The Exchanges

Q Can you potentially bring it to life by explaining what shared values looked like in the context of maybe Dropbox and what is shared values look like in the context of frame?

A Yeah. So I can talk about in Dropbox, a shared value and a value that wasn't shared. So in Dropbox, there were a couple of shared engineering values. I mean, there's sort of the values that Dropbox talks about, but like the engineering culture at Dropbox is one fundamentally built around scale, you know, and, and being at a really large scale with a relatively small team and trust and privacy. Like Dropbox like takes data retention and data privacy incredibly seriously. And you never speculate about some other team is doing this. Like there's no other team that's going to be like sneaking looks at the data or, you know, doing a creep creepily trained AI model, or it just doesn't come up. You never ask is this person doing this for, for sort of reasons that aren't aligned with that values around trust and privacy. A value that wasn't shared at all was the idea that you could build products and that would change the direction of the company. You know, Dropbox had built one product once. It had been very successful. It had gotten more successful by keeping that product scaling up with demand. And there was a real skepticism that a second product could ever emerge from the company. And when you showed up and said, Hey, I'm going to build something new. They're like, you're just trying to build an empire, aren't you? Which didn't come up at all when you said, Hey, I need to access t…

AI assessment note: “in Dropbox, there were a couple of shared engineering values”

Q Can you talk more about when you use the word coaching, what you mean by it?

A So I, I don't mean what you might be taught to do as sort of part of like a formal coaching education, which I feel like the heart of that is not giving people answers. It's asking questions and not giving them answers. So I don't do that. Get curious is my single most commonly repeated piece of advice to people. I spend a lot of time being really curious and asking people a lot of questions and then asking them how they're going to deal with the problems that they've identified. And then talking about a couple of different approaches that might work and asking them to maybe try it. Like that's, that's the simplicity of the practice. You know, I had a one-on-one with EM today where they're like, look at, I'm thinking about assigning ownership areas to everyone on my squad so that, you know, we know how to route bugs. And I'm like, cool. You know, this is the thing that's been tried about a million times before an engineering org. Some things are going to work well, some things are not going to work well. You know, what are you concerned about with doing that? And what's the problem you're trying to solve? And what are you going to do when JP goes on vacation? You know, it's just that that's coaching. Um, and I tend to do it both at work and also outside of work. I mean, I do a fair amount of advising and I do coaching when I'm in between gigs. And I'd say it's probably just my …

AI assessment note: “I spend a lot of time being really curious and asking people a lot of questions”

Q Can you talk a little bit more about capacity building?

A Sure. I mean, you know, you think about the capacity of your organization to produce a thing, to have a, have a result. What are the ways that you increase capacity? You increase the skills of the people, you improve the system under which they operate, so the tools and practices they operate, you grow the team, and those are kind of your tools, like those are kind of your levers. And so you can either skill up the individuals, you can improve the environment in which they're operating, or you can hire additional people, and that's how you grow capacity. And ideally, you're doing some mix of all of those, and different parts of your organization probably need different ones. But, you know, at the end of the day, you have An organization, which is highly effective. And then for me, now that I've been doing this now, my first engineering management job was almost 25 years ago. I kind of think of myself as like increasing the capacity for the industry.

AI assessment note: “What are the ways that you increase capacity? You increase the skills of the people”

Q An interesting place to end would be, I'm really curious, given what you shared in our conversation, what are the things that have influenced your thinking on these topics the most? Maybe that are potentially unrelated to engineering management. If there are specific things that You found a lot of inspiration in.

A I mean, I would say that the first inspiration is not engineering management, but just software engineering, you know, and just going back to that feeling of being a software engineer at the start of my career and what it felt like and the agency that came with that work. Cause you know, I was doing it at a time when the web was brand new and I was dropping out of college to do my own startup and just the discovery and joy and fun of that work. And so that, that, that is a, that is a bedrock is, is that experience of what this can be like at a very different time and phase and maturity of the organization. You know, the other piece, uh, you know, part of my secret weapon is both my parents manage, you know, both my parents are executive directors of nonprofits and seeing the way they worked and the way they worked with volunteers and the way they worked with boards and, you know, talking about that with them over the years is just, I think, Brought a set of management practices from a industry that's been around longer, um, and has a different set of challenges and constraints. But I will say, particularly when the, when the industry is on an upswing, there is something similar to managing volunteers and managing engineers, even though you're paying the engineers a lot of money to do it. Um, so that was pretty key. And, you know, I think that the, the other piece is just Being …

AI assessment note: “both my parents are executive directors of nonprofits and seeing the way they worked”

Q a lot of different companies and a number of different market cycles. When you think of About the underpinnings of what it means to run an excellent engineering organization, say, 10 or 15 years ago. What have you become more certain about? And maybe what are things that you once believed that maybe you updated your thinking or you changed the way that you, um, you think about those things?

A Sure. That's a really interesting question. Hit me with the having to remember something from 10 to 15 years ago. You know, I, I will say that I've always approached the work with curiosity, so it's, it's constantly changing, so there's not sort of a bifurcation. I like to think that that means that it's always been, uh, relatively correct because it was based on data, but no, that's a really interesting question. I mean, so I would say that the things that haven't changed are, I mean, the things that make software possible are like small teams, high degrees of clarity, lots of trust, Good communication. Iteration. Customer focus. Like these are the things that we kind of already knew 10 to 15 years ago. They're still true. They're still hard. And I think that's kind of a reoccurring theme of a lot of this stuff is just because you know the answer doesn't mean it gets easier to do. But as of what's changed, I mean, certainly we are embracing larger teams these days and Having to think more creatively about how we handle the complications and concurrency that brings to our teams, and I think that's a thing where my thinking has evolved over the years to sort of be some of the value as well as the downsides. Flickr was very famously a team of 20 people, and we never wanted to get larger than 20, which meant that once people started leaving, we didn't have a lot of resilience, and…

AI assessment note: “things that haven't changed are... But as of what's changed, I mean”

Q So you're sort of getting at this, but what is creating clarity and setting goals in the context of an engineering team look like when done well?

A I mean, the first, it has to be simple. And the second is You have to be willing to sit with people while they poke holes in it and ask why, because that's what engineers do. And so it's a simple message. It looks measurable. People are going to want to poke holes in it and ask questions. I have a nine year old, so it's a little bit like, you know, she keeps finding, keeps taking what I tell her literally and wants to like turn that around on me. It's a little bit like that. And so that's the work. You go out and there's the things that come up every time. Okay, but what do you want me to do if the site's in danger? Or what do you want me to do about tech debt? And we can talk about that. How do I find time to do these other things? And so you just got to layer that in there and layer that in there starting again at the cultural level. Look, we should be making things better every day. You know, we care about developer experience. We care about the customers, you know, the customer experience every day. When you start laying those things in there over something like predictability, over something like Doing what you committed to. And you get to the end of that, sort of all those other things that you're putting in your budget, and you may not have a lot left. And that's the other piece about engineering leadership is if you're trying to build a new product, you need to start fa…

AI assessment note: “the first, it has to be simple. And the second is You have to be willing”