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Episode 14: Naturally growing into a managing managers role with Alexandra Sunderland

    Guest Biography

    Alexandra Sunderland is an engineering leader with over a decade of experience working in both hybrid and remote roles, at companies ranging from 10-person startups to public corporations. She is currently a Director of Engineering at, where she is helping to build the future of work. She prides herself on building emotionally-intelligent processes for teams, and sharing her knowledge of management through conference talks and written works. Alexandra is the author of the book “Remote Engineering Management”, the guide for empathetic and people-first management in a remote world.

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    Patrick Kua: Hi everyone. Today we have Alexandra Sunderland. Alexandra Sunderland is an engineering leader with over a decade of experience working in both hybrid and remote roles at companies ranging from 10 person startups to public corporations. She is currently a director of engineering at where she is helping to build the future of work. She prides herself on building emotionally intelligent processes for teams and sharing her knowledge of management through conference talks and written works. Alexandra is the author of the book, Remote Engineering Management: The Guide for Empathic and People-First Management in a Remote World. Welcome to the podcast Alexandra.

    Alexandra Sunderland: Thanks so much. It’s great to be here.

    Patrick Kua: It’s really wonderful and I think your book resource is going to be a fantastic resource given our current day and age. We’ll get to that a little bit more but first I’d love to hear a little bit about your leadership story. So how did you start getting into leading teams?

    Alexandra Sunderland: Yeah, well I’ve been an engineer for quite a while now. I started about eleven years ago as an engineer. Went remote almost right away and I joined the company I currently work, at Fellow. I joined about five years ago as employee number twelve. Engineer number four. So very very early on and the great thing about working at startups that early is that there’s so much room for growth and so much room for creating processes and building up teams. When I joined, I was an engineer but very quickly turned into a manager within the first year or two, I think, of joining. Because the team was growing so much over time. It got to a point where I think there were 10 people reporting to the CTO and so we just needed to do a split because that was too many people reporting to one person. I naturally became the first engineering manager there and then a little bit after that I grew to have nine people reporting to me which was too many for me to manage at that point. So we split the teams again and kept doing this over and over until I ended up managing a team of managers a little while ago. But I feel like we’re always growing as a team and so I’m always on the lookout for new people to help develop skills of leadership because I know there’s going to be more opportunities very quickly for them to move into that role too.

    Patrick Kua: Yeah I mean that is such a fantastic opportunity as you describe with startups getting in really early. Particularly as they’re growing of just having more opportunities. Obviously the timing becomes a little bit hard when suddenly, yeah, you have nine people that you have to manage. It’s quite a large group. Needing to split that. wWhat was your transition into managing a team? Like what sort of support did you have as you transitioned into managing people for the first time?

    Alexandra Sunderland: I think. It felt like a very natural transition to me because even as an engineer I had been doing a lot of management related tasks. So I had been creating onboarding processes. I had been setting up the interview process and making sure that everything was going very smoothly with the team. So it felt very natural and I didn’t get the, as most people don’t get, I didn’t get any sort of formal training or anything like that at the time. But I did have a lot of support from our CEO and CTO. They were sending me so many book recommendations to read about how to be a great leader and a great manager and came across your resources as well actually. And watched a lot of your talks and read some of your works.

    Patrick Kua: Thank you.

    Alexandra Sunderland: All of that was very helpful.

    Patrick Kua: Oh that’s really fantastic to hear and there are so many good resources out there today and a lot of people don’t know about them. Unfortunately. Until you find yourself in those roles. But it’s great that you had people who redirected you and pointed you at these resources as well. Let’s talk about that transition as you started to lead other managers or manage other managers. So what was that transition point like? So you had a team you were managing. It grew really rapidly. What was that timeframe before you decided to split that team and how did you decide to split it?

    Alexandra Sunderland: Well I don’t even remember now because there was a period of time where I think every 3-6 months we were doing like a little bit of a reorg on the engineering side because we were just hiring at such a rapid pace. And because we were a startup as well the needs of the business were constantly changing. So there would be one period of time where we’d be really focused on app development and then the next where we’d really want to focus on our notes editor or calendar or whatever it is. So it felt like the team structure was just always evolving to best support that. So I think that when I started managing managers might have been, if I’m getting the timeline right, it might have been actually a year ago. Now I remember. Yes it was a year ago that I started managing managers. It felt very natural because I had started to take on a lot of the product engineering type of decisions being made. So I was doing a lot of work directly with the design leaders. The product leaders. It felt very natural for me to look after all the teams that related to product engineering very specifically. Because I love that side of things. I see code. I love code. But I see it more as a tool to create a great product instead of code being beautiful for the sake of code. So I took over that side of things while our CTO kept the teams related to SRE, infrastructure. The more, like, heavy duty code that I’m not quite as well versed in as he is.

    Alexandra Sunderland: So the transition went very well though. I think what we ended up doing is dividing up the team so that I manage the Enterprise team, the Apps team and the Meetings team. Which I find is a very cool concept of a team because we’re… so Fellow is a meeting management platform, where we help you create agendas, take notes, do all these things related to meetings. And this is such a core concept to us. So we created just a meetings team overall that looks after the notes editor, the calendar and all of these things. So I took on these teams and he took on the growth engineering team and the SRE team.

    Patrick Kua: Amazing and it sounds like some of your interests also gravitate towards that product space of thinking more holistically. I heard you say code is not just about code. It’s really a means to an end. Of solving some problem. It’s nice that it’s beautiful, but it’s not really The only thing that matters. What were some things that helped you transition into that area? Was that already something that you’d taught with your manager around? Around wanting to have more ownership of the product? Or was that just something that you started to keep helping out because it was kind of needed?

    Alexandra Sunderland: It was a little bit of need based and also it’s something that I really wanted. Because I love it when teams work really efficiently together and I really really love communicating with other teams and making sure that things are going well. So I was seeing that we were kind of falling through the cracks in some places because there was this division originally of, you know, like I’ll manage the Enterprise Team. He’ll manage whatever other teams we had at the time. Both kind of product related and it felt like not everyone was always on the same page. Things weren’t going super smoothly. So I was naturally stepping up and creating new ways of communicating with a product team. Making sure that everything was going very well.

    Patrick Kua: I was just trying to understand how you found yourself in that space? If it was something that you’re pushed into or more of your own interest? It sounds like it was something that you were, once again, filling in a need of what the business needed. And then somebody gave you that official title. Saying, hey, you’re already doing these things. Do more of it.

    Alexandra Sunderland: Yes. Yeah, and so I at some points asked for the ability to manage all of these other teams because I felt like if everything falls under one person then it will go more smoothly. In January of this year I think is when we made that change, so that everything that’s under product engineering would fall under me.

    Patrick Kua: Amazing. And if you think about some of the responsibilities or activities that you do now managing others managers, that you wouldn’t do as a, say, engineering manager, what would be some concrete examples?

    Alexandra Sunderland: I think in my case, a lot of the things that I do now are very similar to what I was doing before as an engineering manager. Probably because we were a startup and you take on a lot more responsibility when you’re a growing team and there’s needs. So even as an engineering manager, I was creating the career ladder. I was creating the onboarding process. I was doing a lot of those things that typically don’t fall on managers. But what I find myself doing a lot more now as a director is taking on business critical decisions and making sure that they’re executed on. Instead of being given a decision and told to see it through. There’s something exciting about that but also something incredibly stressful.

    Patrick Kua: Scary.

    Alexandra Sunderland: It’s so scary. Just making a decision but also not having direct control over its outcome anymore because you’re trusting your teams to follow through on it and make something happen. So that is something that is very different from what I was doing before.

    Patrick Kua: That’s a really great example. It resonates with a lot of people in a director-like role of where you have more scope, but ironically less direct control. You have these objectives that you need to deliver and you need to see these out. What are some of the things that help you influence and give you confidence that things are on track? So can you think of an example where you have a critical business decision that you need to make happen now and how do you make sure that happens?

    Alexandra Sunderland: I think that we have a lot of checkpoints set up between me and the managers of different teams which help out a lot with that. So, for example, every Monday morning we have a Dev Lead sync meeting where it’s me and all the other engineering managers in the company. Our CTO included. That’s where we’ll talk through some of those decisions that’ve been made. How they’re going. How they’re being carried out and just for more visibility for everyone in the company. Or everyone on the engineering leadership team. 1-1s are also a great place to really drive down a decision. Make sure that it’s being followed through and ask deeper questions. But something that I love as well for understanding what’s going on within the company is that almost all of our channels in Slack are public. So unless there is a reason that some information needs to be kept private. Which is a very rare reason. Then we default to public always and that means that any project that’s going on. Any sort of initiative. Whatever it is will have a slack channel that’s public that I’ll join. Maybe I’ll mute it so I don’t get the little red dot all the time that’s like constantly interrupting me. But I will have that insight to be able to, at any moment, go see what is going on with this. Is progress being made? Are the decisions being carried through?

    Alexandra Sunderland: And within all those slack channels too, like for a project, we’ll set up automations. Because remote work sometimes it’s hard to update people on what’s going on and to remember to communicate, so one of the things I love that we’ve done is set up these workflows in Slack where every day at a certain time there will be an automated message posted just saying how are you feeling about the projects? What’s going on? What issues are you running into that we can solve together?

    Patrick Kua: I love it.

    Alexandra Sunderland: Yeah, it’s great. Everyone will reply to that. We have different versions of this too where sometimes we do like the stoplight method. Where people are supposed to react with from red to green, how are you feeling about the situation?

    Patrick Kua: The pulse of the day.

    Alexandra Sunderland: Yeah, it’s so useful. Because if you’re feeling bad about something you might not always say it. But if you put like a red emoji. I think this project is off track. That opens a conversation and people are going to talk about it sooner than the weekly check in or whatever it is that you do.

    Patrick Kua: No, that’s great. You’re really building into some of the tools and really taking advantage of that. I think that’s such a great idea and exactly what you talked about when people are remote is people forget about things. People in different time zones and just having that heartbeat regular cadence is really nice to have some of that tooling in place. One of the things I heard you say and I find it interesting that everything is public, which is, there’s probably a lot of information. In your role you also probably are interested in a lot of information but you can’t read everything. So what’s your strategy for dealing with so many different teams? So many different topics? How do you manage your time as a director?

    Alexandra Sunderland: Yeah, oh it’s so hard because at first when I became a director I felt kind of odd to be handing over the teams to other people because I’m not directly involved in the work anymore. So at first I went through a phase of like I need to know everything that’s going on because I need information. I need to make sure things are on track.

    Patrick Kua: FOMO (Fear Of Missing Out)

    Alexandra Sunderland: Oh so much. It was way too much information because there’s way more going on than you can ever realistically keep on top of. So we created all these communication paths and updates and then eventually just muted everything. So that I can go check at will instead of reading everything that comes in all the time. One of the things that we do as a part of the Monday Dev leadership meeting that I mentioned is each team lead will write out what’s going on on their team. So it’ll be just the high level here’s how the project is going. Here’s the good. Here’s the bad. Here’s what we need to talk about and I find that very very useful because that also makes sure that our 1-1s aren’t used for status updates. Status updates are okay once in a while in 1-1s but I am pretty big on making sure that the 1-1s I have with my managers are related to them and issues on their team rather than just how the team is functioning as a status update. So I find that having them send information to me that way is very useful but then having the channels available so that whenever I feel like I need a little bit more info I can go check there instead. I find that very good to have those channels publicly available because then I can self-serve information instead of going to the manager and asking questions when they probably have better things to do than answering my little questions here and there.

    Patrick Kua: Now that’s a really great example. The fact that it’s also public means that other teams can also get insight into what’s going on with other parts of the organisation. Which I know from startup land can be often very difficult considering everyone’s just working in their different team silos. Without a lot of transparency. So it’s not just helping you but also helping other parts of the organisation which I think it is a good habit to have. I think what’s interesting is that sort of standardisation perhaps of the weekly update, as to what teams are doing. What other standard things do you have as mandates or encouraged things that teams should be doing? So each team can run their processes differently but where do you say every team has to do these things in a similar format?

    Alexandra Sunderland: We have some very similar processes around Linear. So we use Linear as our project management tool and we make sure that everybody has the same statuses across that so that we know when something’s on staging, when it’s deployed. Because the QA team works across all the teams and so if every team had a separate process that would be that would be a little bit difficult for them to deal with. We also make sure that everybody has the same bi-weekly 1-1s on their team. 1-1s are just so important in our company.

    Alexandra Sunderland: So we make sure that that is standardised across all of engineering. We also have team meetings that are not standardised in format but standardised in that they need to happen. The team meetings are more about connecting as people and socialising rather than accomplishing work together. Which is a little bit of a departure from other people. I think it helps that we’re not doing sprints or things like that. We have longer 8-week build cycles. So we don’t need to be constantly going over a sprint board. Another process that I love that we all do together is our engineering retrospective which is super important on our team. It’s something we’ve been doing for, I want to say, four years now.

    Alexandra Sunderland: But consistently every six months we, as an entire engineering org, get together and sit down and do this like half async remote retro. It’s really really good because it’s something where everyone gets to talk about what they like about the team. What’s not great about the team and we should kind of figure out relatively soon and then what is just going so poorly we need to solve right now. Is the worst thing in the world. I love these processes because it allows everyone to talk very freely about things that are bugging them and that makes everyone feel more like they’re a part of a team. There’s something so nice about listening to other people complain about the same things that you encounter and then working together to come up with a solution. It’s one of my favourite things that we do.

    Patrick Kua: Yeah I love it. I’m also a passionate fan of retrospectives. Of creating that safe space, as you say, to create visibility as to these pain points that team members are having. There’s often that empathy of, oh yeah, you’re facing that same pain point or you feel that way as well. And you’re right, which is, that channeling that energy not just to complain and mope, but also to then do something about it. To hopefully improve the work environment. So that’s really fantastic to hear. I’d like to change topics a little bit to your book. So you recently published a book on remote engineeringing management. So congratulations first.

    Alexandra Sunderland: Thank you.

    Patrick Kua: Given the current state of the world. A lot of the people that I work with they’ve settled probably more on a hybrid, with fewer probably remote or fully remote. But I think it’s going to be a really valuable resource. So why did you decide to write this book?

    Alexandra Sunderland: So my husband had been trying to convince me to write this for quite a while actually. I finally sat down and did it because a friend of mine was doing NaNoWriMo (, which is the national novel writing month of November. She wanted a writing accountability buddy and I was the only friend who said yes. It was a very big thing to do. The point of it is you write 50000 words over the course of November. Which is a lot of words.

    Patrick Kua: That is a lot.

    Alexandra Sunderland: That’s a long blog post every single day. I thought I’ll do it. I’ll write about this topic that my husband’s been trying to convince me to write about for a while. I ended up at the end of November with a book that I managed to get published. But I wanted to write about remote engineering management specifically because I had been working remotely already for, at that point, it must have been eight years or so. But now it’s been eleven. I felt like everybody in the world had done a good job of embracing remote work and people were good at knowing to mute themselves on video calls when they weren’t talking. You know, the basics like that. But I felt like there’s still a lot of stuff missing that people didn’t know about yet that could really like uplevel how they were working. There were a lot of lessons that I had learned over the years that I felt would take a long time for others to pick up on so I wanted to just put that all out there so that everyone could be the best remote manager that they could.

    Patrick Kua: It’s really fantastic. I think we definitely need more of those resources. So definitely recommend people check it out. We’ll make sure that the link is in the show notes as well. From your perspective, how do you think remote changes management or the role for engineering managers?

    Alexandra Sunderland: There are a lot of obvious answers to that. Like I think the first one everyone’s going to say is you have to be so much more intentional about communicating and building team culture and all of that stuff because you’re not seeing each other day to day. But I think the biggest one that stands out for me is there’s a lot more conflict resolution that happens when you’re a manager when you’re remote. Not specific to engineering but I think there’s something about, when you’re in the office, if something happens and you’re a little bit frustrated. That, you might appear frustrated and someone else in the office might pick up on that and go, hey, what’s going on? Let’s talk about it. Things don’t seem to be going very well because you have this body language and you can just talk it out. But when you’re remote I find that when you’re on a video call people have kind of this veil. Where they might present themselves very differently than how they actually feel. I’m sure we’ve all had video calls where we’re in a meeting, we’re happy, whatever. We do the call and then you press end and you just go collapse on the bed. You’re like, that was the worst. I don’t want to deal with this. I’m over with meetings.

    Alexandra Sunderland: It’s great and all that you can present yourself in the remote world without showing your emotions all the time for some situations. That’s great. People prefer it. But it also means that it’s harder for people to pick up on things when there is a bit of conflict. So I find that because of my role I have a lot of people coming to me saying like, oh, this thing is so frustrating. I don’t know what to do. Then maybe the other person involved in that conflict will also come to me saying, oh, I’m so frustrated by this. I don’t know what to do. The answer is almost always just go talk to each other. This is very simple. If you just talk about it together, it’ll get resolved. No problem. But I do a lot of that. Just people coming to me with problems and the answer is always just go mention it to the other person and it will be fine. That was not something that happens in person.

    Patrick Kua: Yeah I mean it’s such a great insight. You’re right. Is that I think people have that difference of being at the end of a camera versus being in person and then I can also think of teams where some of the team rituals mean that people don’t have their video on all the time. And so it’s even harder from that side because you just have whatever text or voice messages that people have. Trying to get a read into that I can imagine that makes it really hard as a manager to understand. I think that’s also really interesting from a mediation perspective because I guess if you’re in an office, you can probably get people into a room a little bit quicker than if you were remotely. Maybe. Depending on scheduling and calendars. Do you have any tips for people about improving mediation in a remote setting?

    Alexandra Sunderland: Yeah. So sometimes, when especially, as engineers, we love solving problems and so when someone comes to you with a problem often it’s easy to just listen to them and then try to solve it for them. Either give them a solution or say, oh okay, I’ll go talk to whoever it is or or the group of people, whatever is going on. I’ll go solve it for you. I don’t think that that’s necessarily the best way of going about things in most cases because then that other person isn’t going to learn how to solve their own problems in the future. It’s often basic communication skills that need to be built up for it to thrive in the workplace. So I find being able to tell someone, that’s great, what have you done to try to solve this? Or what did the person say when you mentioned this? Asking questions like that will get them to, in the future, more often, go directly to people and try to figure things out for themselves instead of coming through you as a mediator.

    Patrick Kua: I think that’s some great tips and I know from experience of working with those engineering managers, it can be hard to turn off that problem solving mode. Because as an engineer you’re used to solving problems. That’s the primary thing but when you’re mediating it’s hard to not do that as well and you turn off that habit.

    Alexandra Sunderland: Yeah, and it feels so good to solve problems for people. I love saying, don’t worry. I got this and just making things better.

    Patrick Kua: Absolutely. In your book you cover 1-1s from a few different angles and one interesting thing I found in the book was you talk about how there are some reasons why 1-1s are actually better remote. So can you provide a little bit more context about that?

    Alexandra Sunderland: Yeah I know it doesn’t sound like that would be a logical conclusion at all. Because everyone’s always saying that in person, it’s a real person. It’s not just a screen. And I agree to an extent there. There is a lot that is great about in-person 1-1s and I still do them when I can. But remote 1-1s I find are… you get deeper conversations. So it’s kind of like the phenomenon of when you’re out on a walk with someone or sitting in a car driving you naturally just talk more in depth about how you’re feeling. What’s going on? I think part of that is because you’re not looking directly in each other’s eyes. So it’s not this odd presence in front of you where you really know that you’re saying something to a person. With remote 1-1s it’s sort of the same thing. Like you might be able to look around the room more easily. If you’re in person together then it’s awkward to not be sitting there looking at their eyes. But remotely it’s totally fine. There are all these other benefits too.

    Alexandra Sunderland: Like you get more comfortable. Like right now, even on the podcast I’m sitting cross-legged. But you would never be able to tell. I couldn’t do that at an office. That would look odd. I mean you could, but I’m not going to because I would feel very awkward about it. So I’m more comfortable here with my legs. My blanket. I can fidget with things. But then another benefit too is that I am able to look at my notes on the screen right next to your face. Notes are very helpful for 1-1s because often there are a bunch of topics to talk about. You want that agenda in front of you and you want to be able to take notes without it being too awkward.

    Alexandra Sunderland: Because I’ve done a lot of in-person 1-1s where one person will bring their laptop and the other won’t. They’re talking to you about some problem they’re having and you’re taking notes and you feel so like something feels wrong about that. Remotely you can go on mute and then they’re not going to know that you’re sitting there typing. So I love that. And I love the fact that you know when time is up. Because as managers you’ll often have meetings back to back and in person I find it so awful that I sometimes pull up my phone to check the time so that I’m not late for my next meeting. Because it feels like you don’t care about the person in front of you, when you do. So I think that remote 1-1s are great because the time is right there in the corner. You’re not obviously looking off at the clock. Like people don’t feel pressured by the time. So there are all these benefits. You get deeper conversations. It’s easier to take notes. You’re not pressured by clocks. I just really think that it creates an environment to have better conversations with people.

    Patrick Kua: Great. I love it and I think there are those tradeoffs. I think it’s interesting to be able to experiment with both. But I love all the points that you talk about. I can definitely see some of them. It reminds me a little bit of when I was doing those interviews in person versus interviewing remotely. Same with the note taking. Doing remote note taking on a laptop’s a lot easier because it’s not distracting. But when you have that laptop in the middle of the room between you and a candidate then it’s a little bit more awkward.

    Alexandra Sunderland: Oh yeah.

    Patrick Kua: One of the other things that you talked about in your book was about peer 1-1s. So what are some peer 1-1s that you currently do? Do you run them similarly or how do you run them compared to your normal 1-1s with your reports?

    Alexandra Sunderland: Yeah I have a lot of peer 1-1s because I find that as a manager your direct team often is the people in the other departments that you collaborate with. And so I have peer 1-1s with the Head of Design, the Head of Customer Success, Head of Marketing, one of our staff engineers, and Head of Growth Engineering. Probably some more people that I’m forgetting. Y

    Patrick Kua: A lot of people I’m getting the impression of.

    Alexandra Sunderland: Oh yeah. Somebody from just about every area of the business because you work so closely with these people. The structure is a little bit different from how I do normal 1-1s. They’re still set up on a recurring basis. So I do these every two weeks and depending on the person anywhere from 20 minutes to an hour. They’re a little bit more social. So my 1-1s with my team are more about coaching and feedback and that sort of stuff. But with peers a lot of it is social time. So we’ll just catch up on what’s going on in our lives. I am lucky that all of these people also happen to be my friends. So it’s nice having that built in.

    Patrick Kua: It’s a great place to be.

    Alexandra Sunderland: But then the rest of the time is either talking about the work that’s upcoming from both sides. So anything that we’re doing that maybe the marketing team should be aware of. Or the head of CS will give us feedback on things. Trends that they’re noticing on the support side. Features that the enterprise customers are asking for and we’ll talk about how our teams are working together overall because very often there’s something that we could do to make how we collaborate better and we’ll try to hash that out together.

    Patrick Kua: Yeah, lovely. Excellent. If you think about 1-1s with your reports, who are managers versus 1-1s with, say, an individual contributor on a team, do you think there are any differences between them? If so, what would be those differences?

    Alexandra Sunderland: Yeah I think so there are a lot of common elements between both types. They’re both focused a lot on things like coaching, giving feedback, answering any questions that they have. I think when I have 1-1s with the managers that report to me though, a lot of it is also focused on providing business context. So going over a lot of the business side of things so that they have a good understanding of what’s going on. Because inevitably, the people on their teams are going to ask them questions like, oh what is this? What does this ARR mean? And how is it impacting the features that we’re building next cycle? We’re very transparent within the company overall so everybody has access to all of our business numbers. So I want to be able to make sure that they’re prepared with the ability to answer those things when they come up. So a lot of that. But I also really love focusing on managers as people and how they can develop themselves instead of just using the time to focus on their teams and how the status updates we talked about earlier. I really want to make sure that they’re growing as managers. They’re still developing their tech skills as well and really talking about them.

    Patrick Kua: Excellent. Great. One of the things I heard you say with 1-1s probably, common across both 1-1s with managers and individual contributors was feedback. So when you’re thinking about feedback for managers in an environment where, maybe, you don’t get to be part of their ceremonies, how do you go about getting feedback for your managers?

    Alexandra Sunderland: There are two kind of sides of feedback that I think of when I think of managers. It’s how they’re interacting with me. Then also how they’re interacting with their teams. For how they’re interacting with their teams I’m able to collect that kind of feedback pretty regularly because I also do skip level 1-1s and I set those up to be every six weeks with each person individually. I set those up as a recurring basis because otherwise it’s so easy to just go a whole year without talking to someone. Unintentionally. But I really want to make sure I have time on the calendar to talk with everybody in the org.

    Patrick Kua: Yeah, your calendar fills up fast.

    Alexandra Sunderland: Yeah. So I have those meetings with people and part of that is how they’re doing as people. How they’re developing. How they’re feeling. But then there’s always a component of like how is the team? How is your manager supporting you? So I’m able to collect feedback that way that I can then deliver to the person outside of the normal 360 feedback cycle because that only happens twice a year and that’s not enough. To be six months is a long time for someone to go without feedback.

    Patrick Kua: Absolutely.

    Alexandra Sunderland: So there’s that side. Then there’s the side of how they interact with me. I think often the feedback will be along the lines of and whether or not I feel like I’m being informed about the things that aren’t going well. I never want someone to sweep a problem under the rug. I want to make sure that we’re solving things together and be really on top of what’s going on. and then how they’re interacting with other teams as well. Which is where those peer 1-1s come in handy as well. Because maybe there will be feedback sometimes. Where it’s, like, oh this team released something and we had no idea it was coming. So the help centre docs are all out of date and this could have been prevented easily. So the feedback I would get from that would be to go to the team and say we’ve got to be better at communicating here with other people.

    Patrick Kua: Great, excellent! No, that’s so really fantastic and you’re right is that the 2, or twice a year 360 degree feedback isn’t really quick enough. So it’s great to have more regular feedback for your managers as well. One of your responsibilities I expect is probably knowing that your engineering managers are doing a good job. How do you quantify that or how do you think about what does an engineering manager do, and how do you know they’re doing a good job?

    Alexandra Sunderland: I think a lot of that comes down to are we hitting our goals? Are we shipping the projects that we say we’re going to ship? And are they high quality? At the same time is the team happy? Because if we’re hitting our goals and we’re shipping things but the team is burnt out and everyone’s suddenly taking vacation because they just can’t work anymore. That is not a good outcome because that team’s not going to succeed long term. I don’t want that. It’s also not good to have the opposite. Where the team is happy but they’re not shipping anything. Because that’s great for them, but they’re not going to be growing in their careers. And I think we’re going to have problems as a business overall if that’s how we operate. So those are the two things I really look at. We have these product engineering sync meetings where we’re able to see, are we on track? This comes back to the public channels I mentioned too where we have these check-ins saying how are things going? What’s being shipped? So I’m able to check that to see are we on track? And then I’m able to use the skip level 1-1s to see are people really happy? How are they feeling about their work and do they feel like they’re contributing to the success of the business?

    Patrick Kua: Great, excellent. As your business has grown, in your role as a director, I can imagine that you’ve probably had some new spots for new engineering managers. Have you grown people into that role or did you hire people into that role if you had any of those spots?

    Alexandra Sunderland: Yeah, everyone who’s a manager at so far has started off here as an engineer.

    Patrick Kua: Amazing.

    Alexandra Sunderland: Yeah it’s great. We haven’t hired externally yet. I think that’s really great because when you become a manager when you’re already on the team, you understand the codebase. You understand a lot of the problems that we’re having. The opportunities that are available and you have the trust of the team already. So we found it very important that whenever somebody moves into management they have to be very well-respected on the team otherwise things go poorly. And like even when I became a manager, I asked our CTO, before making this decision, you have to go ask every single person if they’re okay with it? Because they’re nice to me but if they secretly don’t think that I would be a good manager I don’t want the role because there is nothing worse than leading a team that you don’t have the respect of the people of. So it’s been very good. But we’re always on the lookout for people who have signs of leadership and want that role too. Because I never want to put someone who doesn’t actually want to manage in that position. But even now there are people who have said that this is something that they would like the opportunity when we have the need for it. So we’re sending them to management training. One of them took your class actually. I think the tech management essentials are so. That’s been very helpful. But we’re creating these skills and giving them opportunities to try out management too. So managing little projects here and there before actually moving them into that role.

    Patrick Kua: Great. It sounds like an amazing environment. It also sounds like you’ve probably put a greater support network as people move into that than what you had when you were going through that the first time.

    Alexandra Sunderland: Yeah, definitely. I mean to be fair, we were still a very small company. I was the first person going into management so it makes sense that there was nothing set up yet.

    Patrick Kua: That’s great. I mean in other places, those things don’t change still. Is that people just get on with execution. So I think it’s also a good testament to the improvements that you’ve made. Leaving it in a better, easier path for newer managers as they transition in. Let’s start wrapping up a little bit and I want to maybe go back to the topic about managing managers. So what do you think has helped you in managing managers over time? So what do you think has been the biggest thing that has helped you in your role as a director?

    Alexandra Sunderland: I think the biggest thing that’s helped me is having our CTO to talk to. Our CTO, his name is Sam. I’ve been working with him actually for 11 years as well. So the very first company that I joined, he was the co-founder of. He’s also the co-founder of So I’ve known him for a very very long time. But I think people always talk about how having a support network is so important as a manager. I found it very helpful to just have him to go to. To sometimes just rant about my problems unproductively, but also sometimes just talk through my thinking. Kind of like rubber duck debugging. Almost where I’ll say something out loud and it helps me immediately just having him there to talk back with me. So that has really been the biggest thing. Just having him there to help me through it.

    Patrick Kua: That’s fantastic. I’m glad that you have somebody like that in your organisation that you can go to with that history and support. If there was any book or books that you would recommend to a person who’s about to step into a managing managers role, is there anything that you would really point them to?

    Alexandra Sunderland: I mean, of course, I’m going to say, my book, Remote Engineering Management.

    Patrick Kua: Of course.

    Alexandra Sunderland: But then the one that really helped me as well when I, a few years ago, was Julie Zhuo’s book, which is The Making of a Manager. It’s such a good book. Such a nice read. Very storytelling based. I really appreciated her approach to management.

    Patrick Kua: Fantastic. And then if you were to give yourself some advice going back to your earlier self as you were stepping into your director role for the first time, what advice would you give yourself?

    Alexandra Sunderland: I would probably tell myself that it’s okay to ask the manager that reports to me questions. It’s not going to seem like I don’t trust them or trust what they’re doing. It’s good to be informed about what’s going on and really dig into things if something doesn’t seem right. So I think it took me a few weeks at least to understand that even though they’re managers, they still need support as well and that is my role. To really be there for them. It’s not to just let them take over and do things on their own without support. So I would definitely want to, if I could redo anything, it would be to be more involved right from the start and not be afraid to ask them questions.

    Patrick Kua: Great answer and great insight as well. So thank you very much for sharing that. My final question then is where can people find out more about you or reach out to you?

    Alexandra Sunderland: People can find out more about me on my website and I’m also on Linkedin and Twitter.

    Patrick Kua: Fantastic! We’ll make sure that all of those links are in the show notes as well. Thank you so much Alexandra for all of your amazing insights and your stories as well. It’s great to have a peek into what your world looks like and also your growth journey. It just sounds like it’s been a fun, really great environment to grow into both a manager and also a manager and managers. It also sounds like there’s lots more growth and lots more opportunity there as well. So thank you very much for being a guest on the podcast.

    Alexandra Sunderland: Thanks so much. It was great being here.

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