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Episode 22: Ethical engineering management with David Yee

    Guest Biography

    David Yee is VP of Engineering at the New York Times. As an engineering leader, he’s built and scaled teams at both small and enormous companies in the worlds of journalism, music, and art—with an emphasis on product-oriented engineering and humane management.

    His career has included roles as Chief Architect and co-founder at 20 by 200, co-founder and CTO at Editorially, and Engineering Director of Chorus at Vox Media

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    Links and mentions

    Transcript

    Patrick Kua: Hi everyone. Welcome to the Managing Managers podcast. Today we have David Yee. David Yee is VP of Engineering at the New York Times. As an engineering leader, he’s built and scaled teams at both small and enormous companies in the worlds of journalism, music, and art—with an emphasis on product-oriented engineering and humane management. His career has included roles as Chief Architect and co-founder at 20 by 200, co-founder and CTO at Editorially, and Engineering Director of Chorus at Vox Media. Welcome David to the podcast.

    David Yee: Hi Pat. It’s good to be here.

    Patrick Kua: Wonderful to have you on board and you’ve got some really interesting experience across lots of really interesting industries as well. I’d love to hear about your story about how you first found yourself in management. How did you make that transition the first time?

    David Yee: If I go back a little bit before the scope of my bio. I mean the last time I was just an engineer. I think I was at Hearst Digital Media, so Hearst Magazine here in New York. I remember my manager at the time coming to me and saying, hey, you’re doing a great job. Would you be interested in actually being the manager of this team of engineers? It was really just one team of engineers at the time. I remember thinking I don’t really want to do that. It’s really a lot of what we sometimes hear from engineers. I really just want to follow the IC (individual contributor) track which I did. Which is the right decision for a lot of people at a lot of times. I became the tech lead there and that was great. I found myself at my next job which was a startup not having a choice in the matter. It was a startup. We were 3 people and we needed to scale. Great news and the person who was going to do that work was going to be me. Becoming a manager in that space went about, as I imagine it does for a lot of startup engineers, which is like, I’ll do it. I can tell people what to do and I can hire people and I can figure out how good they are at being engineers. But I’m just going to keep doing my thing. I’m going to pretend it’s not happening and it’s more or less what I did.

    Patrick Kua: Wow.

    David Yee: So that was the start of it.

    Patrick Kua: Yeah. I mean that’s quite a long time ago and I know that your management journey has grown. You’ve evolved and developed a big leadership toolkit. At what point did you start to manage managers? Was it in the same startup or was it in a different company?

    David Yee: No, that came later. From 20×200, I started Editorially. From Editorially we were acquired by Vox Media. At Vox started out as an engineering manager working on their content management product. Then at the time when I joined there were exactly 2 managers of engineers for, I think, at the time it was a 30 or 40 engineer team. That’s not a best a best practice. tThat’s certainly not something that served those managers well or their engineers well. So as they thought about restructuring the management team, we moved into a situation where I was going to be a Director of Engineering. It was really at Vox Media that I began to manage managers. At the time picking up 3 managers in that process.

    Patrick Kua: And what was that experience for you like as you transitioned to managing managers?

    David Yee: At the time it felt totally fine, right? It felt like I know how to do this. I manage people today. I’m going to manage these people. I’m not going to micromanage. I’m gonna take 2 engineers and promote them to managers. I just had it all figured out. At the time it felt fine. When I look back on it, there’s so much that I didn’t understand about what was happening there. I don’t think I truly understood what it meant to be a manager until I was managing managers. It was interesting. I had 1 seasoned manager reporting to me and so with that manager I said okay, well you more or less have this figured out. It was mainly one on ones. Tell me what you need. What’s going wrong? What are you doing about it? Then I had 2 first-time managers reporting to me. What it looked like a lot was like me going around them and not quite letting go and keeping an eye on the dashboards and getting in the weeds and so here I was saying well I’m not going to really micromanage and nonetheless I hadn’t set this expectation either for myself or for my staff of how far I was going to be from stuff. That was when I first realised it’s a different job. This is not the same as managing engineers?

    Patrick Kua: What brought you to that realisation? Was it some feedback? Was it, a it’s not working how it is after some time or how did you come across that realisation that it’s a different type of role?

    David Yee: Well I mean it first came to my attention because one of the new managers I had promoted didn’t want to be a manager. Which is great and there’s a whole other lesson in there about giving engineers the opportunity when you can to try out management and giving them a really clean out. For what that would look like that allows them to make the transition back safely. But I think when one of them went back to being an engineer I remember thinking, how much of this was he doesn’t like doing it and how much of it was what it looked like to be supported in that work and what it looks like to be supported as a manager and what it looks like for me… to what delegation really looks like. For me, at least in my career, you reach several moments both as an individual contributor and as a manager where you have to think about delegation but the rubber meets the road as a director because it is the same task. You are asking somebody to perform the same task as you at a different level. It’s not really what it’s like as a manager managing engineers and so I really wrestled for a while with understanding what delegation looked like. I realised that I didn’t fully understand it.

    Patrick Kua: Thank you for sharing that interesting insight. One thing I heard you say was around that support. So fast forward. You’ve got lots more management experience for managing other managers. What would you do differently managing a first time engineering manager?

    David Yee: I’ve continued to do that. I just do it in a very different way. First is to stay close in the right ways and to focus on principles is a different task than focusing on tasks. Let me give you an example of the contrast a little bit. With the first time I helped an engineer become a manager. I put them in a managerial role. I said, well, here’s what I expect you to do. Do this, this and this. Run one on ones. Set up a standing meeting with your product partner. Make sure the trains run on time. I didn’t talk about the principles. So the principles would come along the way. How is this going? Okay, let’s talk about this instead. Now I think I would focus more on the principles. This is what I expect of an engineering manager and in that there’s two ways I talk about that. First is that your job can look a lot of different ways but you bring together 3 things. People, problems and time. Your job is to navigate the space between those things.

    David Yee: So tell me how you think about that? How do you think about how long it should take to do something? How do you think about how many engineers need to work on a specific product? We can talk about those kinds of things. Then the second way of thinking about it is that you are building great teams. You’re building great engineers who build great software. If you stand back and you hold those 2 sets of things in place then what you actually can coach is the tasks as opposed to coaching the principles. So I would probably start there. I think I did the right thing at the time, which is to say, let’s give this a try for ninety days. You see how you think. You can back out of it if you want. I’ll be there to catch you. I’ll maintain biweekly or monthly cadence conversations with the team and I think that part would stay. But I think I would lead with principles rather than tasks.

    Patrick Kua: Yeah, it’s a great approach. I love that you can articulate what those principles are. I think that sometimes the challenge for probably some of the newer manager of managers is the reflection of, well, what is exactly the principles that I’m looking for innately. But as you have to articulate them to somebody else then you realise maybe I don’t know how to succinctly put it that way. I think there’s also an interesting thing here where you have managers perhaps at different levels. So the principles and the coaching on tasks are probably very useful for those first time managers. What would be different about perhaps a really experienced manager? How would you approach that?

    David Yee: That’s a good question. I mean what’s interesting about experienced managers… it gets back to what you just said. Like one of the things that’s really interesting about management when you’re doing it is that unless you’re articulating that work to somebody else, I’m probably not the only person, the only engineering manager who would say there are times when I don’t know what my job is. Like I just don’t know what it is. That was true when I was an engineering manager too, and to a certain extent there’s to varying degrees, all of us walk through our day-to-day at moments doubting whether we’re doing the job correctly. Because we’re in positions of authority we have to project that we do think we’re doing it correctly. So with an experienced manager in many cases, they’ve gotten very good at projecting that they know what they’re doing. So with an experienced manager, for me, I think the job ends up creating a sense of vulnerability in our conversations. Because I’ve been in this situation before, and I often continue to find myself in the situation where I have to tell my manager, I’ve got this. Don’t worry about it. If something is wrong I will tell you. That’s fine and I believe it. But at the same time, my job here is to help you read your room and to give you context that you might not have.

    David Yee: I might not always know what context to give you. So I have to create that sense of vulnerability with experienced managers while at the same time really honouring that contract and say I’m going to stay away. I hired you because I know you’re already good. There are managers that I’ve hired that I’m very very proud of. And just won’t get in the weeds but at the same time have to say things like, there are times when I have to raise my eyebrows, and said what’s true about this? How do you feel about what’s going on right now? Creating an opportunity to explore doubt.

    Patrick Kua: Yeah. I think what you describe there is a really good example. I think of adapting that style to supporting a different type of manager with more experience. In the example that you gave I think it really really nails it. You talked about both hiring managers and also growing managers or picking potential engineers who have that management. What is it that you’re looking for in a potential engineering manager of what makes them potentially great as an engineering manager?

    David Yee: First of all, it depends on the organisation I’m working in. Second of all it depends a little bit on what the team needs. However, there is a consistency to my hiring in that I tend to look for people who are capable of interrogating and understanding ambiguity. We often talk about this for engineering directors and for VPs, the higher up you go, the more ambiguous things are. But even at the line, you’re dealing with human beings. We want things to be systemic. We want things to work in lockstep. We want the trains to run on time and for your agile processes to run smoothly. But at the end of the day these are human beings who are building software. So that introduces a tremendous amount of ambiguity into your day.

    David Yee: When do you break the rules? Why do you break the rules? How do you infer that somebody is thriving and delivering a lot of work? How do you discern whether they are burning out and delivering a lot of work? I look for people who are capable of understanding systems of human beings and understanding human beings at the same time and sometimes finding the juncture between those two things and how they sometimes conflict.

    Patrick Kua: I think that’s a great summary as well. Of dealing with ambiguity and, you’re right, I know this from personal experience as well. As you mentioned as your scope increases the ambiguity and uncertainty increases with that role. I think back to the days of when I was an engineer I would be like here’s a nice user story. Let’s get the acceptance criteria and nail it all down, right? So it’s very clear and you don’t really get that when you’re in those management roles alone in higher levels. You’d never have the time. You never have all the information and you definitely have to deal with a lot of ambiguity. So I really love that.

    David Yee: Yeah. People. It’s true. I mean it’s not a particularly easy role to take up. I always talk about this. Like if I had a really gnarly engineering problem, it would keep me up and then I would solve it and I would sleep well at night. When I have a really gnarly people problem, a really gnarly person problem, human problem I can get to the end of it but I never really, you never, really solve anything. You have to wrestle with the circumstance. You have to wrestle with the consequences and so that is something it takes some time to get through.

    Patrick Kua: Absolutely. The emotional side if you really care as a manager I think makes a huge difference as well. I’d like to jump to a topic on your website. So on your website it says, if we should ever meet, we should talk about ethical engineering management. So this is a fairly new term for me. I mean I understand ethics and it’s very rare to see them together in that phrase. So what do you mean by that phrase?

    David Yee: It’s funny. I was thinking about how I infrequently update my website. The phrase ethical engineering management, to me, does leap out as like a statement from the past that I still believe in. But it’s gained a lot of nuance and complexity since I first wrote that sentence. I guess there’s two ways of thinking about it. The first, when we think about ethics, we often think about business ethics, right? And so what is my obligation to a business? How do I think about how my moral code fits in with that business? That’s going to be different for everybody. How do you create change where you need to create change? How do you accept fuzziness where there’s fuzziness? But when I think about it really, if I think about ethical engineering management, it’s really about the discernment of right and wrong. This gets back to that sense of ambiguity. Our jobs are not really job descriptions. They are the intersection between a group of people and a series of mandates from the business or job descriptions from the business.

    David Yee: This gets to another way that I talk about work, which not everybody who works for me is always comfortable with, which is, listen, if I’m going to say one thing to you it’s going to be to do the right thing. Do the right thing. If it doesn’t serve the business but it’s the right thing to do I want you to do that thing. You can come to me to talk about what’s the right thing to do. I love having those conversations. I have a lot of 1-1s and coaching conversations that revolve around the notion of what the right thing is to do. A sidebar here. This might be the reason I use the words ethical engineering management. When I was a kid, my dad was a lawyer by trade and this is like one of the nerdiest lawyers kids’ things to do. We would be sitting in the parking lot of a grocery store and my dad would just grill me on ethical dilemmas. Like what is your obligation if somebody passes you too close on the road and it damages their side mirror on their car but your car is effectively fine? What is the right thing in that situation to do? There’s a number of ways that we can explore right and wrong and so I really enjoy doing it. Ethical engineering management, for me, is about bringing the question of what is right and wrong in every individual moment to the practice of shipping software and the practice of building teams and supporting the human beings who do that.

    Patrick Kua: Wow. I’m getting some flashbacks actually to university. Because I was also forced to do a course in the law school where there were some ethical dilemma type things here. I can only imagine what that would be like as a kid.

    David Yee: Weird. Weird. But strangely fun because you don’t know you’re being taught law school ethics.

    Patrick Kua: Yeah, absolutely. I think that’s interesting when you ask about the right thing because I think this is the difficult thing, is that particularly people who come from that individual contribution, particularly engineers, they’re often very certain about what is right and wrong in their perspective. They often have this position of well now I’ve decided what’s right and now I’m just going to debate my way through that. Have you found that comes through with engineering managers as well. They’ve already decided on a position and regardless what you say they’re not going to move from that in these ethical debates?

    David Yee: Yes to most of that question. To the very end it’s complicated because I have a title that confers on me a lot of authority and power. So I have to wrestle with when I’m telling somebody what I think that what they’re trying to do may not be the right thing. So that’s actually one of the greatest challenges of my job. If somebody comes to me with a preconceived notion of what they should do and I disagree with it, what am I supposed to do? In general when these kinds of things happen, and this does happen a lot, people come and say this is what I’m inclined to do, and I have to ask myself how I interrogate that. It’s like, how did you arrive at that decision? What are the consequences we have to think through? How are we going to mitigate risk here? Is this a decision that we can back out of?

    David Yee: So rather than say, hey, you have position A in mind. You’re pretty confident about it and I would have done this early in my career too. Instead I have position B in mind and so let me sell you on position B, not realising that no one is going to reject my sales pitch. People are going to do what I tell them to do and so I have to ask questions to get them through it. Sometimes they don’t bite. Then I have to accept that this is the job. That I am not close enough to the work. They’re close to the work they have to make a decision. We’re going to explore the consequences of that decision and in many cases it’s totally fine. I’m like why am I so worried about these things? But yeah, it still happens quite a lot and because people are operating in ambiguous spaces it’s a little harder to discern the outcomes. So I’ve had to learn to let go a lot.

    Patrick Kua: Yeah. I think what you described is a very common challenge for managers of managers. Of that difference, because you’re in a different role with more authority typically, changing modes from coaching and inquiring and telling can be very hard. Do You have any tips or heuristics about how that’s been easier for you?

    David Yee: No. But.

    Patrick Kua: Still not easy. Completely agree.

    David Yee: Listen. I lean into trying to paint the background of a painting as much as I can with my work and letting the people who are closer to the work fill in the foreground. I’m always going to do that first. There are some situations in which I’m aware of context that constrains and I might not have painted that part of the background. And so that’s often what I’ll yield with. What you don’t know. What I haven’t shared with you before and I have to own that in some cases is this. The company is moving in this direction or the budget is not there and therefore what would you do, you know return the question, what would you do now if you know that? What would change about your assessment? They may still say I still need three engineers. I don’t know what to tell you. I’ll say okay, then I’ll paint a new picture with them. So if you keep in mind that there’s no budget there, who are the 3 engineers that you need? What would you let go of if you didn’t get those engineers? What are other approaches that we could take? And I’ll do that. There are very few instances in which I’ll say, after the fact, this is the decision because I don’t want to tell somebody to solve a problem and then come in and say, actually I already solved the problem for you. This was all a preconceived trap and you guessed wrong. Because there’s so many ways in which that creates a sense of helplessness on the part of the manager who’s reporting to me. So I try never to say, well, the company says this so you’re going to have to do this.

    Patrick Kua: Yeah, it’s a great thing to keep in mind. And a great realisation or self-awareness that you have. bBecause I have still seen managers and managers and managers or directors who’d like to still solve those problems for their managers and, you’re right, it creates that weird dynamic between them and their manager as to who’s responsible and it muddies up the waters quite a bit.

    David Yee: Yeah. tThis is one of the benefits when once you’re a director for a while, or once you’re a VP for a while, once you’re a manager for a while, things change a lot. I was thinking about this this morning. You were talking about like IC’s becoming managers earlier. There’s a really powerful moment when you first become a manager because all of your technical experience is still relevant. And you now have the authority as a manager to build teams around that. So you can actually get some really incredible things done early on as a manager. The same thing is true of directors. You still know the team. You still know their work. You still understand the structure and the challenges. You understand the cross-functional players in play. So for first time directors, wow, they can get so much done. They have a close relationship with the engineers and they have a manager who they’re supporting and then in both situations it goes sideways, I find. Somewhere about six months to a year in because all of those things that were gifts early on are now curses.

    Patrick Kua: The flip side.

    David Yee: It’s like, whoops, there’s a downside to this. Later on you lose all of those blessings. I try to stay relevant. I have to try to stay relevant with my technical decisions. There’s no way I would ever rule an engineer in their decision. There’s no way I would ever overrule a manager and in their technical decision making. I find that distance can be very helpful. Because that delegation is actually part of the toolkit.

    Patrick Kua: Yeah. I think that’s also a really great realisation. It did trigger something for me as well which is that when people are going through their careers, it’s often the thought, well, I need to climb that ladder. I need to get the next role. You see this with sometimes individual contributors going into a management track. Maybe they’re forced to because there’s no two tracks. You talked about reversibility and I’m pretty sure you’ve probably seen instances of managers who go I know want to be a director. What are some bad reasons why people want to be a director or where have you seen it fail?

    David Yee: I have a colleague who I really love who I disagree with on this point. He has said in the past, the only thing that drives people’s career progress is always money. It’s always money. I disagree with that. I mean I think there’s something about recognition and belonging and position in society that drives things a lot. Yet, despite the fact that I disagree with him, I find that most people want to be… I’ve never talked to anybody who wanted to become a director because they wanted a more abstract view of their team’s work with greater accountability and less control. That’s not something that you generally hear from somebody, a manager, when you’re talking about a career path. Usually it’s where do I go from here? I’m a senior manager. What is my sense of progression in my work? How am I going to get paid more? So a lot of people make that decision and they treat that work as a promotion and the same colleague, with whom I disagree on this matter, nonetheless I agree with on this next point, which he made numerous times, which is that becoming a director is not a promotion. It’s a new job.

    David Yee: It is every bit as much of a new job as becoming a manager for the first time. So you cannot treat it as a promotion. So I don’t. I talk to people about here’s what the work is. Here’s how it’s different. Here’s how the additional X thousand dollars doesn’t really account for how different this is. So when people make that transition to director, sometimes the things that go wrong, is they stay too connected. Sometimes they get too disconnected. Sometimes they think of it as just 1-1s. Just having 1-1s with managers. Sometimes they find themselves in conflict. Suddenly you are in many ways more connected to cross-functional peers who have more at stake than the product managers you were working with before. So they find themselves in conflict with those people because they say I have all this authority. I’m a director. I now have all of this power and you’re working with other people who probably feel the same way. So negotiation is different. If you don’t learn those lessons or you can’t be vulnerable about the fact that you have a new job and it’s not just I’m really good and now I’m in the really good club then you can just drive straight off the cliff.

    Patrick Kua: Yeah. I want to delve into a couple of some really great insights into what you’ve just talked about. The last one which you talk about that it’s not a promotion but it is a different job. A different role often that means that somebody is going to be doing something with different skills that they’ve never really built before if it’s a new role. So what would be an example of a couple of skills that new directors would need to build that they may not have built before?

    David Yee: Yeah, I mean we talked about delegation as being one of them. Really thinking in a sophisticated way about delegation. Thinking about how people collaborate, for some reason, is like an order of magnitude more difficult at the director level because you don’t have these clean boundaries. Suddenly you have, not just the power to change the shape of an organisation, but in some cases the obligation to change the shape of an organisation. So thinking of more complex groups of people and how they interact. Thinking about large scale multi-year strategic initiatives. What is your organisation trying to achieve? What does that look like next year? What does that look like in three years? Who do you need now? Who do you need later? I think you suddenly end up in various executive level meetings. People actually talk about this all the time. I need more executive presence. Somebody tells me, you need more executive presence. Understanding what that presence means for the executives in your building. Like there’s no one executive presence. There’s like being in the presence of executives, which is a whole other podcast that’s worth exploring and carries with it all sorts of existential dilemmas.

    Patrick Kua: Lots of trauma I’m sure.

    David Yee: Lots and lots of trauma. I think also as a middle manager, I think this relates to this, you’re privy to the fallibility of all the adults in the room. A lot of people can probably recognise a moment in their personal lives when they recognised that their parents were human beings and were flawed and anxious in all of the ways that we can be. As well as experienced and challenged. And challenging in all the same ways. That’s true of your executive suite as well. And so learning to understand the complexity and the fallibility and the humanity of your executive team. And if your VPs of engineering is like, that’s an important step as a director because you have to be able to respond to that and not simply say well, the boneheads in power, say X. It’s, like, well what’s going on in those bony heads, that’s helped them arrive at this conclusion and what can you do to align with it? Nudge on it. You have a lot more of that responsibility as a director.

    Patrick Kua: Great. Some really wonderful examples of how things are different. The skills and responsibilities of people who might find themselves managing managers. I’d like to go back to one of the other things that I heard you say, which is that in these roles you have more accountability and less control. So can you give us a concrete example about what you mean?

    David Yee: Yeah, so I have the luxury of being able to give you a perfectly hypothetical example. I was thinking about this a couple months ago. You’ve probably seen a recent study that an organisation in the UK came out with that said the four day work week results in higher productivity and greater satisfaction. This, of course, builds on the fact that we have a five day work week to begin with which was an outcome of industrial research in the twentieth century that said, actually, probably, should give two people off a week. Which, at the time, was a revolutionary notion. So the four day work week is, of course, an even more revolutionary notion that a lot of people aren’t behind. I would say I have no idea whether a four day work week would work well or not but you can pretty much predict how any large organisation would respond to somebody saying, hey, we’re going to try a four day work week. I was thinking one example of why this is tricky is I have a lot of authority in my role. I could say to all of the 80 or 90 engineers in my organisation, we’re going to have a four day work week. Here’s how we’re going to do it. Here’s how we’re going to make sure that we’re covering everything else. We’re going to see how it goes. But the scope of visibility and impact of my work and the authority, not just vertically, but laterally that my edicts have means I could never really do that. I can’t really do that.

    David Yee: However, if I were a manager and I had 6 engineers reporting to me, I could say, for the summer, we’re going to have a four day work week. There’s always going to be someone on staff. We’re not going to talk about it. We’re going to see how it works. We’re going to see how it feels. From there I might talk to my manager and say, hey, just so you know, we’ve been trying this out. Now in that situation, I don’t have a lot of power because my manager can then come to me and say, that’s absurd. You should have told me. You’re fired. But I had a lot of control at the moment over that situation. For six engineers I was able to make that work. I wasn’t able to make it work. It’s not something I’ve tried. But I think that’s an example of somebody, and that’s true of any organisational decision. Any personnel decision. Any cultural decision. If I stand up on stage I say we’re doing x and this is one of the lessons I think that you learn as a director and certainly as a VP.

    David Yee: Everything you say is taken as gospel. So all of the consequences accrue directly to you. So you end up making sharper, finer decisions. You end up running more experiments. You end up taking the long road a lot of times in ways that, as a younger, earlier career engineering manager, I was a bulldozer. I would just say we’re doing this. This is what we are doing now. We’re trying this and great things came out of that. But I couldn’t do that now without a different set of consequences.

    Patrick Kua: It’s really interesting what you say. I’ve seen this. I’ve been that bulldozer as well. What has helped you change your approach?

    David Yee: The tongue in cheek answer is constant scolding.

    Patrick Kua: Feedback?

    David Yee: Yeah, exactly. Feedback. Have you thought about this? But that’s not entirely true. It is less the case, it is less frequently the case that I do something or or have done something as a manager and received feedback from my manager that wasn’t the right thing to do. Although that happens. Different organisations value bulldozers in different ways. So you have to assess. I’ve had to assess the appetite for that behaviour in every organisation I work in as well as the unforeseen impact.

    David Yee: I think that over time what’s mattered more to me is the reflection of the people that my statements affect. People come to say I found that really confusing. Or if we do this, what does that mean? If I suddenly have to do this work, what do I do with all this other work? I’m like, oh, it sounded so simple when I was thinking about it. But again, against the background of like 100 people or 200 people, it takes a new shape. I think that’s what’s led to a change in my approach to talking about work. To making decisions. Balancing consensus and authority. That, what I was saying earlier, about painting backgrounds letting other people paint foregrounds is about making sure that people actually understand what’s happening and reckoning with that, with that shift in context.

    Patrick Kua: Yeah, it’s a great example and I think what you were talking about there, yeah, it makes a lot of sense. I’d like to jump to a different topic which is about your own journey. So you’ve managed managers for quite some time. You’ve probably grown a number of people into director roles or other people who have to manage other managers. Is there a typical book that you give to people as they make that transition into a new role or what resources would you point people to?

    David Yee: I think Camille Fournier’s book, The Manager’s Path, is basically… I mean I don’t agree with everything that Camille says. I don’t agree with everything in that book. But I think the book is comprehensive and well written. The structure of the book lends itself to ascension in that way and to increase responsibility. So I think her chapters on directors are really good. I tend, in general, though not to be so much of a book person. It’s not that I don’t value… I do value books. But I tend to find that everybody’s journey is a little bit different. Either they’re different or their team is different and so the things that they’re learning in books or conferences, they have to interrogate a little bit more. To a certain extent, they have to question authority. So I tend with folks who are doing that to, again, lead on principles. Say, okay, well here’s what I’ve done. Here’s what I think is happening in the organisation. I’m going to give people a little bit more context. A little bit more room to move and we’ll see. I will say that it’s, in the same way that as a director you learn to be a manager of managers, as a VP learning to be a manager of directors is another phase shift.

    David Yee: I’m not yet at the point of my career as a VP, which I’ve been for about a year and a half where I feel like I could tell you cleanly that I feel as confident managing directors as I did managing managers. I have found it really instructive. I’ve found it really instructive to help directors grow and help managers of managers grow. By watching the places where they get stuck and realising, am I also stuck there? Have I been stuck there? What did I do to get out of it? What did it mean when this product partner said that they didn’t know what I was doing at a particular time? Or that I made a decision that felt abrupt? So I can match those. I can pattern match those against my own experience while being able to turn to colleagues and other organisations or turn to books. To try to inform from an outside point of view how those directors operate. and how those other managers operate. It’s been a really fascinating journey.

    Patrick Kua: Yeah, thank you very much for sharing that insight and your own personal journey as wWell. I find it also interesting because I think it requires quite a lot of self-reflection and also an observant nature of people in the system. I know many other VPs of engineering and directors, or directors in large organisations where it’s all about running from the next thing to the next thing and they miss out on these opportunities. I think it is also a testament to yourself to notice these things. Also asking yourself how it relates to your own journey and so I think that’s a great thing to celebrate.

    David Yee: Yeah. I hadn’t really thought about that until you just said it. Like how much of the work of being a senior leader does feel… and this gets to the ambiguity. I don’t remember who said this. Whether it was the person who told it to me or somebody who told it to them. But if the problem has gotten to you as a VP it’s pretty complicated and it’s probably really urgent. Because it’s had a chance to percolate its way up. Or percolate its way to the side. So you’ve got to move very quickly. There’s a lot of running around and putting out fires. Things that I really valued about my work when I was an engineer that feel relevant again to me as a VP but I do think that means you have to strive to be a slow thinker. That balance between needing to run and striving to think is extremely difficult.

    Patrick Kua: Absolutely agree. I have two quick questions for you then. Imagine that you can provide only one bit of advice to a person who’s stepping into the managing manager’s role for the first time. What would that bit of advice be?

    David Yee: Make no assumptions. By that I mean make no assumptions about your organisation. Make no assumptions about yourself. Make no assumptions that don’t lead with anything that feels like you have to demonstrate expertise. I think there’s so much about becoming a director and we talked about this earlier about being a director as a super manager. You have to allow yourself to be bad at something before you can become good at it. You can deal with that however you want but don’t assume that you’re a projection of authority or expertise before doing the right thing.

    Patrick Kua: Great bit of advice. I also think it’s one of those things where when somebody’s doing something for the first time you need to make mistakes to learn. I think that’s probably related to that. Which is you can’t just ignore them and then hope everything continues to go although you won’t really learn and grow. So I think that’s a really relevant bit of advice for a first time manager of managers. My last question for you is where can people find out more about you or reach out to you?

    David Yee: Well, you can go to my, not recently updated, website which is tangentialism dot com. The dissolution of social media has been a really fascinating thing. Because it means that all the short things that I say can live in multiple different places. That said I’ve backed away from Twitter and I’ve moved into Mastodon. So against probably my better judgement I’ve created my own Mastodon instance. So you can find me at @yee@yee.camp and that’s where I tend to do a lot of my writing. There I’ll talk about places when I’m speaking. I speak often at LeadDev. I host LeadDev New York. And you can always send me a note. So david dot yee at nytimes.com is a great way to get in touch with me. I have contact information on my website. Or just if you see me around, just say hi.

    Patrick Kua: Wonderful and we’ll make sure that all those links appear in the show notes as well so people won’t have any difficulty finding them. Thank you very much David for spending the last hour with me and the listeners on this podcast. You’ve got some really great insights. I think we could talk about many other topics for hours. But we’re going to have to call it a wrap for today’s show and I really want to thank you for your time.

    David Yee: Pat. Thank you so much. It’s been a real honour speaking with you. I love talking about this stuff. So thanks for inviting me.

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