot of the individual team ceremonies. Just to give my managers the space and authority to run their teams in the way that they see fit. But I will occasionally drop in on a meeting from time to time. Mostly a retro. Just because I want to hear how things are going.

    One thing that I’m about to kick off this month that I’m pretty excited about is I’m going to start this new meeting called engineering radar. And what that is is I want to take all the senior most ICs in our group, which is not just the staff engineers, but just the appropriate level of seniority and I want to come together in a meeting with the managers and I want to give them the space to surface things. Like wins. Pain points. Stuff like that. I think my concern here is, even as a manager, or even as an IC, I often felt this thing where I’m like, “Mman, the things that people talk about as our biggest problems, I don’t feel any of those. But I feel all these like developer experience problems that no one ever talks about, how come we don’t talk about that?” I feel like there can often be this gap – people at the higher level and then people doing the work. And it’s just one mechanism by which I can potentially close that gap. So my hope is that when they surface things, if I can fix it, I’ll fix it. If I can’t then I’ll use my management chain to escalate things through the org.

    Patrick Kua: That sounds a fantastic opportunity and I think a reflection on your own personal experience of being an IC and that empathy there. And shortening that feedback loop. So I wish you luck with that experiment.

    Dan Na: Thanks. I’m excited. I have high hopes.

    Patrick Kua: Yeah, no, it sounds good. One of the situations that you were talking about was one of your reports going on parental leave. So that can often mean you end up doing a lot more, perhaps, as a director. So what was your strategy? How did that go? How did you make sure that their activities were covered without your schedule then suddenly exploding with lots of meetings?

    Dan Na: My schedule did explode with lots of meetings. But it’s fine. It’s fine. So first thing I’ll say is that I love parental leave. I think it is honestly one of the most humane and generous employee benefits an employer can give. We give a very generous parental leave. I believe it’s twenty weeks or something.

    Patrick Kua: Oh that’s very impressive for the US.

    Dan Na: Yeah. I’ve personally had two stints of parental leave at Squarespace. When I hear someone is taking parental leave, I’m honestly filled with more happiness for them than I am the dread of like, “Oh no, we got to cover them.” I mean when you think about a thing like parental leave and if it causes you a sense of worry, it’s usually because… the pain points of parental leave are obvious. It’s someone’s leaving, hey have a lot of responsibility, how are you going to cover them?

    I’ve done this enough both personally taking my own parental leave and also having ICs on my teams take parental leave that I have a pretty good template. That template is a handoff document where you explain: what is the work in flight? Who are you going to delegate it to? What’s the context that might come up that you really need to make sure is said, so nobody has to call you? Nobody wants to call anybody on parental leave when something goes wrong. I think that rigour really helps alleviate a lot of the pain points. There’s also sufficient notice where… for example, it was pretty interesting. The most recent stint of parental leave I’ve had on my team was the engineering manager of the enterprise team and it was pretty interesting because market expansion was formed. I had just assumed the enterprise team leadership and shortly thereafter this person was going on parental leave.

    So I was like, “Oh man, I’m kind of new. These people don’t know me as well.”But at the same time, that was the opportunity for me to get to know a lot of the ICs. So I recognised my limitations. I cannot frontline manage this team. I don’t have the bandwidth to be in the product engineering triad at a team level anymore. However, what I can do is I’ll take all the management responsibility. I will meet one on one with all the ICs. However, is there an opportunity for a senior IC on your team to step in temporarily in this leadership role to get the reps? To build some career growth for them? And there was. So we delegated. We formed a new triad with a senior IC on the team. I took over all the one on one responsibility.

    So the outcomes are really good. This person went on parental leave. Their baby’s super cute. The family’s super happy. A senior IC got a lot of really valuable technical leadership reps that I think they wouldn’t have normally gotten if their manager was here. I got to build a rapport and some trust with the ICs in a way that I probably wouldn’t if they hadn’t gone out. And it was just setting up the systems and making sure that all the boxes were checked before they went out.

    Patrick Kua: Yeah. It sounds like there were a lot of really good outcomes. I think one of the reasons for that is probably because you had this approach that you talked about. This template. Thinking through those activities, working out who to get involved at what level, recognising your limitations and which things you definitely weren’t going to take on. I think that’s definitely a good outcome and result as part of your process.

    Let’s talk about the experience of your managers. So if I understand right, maybe you had a manager or a couple of managers who were maybe stepping into that for the first time. What was your approach to growing them if they were moving from being an IC to an engineering manager?

    Dan Na: So the managers I have today aren’t that new but I have done that in the past. I think the approach is, for example, in terms of international, part of the organic growth of the international engineering team was I moved… We had to split the team and one of the ICs moved into the management role. Given the context at the time, one thing that I think we did really well is they gradually took over more and more responsibility over time because I was actively managing that team. So what that meant was we slow rolled it. So if we were like, “Okay, you’re going to move into management at the end of eight months. “So what we would do is, “Okay, this planning meeting on Mondays, you’re gonna start running it. I’m gonna step away.” And then just started doing that. And then we were like, “Okay, this planning artefact for H2, you’re gonna write the first draft and then I’m gonna step away.” So that worked really well.

    I always give people the same prescription when they move into management. Management is two sided.

    Number one, read Lara’s book which I think is the best book on the human side of engineering management. And then number two, read High Output Management, by Andy Grove, which is my favourite tactical book about management. There’s a lot of development conversation there. And then at some point, after the slow roll and after they feel a little bit more comfortable, you just kind of jump in. You assume the one on ones. You own the planning process. You operate within the triad fully. I step away and, yeah, like many things, there’s no better way to learn this than by doing. You can read books and I think that gives you a nice mental model to operate off of, but really, it’s not the same as doing.

    Patrick Kua: Great. I guess what I’m hearing here is that your approach is, in this situation as well, is that you had the opportunity to have those conversations early. So I heard you say around that eight month period. And therefore you’re able to take your time at thinking about activities and give them the opportunity to have it but also to do with some support. Versus simply going, congratulations, you’re an EM. Good luck and then off you go.

    I think a lot of people have that experience.

    Dan Na: Yeah. I mean again, we were kind of lucky that that was possible. I do think management is a different planet. It’s just a different job. The incentives are very different, the emotional toll is incredibly different. One thing that Andy Grove actually says is that when someone is new to a role that means that you flex into a different level of managerial oversight. So if someone is new, maybe you need to micromanage them more tightly until they develop their own smells and muscles around doing certain things. I think that’s a thing that you would normally want to do. If you had to just thrust someone into a role and they were really flying blind, I would probably be like, “Okay, we’re going to do all this stuff together for the first month, month and a half.” But in an ideal case you can have that slow ramp up where they learn over time and it’s less of a frenzied onboarding.

    Patrick Kua: Great. Great reflection. Let’s change the topic a little bit and talk about your experience with managing managers. If you were to reflect on your experience, what would you say are some differences from managing managers versus managing individual contributors?

    Dan Na: I think it’s pretty consistent with what I said before. I think it’s a different planet. It’s a different job. It’s like.. It’s truly a different job. The whole trope of, oh, you’re the most senior IC, you should be the manager. I think that’s pretty much dead. That’s why we have two different tracks. That’s why we have different conferences. I think, yes, you’re both rooted in the technical outcomes. But I feel just the emotional investment of management is infinitely higher than being an IC. It’s also much less prescriptive. The thing about technical work – and I’m not trying to discount the glue work that’s required to get really hard things done, that is 100% real. The most effective engineers are the most mature ones that can operate within a system of incentives and emotions – But it’s a really different job to have to fire someone.

    Patrick Kua: Absolutely.

    Dan Na: It’s a really different job to know that one of your reports is going through a really hard time in their personal life and trying to support them in the best way and there’s no playbook for that. I think when it comes to managing managers, that’s why I think the player coach thing is really appropriate. Because, at least for me, when I first encountered these things, I was like, what does this have to do with engineering? These are like psychological things. These are emotional intelligence things. These are challenges that challenge my morals and my beliefs on how I should treat people. So because of that dynamic, it’s much more… managing managers is more involved because the problems they face are so context dependent. Just the tradeoffs are often really emotional and bad.

    Patrick Kua: Yeah, yeah. It’s a tough situation and it probably gets worse, or it gets harder as you have lots of other things going on. If you were to reflect on your path, if you were to go back to your previous self, as you were stepping to this role, what piece of advice would you give yourself as you started to transition into managing other managers?

    Dan Na: It’s really interesting though because I haven’t done everything right. I think there are things I’m still learning. So, for example, one thing that I’m still learning is what is the right altitude to be involved. My job only scales when my managers are really autonomous and strong. And I do have that. I’m super lucky. My managers are excellent. However, I still feel accountable to outcomes. I feel I’m still accountable to outcomes too. So “what is the right way to be accountable to outcomes without undermining the authority of my reports” is a thing that I think is much more art than science. It’s hard for me to give advice though because I feel like the only way to learn is to have the reps of doing it and kind of screwing it up a little bit and trying again.

    Maybe the one thing, it’s not really advice either, but it’s kind of a thing I’ve noticed, is that I feel like one really weird thing about my title change from senior manager to director is that for some reason, people at the IC level are a little bit more reticent to tell me the truth. And I don’t know why. Even if I work with them for years and was part of hiring them, it’s a little bit harder to get the truth out of people. I’ve talked about this with other people at the director and VP level and they’ve echoed a similar sentiment.

    Patrick Kua: It’s not uncommon.

    Dan Na: Yeah. So I think that it’s good to know that. How can I account for that behaviour? I can try things like this new meeting: the engineering radar. I can make sure to never bite someone’s head off for giving me critical feedback. That’ll undermine that forever. So it’s just a thing that… I don’t know if I have any advice. It’s just, this will happen. So understand that the optics of your behaviour will either reinforce this behaviour or will hopefully mitigate it.

    Patrick Kua: I think even simply pointing out that these things are happening is useful advice in terms of at least people aren’t going to be as surprised. Each person can choose how they’d prepare for it differently. But at least they know it could be on the horizon at some point. So that’s still very useful for a lot of people who’ll be listening. My final question for you is where can people contact you or find out more about you?

    Dan Na: Yeah, so this is a good question that’s gotten more complex over the last six months. I used to be really active on Twitter. I don’t really know what’s going on there anymore.

    Patrick Kua: Nobody does.

    Dan Na: I really liked management twitter for what it’s worth and now it’s different. I have a mastodon that I’m not that active on but I’m reachable there. I think the thing that I’m trying to double down on a little bit more, I’m trying to write a little bit more. I do enjoy it. So I do some engineering management writing on I do have various types of contact information there. So if someone really does want to contact me that’s probably the best way.

    Patrick Kua: Fantastic and we’ll make sure that all of those links appear in the show notes.

    Dan Na: Perfect.

    Patrick Kua: With that, I’d like to thank you very much for spending the last hour with me. It’s been really insightful. I’ve loved hearing your story and the insights that you have. And I want to thank you very much for appearing in the Managing Managers podcast.

    Dan Na: Thanks Pat. I enjoyed it.

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