In this week's episode of Dev Interrupted, host Conor Bronsdon is joined by David Yee, VP of Engineering at the New York Times. They dive into the often unseen aspects of organizational structures, discussing how every organization regardless of their defined values and principles, operates with a 'shadow'. 

David discusses the role of senior leaders in addressing systemic problems and navigating the tensions between innovation and consistency. He highlights the importance of recognizing and integrating these organizational shadows to foster better decision-making and operational efficiency.

Drawing from his rich experience leading engineering teams in media, this conversation offers a unique perspective on the complexities of engineering leadership and explores the challenges of aligning technology with the century-old tradition of news reporting at the New York Times.

“Every organizational leader has sat down at some point to think about two things. One, should I reorg? And two, what are the values and principles of my organization?

When we do that, We often ask ourselves what we're optimizing for. That's a very reasonable question. What we don't ask is, what do we do with the things that we're repressing? How are we going to reconcile with that?”

Episode Highlights: 

  • 1:48 All Organizations Have a Shadow
  • 10:45 The Two Questions Every Organizational Leader Has Asked 
  • 18:26 Solving Unseen Problems: The Role of Senior Leaders
  • 25:54 Balancing Tensions in Organizational Philosophy
  • 31:35 Technology Meets Tradition: The NYT's Unique Challeng

Episode Transcript:

(Disclaimer: may contain unintentionally confusing, inaccurate and/or amusing transcription errors)

David Yee: 0:00

every organizational leader has sat down at some point to think about two things. One, should I reorg? And two, what are the values and principles of my organization? When we do that, We often ask ourselves what we're optimizing for. That's a very reasonable question. What we don't ask is, what do we do with the things that we're repressing? How are we going to reconcile with that? Or

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Conor Bronsdon: 1:11

Welcome back to Dev Interrupted. I'm your host, Conor Bronsdon. And today I'm joined by David Yeat, VP of engineering at this little company called the New York Times.

David Yee: 1:18

We're going to make it someday.

Conor Bronsdon: 1:19

Yeah, I believe in you. This regional paper is scrappy. Um, the amazing thing about your career, David, is you've scaled both small organizations and frankly, enormous ones in the world of journalism, music, and art. And you have an emphasis on product oriented engineering and humane management, as I've heard described. And that diverse perspective has led you to identify something that you think is that organizations all have a shadow. Can you define what that means?

David Yee: 1:48

Yeah, so what's interesting about talking about organizations is we sort of define like what they look like. So if you think about like the values that an organization has or its org chart, these are all things that you see. But The thing that I've been obsessed with is this idea that every organization is bigger than that, and the parts that you don't talk about still operate, and they are excluded for a reason. So, it's those bits that are left on the side that are still operating that show up in ways that kind of like can irritate an organization.. And so the things that I've really been thinking about is how you bring that together.

Conor Bronsdon: 2:19

What are those bits?

David Yee: 2:20

It depends on the organization. So, these things are in con, either in conflict with the way you operate. So you could say like, all right, well we are the kind of organization that makes like really crisp decisions. you know, and everybody owns their decision, something like that. But there's always gonna be a class of decision where people are like, oh, well I really need to ask a bunch of people, or We need to agree on this. That might not be in your org values, it might not be the way you identify as an organization, but it's still something you need to do. And so if you're going around trying to make sharp decisions about things that need consensus, everyone's going to get just annoyed. and so that's an example, but it shows up in all sorts of different ways.

Conor Bronsdon: 2:57

What are the impacts of the shadow? I mean, you mentioned one, but it seems like there would be a variety of ways this would impact different organizations.

David Yee: 3:05

Yeah, generally speaking. the thing it tends to do is cause dysfunction, slow you down. And it's not that the shadow does that. It's the fact that you're not engaging with it meaningfully. You're not really acknowledging that this is happening. The example I was giving at lunch was when you think of an organization, I had this debate a couple of years ago with my product partner where I said we really have to be We have to make sound technical decisions. And my product partner was like, we need to move fast, we don't have time to make sound technical decisions. And so we worked this out, just the two of us were working this out, debating back and forth for a long time. Finally I said, we have to move quickly while aiming for technical consistency. Now the result of that debate between two people means that there's still this question that the engineers would ask about. And this is in a different organization about like... Where do, where do we value, show me where we value technical consistency, but I do value it. It's just that when it shows up, it tends to fly in the face of the world, the org values say that we're supposed to move quickly, why would we do this? But the answer is you have to do it. And so it causes confusion, it can cause delay, it can cause debate. And frankly, for people who find themselves in roles where that, where the shadow, where you're sort of acting on behalf of the shadow, you can actually get really marginalized. And so there's both an organizational process problem, as well as sort of, you really have to think about what it means for individual human beings who, who really aren't acting in service of the publicly stated goals.

Conor Bronsdon: 4:44

I think it's interesting because it sounds like this dissonance between kind of the formal structure of the organization and the way the organization actually functions is likely to cause misallocation of resources, both if you wanted to find human beings as resources, which is controversial at times, but we think of them that way in a lot of ways. And also I'm sure how money is spent in the organization, how time is spent. Uh, would that be a good way to characterize this?

David Yee: 5:08

I mean, that, it's certainly one aspect of it, right? So if, if you, I guess I hadn't really thought about it from the perspective of like OKRs or metrics, but it's, it's true that if you say, let's say that you have an organization where, uh, the goal is to invent new things rapidly. And you're not going to be able to depend on a framework to do that. You're going to have to hack everything from scratch. You have a team that happens to be in your organization that is responsible for a consistent design system or something like that. If those two things are paired in one organization, you're always going to prioritize the resources for invention. You're never going to prioritize the resources for consistency, even though that consistency is really important. But at the end of the day, where do your priorities lie? Where do your values and principles lie? That's where you're going to be paying attention. And you have to ask yourself, at what cost are we not paying attention to this other thing? And this other thing is just nagging us in the back of our mind. And you can ask yourself, why are we wasting so much time inventing new things? We should be spending time building a design system. He says, well, that's not what our org is about. Our org isn't about that. That's something else. So there is a larger question about how organizations intersect and how you really want to sort of bring those, you know, bring that shadow into light is one of the things that I talk a little bit about. sometimes you bring that shadow into light inside your organization. You can also find the shadow of home in some other organization.

Conor Bronsdon: 6:40

I'd love to, for you to expand on that. That's a really interesting concept.

David Yee: 6:42

Okay. So first of all, I have to explain that. of an organization's shadow, and this was sort of part of my talk, it actually emerges from psychoanalysis, and it emerges from Carl Jung. A whole section of my talk is just about Carl Jung. It's a really risky thing to get on stage at an engineering management conference, but I'm going to talk about the Swiss psychoanalyst. But let's just acknowledge the Swiss psychoanalyst Carl Jung has this notion of shadow, which is about the psyche, and it's about personality. If I'm the kind of person who says, I'm a confident leader, that's my persona, right, to use also a Jungian term, like my persona is, like, I don't know that I am this, but let's say that I am a strong, confident, convinced leader. that's how I define myself. That's how I see myself. That's how others see me. That's my conscious self. The unconscious self right behind that, contains a shadow, right? So that's where we talk about the shadow. And the shadow contains all the parts that are part of me that I, that don't fit my conception of the person I am.

Conor Bronsdon: 7:49

Does it also contain the parts that do fit the conception, or do you view it as a separate entity?

David Yee: 7:54

It's a totally separate entity, right?

Conor Bronsdon: 7:55

So, so maybe you're not confident in the shadow?

David Yee: 7:58

Right. Maybe you have doubt. Maybe you're the kinda person who, who has doubt. The reason it's in the shadow is because doubt doesn't fit my notion of being a confident Right, convinced, strong leader.

Conor Bronsdon: 8:07

That's not how I wanna present to the world. It's not how I want to act in the world. That's, and therefore I push it, push it down,

David Yee: 8:11

I push it down, I repress it,

Conor Bronsdon: 8:12

but eventually. It'll come to the forefront. Maybe

David Yee: 8:15

it's there. Right. Like and you know, any confident leader, like, something, if you invert that any leader who is devoted to consensus may have a gut instinct. That gut instinct. And so there's nothing wrong with doubt. Doubt's not bad. It's, it is a tool, right? And so ultimately, this kind of gets to the point, it's like the goal, the way I close the talk is basically talking about integrating the shadow. And both in psychoanalytic terms, but also in organizational terms. What you really want to do is bring that to light and say listen sometimes as a leader I kind of doubt myself. It serves me in the following ways, and it actually helps get make sure that I'm making more More informed decisions in moments that are not certain.

Conor Bronsdon: 9:08

Maybe I understand the risks whereas if I was fully confident I would ignore the risks.

David Yee: 9:12

Right exactly and that's what happens to a lot of people so if we take that hypothetical leader That person's gonna run you off a cliff if they ignore that shadow. So it's really important to integrate the shadow. The same is true of organizations. So if you take that same model, and I, I don't know that necessarily, this is the best example, but let's, let's follow it, that you've got sort of design consistency in your shadow. Okay. Right? Yeah. I have to make consistent design, like it makes the my product easier to use. But that gets in the way of innovation, gets in the way of your public persona of innovation. You have to ask yourself, how am I going to invite this consistency into the work? How do I acknowledge, listen, nonetheless, this is something that my organization needs to do. How do I bring it in? In a complex organization, the answer might be platform thinking and you wanna move that into a platform space. Sure. Someplace that's gonna be able to have the leverage, that's gonna be able provide the leverage.

Conor Bronsdon: 10:06

So maybe building a platform team or something.

David Yee: 10:08

Exactly, exactly right. And you bring that to light and you say, look, we need a platform team. Even though our job is to innovate, we need a platform team because ultimately it's going to help us move faster. one way of thinking about the reintegration of an organization shadow.

Conor Bronsdon: 10:24

This is fascinating because you've also just given me a great argument for why people need platform teams. Enable innovation in your organization by getting rid of your organizational shadow and orient it to the platform team so they can solve your problems. I love it. It broadly sounds like you think engineering orgs need to think more in depth about organizational design and the psyche of that organizational design.

, David Yee: 10:45

every organizational leader has sat down at some point to think about two things. One, should I reorg? And two, what are the values and principles of my organization? We do that as an organizational tick. We do that as leaders. And of course those things are necessary. When we do that, We often ask ourselves what we're optimizing for. That's a very reasonable question. What we don't ask is, what do we do with the things that we're repressing? How are we going to reconcile with that? Or sometimes on the line, how do you find yourself in a situation where something is happening and you're confused or annoyed and you're saying like, but I thought our value was this. How do you look at that, at those, at that moment of decision when you re org ed, when you sort of wrote your values and principles and said, Oh yeah, I made a conscious decision not to include that in the values. Nonetheless, it is important right now. Like, your organization still needs those things. If it didn't need those things, they wouldn't be coming out. And, I'm not saying you have to write like a 33 point org values document, but sometimes you need to ask yourself, How do I invite these tensions? into conscious view so that I can reconcile them.

Conor Bronsdon: 12:01

Interesting. So because they're out of view, they continue to cause extra problems. Almost like having like, I don't know, like a, a burr in your clothing that you, you can't get ahold of. And once, once it's out, you can get rid of it, you can deal with it, you can leverage in whatever way you want to. Mm-Hmm. And so you're looking to say, how can I leverage these challenges in a way that's positive for the organization because we know we actually do need to solve them or. Or use them or else we're going to invite more risk.

David Yee: 12:29

Yeah, we're going to invite more risk and frankly, we're going to waste a lot of time and energy.

Conor Bronsdon: 12:32

And frustrate people.

David Yee: 12:33

This is in, I mean, I'm not the kind of person who says, well, this one simple trick to fix your organization, but I do.

Conor Bronsdon: 12:41

That's what we're going to title the podcast.

David Yee: 12:43

This one simple trick, the, I think that the, When I think about operational efficiency, and this is just my, this is the way that I think. When I think about operational efficiency, I'm not thinking like, okay, if we could just use AI for this, or if we could just have engineers work longer or harder, we could get more done. A lot of times when I look at the things that slow us down, it's related to confusion, disagreement, and delay. And that delay often emerges from a sense of uncertainty that says, I usually know what to do, but in this moment I dunno what to do. And I'm really afraid of making a decision because I'm afraid I'm gonna be held accountable for doing something contrary to the values of my organization. Or I'm gonna be acting out of turn, or like, I don't know. I feel like I should ask the VPE about this, when actually sort of acknowledging no, sometimes like. There are decisions that need to get made in ways that don't mirror the values or don't mirror the hierarchy of your org.

Conor Bronsdon: 13:39

Right, and then that creates additional communication costs by that confusion because now suddenly you're talking to the VP, you're spending their time, you're spending your time, you're diving into this problem that hopefully if the shadow is better integrated into your organizational You'd be able to solve because you understand how to think about this prioritization, how to think about this context.

David Yee: 13:58

Yeah, because at that point you would have said, you will have said, and it's really funny actually because recently we had this conversation in my part of the organization where rather than sort of stating the values, we actually stated the tensions. So, so one of those tensions, I'm trying to think of like a really good one of those tensions was sort of, I need, on one hand you say, I need the liberty to act independently. And on the other side, you say, I'm afraid of stepping on people's toes. And both those things are in play, right? if I look at the organizational values of the New York Times, one of them is independence. Right? So, the former is really independence. I'm going to Act independently, I'm going to like depend on my research, I'm going to make a thorough point of view, and I'm going to arrive at a decision. But you'd be surprised how much in my organization there's a fear of stepping on people's toes. Now, don't step on people's toes is not written in the organizational values of my business. But it's there, and you have to be able to talk about it, and so I, like, one of the ways we did that recently was bringing those up as tensions, and saying, how do you want to reconcile these tensions? That's the work of integration, you have to say it out loud.

Conor Bronsdon: 15:03

Do you think that's the result, this specific tension of not wanting to step on other's toes? of a way that the New York Times culture functions, or is it a result of people's previous experiences that they're bringing to the table?

David Yee: 15:16

I tend to think it's all the manifestation of past experiences. I don't think, for example, I don't think that the New York Times would say, would say that in any way. I don't think it's representative of, like, what the New York Times would be about. There's no reason to make that sort of part of the values. I think that there's historically, in any organization, there are past experiences that an organization has had. Or that individual people have brought to that organization that have caused pain. And as a result, you repress that. You say, I'm not going to do that again. And it could be one of the things I think a lot about is it could be that the, that the people involved in those events and those decisions and the way they unfolded, they're gone. Or those, those conditions are no longer true, but you have. You've made a decision.

Conor Bronsdon: 15:59

You carry that cultural baseline or foundation that was created by folks at an organization. I mean, frankly, we do as a society, right? Like we're still building off of the culture that was here beforehand.

David Yee: 16:10

That's absolutely right. And like frequently those things, because, because you, if, when you look squarely at them, you, like I said, you wouldn't say like, yeah, I'm going to go ahead and put this one in the constitution. Like it's there that operates. And so you have to be able to ask. Well, what am I going to do about this? And you have to be able to acknowledge that it's happening, because if you don't acknowledge that it's happening, you can't solve for it.

Conor Bronsdon: 16:33

What prompted you to apply this concept of the shadow from Carl Jung to org design? What, what inspired this?

David Yee: 16:41

So, originally, when I was thinking about this... So, you know, lead dev said, Oh, hey, come give this talk about influence at scale. And I said, okay, how am I going to do influence at scale? So I could talk about like communication practices, I could talk about, tailoring a message, I had all these ideas and then I said, Why is it that our org charts don't work? why is it that... A manager can't make a decision in their scope, or the VP of engineering can't act without getting full buy in from the product partner of another vice president of engineering someplace else in the org. There's something happening. It so happened at the same time I was part of this coaching program. That thinks about Jung a lot and was talking about Jung a lot. And so, it was surprising like as you dive into shadow work and Jung's concepts of shadow, it's really hard to internalize what that is. and so as I was, I was thinking about these two things at the same time. And so I was telling, my friend Neha, who's presenting also today, I was like, I think of these things as shadows. there's a book that I cite in my talk, about, uh, about sort of managing the organization shadow, or mapping an organization shadow. and it's, and it, I discovered it and it sort of connects these two bits. It connects Jungian psychology with organizational thinking. Uh, and so actually that leaping off of that helped me sort of formulate the connection between these two things that were going on in my head.

Conor Bronsdon: 18:07

I would be curious if you could share an example of an organization that is either doing a great job integrating its shadow, or maybe a terrible job.

David Yee: 18:16

I mean, honestly, my assumption is that all organizations are doing a terrible job of this, right? If they weren't doing a terrible job of this, then we wouldn't have our work. The reason why I'm giving this talk here today is because as senior leaders, as directors and vice presidents of engineering, An engineering manager is having a problem with another engineering manager, or this process that you set up isn't working. and so, the natural process organizationally is to, pump this up and you go this up to the next, up to the next level. So you're talking about directors, VPs of engineering, other kind of senior leaders. So, by definition, our job is to solve problems that our designed systems are not equipped to solve. Which means that, like, you have to look at the prob you have to look at the problem and say, Okay, well, what's at play here? All of us do a really bad job of this because we've, we've worked really hard to create working systems, healthy systems, uh, to be able to serve these needs. you know, I can, you can imagine sort of any number of organizations that, that are well known for sort of healthy, uh, healthy culture. So Netflix, for example, and I don't work at Netflix, so I can't speak for Netflix, but legendarily from the outside, everyone says, you know, Netflix has this figured out. They have this culture document. It defines everything. If you follow the culture document, it's just gonna work. It didn't work for them as they scaled. Everything that they've done in the last year of their existence has been to sort of question their culture document. So in a sense, you might say, okay, Netflix is looking at the shadow and saying, like, , this isn't working. and you could talk to anybody at any high functioning organization and say, wow, it looks like a great organization to work on this. And yeah, well, on the ground is a little more complicated. Right? Right. That's real. So if it's more complicated, what do you do with that? And so you could imagine that an organization like Netflix in making the decision to sort of like question their culture document and change their processes, is trying to integrate the shadow, whether they're doing a good job or not. I, I don't know, but that's just one example. Again, I think most organizations of any complexity and probably the more complex or the more tenured the organization, the harder they have, the harder time they have of doing this. Find difficulty in reconciling the shadow by design.

Conor Bronsdon: 20:34

This is really interesting. I love to use Netflix as an example because I spoke with Carol Barrett at Netflix about their transition as they've started to hire more junior engineers and some of these changes they've made. What you're saying resonates. Netflix, we're speaking for them. We don't work in Netflix, but, I think by your definition has been wrestling with that shadow where maybe that shadow, and again, I'm just guessing it grew over the years where they said, this doesn't now work for us as well as it used to. We've, we've added these cultural pieces that maybe we haven't fully accepted or that we, if we need to adjust to. And now they're saying, okay, how can we integrate parts of that shadow to improve the organizational and I would be curious if, if they think that's what they're doing and that's how they're improving the organization or how they would think about it. Maybe an interesting follow up for Carol or Catherine here today is asking them like, what do you think? Is that what Netflix has been doing? Integrating the shadow? Does David's talk resonate?

David Yee: 21:28

Yeah, I will ask. So did I really change your mind? Are you convinced now that I was right about the way Netflix ought to work?

Conor Bronsdon: 21:35

Let's get someone from Netflix in here. Come on. Producers, can we grab someone? Gimme a call. They're shaking my head here. Yeah. But maybe they'll, maybe they'll call David after this. Yeah. I, I'd love to add some more context to this. Sure. So let's talk a bit about what you do at the New York Times and your organization there. Mm-Hmm.'cause I think that'll be a, a great corollary to this, you know, the, the shadow side of the organization versus the tensions versus how your organization functions. Mm-Hmm., how big's your org at the New York Times?

David Yee: 22:01

So my organization in the New York Times, I have nine direct reports. I have about 70 engineers all told. and it's an organization called Subscriber Experiences. Think of this as the organization that is responsible for the homepage of the New York Times. the News Reader application, if you like, read the New York Times on your phone. Like that, that app, that is an app that we own. It's in conjunction with a lot of other teams. Things like personalization of the experience and the emails you receive, right? All of these are like sort of how do you bring, uh, how do you bring the product to subscribers? So when you describe me as a product oriented engineering leader, That's my bread and butter. That's the kind of organization that I'm in. so that's, that's kind of my zone. and You know, it is a, it is a discreet mission. We use a mission system. So we use a discreet mission inside the New York Times, inside an organization called XFUN. and so we have our own practices. We have our own principles. We have our own values that supplement those of, of the New York Times. We don't operate exactly like the organizations around us. and yeah, like we have, like you said, we have our own tensions, our own problems that are unique and like we also reflect on the problems and tensions of the organization as a whole in our work. You have to,

Conor Bronsdon: 23:11

would you be open to sharing some about how your org works and then some of the tensions you identified? I know you mentioned one earlier.

David Yee: 23:16

Yeah. So,, this is always the classic engineering debate. It's like, do I move fast and break things, or do I make the right decisions up front, right?

Conor Bronsdon: 23:22

Which is hard to do.

David Yee: 23:24

You can't really live by one or the other without, you know, you have to eat your hat eventually. And so one of the things we're figuring out now is, Okay, how do we, how can we bring products to market really, really quickly? while pointing, and so this is, so if you, let's, the process of reconciliation looks a little bit like this. if we were writing an org value for subscriber experiences, we might say, we need to bring products to market as quickly as possible to evaluate whether they serve our readers and serve our newsroom in the right way. Right? And then we would leave everything else on the floor, but by bringing up as a tension. We can say, we're going to build things as quickly as possible to bring them to market and experiment. But as we do it, we're going to identify the journey we're going to take to a consistent, scalable, resilient, extensible user experience. Right, so we're not, we're still going to be optimizing for one thing, but we're going to be doing it in tension with this thing that would otherwise live in our shadow. Which is making sound technical decisions as we work. We are going to do this today, but in six months. We're going to be lining up this batch of work that brings it along. That's not like an uncommon gesture in engineering, but one of the things I appreciated about the way we've been thinking about this is that you can say it up front and you can say, this is, it's not this, but that it's more like this in light of. The long term goal, the short term in light of the long term.

Conor Bronsdon: 24:54

How do you measure your success? I

David Yee: 24:56

mean, in our organization, we measure our success through business success. That's, that's why we exist. We're not a platform. My organization is not a platform organization. We are defined by whether or not we're able to engage our readers in ways that keep them coming back and keep them informed. I mean, that's the, that's the heart of it.

Conor Bronsdon: 25:14

I love that there's this key core mission that drives how you do the org design and also how you think about the tensions with your shadow work. I think that's important because it, I'm sure it makes it much easier for you to prioritize even when there is conflict that happens with the shadow org because you have a defined clear mission.

David Yee: 25:32

Yeah. The clear mission doesn't. It doesn't mean that you can't wrestle with these things. I would, you know, I'll cite that mission left, right, and center, no matter where we go. I mean, that's, that's still a very reasonable place to be. It's a good goal to have. But being able to say operationally, philosophically, as we approach these things, we are living with these things in tension. And there's no, I'm not, like in all of these tensions, I'm never going to arrive at a clear statement. It's going to be a continual body of work. It's going to be shifting between that sort of move fast and like that consistency. It's going to be shifting between independence and stepping on people's toes. it's going to be shifting between flexibility and rigidity of teams. Like we're always going to have to sort of reckon with that and like figure out what lives in the light and what lives in the shadow and how are we going to sort of bring these things together to have a healthy conversation.

Conor Bronsdon: 26:22

It's interesting to look at your career in the context of this. You've been someone who's been involved in media engineering, uh, as you put the phrase for a while. You know, you were a director of engineering at Vox, you were a CTO at Editorially and co founder, and you've had other roles in this space. Do you think that there are unique aspects to the organizational shadows at media engineering orgs, or is this something where it's fairly common across the engineering space?

David Yee: 26:51

That's a really good question. I, yes, this is, there is something and, but it's not unique to the media engineering space. Let, let me, I'll give you the sort of broad strokes on it. and then I'll get a little bit closer because there's a really interesting contrast between Vox and the New York Times. so broadly speaking, I would say any time, especially in engineering, there's always a, some sort of foil, right? I remember talking to a friend of mine, at an organization I won't name. And, you know, at the New York Times at the time, there was a sort of this question of like, who's in charge, product or engineering? It's going to be product or engineering doing this. And I was like, and I was talking to my friend, I was like, well, what do you like, you know, what's your relationship between product and engineering? He said, well, it's fine. I said, well, like, there's not a tension there? He's like, no, not really. I was like, well, you know, uh, how do you, How do you reconcile with the needs of the business and like being pushed to do things that you don't wanna do? He is like, oh, that's marketing , . That's marketing. Oh yeah. Marketing's you're thinking about marketing. Marketing's the team that screws us up all the time. but of course that's just from his point of view. Yeah. I'm sure if I, if I was friends with somebody in marketing, I said, well, what's your perspective on engineering? Like, oh, engineering's always like, we wanna move slower. We gotta make sure we do this the right way., like, you know, and, and I think, so there's al so first of all, there's always that dynamic. Right, and that often the shadow organization, you could pretty cleanly find some corollary in the relationship between two functions or branches of the organization. So when I think about usually what you'll hear if you talk to people at the Washington Post or you talk to people at the New York Times or Vox Media. It's this tension between, quote, the newsroom and the product, business, technology organization. Not that that is, not that that's a contentious relationship, but what often happens is, it is the job of somebody in the newsroom to be able to report the news and to be able to present that news as effectively as possible to their readers as quickly as they can. if you think about any organization, you think about CNN, you think about WAPO, you think about the New York Times, The difference between, reporting on, The kinds of things that are happening in the world today in the next two minutes versus the next 20 minutes is everything. So that need to be able to meet the news and move with the news is really, really critical. And then on the engineering side, if I just approached and didn't have any background in that, didn't understand how important it was to be able to say, like I've talked to partners in the newsroom during an election year and they've said like, I was like, what kind of availability do you need? It's at 99. 9, 99. 99, they're like, how about 100? And you're like, well, what do you mean? It's like, no, but what if we're down for 5 minutes when the Supreme Court makes its ruling? Or something like that. We cannot afford any downtime. The answer is 100%. You have to be able to have, you have to be able to engage in dialogue there.

Conor Bronsdon: 29:39

And that is tension, as you point out.

David Yee: 29:41

That is a tension, right? Okay, I get it. We need to be up when the Supreme Court makes its ruling. That doesn't mean that our systems need 100 percent uptime. It means that we have to find ways to be able to meet our readers and consumers in the ways. that can follow the news, even accounting for the possibility that some system or another might be down. You can design a system accordingly with that, but you have to be able to have that conversation and that tension in play. when I think about, The unique challenges of media engineering, it relates to how an organization came to be. So the example I always give is that at Vox, Vox Media more or less started as a product organization, started as a technology organization, and it really started with sports blogs. So we're going to make it possible for fans of the Cardinals to be able to write about games, alongside the journalists who cover those games. and so it was effectively a product organization. You add a bunch of sites like Vox. com and The Verge and Eater and all of them. and so what you effectively have is newsrooms that are built on top of a product organization. The New York Times is very different. You're talking about like a century and a half of journalism and of a newsroom that is sort of steeped in tradition and systems and a newsroom that talks in systems and you've got a technology organization built on top of that newsroom and

Conor Bronsdon: 31:09

And to the New York Times is credit. The New York Times is held up as a paragon of a successful digital transformation. Yeah. Into this era. But to your point, there's this massive. Cultural foundation that's already been laid over 150 years.

David Yee: 31:23

Yeah. And that cultural foundation also is an operational foundation. And so at Vox you were able to say, this is how software works, this is how technology works. How would you tell the news in that context? And in the New York Times, it's like we have built. A tradition from over a century of how to report the news. Yeah. So then how does technology meet? That is very, very different tension and it creates a very different shadow.

Conor Bronsdon: 31:50

I'm a big fan of the acquired podcast, which does like breakdowns of businesses and they did a really interesting episode for me as someone who, you know, I'm, I don't work at the New York Times, but they did a whole breakdown of the New York Times as transformation into digital organization. Yeah. And it was. It was fascinating to think about, and particularly in the context now of rethinking about it through, uh, the Shadoworg piece, because I can only imagine the amount of... Institutional thought processes and culture and ideas that have developed and some of that has been calcified and like, this is how we operate. I'm sure some of it is, you know, tribal knowledge too and like, oh, this is how we adjust that and making that transition to, okay, now we are extremely digitally transformed. We have applications, we have, you know, made purchases. We have a massive digital subscriber base, must bring a host of challenges.

David Yee: 32:43

It does. I mean, it does bring a lot of challenges. At the same time, I think what I've witnessed as this has unfolded is the willingness of the organization to meet those challenges. Which is not to say that it's easy, or that people are comfortable with it, but we have an executive editor who is relatively new to his role, he was sended to that role, but before that, like, we were working directly with this executive editor to figure out What is the role of technology in telling the stories of the New York Times? The fact that we are in the position we are in right now as a business, with the digital subscription model that we have, is a testament to how flexible the organization has been to be able to say, you know what, we have to be able to figure out how to integrate these two different cultures, these two different businesses, and these two different conceptions of the New York Times. So, you know, you asked me earlier like, who's doing it well, like I'm not, I'm, I'm not here saying that it's, that it's perfect or easy. We're doing pretty well. We're, I'm just saying, you know, New York Times reconciles, its shadow pretty straightforwardly. There's always gonna be something that's gonna piss you off. There's always gonna be something that gets in the way. Those, and, and I say this in the talk, like there is no perfect reconciliation. There is no perfect resolution. The work is ongoing and the talk is Titled shadow work. And so it is an constantly evolving

Conor Bronsdon: 33:58

process.Thank you for taking the time to dive into this with me. I, I've really enjoyed the conversation and it has, I think, opened up some new thought avenues for me. I I really appreciate you coming to Upon podcast to talk about it with us. If you are a listener and you wanted to follow along with David, where can you find him?

David Yee: 34:17

Yeah, so in the roiling hellscape of social media, I've sort of pulled sharply back from the company, the company known as Twitter, but like my handle there and in a lot of places is tangentialism, which is like a handle I came up with when I was in my 20s. So that's, that's, that is what it is. So you find me there, but I actually post a lot on Mastodon. And so if you're looking for me on Mastodon, you can look for at David at yee, Y E E dot camp, C A M P. and that's where I do most of my writing now.

Conor Bronsdon: 34:47

Fantastic. Uh, David, I've really enjoyed this conversation. Thanks so much for coming on the podcast. And, uh, if you want more insights from leaders like David, you can check out our sub stack at dev opted dot sub David, thanks for coming on.

David Yee: 34:59

Thanks for having me.