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Become an Effective Software Engineering Manager

James Stanier • Gergely Orosz | Gotopia Bookclub Episode • January 2024

Software startups make global headlines every day. As technology companies succeed and grow, so do their engineering departments. In your career, you’ll may suddenly get the opportunity to lead teams: to become a manager. But this is often uncharted territory. How do you decide whether this career move is right for you? And if you do, what do you need to learn to succeed? Where do you start? How do you know that you’re doing it right? What does “it” even mean? And isn’t management a dirty word? This book will share the secrets you need to know to manage engineers successfully.

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Software startups make global headlines every day. As technology companies succeed and grow, so do their engineering departments.

In your career, you’ll may suddenly get the opportunity to lead teams: to become a manager. But this is often uncharted territory. How do you decide whether this career move is right for you? And if you do, what do you need to learn to succeed? Where do you start? How do you know that you’re doing it right? What does “it” even mean? And isn’t management a dirty word?

This book will share the secrets you need to know to manage engineers successfully.
Join James Stanier, currently director of engineering at Shopify, and author of"Become an Effective Software Engineering Manager.” as he discusses all of the above and more with Gergely Orosz.

The Real Stories Behind the Book

James Stanier: My name is James Stanier, currently director of engineering at Shopify, and I wrote a book, which is I think what we're talking about today, called "Become an Effective Software Engineering Manager." And yep, there we go. That's the one. It's the one with the flock of birds on the front. Nice to be here, have a chat.

Gergely Orosz: Yeah. And, I'm interviewing James. I'm Gergely Orosz. I write "The Pragmatic Engineer." Before that, I was a software engineer, and then an engineering manager, and I've also just recently published my first longer paperback book, called "The Software Engineer's Guidebook," so I guess we have author-to-author here. But today, we're going to be talking about "Become an Effective Software Engineering Manager." This is a book that I had the privilege to read a little bit before it was out, and I believe, yep, I'm on the back of this, with my recommendations. So, a book that I really liked from the start, and I'll just kick on with why I like the book.

A very, kind of, typical part of the book is any chapter that you open, what I like is it starts with a story. And for example, there's a chapter...there's a "Humans is Hard" chapter, which is, I'm just checking, Chapter 10, it's called "Humans Is Hard," and when I open that chapter, it starts with this story of you're a manager, or maybe even a director, whatever, and your manager, so, your boss, is upset with you because your team has not been delivering for six months, and they're telling you you're not working hard enough. There's a story, you're kind of, like, almost feeling yourself in the shoes. I've luckily not been in this situation, but I've seen other managers be in this situation. Then the book goes into, like, all right, how did we get here, and how do we fix it? For example, when this chapter goes into explaining that, as a manager, you're under way more scrutiny, both from the people that you work with and your management. It goes into, the upper you go, the more wobbly things are. You just need to balance all these things, and that, as a manager, for example, your team is behind schedule, now what do you do? Do you use the whip to tell people "We're gonna work more," or do use motivation?

The book is just, like, I feel, you know, this chapter was really, it's one of those things where, even though I've not been in that situation, that specific one, as a former manager, I, well, at the time I was a manager, I just empathize with it. And every single chapter, I like how it pulls you into this, like, real situation. So, I wanted to start to ask you about that. Like, were these real situations, or were there ones that happened to you, or ones that you observed? Because they feel super real-life.

James Stanier: Yes. I think they all did happen, obviously not exactly as they're written, but the thing that I noticed in sort of my early years as a manager is that there were just these patterns that you notice. It's the same as writing software. There are software patterns. There are also patterns of organizational function, or even dysfunction, that you find yourself in, time and time again, and I think the way that the book was constructed was to try and make sense of those patterns that I'd seen and experienced, and talk to other people who's also seen and experienced them. And then try to extract frameworks or tools out of those situations, that are then generally applicable to people going forward, because I think the whole way the book was put together was, "Here's a whole bunch of stuff that I've experienced. Here's how I think if I knew this beforehand, I would handle it better." And the book was a process of kind of committing that to paper as I went through.

Gergely Orosz: And what are some, like, frameworks and tools that you mentioned? Like, what ones that maybe are a bit more memorable for you?

James Stanier: Yeah. You mentioned a few there. So, the one was the kind of, wobble analogy. And if you think of an org chart, and the kind of the pyramid shape, and then you think of, like, a jelly, for our European folks, or a Jello for our American folks, kind of superimposed over the org chart, you know that if you sort of poke the jelly at the bottom, it doesn't really wobble very much, because it's at the bottom. So, like, little crises can be contained in teams quite well, without needing too much effort. But the higher the org chart goes, and the higher up the top you are, just one tiny little prod can send the entire organization going crazy. So, for example, if a CEO gets involved in something, and then suddenly there's a burning issue, the whole org chart just goes all over the place, and it all wobbles, and it's all a mess. So, I think what I've tried to do is just kind of extract all these little metaphors and analogies that I think are quite easily memorable, so that you can think, "Ah, okay. This applies to this situation going forward."

Gergely Orosz: How did you get about writing this book? You mentioned you're a director of engineering right now, at Shopify, but I guess, related to this is both how you wrote the book, but how you became a manager, and pick up these interesting lessons that are now in the book in a more condensable format.

James Stanier: It was pre-Shopify that I wrote this book. So, I've been at Shopify for a few years, and I think I finished this three years ago now. So, this was very much written during my journey to get into management. Four years before the book, as I first became a manager, and I'll talk a little bit about that in a second, I just was trying to synthesize what I was learning. I think back then, which was probably 10 years ago now, there just wasn't the same amount of books or blogs or newsletters out there that were there as an example of how to be a good manager. So, I was reading around as much as I could, but a lot of the information was either very autobiographical, it's kinda like, "Here's a book on Steve Jobs," and, like, I'm not Steve Jobs. Or "Here's a book on Jack Welch," or whatever. It's like, I'm not running General Electric. Or they were very sort of pie-in-the-sky, very abstract.

Gergely Orosz: That's the, I think that book was the, either the Jack Welch one, and there's the other one that's very often recommended. The one, I forget the name. I think it's not on GE, but there's also one, it's a managerial book. It'll come to me later, but yes. But they're very old books, and they're non-tech companies. They're kind of more traditional management books.

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James Stanier: Absolutely. And I think the only one that connected with me in the early period, which, was when I was trying to learn the ropes... And I'll tell you, rewind a bit. So, I was in this startup called Brandwatch, which, we successfully exited, 10 years later. It took a long time. But I was there just after the seed round, and I joined, just, a period where everyone reported to the CTO because there weren't enough engineers. And then when we had the seed funding, and then some Series A funding, it was, okay, we need to grow the engineering department. And I always remember, when I joined, I ended up reporting to the guy who was effectively a principal engineer, and I remember the first ever time that we sat together him telling me, "I don't understand why I'm a manager. I was sort of just told I'm the most experienced person here, so I need to manage everybody." So, I think the company was working itself out as it was growing, and I think I was just very interested in, okay, well this feels like this isn't how it should be. And then I wanted to do a good job of management, and then I did a lot of reading, and then I sort of placed myself, as we grew, to say, "Hey, I'm interested in management as a craft, and I think, leading on from that, you know, how do we define career tracks, the dual ladders of management and individual contributors," all of these things started to sort of come out. And back to your question about where the book came from, well, I started writing a blog post once a week, which was effectively just on my website, trying to synthesize what I was learning as I was reading.

Gergely Orosz: And this is theengineeringmanager.com, right?

James Stanier: That's correct. I think it came from the typical way that it works with techie people, which was when I saw that the domain was available, I bought the domain, and then I decided to write the blog. But the intention was there, to try and write something once a week, just something small, just what I was learning. And I think, in terms of audience, I didn't have that as front-of-mind when I was doing it. I had a few colleagues who were just interested in what I was reading, and I thought that if I could write some stuff that maybe just five of my colleagues would read, that would be a success. And I only really cared about that. And, yeah. Just wrote every single week, trying to get better at writing, get better at synthesizing what I knew, and then, slowly, I saw that posts would be picked up on Hacker News, and it kind of just very organically grew. So, it was nice. And, to answer your question, finally, sorry, the book, when I'd written the blog for years, I sort of stepped back and looked at everything that I'd written, and started to sort of categorize it all together, and sort of, okay, there's a sketch of what could be a book here, and I wrote to a few publishers. So, I wrote to Manning, wrote to Pragmatic Programmers, and I got on very well with the Prag Prog folks, and they offered me the chance, and went from there.

Gergely Orosz: How long did it take to write the book? So, you already had a lot of ideas in the blog posts, right?

James Stanier: I'd say that the material was there. So, if you put all the blog...if you imagine printing out all the blog posts side-by-side, you probably had about half a book. But the thing that took the time was making it all flow as one coherent narrative, and I think, as a fellow author, you will sympathize with that.

Gergely Orosz: Yes, very much.

James Stanier: People just go, "Oh, you stitched the blog posts together."

Gergely Orosz: I think this is the thing that, it's hard to maybe empathize with, or see until you write it because the book does flow well. I like that. You know, the book has, do you have four parts or three parts?

James Stanier: I think there's three main parts, yeah.

Gergely Orosz: No, it's three main parts. There's a bit more of an introduction of a, like, general stuff orientation. There is working with individuals, which is more of the line manager part, and then the bigger picture, which is, feels a bit more like managers of managers and above. So, like, senior EM, and, you know, well, you were, at Brandwatch, in the end, were you a VP of engineering or senior VP of engineering?

James Stanier: I was VP of engineering for the last sort of five years of my time there.

Gergely Orosz: Yeah. Which, I mean, I think this is a nice split, because, like, as, what I found when I was reading the book, I was reading the book when I was already an experienced engineering manager, and I was starting to get my first managers under me. I might've already had a manager under me. And so, for example, for me, you know, the first parts were maybe a bit less relevant, because I've already kind of gone through the one-on-ones, performance management, all that. It was nice to see additional approaches, but the big picture was really useful for me, which is... I've heard from friends who I recommend it to, the engineering managers who are brand-new to this, just really, like, the beginning, and it's kind of nice, but for them, the second part was not as relevant. So, I think it's a good balance because it does similarly cover a lot of it. Did you find writing some parts easier or harder? Because I guess by the time you were writing this, you were more on the lot more experienced side, and further away from the line management side.

James Stanier: I wouldn't say any individual chapters were difficult, but I think that as you've probably also experienced now, like, it takes writing something down to understand whether you know something or not. And you can sometimes feel that you really know something, and then you try to write it, and then you realize you don't know anything about it at all. I think that the one thing that I've taken away from writing books is that it's the way that you understand what you know and what you don't know. And certainly, those latter chapters, I remember when I was writing the one about the dual career tracks, you know, that was all about the time where I think I'd just about put Brandwatch's career tracks on progression.fyi, the career track site. So, I think I was pretty much writing that kind of, like, hand-in-hand.

Journey to an Engineering Manager

Gergely Orosz: By the way, I think this is the only book so far, I might be wrong, I may be missing some, but I haven't seen another book that talks about career tracks and putting them into place. I get this, a lot of questions from people, especially senior managers, or people who are starting as a CTO role at, like, a smaller company, who want to do this thing, and obviously, there's a lot of online resources, but so far this has been the only book. So, it's interesting, because I feel it does go through a lot of the tracks. It's probably helped that you grew with Brandwatch, right? Like, by the end, as context, can you give, like, how small the company was when you joined it, and then, by the time you were kind of finishing this book, how big it was?

James Stanier: When I joined, I think the company in total was about 20 people. And that includes everybody, from CEO, engineers, commercial. And at the time that we exited, it was about 1000 people.

Gergely Orosz: Wow.

James Stanier: So, it was a good size.

Gergely Orosz: So, you went through that growth?

James Stanier: I think, to answer your question as to why I was able to write about it, I think it's essentially because I had the privilege to do that work. And I think that's the one thing that, you know, certainly, now, at a larger company, Shopify, I have influence into these things, but I'm not effectively the decider on what our career tracks are. That is above me now. So, when I wrote this book, I was fortunate to be able to do it.

Gergely Orosz: Well, who knows? So, the person deciding might be reading this book, so you never know. And so, this book launched three years ago, or almost three and a half years ago, in May 2020. What was the reception so far? Because now you've probably got a lot of feedback.

James Stanier: Overwhelmingly positive, actually. I think it's very nice that every in-person conference that I go to, typically I end up meeting someone who says, "Hey, I read your book and it was really helpful." And that's the bizarre thing, and again, I think this is something that you, you know, with your newsletter, is that being able to commit things to paper is just such a bizarre thing, because it introduces you mentally to other people. And you meet someone who's read 350 pages of what you've written, probably understands your ideas better than you do now, because you've kind of forgotten them a bit since you wrote them down. But it connects you with people. And the sales have been brilliant, sort of, like, really nice, meaningful, five-figure sales, and it's just, it's been a really lovely experience, because it's felt that I've connected myself to the world in ways that I don't put myself out there typically. I've never really enjoyed playing the social media influencer game. But, I can write, and I think this is really nice because it's connected me to people in a way that I feel is more genuinely interlinked with my passion.

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Prescriptions versus Tools: Why This Book is Different?

Gergely Orosz: Amazing. I mean, one thing about management books in general is, you know, like, I guess one of the best ways, you've seen this, I've seen this, the best ways to get better at managing is to just do it, and you're gonna make a bunch of mistakes and you're gonna learn, and if you're lucky, and hopefully you are, you either seek out mentors or you have mentors, but, like, it's hard to generalize some of these things, but you still did generalize things here, and I just wanna ask you, like, how prescriptive is this book, and also, how do you feel this book is different to the books that you previously picked up on management as you were becoming a manager? Because clearly, you were trying to do something that didn't exist, and clearly, there's a demand for it so far. So, how is this book different, and how prescriptive is it?

James Stanier: Good question. I think there's a few things in there. I think prescriptiveness, there's a little bit at the beginning. Obviously, the management 101, here's how to run a decent one-to-one, here's how to do a performance review. The very basics, that, sort of, the bottom of the scaffolding of the book, is fairly prescriptive, but it is written in such a way to say "this is one way of doing it."

Gergely Orosz: But by the way, I did like, so, like you mentioned, there's one-on-ones, there's hiring people, there's figuring out how to kind of put people in your team, figuring out the right motivations for the people, and then what I really liked is there's how to deal with people leaving, and also just firing people. I mean, I think this is something that, I mean, no manager signs up to do this, but sometimes you have to. So, like, those parts, I kind of appreciated, that it was a bit prescriptive. Obviously, as you said, it didn't say "this is the only way to go," but it's a bit reassuring. For example, you write that people leaving is normal, like, and because, like, whenever this happens, especially as a first-time manager, I think you just take it personally, even if you're just, like, you become a manager and, like, someone stands up and says, like, "I'm sorry, I'm leaving." So, like, those parts of being, I guess, maybe prescriptive is not the right word, but opinionated, I thought, was very helpful, of, like, okay, this person, or James is thinking that it's okay that people are leaving. I guess, okay, that's good, because I was a bit worried that it's not.

James Stanier: I think it's because, you know, and going back to the motivations for the book in the first place is that typically, and I think there's a strange thing with management in technology, is that everyone enters into the technology industry, typically, because they are either passionate about programming, they've done some education around computer science or programming, and that's their expertise. And then they come in, and then they demonstrate that they're excellent at that thing. And then they get to that career juncture in the career tracks, where they go, "I want to do management." And pretty much everybody has not done a course in management. They've not done any formal education. And I wanted to try and, almost as a curriculum, lay out, here's all of the pieces of the pie that you are gonna be expected to do. And going back to your question about prescriptiveness, the way that it's written is that I've kept myself out of it. It's very much a book about the hero's journey, which is you, as the reader. And that isn't necessarily something that I made up. That's actually why I really like the publisher, because Pragmatic, they want you to write the books like that. It's part of the editorial theme and process.

What I like about the book is I'm not present at all. Obviously, I wrote the words, but it's not about me. I don't care about me. I don't want you to care about me. I want you to care about the ideas. That's me. And I think, as the book goes on, and it gets slightly more abstract, we talk about things like leadership, and strategy, and how we piece together good culture. This is where there are no prescriptions. And I think that something that, again, I really like about books, because they give you the length and the space to explore, is that it acts as a really nice anecdote to, so, antidote rather, to a lot of the blog posts that you see get lots of traction these days, which are very much, "Here's seven things that you need to do to be an amazing manager." "Here's the three things that you shouldn't do." And it's just, as you say, you have to do it. You have to learn. You have to apply your own pattern recognition to situations, and try to work out what to do. So, telling people exactly how to do a good job as a manager is impossible. Every person is different. Every organization is different. And that's what I quite like about the book, is that it recognizes that, and it's like, "Here's a bunch of tools." It's almost like a toolkit that I give to you. Use the tools as you see fit, and here's some guidance.

Gergely Orosz: It's interesting, because I've yet to come across a book... Like, I was wondering why I like, because I really like this book. And I think there are two types of books on management. There's some, again, really good books that are kind of like, all right, here's how you do things. It's opinionated. It kind of lays out different approaches, and it's more of a reference book. And this one, like, I think the difference is, like, as soon as picked up, every charter, as you said, it's not about you as James. In fact, I never thought of James, but I'll just, like, read, like, three sentences from the book, of how, a chapter first, which is chapter two, "Manage Yourself First," and it starts, and it just pitches, like, you, as a reader, and says: "Today started so well. You felt like you ended on a first week high. You'd met your team and your [inaudible 00:20:38] manager, and you'd made notes that you're going to follow this week. You saw good in the world, and the world saw good in you. And then it happened: a production issue that started in your team brought the whole site down." And I'm like, you know, like, suddenly, I just feel like, two things. Either, like, I've actually been in this situation. Like, I come in, it's a great day, and then it just blows up. It's an outage, production issue, and I'm the manager of the team, so now it's my problem and my responsibility. And of course, the book goes on with this.

But there's also situations that never happened with me, and I'm reading it, for example, the one that I talked about, where your manager, let's say the VP of engineering, walks up to you and saying, like, "What is your team doing? We are behind schedule. We need to get this out. Are you guys lazy or what? Like, you've been on this for four months. This is not acceptable. It should have been done in a week. Like, I talk with someone else." And so, I like how it, like, I feel it just by, even if someone just reads the introduction of the book, of these, like, I think 20-something chapters, you just get an empathy of what it's like to be a manager, even if you're not a manager, by the way. I think this is a great way to think, like, do you wanna be a manager? Because these are situations you're eventually gonna find yourself into. But more importantly, like, every introduction of these chapters just made me pause a little bit, and think about, because it is a real situation, and it feels that it's about me, as the reader. So I think that was a really smart choice. And you said this was not your choice. You said this was help from the publisher, or how did you come up with this? Because this is a very consistent structure, and I think this is one of the, I guess, trademarks of your book, if I even might say so.

James Stanier: I mean, the story at the beginning of the chapter thing was my idea, for sure. The hero's journey, as how it's generally written, is definitely the publisher. I did have to pitch them this idea, of, like, some stories, and I can understand why initially the publisher was, "Are you sure?" Because, I mean, engineers probably aren't the best fiction writers in the world, but I think I sort of managed to pull it off.

Gergely Orosz: I feel it's not fiction. I feel it's a bit like Silicon Valley, when you watch the series. It's actually just real-world. Like, if you've been there, you're like, "Yeah, this actually happened."

James Stanier: There's a bunch of jokes. There's little Easter eggs in it. There are little Easter eggs throughout the books, like the illustrations, you know, got my dog in there a few times, if you notice. Some of the names of the people in the diagrams are the people in my family and so on. So, there's lots of little nice touches I throw at it.

Getting Into Management: How to Make It Happen?

Gergely Orosz: Nice. So, one of the things I think this book is wonderful for is people who are just new into management or just getting into management. But can we talk a little bit about that? I mean, you're an experienced manager. You actually helped a lot of people get into management. If someone is listening now and they're thinking, "Hmm, I actually wanna become a manager one day," you know, like, maybe in a few months or a few years, how do you make it happen, based on your experience?

James Stanier: That's a good question. So, we've already mentioned that if you happen to join a startup in the earlier days, then if you haven't had experience with it before, you have this wonderful environment around you where lots and lots of people are coming in, and these positions will get created, and you do have a chance. And certainly, I guess we'll touch on the current mood and economy at the moment, where there are limited positions in our industry, where trusting sort of an outsider to come in as a manager with no prior experience rarely ever happens. So, certainly, if you're looking for it, try and get into a company that is growing, or will grow, because those slots will open up. And if you've already demonstrated that you're good at your job, and you've demonstrated leadership, and the ability to get things done, and you're reliable and trustworthy, and you have great rapport and all that kind of thing, then you can step into those roles as they occur.

I think the one thing that is important, though, which is something that we did at Brandwatch, and also we do it at Shopify too, which is that, if someone is definitely high-growth, and really is intentionally wanting to get into management, you can basically come up with a safety net, to say, "Hey, like, why don't we do this for some fixed period of time," maybe six months, maybe a year, because I think some people do get worried that, say you're a senior engineer, and you know that you're pretty much on the route to being promoted and you get to choose, you're worried about that choice being a one-way gate. Where, if, for example, you go into a management role, and either you really dislike it, or maybe you're not as good at it as you think you would be, you get worried that you're gonna lose your job. And what you have to do is, if you're in the position to create an environment where that doesn't have to be the case, but hey, try this out. If it works, then fantastic. If not, then we can always hire externally or give the role to somebody else. Because I think you can switch back and forth on the tracks, and it's not seen as a failure.

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Gergely Orosz: You're talking this from perspective of the decision maker, the manager who is creating this position. But, would you recommend, as someone who is being offered, like, okay, you know, I'm a senior engineer. My manager said, like, "Hey, Bob, I think you're ready to go into management," would you recommend, if they don't offer this up front that we're gonna create a safety net, would you recommend negotiating something like this, saying, like, "Look, I'm open to this, but can we try to figure out a safety net? What happens if it turns out either I'm not as good, or this just really doesn't resonate with me?"

James Stanier: Definitely speak about it. I mean, it's for the good of the organization after all, for that to be the case. Because if it doesn't work out, and you get the chance to go back to being a fantastic individual contributor, then the organization wins either way.

Gergely Orosz: Yeah. I think more and more places are seeing it like this, so I've definitely seen these things. I used to work at Uber, and Uber, at some point, did not have the best reputation in terms of the perception of the company or how things were. But I will say this, Uber has always had a safe path back from being a manager. So, they...in fact, Uber actually, like, contrary to popular belief, they're one of the first companies that I've seen to get into,maybe Facebook, who have an apprentice management program. So, that means that when someone becomes an engineering manager, they get dedicated training, they have a cohort of first-time managers, and then they have a support group, which I just very rarely see, which, again, the irony is strong on this one, because this actually happened not as a result of the negative press. This was there even beforehand.

So, I guess it is just, like, you know, if Uber did this, then there's... It is harder to do for smaller organizations, but at a larger organization, it is very useful to do them. And what I have found work well is having this apprentice manager title, which is a safety net itself. It means you're not yet a manager. You're in this, like, transitionary title, and in the end, you're either graduate, or you will go back to where you were. And again, it might feel a little degrading. I was an apprentice manager at Uber, and at first I was like, "Oh, why am I not a real manager?" But then I realized later that this was a safety net, because there were some people who went back from apprentice manager to software engineer, and it was not a stigma. So, I think like playing with those titles could be interesting as well.

James Stanier: Yeah. That's fantastic. I didn't know about that. That's a really good idea.

Trends in Engineering Management

Gergely Orosz: And let's talk about management right now, in 2023, or almost, like, coming up 2024. How are you seeing the world's changing? You're obviously working at an organization, but even more so, you're talking with a lot of other managers, with peers in the industry. Are we seeing more demand for managers, less demand for managers? Are the skill sets changing? And maybe let's focus initially on just line managers, and then we can expand into managers of managers.

James Stanier: I think it's clear that since the pandemic ended, we've had economic woes across the board, in many different ways, and we've seen many large companies, tech companies, firing many people in layoffs. It's been pretty tragic, and that means that now we have organizations that are not growing. And the one thing that is tricky about management is that you need people to manage, and that's just how it is. So, if these organizations are not growing, then there's only the amount of managers that the org can produce, and I think also we've seen, during these rounds of layoffs that have happened in many different places, that we're trying to also make sure that managers have enough people, and this has been quite challenging because, during a heavy growth period, you're putting managers in place and you're slowly building up teams around them, and then that all stops. And then you end up managers with, have two direct reports, three direct reports.

I think there's been a consolidation of trying to make sure that, look, we all need managers. They're essential. But we want to make sure that they have sizable teams that can get things done, clear purposes, and so on. So, skill sets, I think also, is an important thing, because the last, what, 15 years has been, like, the longest bull market that we've had forever, where it felt like if you were in the right companies in the right time, everything's always growing all of the time. And in terms of bad news that you have to deal with, okay, your project might get canceled or it might pivot. Maybe some people will leave your team. Maybe there'll just be some general sort of work-related stress, but very few managers from the earlier generations have yet to go through a downturn like we have, where you have to deal with layoffs, you have to deal with budget cuts, doing more with less, all of this kind of consolidation stuff. 

Gergely Orosz: Well, and I guess, interesting enough, like, not just dealing with you laying off part of your team, but you laying, like, I think it's important to recognize that, like you said, the jelly, wobbly, the higher up you are, the more wobbly your position, so a lot of times, like, for example, when we had layoffs at Uber, they asked me, like, if, I mean, it was not as direct, and we were in Amsterdam, where that you cannot pick and choose who to let go. But they still asked me, like, if you had to let go 25% of your team, who would it be? And I just said very clearly, like, okay, well, it will be these people, and it would be them because they're the latest joiners, and I don't have anyone on performance issues.

But then, I was thinking, like, what they didn't ask me is about me, because a lot of times, the manager, you know, like, when these things happen, often you help the company become more efficient, but then your role might become inefficient. In fact, I also know, like, some companies who, for example, let go of the middle management layer, at a scale-up. So, I feel there's that, this is type of stress that no one really prepared you for it, and again, like, not to downplay the stress that individual contributors, but I think as managers, you have more information and more stress to deal with, and especially during a downturn, I feel that stress really, really gets on you. Like, at Uber, I remember, after the layoffs, most managers were not impacted, but most managers left. And I keep in touch with some of them, and it was just a lot of stress. I don't think anyone was ready for this. So, like, given that we have seen this market, and hopefully it'll turn around, but let's assume that it'll stay how it is, like, what are some strategies that you could suggest for managers, new or existing ones, to cope with this a little bit better, and to find ways to maybe reduce the stress on yourself, have a bit better wellbeing? Because that's something I don't really see managers focus as much. I think on your book, you touch a little bit about this, but I'm not sure how much.

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James Stanier: Yes. I speak] a little bit about that, especially in the sort of parts around stoicism, and, like, understanding what you can control and what you can't control. And I think that, I mean, in terms of strategies for managers in this environment, I mean, I think one thing, in the course of an entire career in technology, I think it's highly likely that everybody, and I would probably put myself in that bucket as well, may get let go somewhere at some point. Because it's not in your control. It's not necessarily something you've done. It's just, it can happen. That's the downside of our industry. It can be very high-growth, but also very high opposite of growth, degrowth.

Gergely Orosz: It's volatile, right?

James Stanier: It's volatile. And so, it's never your fault. That doesn't make it any more easy to deal with, but I think you always have to remember that it's not on you. So, strategies are, I mean, obviously, from an individual level, always try and make sure that you are doing high-value work, and you're doing a great job. That's all the baseline. I think I've seen some managers being very open about saying, "Hey, like if anything happened, I'm really happy to go back to doing individual contributor work. I'm still super high-context. I understand all the systems we work on. I can write code. Like, don't see me as just a manager. I can do whatever you need." So, having the ability to be a manager but still be close to the details, to still really understand what the team's building, to contribute code if you can, like, that's all great as well, because it gives you different paths.

Going back to the more sort of philosophical side, you just have to understand that there are things that you can control, there are things that you can't, and for the things that you can't, you just have to try your best, and set yourself internal goals, where you're like, "In this situation, I'm gonna do the best for my team. We're gonna build the best software we can. We're gonna hit all of those goals that we can control, and the wider thing is just not under our control." And if it isn't, you just have to learn to let go. And that's really challenging, and it goes through the whole of life, right? It's not just work.

Gergely Orosz: I guess maybe one thing I would add is, like, during the good times or even the decent times, like, we do work in technology, which is a pretty good sector, in many ways, in terms of the flexibility of work, the fact that many of us can work either partially or full remote. Compensation is often, compared to other industries, just pretty decent, when I look at my peers who graduated high school at the different industries. So, like, based on this, like, building a nest egg, or putting aside some, a bit of a safety net, because it is volatile, right? It can be very good, and then at some point, it for a short time, hopefully, it can drop. But I feel just having that safety net, it just gives a peace of mind, because yeah, as you said, the reality is, again, unfortunately, I've seen this, you know, people, like, very specifically at Uber, have joined, and COVID hit. The company had to have layoffs. Like, I saw the numbers. This was not one of those, the stockholders are doing something. It was actually just, like, revenue was going to zero, like, literally, like, on the graphs. So the company had to let people go, and those were people, in my case, who have recently joined, but they obviously joined with high hopes, and most of them, in fact, I think everyone I know, within a few months, they were back in a different position, but I'm just going to assume that the ones that did have a bit of a safety net of a few months, they were probably just a lot less stressed, and a lot more picky in getting up in whatever that next role is. So, that's probably something that we should all remember, that, like, when it's good times, it's good to, like, I feel until now, we've always assumed it will be good times. Now it's a bit of, you know, not as good, but it just goes up and down, so just save up where you can.

James Stanier: Yeah, I completely agree. There's, like, basic sort of personal finance things, where, if you are fortunate to get a good job in technology that pays well, don't spend that much money, you know? Save it. Put it aside. See if you can get three months of emergency savings, six months of emergency savings, maybe even a year, where you give yourself that safety net, so that you can definitely ride out any bad times. Don't get that promotion or that new job, and then suddenly buy a house that's twice as big, and assume you've got that pay forever. Never do that, ever.

Three Must-Have Tools in Management

Gergely Orosz: That's good advice. So, can we just touch on, like, three of your favorite ideas in the book, that you go through, that are maybe unique to this book, or, well, unique to you?

James Stanier: I guess the first one that comes to mind is the diagram around delegation. And delegation is such an interesting thing, because it sounds very basic. It's kind of like, give someone some stuff to do and they'll do it. But I think that's where managers get that wrong a lot, because delegation is kind of an art, and it's sort of a gradual spectrum, where, fundamentally, yes you are giving people things to do, but the important thing is, as a manager, that you are still accountable for those things getting done. And I think that's where managers can sometimes get it wrong, and they abdicate. They just give things to their staff, and then just abdicate all responsibility and accountability to them. Fundamentally, managing well is always remaining accountable for everything in your organization that you've delegated out. And the way that you delegate also, it depends on how skilled or experienced or high-context the individual is. If someone's extremely skilled, then you can delegate a thing to them. They'll tell you when it's done.

Gergely Orosz: And I'm just showing the diagram...

James Stanier: The spectrum is there. 

Gergely Orosz: ...that you were talking about. This is the delegation spectrum. It's a bit hard to see here, but I feel, in an image, it kind of explains what you just did, but with a glance, basically, like, how much you delegate and how much control you have.

James Stanier: I come back to that all the time. I've used that as a coaching point in my staff over and over again since I wrote that book. Another one. Contracting is something I learned from some management training we did at Brandwatch, which was great. And it's all to do with that kind of, like, awkward first few times that you meet new staff or even your own manager. This works upward as well. But, how can you, at the beginning of a management relationship, spend some time with someone to understand what is it that they want from you? What do you want from them? What are some of the ways that it can work well? What are some of the ways that it could go wrong? And also, how can you let each other know when there's a problem? And then it just sort of, at the beginning of a relationship, just by preparing some answers to those questions and sharing them, you can understand, like, what you both need or want from each other, and how you can sort of frame and build scaffolding around your relationship so it's successful going forward.

Gergely Orosz: So, you called as a contracting exercise, so I guess, is it a bit of a getting to know how the other person works, preferences, etc., in what sounds like is a little bit more formal way, that can also be just very efficient, right? Or helpful?

James Stanier: It's sort of almost like a manager read me type thing, collaboratively together, where you understand how they work, you understand how you work, and you share, and you try and, ahead of time, spot ways in which you may have friction or ways that you can work together really well. And it does look kind of formal, but I've done it with every member of staff that I've had since I wrote the book. It's really useful.

Gergely Orosz: I guess it is one of those things which, like, I feel a lot of managers, like, "Ahh, that sounds, like, very, ahh, you know, old school, or formal," or, like, again, like, I think as engineering managers, we wanna think of ourselves as cool, and approachable, but you've said you've done it, so, like, okay. Well, I guess, if you're a manager listening, either check the book or just as we describe it, I don't think you need the book specifically for this. You can try it out, and probably, hopefully, be surprised.

James Stanier: It's on the blog as well, so I can stick a link in the description.

Gergely Orosz: Awesome. We'll have a link there.

James Stanier: And we already touched on it, just as the last thing, was the sort of the stoicism part, which, there's a really good book called "The Ancient Art of Stoic Joy," which, by William B. Irvine, I think it's called, like, "How to Live Well," and it just dives into sort of the trichotomy of control, which is, like, three things, like, the things that you control, the things that you don't, and then the things where you have some influence, and you can try your best. And I think that very much sums up what it's like to be a manager because you kind of exist in this kind of vortex of things that you definitely can control, amongst a whole whirlwind of things that you don't. And really, just understanding what you can affect.

Gergely Orosz: So, is this about just, like, so I also get it, like, it's just, like, acknowledging what are things that you cannot control, and, like, not being stressed out about it, like, and focusing on the things that you can control, which might help influence some of the other things, but ultimately it's not your decision. 

James Stanier: Absolutely. It's seeking clarity throughout all of that. It's like, how do you lead a team confidently, and work on a team confidently, in a way that shows that you are in control of everything that you can be in control with, but knowing that fundamentally, things can happen that have nothing to do with you. Anyway, we touched upon the economy.

Gergely Orosz: I think this is a good one. I just recently talked with a VP of engineering whose company was acquired, and he was telling me that the next day, the new company is going to decide who to fire, and, well, because M&A went through, and they're gonna fire, like, 10% of staff or something like that. This was known. He didn't know, like, how much of his team would be fired exactly, and if he would be fired. And I was asking, like, "Are you worried?" And he said, like, "Well, I am a bit worried, but my grandma told me that worrying is just moving back and forth, but not going anywhere." And I was thinking, wow, that's so apt. So, he was like, "Look, I'm trying not to worry because it's out of my control," but I feel as a manager, a big part of the challenges that I've seen is there's just, you get so much information, and you start to worry about so many things. For example, again, you know, like, the negative thing is layoffs, when layoffs are coming, and this is happening. But even the positive, with promotions, you know, like, we had a promotions committee. Well, your person on your team is about to be promoted, you want them to be promoted, you put in the case, and then someone else is going to decide, and I found myself worrying so much about this, whereas now, knowing what I know, I would've been just like, I put in the effort, I'm gonna walk away, it's not on me, and take it from there. So, I feel this is much easier said than done, but maybe managers will be better off reading and listening to some of these stoic thoughts. There's a lot of literature on this, isn't there?

James Stanier: There's Ryan Holiday's blog and podcast, "The Daily Stoic," which is excellent. But I think it has to do with, like, then you build on that, to be transparent. If you know what you can control and what you can't control, then you can be incredibly transparent with the team, in a way that then doesn't make you feel like you are responsible for all of the outcomes. 

Gergely Orosz: I think that's important, because, like, the best managers I've seen are the ones who just felt calm. So, I once said, I'm like, "Oh, we have a production outage," and, like, "It's okay. Relax. We're handling it right now. Here's what we can do. Here's what we're gonna do." And the worst managers have been the ones, well, not the worst, but the ones that just were not helpful, who were like, "Oh, my gosh. Oh, my gosh. Okay. This is bad." And I feel it had to do with those managers, and I'm not gonna say it's through stoicism, but they found their peace. They knew what they could do, and when they did, they were very decisive, right? Like, so, those managers, they're sometimes calm, but sometimes said, like, "Okay, we're doing this right now. This is urgent." And I feel it's like finding that peace, finding that...which, over time, I think it came to you, but if you can speed it up with mental models, it's a great thing to do. 

Book Recommendations

Gergely Orosz: So, this has been nice, James, going through the book, but with just one note. This is not your only book, right?

James Stanier: No.

Gergely Orosz: What other book do you have? Or books?

James Stanier: So, I have a book called "Effective Remote Work," which, if you like the style of this book, it's all to do with how you work remotely well, both for yourself and your organization. You know, a very, similar kind of narrative arc of individuals, teams, and company, but to do with how to do remote properly, which is very relevant to how I work now. And there's another book on the way, which is, where we address the middle management layer upwards, which is very much where I live in my current world. And I'm writing that right now, so I'm maybe about a third of the way through, so that's a next-year thing.

Gergely Orosz: Is the title done, or not yet?

James Stanier: TBD. TBD on the title. I do that in the end.

Gergely Orosz: TBD. Okay. So, that's expected to be middle management and up.

James Stanier: It would deal with sort of, like, middle management to executive at large orgs.

Gergely Orosz: No, that is very exciting. And I have this book, "The Software Engineer's Guidebook," so I feel this is a really good series, because, if you're a software engineer, there's this book, if you're an engineering manager or a senior manager, you have your book, "Become an Effective Engineering Manager." If you're working remotely, you have a book on working on that. And then if you're an executive, who knows? You'll have something coming out. But again, well, thank you. This was a really good discussion. Again, I still feel like more books are coming out in management, which I think is very good, but this feels to me like one of the most hands-on ones, where it does feel like you have someone sitting next to you. And just to close it, I like the stories, and the fact that it has opinions, but it doesn't force it on you. This book is three years old, but it feels very relevant to me, especially since we still don't have any manager training. If you do have an apprentice management program, you might be able to skip this book. Otherwise, I'd still recommend it.

James Stanier: Thank you very much, and congrats on getting yours out, it was two weeks ago, three weeks ago now?

Gergely Orosz: It was two and a half weeks ago, so it's still very fresh.

James Stanier: Awesome. Thanks very much. Been a pleasure.

Gergely Orosz: Same. See you later.

About the speakers

James Stanier
James Stanier ( author )

Director of Engineering at Shopify & Author of "Become an Effective Software Engineering Manager"

Gergely Orosz
Gergely Orosz ( interviewer )

Writing "The Pragmatic Engineer" & Author of "The Software Engineer's Guidebook"