The Stack Overflow Podcast

Writing the roadmap from engineer to manager

Episode Summary

Former co-host Sara Chipps, now an engineering manager at LinkedIn, joins us to chat with Sarah Drasner, a director of engineering on the core developer web team at Google. We discuss the challenges of transitioning from an individual contributor software engineer to an engineering manager. Co-host Cassidy Williams knows exactly what kind of manager Drasner is; Cassidy used to report to her at Netlify. It's a whole former co-worker reunion!

Episode Notes

Former co-host Sara Chipps  now manages engineering teams at LinkedIn, but her best content is still on Twitter.

Cassidy's former boss, Sarah Drasner, recently wrote a book to help engineers level up to management: Engineering Management for the Rest of Us

Cassidy's new favorite software tool is Astro, a single-site generator that looks to minimize the amount of client-side JavaScript in a site. 

The two books Ms. Chipps mention as the old standbys for new engineering managers are Peopleware and Smart and Gets Things Done

Episode Transcription

Sarah Drasner So you need to have some rapport with your colleagues where you feel comfortable, not challenging them in a way where you're like, trying to get them. But that you're really trying to work on a shared goal and it's okay for you to have a little bit of conflict, a little bit of disagreement, so that you can get to good things. I think that that does build and happen when you can joke with each other.

[intro music]

Ben Popper Stack Overflow is supported by CircleCI. Now that every company is a software company, getting code to market quickly and securely matters. Learn why developers rely on CircleCI to manage their continuous integration and delivery pipelines at 

Ryan Donovan Hi, everybody. Welcome to the Stack Overflow podcast. I'm Ryan Donovan, Content Marketer here at Stack Overflow, covering for Ben popper while he's on vacation. This is a place to talk about all things software and technology, programming, all that good, nerdy stuff that y'all are into. Today, I am joined by my co-host, Cassidy Williams. Hi, Cassidy.

Cassidy Williams Waaassap? Hello, everybody. 

RD So Cassidy, what's exciting you about this software right now?

CW Exciting about software right now. You know, I think it's a very cool time to be in the Dev Tools, space. There's a lot of cool Developer Tools coming out right now. And because everybody has been indoors, we get more time to play with it, I guess, cuz we're not going outside. [Cassidy laughs]

RD Do you have a favorite? 

CW Honestly, I've been playing a lot just with a bunch of different things. Lately, I've been really interested in Astro, which is a static site generator framework. It lets you use all of the libraries together. And so I was able to do some cool state management stuff with React and Vue at the same time, which you don't normally get to see.

RD That sounds cool. Well, our guests today are the prodigal daughter, Sara Chipps, who's now an engineering manager at LinkedIn. And Sarah Drasner, former VP at Netlify. Ladies, how are you doing?

SD Hey, good. How are you? 

RD I'm good. 

SC This isn't the first time I've been referred to as the prodigal daughter, surprisingly. [Cassidy & Ryan laugh]

RD Well, it seems fitting.

SC Yeah. Well, and speaking of Vue, Sarah, you are on the Vue core team. Have you played with Astro at all yet? Because it's pretty neat.

SD No, I haven't played with Astro. I know you've mentioned it a couple of times. It's on my list. But yeah, mainly I use Next. But also really excited about Next moving over to V, which is something that was also built by Evan You, the creator of Vue, but it works with React and Svelte and other things too.

CW V is so fast.

SD Yeah! So that's really exciting.

RD So we should mention that not only is Sara Chipps a former coworker of mine, Sarah Drasner is Cassidy Williams' former boss.

SD That's right. I can't you know, expounds things about management and have her not call me out.

CW I'm just like "Actually, that's not what you said in our one on one!" [Sarah laughs]

RD Time to settle all the old scores.

SC That's great. Can you give us the goss? What's it like to be Cassidy's manager?

SD Well, she's very serious, never cracking jokes. 

CW Ohhh, that's super true.

RD I could see that. 

SD No, Cassidy is wonderful. She's a hard worker. And, let's see, am I like your marketing department right now?

RD Cassidy has her own marketing department. [Cassidy & Sarah laugh]  So Sarahs, you're both engineering management. And also come from an engineering background. Sarah Drasner, you've you've written a book on this. What's it like moving from doing the work to overseeing the work?

SD Yeah, I mean, it's great question. Actually, that's kind of what the book is about. Because I felt like, I got to be a really good engineer. And then all of a sudden, I was moved into management. But there wasn't really a guidebook to transitioning those roles. And I think there was a bit of an expectation that I would already know how to do all of the kind of managerial work that engineering management entails. And I didn't. I had to learn a lot on the job. So that was, the reason why I wrote the book, right, is for people who are engineers who are either curious about what it's like to be an engineering manager, or people who have transitioned into engineering management and didn't really see that there was a formal path or way of learning are a way of, you know, kind of structuring your team, how to prioritize things and work with other groups, how to have one on ones, how to get feedback. So I kind of tried to encapsulate all of those things to help other engineers.

RD Yeah, 'cause they're kind of two separate skills entirely, right? Like, engineering is a very technical skills and management is very people focused.

SD Yeah, it's kind of like, okay, you're really good at building these bridges, you should be a baker. [Cassidy laughs] So yeah, I think that there's, you know, a few good resources out there. But I thought maybe adding, you know, another voice.

CW It's a very common story, not just in tech, but like even in academia, you see all of these professors who actually want to do research and focus on this thing. But instead, they have to teach students and as a result may not always be the best professor. And you see that with managers a lot. And some people are natural managers, and it's great. But it definitely does take training and education to take on these new skill sets.

RD And there's the old joke, everybody rises to their own level of incompetence, right?

SC The Peter Principle. When I found out about the Peter Principle, I didn't sleep for six months. [Sara & Ryan laugh]

RD Hopefully you find those people who there is no level of incompetence, they just keep excelling. Or they have good books in front of them. So Sara—

CW Which one? Ha ha ha! 

RD Sorry, ms Chipps, how do you deal with management? You also come from engineering background, and have risen to your level of competence, I assume. 

SC Yeah, I think I really agree with Sarah, that there's not a lot of resources out there. It's pretty, you know, like, 10 years ago, when I started, there was like three books people told me to read. It was like Peopleware, Joel's book Smart and Gets Things Done, and then like one other that people are like, then you'll know everything. And so it's great that people like Sarah are coming out with books now. Because that's really helpful, especially in the modern world of management, which I think has changed. When I became a manager, and I think this is a typical ICE story. It's funny, when you talk to a lot of ICEs. And you say, you know, what's your next play? Like, what, what are you working to grow towards? And they're like, well, it's not to be a manager, and you're like, okay, well, you know, it's not that bad. But at the time, I really felt like becoming a manager was quitting, because it meant like, I wouldn't code anymore. And that was something that was very important to me. But what I learned is that being a manager is not that different from being an engineer, it's just instead of, you know, computer processes, you're dealing with people processes. You're still fixing machines, and you're still, you know, making things better. And really, you know, the things that you can do as one engineer gets multiplied exponentially when you know, your job is just empowering engineers and helping them love their jobs and helping them get to the next level. I think that's a really fun part of it.

RD Yeah, I've read a good amount of stuff on know engineering performance and metrics. And almost all of them talk about, it's no longer individual. It's a team. Like the whole idea of the 10x engineer is sort of nonsense, you have to support your team and your team has to excel.

SD Yeah, I mean, that's I have this, you know, open source career ladders for the team, that the teams that I manage. And I think that like the kind of TL;DR of that was what you're saying, right? But when you're becoming senior, you're becoming like the best you could be. But beyond that, when you get to staff and principal levels, you're really empowering the people around you, you're helping them be the best them and making sure that everybody's scaling appropriately. And I like what Sara said, about really like that your scale as an engineering manager is touching many people's lives, getting pulled systems of people to work, that part feels very rewarding. The thing that's a little strange about engineering management that took some getting used to coming from being an engineer is that the kind of feedback cycles when you're an engineer is, you know, you see your code working or not working fairly soon, with management, you can put something into play that you don't see working for months, maybe even a year, so those types of cycles are a little bit different. I would say like the fact that you're no longer flow driven, and you're now interrupt driven, like you are supposed to be interrupted constantly so that your team can stay focused, and you know, provide that kind of clarity from having those conversations is also quite different. And the last thing that is really, really different is just that people are not pure functions. I wish they were. [Sarah laughs] But you can, I mean, you can put one input in one day and get completely different output another day. Because people have things going on in their lives. There's other team dynamics, there's other things going on at the company that is affecting their work. And so you're still doing those kind of like, figuring out what the state of the thing is, figuring out like what is you know, impacting and what's going on with each individual and what's going on as a group. But there are times where it's really challenging because you don't necessarily have that like strong input output that you can kind of rely on day to day, which makes it actually really fun and challenging, as well.

RD Yeah, people that are not deterministic functions. 

SD Exactly. [Sarah & Cassidy laugh]

RD Cassidy, have you been a manager at all? 

CW Yeah, I am one now actually.

RD You're a manager. 

CW Yeah. And I've done it, I've done it a few times both like going from management to I want to be an ICE again, and then going back and being like, Yeah, kind of like management, too. It's like a management sandwich. And I think when I was first going into my career, I was just like, I want to be a manager right away, because this is good for my career. And it means power, yada, yada, yada. And I very quickly learned that that is not what being a manager is about. If anything it is kind of the opposite. In a way, it's really just about providing resources to your team to be successful. And not just about bossing people around, which I think some managers need to learn that lesson still. But yeah, I've started management actually, in my first job straight out of college, but just with interns. And I was managing interns early. And then in my next few roles, I managed small teams of like one or two, and then larger teams of six and more. Now we've got a little team of three that I've gotten. And we mostly just share memes with each other, but we get some stuff done.

RD Those are valuable resources. I think a lot of times, engineers will go into management because there isn't really the individual contributor track. Is there a way we can fix that?

CW I think the leveling stuff that Sarah Drasner put out is super, super useful for that kind of thing.

SD Yeah, I did try to open source not just the levels themselves for the ICE track, but also the process that I go through when I try to figure out with the person where they want to be, what are you communicating when you talk about the level with the person because I actually had a friend who went into management recently, it was like, Am I supposed to talk about promotions with them? If they're not? If they haven't brought it up? I'm like, Yeah, you're supposed to talk about what level they're at. And, and so I think sometimes people don't realize that people do kind of want a sense of where they're at, what it will take to get to the next level, provide clarity for what you're expecting, you know, what's great that they should continue doing, where they can grow. And then, you know, follow through on those things, right? Like, once they do all of those things. It establishes trust between a manager and employee, if you show this is what we're looking for, and then they go through and do it. And then they do get a promotion or a raise, you don't just like leave them in limbo forever.

RD Right. You set expectations, and you meet them. Sara Chipps, what's the hardest thing you found about being a manager?

SC I think the hardest thing about—is giving people opportunities to learn and watching, not watching them fail, giving people opportunities to fail and watching them fail. I think it's really hard. I think it's very important that we all need those in our jobs. We all need those in our jobs, like opportunities to stretch ourselves, as individuals, try things we haven't tried before, do them badly. Do them again and do them better. You know, like, that's the really important part after that is make sure that the person gets that feedback that they need to next time, do a better job. But I think the instinct is always to jump in and tell them oh, you know, here's what you need to do. And you can always give them that advice. But you know, like, one thing you mentioned was like, being an engineering manager. You know, being the boss of people, you're really not. Like, if that's your goal, to be the boss of people, being an engineering manager, you're just going to fail, I think. Especially like engineers, they're very, they love autonomy, and they love their ability to make decisions. And if you're going in, because you want to tell them what to do, I think you'll end up with a pretty unhappy team. So a lot of that means giving them your best advice and letting them decide what to do with it. And so sometimes when you see someone do that, and it's not successful, that could be hard to watch. But the best part afterwards is coaching them, and helping them, you know, nail it a second time.

RD I always say failure is a first step to succeeding. 

SC Yeah, that's nice. 

RD I'm a pretty new parent. So that's the thing. I'm going through a lot where it's like, you got to let them fail. You got to let them fall on his face once in a while. Can you all talk about instances where you had to let somebody fail and then kind of pick up the pieces?

SD Well, I let Cassidy fail at puns all the time.

RD Oooh.

CW Yeah, it's really upsetting, actually. Sarah has seen me at my worst.

SD I mean, there, there are definitely even times where it's not about—I mean, I completely agree with all of the things that Sara just said, where it's not even an individual failing, but it can also be a team working on something and failing. Because if you're trying to—if you're pushing the boundaries of something, if you're creating something truly innovative and unique, then there isn't as much of a clear path, right? Like, I've definitely been at companies where we're just building a thing that is a feature that's very obvious. And we know exactly what we're doing. And we just do the thing. And then there are times where you're building something that has never existed before in the industry, and you're trying to see if it's going to work and trying to see if it's going to be successful. And that means that at times, you're going to find that there are, you know, dead ends, there are things that people that didn't resonate with people, they're things that didn't work that you have to re-do. There's also the communication aspect of trying to understand that, like, it's not just your team, right, you're communicating with peers, you're communicating with stakeholders, above your head about what the nature of that work is, how much of, how much success and failure is, you know, to be expected when you're doing something innovative. And that can be wonderful and challenging and interesting. And gathering all of that kind of input and synthesizing it in a way where the goals are something that is like way beyond maybe your, like current capacity. But trying to stretch yourself as a team together is an interesting challenge can definitely have some failures, but also hopefully, it's rewarding when it does succeed.

RD Yeah, that relates to a post we just put out on the blog about safely creating stretch work assignments. That's the way to get somebody to grow, give them something that's a little bit outside of their current ability, and see if they get to it. So Cassidy, I think it's time to spill a little tea. How is Sarah Drasner has a boss?

CW Oh, unfortunately, there's not much citta spill, she's really good. I say it without irony that she's one of the best bosses I've ever had. She's a really good manager and knows what she's talking about. And that's why that book is probably going to be one that everyone should buy. [Ryan laughs]

SD My heart strings.

SC Sarah, what level of manager did you write the book for? Like, is it like general like if you're a manager this is valuable? Is it I'm a new manager? Is it I've been doing this forever?

SD I think like the intent is for people who are either starting management or have begun a management journey within the last three or four years, anywhere from beginning to three or four years. But I do think that there are things that I've seen even experienced managers like, like some learnings in there that like I have recently learned, even though I've been managing for a while and thought that I should share because it's like, oh, don't do this. Or like, Oh, this really worked out, you should try to do X, Y and Z. There's particularly pieces in there that I'm still working on and learning. So I'm trying to capture things that I'm iterating on as well like one of the last section of the book—so the first section of the book is your team. The second is about collaboration with other teams and other stakeholders. And the third is, is about you in the last chapter is one that I'm really like not super—and I try to be honest about like scheduling your time, what do you do when you're a VP and everyone wants to meet with you and you want to meet with everybody, we just don't have enough time. And that where you get into some of these higher prioritization levels of like, what is your value at the company? What are you providing for other people? Understand that you can't do everything in the world anymore. So hopefully, there's something a little bit for everybody, but it's definitely like the key audiences is people who are kind of transitioning or have transitioned in the last three or four years.

CW Does it cover like when your reports troll you and just really mess with you? 

SD Actually it does! [Sarah laughs]

CW Nice! [Cassidy & Ryan laugh]

RD Cassidy, did you troll her?

CW Yes.

SD For sure. [Sarah laughs]

CW I'm not even gonna lie. It was an active goal. It was great. 

SD They all did, though. 

CW Yeah, no, that's kind of just like our entire team's dynamic. Even in Sarah's absence. It's a very active, just how can we mess with each other as much as we can?

SD Yeah, I think the day that I left, a few of them set their backgrounds in photos to a picture of me as a child picking my nose. [Sarah & Sara laugh]

CW Yeah!

SC Sounded really sweet up until the picking your nose part.

RD Little salty. Little salty. Do you think that kind of casual relationship with your direct reports helps a team perform?

SD Oh, 100% Yeah, I do talk about that a little bit in the book too. Because I think, you know, not every team's gonna have the same sense of humor. And I don't think that it's good for people to try to even do that. But I do think that having team dynamics where, you know, Sara was just talking about failing in front of each other and that doesn't happen unless you have some trust. You really need to create trust, vulnerability and, you know, shared humor, traditions, things like that are ways to build that trust. It's not the only way. But it is a really important way to make sure that people feel comfortable saying something doesn't work. Like let's say, given two situations, you, you're presenting to a group an idea or a concept for what you're going to be building in the future, if you say, we're going to be doing this, and people disagree, and they're quiet, that's not good. [Sarah laughs] You want a team who feels comfortable saying, you know, I don't know if we should be doing this, because did you know about x, y, and z, because sometimes you don't know. So you need to have some rapport with your colleagues where you feel comfortable, not challenging them in a way, where you're like, trying to get them, but that you're, you're really trying to work on a shared goal. And it's okay for you to have a little bit of conflict, a little bit of disagreement so that you can get to good things. And I think that that does build and happen when you can joke with each other.

CW And then it's also important to acknowledge, like the power dynamic too. Like it's fun to have a casual relationship, but at the end of the day, you are still their manager to. So there's a fine balance there, where you will have the serious moments where not everything can be a joke, but it is good to have that vulnerability and good relationship enough where you can talk about everything.

RD And being able to, you know, call out somebody when they're wrong, or when you disagree is important.

CW Or when their joke is bad.

RD Yeah. At my last job, I ended up at some point reporting to the CTO, and she managed, you know, 600 engineers. And I remember sort of trying to squeak out a disagreement, and she's like, no, this is good. Disagree with me. And then she stepped on it. She crushed me. [Sarah & Cassidy laugh]

SC My favorite part of being a manager is when there's someone on my team and I'm not managing them anymore, and I get to be their friend. It sounds like Sarah and Cassidy, you guys have done that. And that's the best.

SD Yeah, I try to make her play Fortnite with me, but she's much better at it than me. [Sara & Ryan laugh]

CW We've gotten some wins though! So, hey.

SD Mostly because of Cassidy. [Sarah & Cassidy laugh]


RD Well, thank you very much for joining us. This has been a great conversation. As always, I'm Ryan Donovan, content marketer. I run the blog here. I am secretly on Twitter, @RThorDonovan, and you can email blog pitches at Cassidy?

CW I'm Cassidy, Director of Developer Experience at Netlify. You can find me @cassidoo on most things on the internet.

SD I'm Sarah Drasner. I'm @sarah_edo on Twitter. I'm on the Vue core team and I'm former VP at Netlify and Microsoft and a couple of other places. And yeah, you can catch some of my writings on my site

SC Sarah with an H dot dev. 

SD Sarah with an H. [Sarah laughs] 

SC I may be the only one in my mind that was wondering. 

RD Sara Chipps?

SC I'm Sara Chipps, you can find on Twitter @SaraJChipps. I'm an engineering manager at LinkedIn.

RD All right. Well, thank you all for joining us today and we'll talk to you next time.

CW Bye!

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