From Mentor to Manager: How to Get Into Engineering Management | Asana’s Amanda Sopkin

0:00If you've been at a company for a long time, you gradually accumulate more knowledge in particular areas. and then suddenly you're the only person who knows about these systems and then you get involved in hiring, so you're doing that. And then you decide that you want to run this particular kind of meeting or be responsible for this other thing. And then it can be kind of difficult to hand those off. On my team, we try to rotate different areas of technical expertise. So someone might be responsible for answering questions about one thing one quarter and then the next quarter we might say, okay, this other person's going to take that over so that we're not building too many single points of failure.

0:38Are you looking to improve your engineering processes and align your efforts with business goals? Linear B has released the Essential Guide to Software Engineering Intelligence Platforms. This comprehensive guide will walk you through how SEI platforms provide visibility into your engineering operations, improve productivity, and forecast more accurately. Whether you're looking to adopt a new SEI platform or just want to enhance your current data practices, this guide covers everything you need, from evaluating platform capabilities to implementing solutions that drive continuous improvement. Head to the show notes to get your free copy of the Essential Guide to Software Engineering Intelligence Platforms today and take the first steps towards smarter, data-driven engineering.

1:19Hey, everyone. Welcome back to Dev Interrupted. I'm your co-host, Connor Bronsden, and today I'm joined by Amanda Sopkin, Engineering Manager at Asana. Amanda, welcome to Def Interrupted. Thank you. Good to be here. Yeah, it's really wonderful to have you on here because you're a passionate people manager. And to be frank, we recently released a series on the career journey of an engineering leader on the show. And I'll say if you're listening or watching on YouTube, you haven't checked it out, highly recommend it. It's full of great advice on one of the topics we discussed on there was trying to understand that kind of fork in an engineering leader's road where you decide, hey, I want to go be a staff engineer.

1:53I want to be a senior engineer. I want to take this deep IC route versus I want to go manage teams. And I'd love to know, how did you make that decision? Yeah. So I started out as a software engineer, like a lot of people. And I think the most formative experience was I mentored an intern early in my career. And I found that experience to be really interesting and fulfilling and challenging in ways that software engineering wasn't. So that was my first spark of interest in engineering management. And I knew I wanted to try it after that. I moved into a tech lead role, and then I went into engineering management after that with the attitude of, we'll try it out.

2:39I could go back to being an IC if I really don't like it. But I was fortunate to enjoy it a lot. I think that's a great point, this idea that you can't go back. Most great VPs of engineering I talk to say that they love to give people the opportunity you to go try it out. And it's like, yeah, if it doesn't work out for you, great. We know you're a great dev. That's probably why we thought you might be a great engineering manager. Let's bring you back to that. So folks who are listening who are maybe thinking about that transition, I would really encourage you to try it out because maybe you'll love it.

3:07But it sounds like you have some early indicators that you notice when you're talking to team members about whether they will be a good fit or whether they maybe won't enjoy it as much. You mentioned that interest in mentorship and really enjoying that process for you. what are some of the indicators that you see from team members about whether there may be a better fit for an IC path or you think they might be a great fit for leadership? I like to dig into their initial reasons and if someone's primarily looking for role level progression or more money those are usually not good reasons to go into engineering management.

3:43I like to look at their relationships with people their mentorship experiences signs that they find that kind of work fulfilling and not draining. And then from there, it's nice if you can try it out in kind of a lightweight way. It's really easy generally to do some kind of lightweight mentorship, either with an intern or a new grad and then see how that goes. And then technical leadership can also be a good indicator. Like if people are particularly interested in process and customer success and those kinds of things. Those are all sort of green flags to look for. And you mentioned some of those red flags are maybe an over-focus on the idea of like, oh, well, this is just a logical next step.

4:27I want to make more money. Yeah. Are there other red flags that you see? Mainly people relationships. So if someone had had difficult or strained mentorship relationships, I'd want to see one that was really successful and healthy on both ends before encouraging them to lead a team. because things can go sour for different reasons and sometimes there are difficult early career mentorship situations. But it's nice to see good signals that, oh, this person enjoys collaborating and mentoring even if it's a little difficult. I have to admit this is a sidebar, but talking about flags, because of the internet phenomenon of beige flags, I just want to ask, what's the beige flag for whether someone's going to be a good engineering leader or not?

5:12Okay, cool. So this is something that maybe isn't totally core to whether or not you'd be. I think people worry a lot about meeting time. And it makes sense because that's a really big immediate change when you go from individual contribution to leading people. I feel like it's not as jarring as it's made out to be. It is a shift, but I got used to it over time. I think there are a lot of really good engineering leaders that are introverted or not entirely extroverted. If someone was interested in engineering management but worried about the amount of personal interaction or meetings, I would say it's not.

5:56Maybe beige flag. Thanks for indulging me. I also know that you're a big fan of tailoring your leadership style, which I think can be a challenge for a lot of early career leaders. Obviously, there are different personalities on every team. I think some leaders take this approach of, well, is this person a fit for me or not? It sounds like you don't always take that perspective. I think that's one of the biggest challenges of engineering management in general. If I ever start to feel like, oh, I've got this down, or I feel like I know these people well, and we have a good routine, that usually means something new is coming.

6:30Because people are really complex, and psychology is really complex. People are always changing, so there's always curveballs. that come your way. And it's hard to screen for personality in general. I mean, obviously I look for certain strengths that'll compliment a team if I'm hiring, but you're not going to find, I mean, just like dating, you're not going to find someone who's 100 % compatible with you in all ways. So it's more about kind of like making it work with one another. Identifying, can they grow in this area? Is this a good long-term fit? That kind of thing. Yeah. What do you do to unpack that in the hiring process?

7:08Or maybe once they're on your team, how can you help recognize the different styles that will fit for members of your team? Mainly I look for balance in a team. So it is, I think, healthy to have kind of a mix of different strengths and weaknesses in a team and preferences. So if there are some people who are more interested in team building and cross-functional collaboration, and then some people who are more interested in technical execution and going really deep in their domain of expertise, that tends to work out well. Whereas if everyone is on kind of one side of that coin, it can be hard for people to grow and it can just lead to imbalances day to day.

7:47I'm hearing you talk about the potential of people. How do you go about unlocking that potential so that they become really incredible team members? Yeah, I think it's a lot about giving people opportunities to try new things, particularly when they're early on in their career. A lot of people have strengths that they haven't had the opportunity to demonstrate yet. So kind of giving them the opportunity to try new things regularly and take on tasks outside their immediate day-to-day. And I know some folks struggle at this because it just feels like more work. It's like, oh, here's the next thing to take on.

8:23How do you draw that line or keep a balance between, hey, I'm giving you challenges, I'm pushing you to stretch, but also making them feel like as a positive for them instead of, oh, you're just putting more on me. I think this gets tough if you've been at a company for a long time, because you kind of gradually accumulate more knowledge in particular areas, and then suddenly you're the only person who knows about these systems. and then you get involved in hiring. So you're doing that and then you decide that you want to run this particular kind of meeting or be responsible for this other thing and then it can be kind of difficult to hand those off.

8:58So I like to check in with people about how much they have on their plate. I think the companies I've worked at have done a pretty good job of encouraging people to redistribute responsibility pretty regularly. So it's good to check in about those things during review cycles. On my team, we try to rotate different areas of technical expertise. So someone might be responsible for answering questions about one thing one quarter, and then the next quarter we might say, okay, this other person's going to take that over so that we're not building too many single points of failure. But when it comes to motivation, there's a couple things there.

9:37I mean, I think if people feel like their workload is sustainable, they're more likely to find it motivating in general. But if there are things that don't totally align with what they want, I try to remove those if possible. So if someone doesn't really want to participate in the hiring process, maybe there's a way that they can contribute to mentorship within the company or other things instead. And it seems like you are kind of tailoring your leadership style to these different personalities. Can you give us a couple more examples of how you're doing that? Yeah, I think early on in my career, I kind of over-indexed on my own experiences.

10:18So for example, I really like to have structured one-on-ones. And when I was an engineer, I remember feeling like one-on-ones with my skip level were awkward and I didn't know what to talk about and I really didn't like that. So when I became a manager, I was like, okay, we're going to have structured agendas for every single one-on-one. We're going to know what we'll talk about and you won't have to prepare. But then I found that that really didn't work well for some of my engineers. And some of them liked having kind of like open-ended space to work through their thoughts in real time. How do you identify kind of which end of the spectrum people fall on?

10:53I'd like to ask about preferences first. So I might ask, how do you usually like to do one-on-ones? And are there things that have worked really well for you in the past? Are there things that haven't worked well? Honestly, frequently people don't have a strong opinion. which means that they haven't had a significant negative experience, so that's good. And from there, I kind of have to feel it out. So I like to start with kind of an optional agenda. I find generally with early career engineers, they like to have a bit more structure. They might not be as sure how to spend one-on-one time. And then senior engineers overall tend to be kind of like more settled into that pattern.

11:33They know what they want from me a little bit more. They have their own approach in some ways. Exactly, yeah. They've had time to develop more of an opinion there. And then we can kind of feel it out from there as we go on. What are other ways that you choose to adapt your leadership style depending on the needs of your team or I guess the needs of the individual really? Yeah, I think methods of appreciation has been kind of a big one. So finding ways to make people feel recognized across different dimensions. So some people, it's fairly easy. They like to receive shout-outs from their manager.

12:07They like their peers to recognize them one-on-one. But not everyone likes that. Some people are kind of shy about that kind of recognition. And then it can be a little bit more challenging. So I worked with someone who really felt motivated when we would talk about their impact in detail and go over feedback from customers. Like one-on-one conversations about it. Exactly, yeah. Yeah, so they wanted to feel like their manager was really recognizing and seeing the impact of their work, but they didn't care for public shout-outs as much. Maybe that felt not quite real to them, or it's like, oh, you have to do this.

12:42Yeah, it can feel kind of like you're putting on a face, and also kind of embarrassing, I think, to some people. So yeah, and then I like to give options if possible. So like for company anniversaries, I'll usually say like, would you like a gift card for coffee or would you like to receive a kudo board of acknowledgement from people on your team or would you like both? And kind of unsurprisingly, a lot of people like the coffee, but it's sort of split. Some people want their peers to talk about why they like working with them and some people that stresses them out. I had a manager give me the feedback that I like negative feedback too much because I love learning, I love growing.

13:25and we were doing a review and it was a very positive review. And I was like, okay, so what criticisms do you have? And he's like, let me finish telling you good things. And I'm like, I really just, okay, this makes me uncomfortable, but okay, sure. So it's interesting to hear that perspective about others because I know a lot of people have these diverse feelings and needs and maybe have been trained, whether it's societally, through their childhood or through their work, to think about these certain ways that they prefer to have feedback. So I love that you're tailoring it. And I think that's something we underestimate a lot.

13:55And frankly, I've been guilty of myself where I'll think, oh, of course my team wants to be appreciated publicly. And to your point, not everyone does. Yeah, and what you just said, that's a big thing. A lot of people don't, you go through reviews and I'll typically highlight ways that you contributed to success. And then we'll talk about areas for opportunity. And you can kind of see people don't, they're just scrolling down immediately to the areas of opportunity. Yeah, guilty. So yeah, I've tried to tell people, I think appreciations are a method of feedback in and of themselves. You can learn a lot from what's working well.

14:30And if you pay attention to that and try not to just gloss over it. How do you keep track of this for your team? Do you have a notes document or is it just in your head? What's the approach you take to operationalize this for yourself? Yeah, so I do have basically a document where I'll just paste things in. If I see, oh, this person had a really great response to this question during office hours. I'll try to just save that for later. I've asked people in the past to share things with me or just send them over to me if they have something they want me to know about. And I love it when people do that because it's really difficult to have eyes on everything that one person is doing.

15:11Yeah, I've talked to some managers who frankly have joined teams where you get asked at the start, what do you want? Do you want to be appreciated in this way? like what's the approach you want to take but to your point earlier I think it's really easy for a lot of folks to say they want one thing or even think they want one thing but maybe they haven't really critically dove into it and you discover through appreciating them in other ways or through that way that oh maybe this is actually what they respond to better they maybe just didn't want to say that or didn't feel appropriate saying that so that kind of like note-taking approach resonates with me and I think it makes sense to kind of say okay let's get some initial data like you talked about I'm going to ask you how do you want to run your one-on-ones but then I'm going to keep track of what actually works with you.

15:52Yeah, 100%. I think either it's embarrassing to say, oh, I actually really want you to recognize me. People feel uncomfortable or they might not know that about themselves. Particularly, like I said, if they haven't had a bad experience in one direction or a really good experience on the other hand. What are other strategies that you use to tailor your leadership style to your teams? I think seniority level comes into play pretty heavily in engineering. So identifying the right kinds of opportunities for people. And then as people kind of move up the engineering ladder, particularly into like staff kind of principal positions, there's more emphasis on initiative.

16:35It's more up to them to carve out projects that are going to have high impact, which is difficult as a manager because I want to help as much as possible and help identify potential areas where you could have impact. But I also need you to take initiative or it's just not staff level, basically. I've struggled with that before when hiring, where I've brought in someone at a senior level and I haven't seen that desire to actually take new things on or tell me that. It's hard when you bring someone in and realize that your expectation of their level of ability to go out there and pick what they want to go after isn't the same.

17:18Where they're like, hey, I want it to be told with you. I'm like, great, your skills are great, but I need that initiative to your point. Yeah, and I think people struggle to make that jump because you can sort of follow along the levels up to a certain point of just really excelling at what's given to you. So it is a mental shift to move into carving out your own opportunities. And I think it's something that's hard to teach too because people often have been ingrained in it throughout their career. I know I have a team member who used to work in government and I talked to him about the mental shift he doesn't make in working in a startup now and saying, okay, people want me to take that initiative.

17:56He's had to kind of reframe it for himself. And it's taken him time to develop on that. And I'm impressed at his work to build that. But it can be a challenging thing for people to do that reframing unless you identify it and talk to them about it with them. And even then, some people don't want to. It's just not how they want to approach work. Totally, yeah. And some people are very good at this. And I think there's a certain level of almost like politics and getting good at building a network and an organization and representing your work that carries you really far in a corporate setting. And it's difficult to explain that because on one level it's like, I would love for it to be totally objective and you don't have to talk about your work and everyone just knows and everyone's judged completely evenly.

18:43But practically that's not really how it works. So it is helpful to learn those kinds of skills like representing your work and networking a little bit. So hearing you talk about developing your team and your approach entering management, I think is a really good compliment to a lot of the context that we get on this show. But I'd love to ask you, do you want to take that next step too? Are you happy where you are or do you see yourself continuing to scale the size of the orgs you work with, the number of teams you work with? What's kind of the goal for you? I'm really not interested in managing other managers right now.

19:19I really like team level line management. And I think you can learn a lot in that role. So I'm mainly focused on trying to have different kinds of experiences and manage different domains and different kinds of people. Go deeper with the individual instead. Yeah, right, and try to get more of a breadth of how to handle different kinds of issues. Why is that, do you think? I think on one level I don't yet feel qualified to manage other managers. I feel like I would want to have more experience under my belt so that if someone comes to me, I can very easily say, oh yes, I've dealt with this at this time.

19:53I also kind of like being close to the team and their work. I think as you go up, there's more levels of obfuscation between you. You mentioned meetings earlier, right? Right, and that's very difficult to understand. Not just hear what the manager who reports to you is saying, but also understand below that what's actually happening on the team. So yeah, maybe someday it seems interesting, but not right now. I think it's interesting to talk to you about this because I feel like I spend a lot of time talking to folks who are already a VP and they're like, oh yeah, I've kind of made this transition.

20:31So something we don't talk about enough on this show is folks who are saying, I just want to be a better engineering manager. I want to be really, really good at this job and maybe someday I'll want to take that next step. So I really appreciate you bringing this perspective on. I mean, it's really fascinating to talk to you. I'd love to give you an opportunity for any closing thoughts, things you'd want to share with the audience or highlight to them. Yeah, I mean, I think along those lines, particularly coming out of school, it's really easy to just climb the ladder as quickly as possible. That's kind of the pattern that we ingrain in people.

21:00And at a certain point in my career, I was like, oh, actually, I kind of wish I had spent more time before I became a technical lead. And then, obviously, you can go back, but it becomes more difficult. So I think there's a lot to be said of just taking your time and enjoying where you are at a certain stage before you move on to the next thing. That's a great message for our audience because I think a lot of us are guilty of being a little ambitious and saying, I want to do the next thing. I hear from these great leaders on the show, oh, they're doing this big next thing, and it's okay to take your time.

21:31It's okay to become deep at something and say, okay, now I want to do the next thing. Yeah, exactly. So I think we've spent a lot of time here talking about your leadership approach and how you're thinking about things. but what are your passions within engineering itself? One thing I've been thinking about recently is representing people's impact equally. So designing good review processes, basically. I think that some companies put a lot of responsibility on the individual to prepare their own promotion packet and get their name out there and decide when they're ready for promotion and all of that.

22:07And then some companies put all of the responsibility on the manager to decide within their team who's ready for promotion and what examples they're going to use, etc. And I think both are kind of difficult on the individual level that's very time consuming. Some people might not know exactly what promotion committees look for. And then on the manager level, you can only have so much perspective into someone's impact kind of like secondhand. So I try to strike somewhat of a balance. I try to kind of like do forensics and try to figure out where people are having impact so I can represent that.

22:43But then I also try to bring people in and say, hey, I'm going to put you up for promotion. I'm not sure if it'll go through or I think it might go through. Anything I should add to this? Which is hard because then if it doesn't go through, I have to say, sorry, I kind of made the wrong call. But I like to sort of balance it there. I think it's really difficult to eliminate bias in that process. and it's this super important conversation trying to represent someone's impact, reward them for what they're doing, but we kind of condense it in companies because we don't want to spend all of our time doing it.

23:19So that's something I've been thinking about a lot. That's an interesting one because I've kind of seen both sides of this. I've talked to managers who say, I spend all my time just doing reviews. I'm constantly in a review cycle and it's exhausting, to your point. We worry about overdoing it on that. We still need to do other work. We still need to help prepare our team for these. I've also seen advice from other leaders who say, you absolutely should prepare your own promotion package. You need to be the one to step up and grab that situation. To your point earlier about how you think about not climbing the ladder as fast as someone else tells you to as far as looking at the corporate ladder, instead saying, am I happy here?

23:57Do I want to take this next step? How do I think about it? I think that's a really nuanced thing to consider here in the context of that promotional package because it's so easy for us to hear the advice of like, oh, of course you want the next promotion. Go prepare the package and not think about, have I talked to my leadership about, do I actually want that next role? Yeah, and there can be benefits to staying at a certain level. Sometimes you get a little bit more freedom to explore your interests or try out different things. And then if you reach a certain level, it's kind of like you have to deliver a lot of impact for the company, which is exciting in its own way.

24:28But challenging. And some people don't want that stress, or maybe it's not where your life is right now. Maybe, for example, you're a young parent and you're like, yeah, look, I have other concerns that I need to balance here. Yeah, totally. Life stages can be a big thing and people kind of naturally move in and out of gunning for the next opportunity or maybe you've got other things going on. You're more focused on woodworking or cooking outside of work. Totally. We had a great article by Gene Su on our sub stack about this, about opting out of the career ladder. I hear a lot of that echoed in what you're saying because it's a tough decision to make sometimes because people just get pushed and fed this idea of you need to just keep moving, keep moving.