Episode 34 | Managing an Engineering Team in a Remote-First World with Alexandra Sunderland

Alexandra: If somebody asks me question, even if it's very personal to me, I'll be honest, 'cause I'm really big on trust, 'cause the more honest you are with your team, the more honest they're gonna be with you, and that element of trust is so important for everything around work and trusting each other. And so I really like building that up by being honest in return with people.

VO: Welcome to Developing Leadership, the podcast for engineering leaders where Eiso Kant and Jason Warner share their lessons on the ins and outs of managing software teams. Today, we have Alexandra Sunderland on the podcast. Alexandra is a senior engineering manager at Fellow App, and the author of Remote Engineering Management: Managing an Engineering Team in a Remote-First World. Alexandra joins us to talk about creating a good remote work foundation and the challenges of jumping back into in-person interactions when needed. The guys also chatted about how remote emotions translate to in-person ones, segmenting emotional reactions, wearing different masks, and more. As always, this episode comes with accompanying show notes, with a deep dive into the main topics, mental models, and key moments from this episode. Find them at developingleadership.co and linked in the episode description.

Eiso: Hi, everyone. We're back again with yet another episode of Developing Leadership. Jason and I have a fantastic guest with us today, Alexandra Sunderland. Alexandra is a senior engineering manager at Fellow.App and we invited her on after we saw that she wrote the book called Remote Engineering Management: Managing an Engineering Team in a Remote-First World. I personally really enjoyed it, it's highly practical and is one of those books that gives you direct advice with the context behind it. And so yeah, a big welcome, Alexandra. Glad to have you on with us here today.

Alexandra: Hi, thanks. I'm excited to be here.

Eiso: When we had a little chat before the podcast, you mentioned that you were listening to an episode that we did a while back with Michael Lopp, where he advocated for, in person as the best. I'm curious. You had a strong reaction to that. I'm curious to hear a little bit more and if you agree with that statement or not at all.

Alexandra: Yeah, so I think when I was listening to that, I was driving my car down the road and heard him talk about how in-person one-on-ones and in-person calls are... Meetings are better 'cause you get a better sense of the person and their body language and there's something that feels so fake about doing a call with them. And I felt what? No, I totally disagree. When you're having calls remotely, there's something that ends up being more genuine about that. And yes, seeing the person on your screen makes that person feel maybe a bit like an avatar and you can tell that they're not real. But in my experience, just having a call with someone makes the things that you're saying more real. It's kinda like that phenomenon where you're sitting next to someone, staring in the same direction. Maybe sitting in a car driving together, or on a bench talking. The conversations you have, you're able to open up more than normal, and you say things that are deeper and say things that are maybe a little trickier to say and more emotionally loaded. But those conversations that happen are just so important.

And I find I get that same feeling when I'm doing remote calls with people, especially in one-on-ones, because you don't get the the kind of imposing, physical presence of having someone sitting across the table from you in a meeting room staring at you with fluorescent lights while you're trying to maybe open up about something that's hard to talk about. I feel so comfortable sitting in my office at home right now. I don't have to look at anyone straight in the eye. I can look around the room and it doesn't feel uncomfortable that we're not making eye contact. And I can have a blanket with me and nobody can tell, and I can fidget with everything on my desk. And having those little things just makes people feel more comfortable. I... Yeah I really think that having remote calls has this... It brings more humanness to it because it's easier to talk about difficult things and really say what's on your mind without that physical imposing presence.

Eiso: You're the first person I've heard say it this clearly. And I think the analogy that you draw the comparison to, the driving the car with someone where... Is to me one of the best ones. It's the first time I've heard it, but it's one of the best ones I, I can think of. And it, it makes a lot of sense. Actually, what you're saying resonates a lot with me. And if I think about the meetings that I have, it, it definitely holds true. Curious to get your thoughts here, 

Jason: Jason.

 I think, essentially what it comes down to, I do think, is that there's... Everyone has personal preferences. And preferences are different across the board. I tend to think... I've been doing this 13 years now. I tend to think that I like the remote stuff more, primarily because it's efficient. I get to, to jump around to meetings and I... And I found and I forced myself to be very good with the human interactions. I like some of the in-person stuff when it comes to groups, much more than I like doing this on Zooms or video for groups. Individuals, I find that the remote stuff is way easier, way better, there's no difference between connecting as... To a human video remote versus in the room in person. But as a group, I tend to like to do it more in person. That's... But again, it comes down to personal preference. And again, we've had... We even had this conversation in a pre, pre episode for the recording here, and I've talked about this. And Alexandra, I'm sure that you've had conversations around this too.

In-person remote is not really the conversation. It feels like stage, context, purpose, all those are the real conversations that we need to end up having. And anyone who thinks that remote is not a thing, j- they're just kidding themselves. Any company over 150 people is effectively a remote company. You've got to communicate, you've got to figure out, you've got to... You've got to organize yourselves in a way that makes it efficient for you to be able to communicate to people across even the city. And I joked about this. Salesforce, when I was at Heroku, had a policy of, we wanted all these people to be in the buildings in, in Salesforce towers and stuff. No one ever left their desks. Everyone stayed there and did Zoom calls or meetings all day. And there was no way that you were being, four floors away from each other and go to a meeting in person. You were gonna take that from a meeting room on your floor or at your desk. So Sensibly, everyone's a remote company once you pass a certain size no matter what anyway.

Eiso: There's something that I would add to this, and I'm not sure if I've spoken about it on the podcast before. But I know you and I have had this conversation, Jason. Is to me, what I value a lot about remote communication, which I don't hear a lot of people talking about, is how deliberate you can be. And what I mean by that, you can have slept really bad the night before, or you might just come from a conversation like another meeting that was incredibly tough, but you can reset, right? You can get before you open that Zoom link, you reset, you set your frame of mind for that specific conversation that you're about to have. Since it's time blocks, you know I have to be in this frame of mind for the next 30 minutes. If that's bringing, what is it? Frank Slootman amping it up, bringing excitement to a meeting that you really know it's going to help drive it. Or if be far more thoughtful or focused on the person.

And you know that you have to turn it on for exactly 30 minutes. And it's not disingenuous, because I don't think it is. But it's deliberate, right? You're there and you're exactly in that frame of mind. And then you turn it off and maybe you turn around and you're, joking with your partner, or you're going to take a nap because you're exhausted and you couldn't do that in an office because, if you're doing that in an office, like, how you feel will shine through the moment you leave that room. And it becomes disingenuous. And that's maybe the weird part that I'm trying to figure out. If you're deliberate, are you actually not disingenuous. But if you were deliberate in real life, you would come across quite disingenuous if you walk out that meeting room and now joke all of a sudden with someone on the floor when you just had a co- serious conversation. I'm curious to hear your thoughts on this, Alexandra.

Alexandra: Yeah I've actually started running to the... Into that quite a bit recently, because... I've been working remotely for the last 10 years, but in the last month, we've gotten a an office to go to downtown for whoever wants to go. It's not forced. But I've been very excited about the thought of going into an office for the first time in my career. I've been making use of that. And I got caught up in, in this thing where I'm so used to just showing all of my emotions at home, 'cause nobody can see me. And so I'm fine reacting to Slack messages and reacting to meetings and stuff. But I'm having to learn how to reign that in when I'm at the office, 'cause I'll go to a meeting and if something upsetting happened or some bad news was shared, I'll walk back to my desk and very clearly be in such a bad mood where people will message me saying, "Are you okay?" And I have to learn not to do that. And that takes a lot of energy, especially if you're feeling stressed about something.

And like you said, It affects how the rest of the team is doing, and they'll see that you're not in a great mood, and that kind of brings everything down. I'm trying really hard to not do that. But working remotely it's great being able to segment those emotions into time boxes on the calendar almost, especially if maybe I'll I think once I had a... I had one-on-ones back to back where awful news was shared in one, and then immediately after that, I had to hang up the call and go to a next one where incredible news was shared. And I had to react appropriately in both situations and not be, like, sad in one and happy in the other when it wasn't appropriate. And if that was happening in person, it'd be awkward. 'Cause if the... If the sad person saw how happy I was, then they're gonna think I'm not taking their news seriously. But I don't wanna give away that they gave sad info. It's just so hard to deal with absorbing all those emotions and figuring out how to display it. It's really tough.

And it is hard because I... Especially in the office if I'm feeling a certain way yeah, like you said, it can feel disingenuous to not actually put that on display and to hide it. But I... And I am always up for telling people what's going on if there's something that is important for them to know, and something bad is happening, that they should be aware of, I'm all for that. But I definitely think that, in some situations, it makes sense to kinda keep it to yourself 'cause you don't wanna negatively affect everybody else when it's not necessary.

Jason: I find that exactly what you said, Alexandra, is true. One One of the things I've noted, if you wanna be good at doing remote and particularly over video, is you tend to have to be more expressive. you know Because you're lacking some physical connection in the room, so you have to use your hands more, you have to use your head more, your facial expressions are much more important. Your tonal inflections are much more important. So You tend to use those as the tools that you have in a remote setting. When in fact, when you... When you're in the office, you're trying to tamp a lot of those things down, even in normal course of business, you're trying to use one mode exclusively. If you're in a meeting, it's the duck on the pond analogy which is you might be spinning below the water, but you're calm above it. Or you're trying to show frustration because the way the meeting's going.

But it's one or maybe a possible two modes in person whereas you're trying to use them all in a remote setting. You have to actually understand how to, it's th- I guess maybe it's like a, an ac- you're trying to throw on several different accents. You've gotta be able to use them appropriately in different settings. But I just thought, to your point, I've actually thought about this a lot because we had this conversation ourselves, you and I, a long time ago. And I realized for me why it worked with the context switchings and the framing at home. And it's because I think of this box, the computer, as the segment. But I think of the office, the entire office, as the segmentation. I'm able to switch because of the box, the computer. But I don't get to switch in and out of it at the office until I actually leave the office, which is why I think so many people, when they're physically located in an office, say, "Let's go for a walk. Let's get out of the building, let's do that sort of thing." Because they're probably very similar, which is the entire office... However many floors, whichever you consider to be your office, is the segmentation.

Alexandra: That's so true. Yeah I hadn't thought about that for, yeah, the times where things are getting crazy at work. I'll go outside on a walk, get a coffee, just leave, and it gives you a new frame of mind. And same at home. If I need a break, I'll just leave this room that I'm working in and go lay down on the bed, go to the couch, do whatever, and anytime I enter this room I feel like this is... This is where work happens, this is where I feel a certain way.

Jason: I noticed it with me when I had another computer over here, and I literally... All I had to do is switch from this computer to that computer and it reset me enough to come back. But I do think of this office as sacrosanct in that way. It's like, all right, I'm gonna go sit on the couch out in the living room for just three minutes, three minutes, that's all I need over there.

Eiso: I know exactly the feeling you have. Do either of you, by the way, when you've been so remote this long, and for me it's now going on six years, something like this. When you... For me, for it's been COVID of course, for many of us, was an example. But even post COVID, if that's even something you can say, [laughs] we... I, I started having a couple of in-person meetings again, but not frequently enough that I'm not longer awkward in them. I actually find myself quite awkward in person these days. And it's not something how most people would've described me four, five years ago. I realize that I take a second because I'm actually not looking people in the eyes anymore. And I'm wandering all over the place or is this just a me thing or is it something... Jason, you've started having in-person meetings, Alexandra, you just started going to an office.

Alexandra: Yeah. I've definitely noticed that. It's very weird, especially because of the whole do you bring a laptop situation, like, how do you sit? Do you face each other? Are you at an angle? Everything. I find that meetings with groups of people are fine those are a little bit easier to do, especially if you're, like, working on a project together and there's some... There's some goal and you know exactly what you're gonna talk about. The ones that are harder are... That I struggled a lot with at first, is one-on-ones, where you... You're sitting next to someone, you stand up at the same time, walk together to some room, sit down facing each other, and then... And then what do you talk about? The hard thing for me especially is just 'cause I find before, whenever I'd go into an office, when I was working remotely to see people there, I wouldn't have a laptop 'cause technology is a distraction and you don't want that in meetings.

And so for one-on-ones now, I've been struggling with we have this whole agenda on our laptop in Fellow, do we sit here staring at each other with our laptops open? How do we know what time it is? Like, how do we know when the meeting's over? When do we go back? I don't wanna be... 'Cause if I don't have my laptop open, I don't wanna be checking my watch every five minutes, and I can't set an alarm or something 'cause then I'm gonna be checking my phone and who knows if it's a call or an email or whatever that's buzzing. And and so I found that part really stressful 'cause having a laptop open in front of just one person when you're talking about personal things and one-on-one type stuff is weird. It's good because, in, in one-on-ones, you should have agendas and things you're talking about and taking notes about whatever is going on. But it's definitely something I'm still getting used to and haven't really found the right way of doing just yet.

Jason: Eiso and I have talked about this a lot in person in the past, and I think we've mentioned this in the podcast. I have not found the awkwardness personally, mostly because I have, for many years, thought of most social interactions as masks that I put on, and for me, when it comes to post COVID, again, if we can say such a thing, it's just slipping on a mask. And so yeah, it was like a... Maybe a little dusty the first couple times I put it on, but it... It was something that I had to practice for years anyway. It was the riding the bike scenario. You just, and my mode of doing it was, slight bit of humor, slight bit of seriousness, but not taking myself too seriously, getting into the mode. Et cetera, et cetera. There's a rhythm to one-on-one meetings that most people know if they've had one with me. And the first couple times might've been slightly awkward, as you get to it. But like 85% of it was still the normal one, and then I was just back to old hat.

Alexandra: I was just gonna say, I'm excited to get to that point, where it's past the peak awkwardness and everything's normal.

Eiso: Are we actually genuine when we do this? I know I'm going a little bit deeper than our... [laughs] Than the usual podcast, although we've been doing this lately a little bit more. When we're putting on these masks or when we're being deliberate, or when we're knowing, hey, I'm showing up to this meeting and I should use a little bit of humor, and I should tone it down here or are we actually being... Are we being good leaders? Are we being genuine? Like, where does the line... Where is the line versus I'm making that other person feel comfortable enough in this situation that they're in, why human beings smile in certain cultures and might not smile in others. Or are we getting to the point where we're actually just starting to be a little bit like the way we'll probably end up training our avatars one day in this situation, this is what you're supposed to show. And I'm curious. Alexandra, you talk a lot about communication in your book. Where do you think that line lies? 

Alexandra: That's a good question. I think I... I tend to veer on the side of being very open and transparent with people, and it's very infrequently that I'll put on a veil of this is my persona for this or that or I'll try to mas- like the... I know I talked earlier about masking emotions when news has been shared, and I don't wanna affect the team. I think that's the limit of where it goes for me. And if somebody asks me question, even if it's very personal to me, I'll be honest, 'cause I'm really big on trust, 'cause the more honest you are with your team, the more honest they're gonna be with you, and that element of trust is so important for everything around work and trusting each other. And so I really like building that up by being honest in return with people. 

Eiso: Do you find yourself... If I think about my company we've managed to meet in person once since we found it, almost three years ago. And we'll still meet again for a second time. And I got COVID 24 hours in. I had about 24 hours with the team in person. And I realized that in those 24 hours with the team, I shared more personal things about my life than I probably did in the whole two and a half years before. Because the moment you're outside of that time box constraint, you keep talking. I know that sounds... [laughs] Sound like we're robots here. But do you find yourself that now you're coming into the office, that there's more room for sharing that personal side? Or do you think it's important for a manager to make room in their remote interactions to go into the personal as well? And how do you think... How do you recommend someone successfully doing that?

Alexandra: Yeah, I think it's very important to make time for that working remotely as well. And especially so for my situation it's not like my entire team is going into the office together and we all get to be there all the time. It's only a handful of people that are going in, and I don't wanna exclude anyone who's working remotely, 'cause I was... When I was working remotely before, it was the entire company in an office together and I'm the one single remote person who's not involved. I know very much how it feels to be not included in certain discussions. And so I, I think that the time to talk and make connections as humans kinda needs to be built into the work day. Not forced. I'm not a huge fan of saying this is the hour where we're all gonna play video games together and just forced fun is never fun for anyone. I don't like it. [laughs]

But what I... But what I've landed on I've gone through many iterations of this. In, in 2020, when everyone first started working from home, we had a bad iteration where every single day, at 10:00 AM, we were all working the same time zone. But every single day at 10:00 AM, we'd have a half hour stand up type thing, where we'd just get on a call, chat, see how everyone's doing. That didn't last very long 'cause every single day is ridiculous and nobody starts at the same time and it's the worst way of doing it. But what we've landed on now, that I really is each engineering team has a twice weekly half hour meeting that's social time. And so we don't call a stand up, we don't do anything work related in it, unless there's something super urgent that people need help with right away. And it's it's like a half asynchronous, half synchronous meeting where we have a note for it and everyone kinda jots down this is what I'm thinking of working on today. Not traditional stand up type stuff, but just getting some work stuff out there.

And then the call itself is just talking about what we did on the weekend, what we're gonna be doing later, like what... We just talk about life. And people bring fun icebreaker questions sometimes. Some of those would you rather fight a duck or a horse size... That one. Those kinds of things. But yeah, so we, we have a lot of time built in for making social connections there. And then we do end up having in-person meetups as well. We do those three times a year 'cause we're spread across the world now. And it makes those even nicer because you're not spending the time getting to know each other as people and building up those outside of work relationships. You already have a good foundation and so you're able to just jump right in, be like, hey, how's your wife doing? Let's go get a coffee and it's just more natural feeling to, to jump right into that.

Eiso: You mentioned something in your book, and I think it's in bold, if I remember correctly. Which is you're not responsible for your team members' personal lives. You're only responsible for them at work. Empathy massively matters as a leader. And like you said you're sharing a lot about your life and that opens up often the gateway for people to do the same. And I personally think having a strong relationship where both sides feel very comfortable to share what's happening in their lives builds for a great foundation of people working together. I think separating those things becomes... If it's only ever about work it's hard to build that strength of a relationship. There is a boundary somewhere in terms of, how involved and where not. And I know you talk about this in your book, and I'm curious to get your thoughts and curious to hear, yours following on that, Jason.

Alexandra: Yeah, this something that I thought was really important to point out, 'cause it's something that I've struggled with and I've seen a lot of other people struggle with as well. Because as a manager, you talk to so many people and you're responsible for the work of so many people, and you do end up learning a lot about people's personal lives. And inevitably, something awful will happen to someone, sometimes multiple people at the same time. And if you're a manager, you probably are an empathetic person already. But that stuff will weigh really heavily on you, and you can't really push it aside. It's not something that is just contained to work. And like I, I've, I feel awful for so many things that are going on for people all the time. But our natural instinct, I think as managers, especially engineering managers, is to try to problem solve, 'cause that's the default there's a problem, we're engineers, we'll solve it. This is something we can we can do.

But you can't do that for people's personal lives. Th- there are things you can do to try to make work easier for them, and maybe make accommodations, make some changes to how things are going. But I think it's really important to just remember that you can't and you should not try to solve people's lives outside of work. It is not your job. You're not... You're not a parent, you're not involved in their lives that way. It's nice that people are sharing things with you so you can help at work specifically, but yeah I don't... I have to remind myself sometimes not to feel like I'm powerless over a situation, 'cause it is not my role to fix these things.

Jason: This is topic that's come up in various different forms over the last 10 or so years, particular in Silicon Valley. And one, one thing I try to reinforce, and I had to learn this myself too, is that you have to separate those things. And exactly as Alexandra was saying. And, you've got to... The easiest way for me to say this is essentially what she said too, which is you got to make accommodations. When something incredibly hard comes up in someone's personal life, you say, "okay, essentially take whatever time you need," if it's at an extreme end of a spectrum, to get this sorted out and figure it out and, come back, et cetera, when you're ready, we'll talk in the meantime. But that's essent- essentially setting up the stage for them to take care of that thing in their life and do that and you to say, this is how we're going to react to this with you. We're gonna give you the space and the time and so you can focus your energies and efforts.

And if you need something from... Specifically from work, whether it be from an insurance perspective or something like that, HR is over here, they can handle some of those things with you. You can't take that stuff on and you can't help with that too. And I push this really hard, is you're not trained to do that. You don't... Have not learned to do this. For instance, there is a... There is a, sub vein inside Silicon Valley where people will talk about... I don't wanna use this word too loosely because people have various degrees of feelings, but bring your whole self to work and all those sorts of things. But let's say you're bringing some sort of emotional trauma to work and talking about it on your one-on-ones on a regular basis. It might be that it's completely inappropriate to, for me as an engineering manager to engage with somebody.

I'll say, "hey, what accommodations do I need to make for you to sort this out? I'm not capable of having that conversation with you to the degree I feel comfortable. If you can have that with me and say, this is, like, why my work product is not where it needs to be, et cetera, et cetera, blah, blah, blah, all the different caveats, but I can't engage with you like a therapist would or a psychologist would or anybody would. In fact, I think it's completely inappropriate." But for some reason, we've seemed to maybe, to some degree or percentage in the engineering management culture say, this is one of the types of conversations we should be having. I feel so strong the opposite. I think we'd be doing people a disservice to do that.

Eiso: Alexandra, when we had a chat earlier, you spoke about hiring. Because we talk a lot about, and we did already today as well about, remote and the setting of remote at the office, but what about our hiring processes? And you said some very interesting things that I'd love for you to share with the audience and how you think about them.

Alexandra: Yeah. When people are starting to get into hiring, normally people will go through this sort of training where you learn how to ask questions, how to talk to people. And questions not to ask and biases to look out for. And I think that when we're interviewing people remotely, there's this whole new set of biases that people aren't talking about, but they're super important. And interviewing people remotely gives you insight into so many new signals that you don't get to see when you're interviewing people in person. For example, if you're... If you're talking to someone on a call, you can see their background, and they might have a messy bed behind them or a bunch of dishes or, you can see their house. And that can give you insight into their socioeconomic status, if... If they clean their house. Things like that. Internet quality is also something that gives insight into that status and what... Where you live. Internet quality is really important to look our for because if somebody's internet is a little bit fuzzy, they're gonna sound less intelligent than somebody who's saying the exact same thing over quality that's really good and they're coming through clearly.

And so there, there are all these new factors that don't exist when somebody walks into an office and just talks to you in a meeting room. And they're gonna affect how people see candidates because, if the internet quality is not great or you can see their messy bed or whatever, those things don't matter. They have nothing to do with how good of an engineer they're gonna be. But you might subconsciously think "oh they're messy, they're not gonna keep the code banks clean." Or their internet isn't good, so they're... They just don't sound as, as smart as they would if you were talking to them in person. There, there are all these things that play into interviews, and I think it's really important for people to be trained on looking out for that kind of stuff and recognizing that might impact your opinion of somebody when you're interviewing them, so that you can try to minimize that as much as possible and give everyone a fair chance.

Eiso: Is this something that you think we can train engineering managers and engineering leaders on to be able to be more aware of it in the interviews? Or do you think it's something that there's just, like... There's just gonna always be that bias and we'll never be able to remove it completely? Like, how... For instance, how do you remove it or try to remove it yourself?

Alexandra: Yeah, so it's not possible to remove any kind of bias completely. There's always gonna be stuff that subconsciously is there and you're thinking about. But I think that pointing it out and saying, this is something that's gonna impact potentially how you think of someone, be aware of it, that is really useful. And I know when I started interviewing years ago, we had to go through all these trainings about how, if you're talking to someone who's really young or really old or this gender whatever it is, just being aware "hey, this might impact what you think of them, try not to". Just knowing that makes it more likely that you'll think hard about okay, they said this. Do I not like that because of the content of what they said? Or is it because of the context around it that is making me think this certain way? I think just knowing about that stuff goes a long way and making that a part of interview training and interview refresher training is a good step to combat that.

Jason: I always wonder on this. Because essentially what's happening in this... In this scenario is you effectively have, as Alexandra pointed out, you effectively have more points of signal towards somebody that you just wanna have before. And one of the things that I've constantly had conversations on with engineers, but even more, business leaders too, is a lot of people want to say something that kind of looks insightful, but ultimately doesn't matter, but they need the... To look insightful. And so they need to have that moment. And so the bias in this might be, like, "hey, I'm looking for something. I'm trying to pick up on a couple of different things." Ultimately, I think always along the way, somebody else has to be saying, does it actually matter? Because these things will come up in interviews. And I see it now, given I'm on... I'm on the VC side. I constantly am interacting with VCs who will point out the dumbest things.

I love this person because they did X. I hated this person because they did exactly the same thing. And they thought it led to a certain signal. None of those things ultimately likely matter, or the set of things that likely matter in those... The outcomes of, in a venture or someone's ability to do their job are actually super small. And what are those? And I think people along the way, in the processes, need to ultimately call out BS on does that actually matter? No, it probably doesn't, so remove it from your evaluation in all likelihood. But more than that, you gotta start doing that pre hoc because people form their opinions based upon those, but you gotta stop the process along the way too.

Alexandra:  Yeah, I agree. I've had so many post interviews calls at previous companies where things were brought up. "Oh, yeah, this person plays the same video game we do. They're gonna get along great on a team." Or "oh, they contributed to this library somewhere. Awesome." And just pointing out "okay, but that doesn't really matter. Let's not put our decision on whether they should join the team based on these tiny signals that don't have any kind of indication on how they'll actually do on the job."

Eiso: This goes way back for me. But about six, seven years ago, I was building a company where we analyzed the source code of developers and we looked at it in context of the code base that they would be working on at a company. And it did things like analyzing their experience or with certain libraries and looking at that in context what the company was using, style of code and a whole bunch of other factors. And what we found, which I found very interesting, is that the people who objectively... And again, this wasn't a perfect measure. But it was definitely able to capture quite a lot. We found it was, like, objectively often the best people for a certain role, or the ones that looked incredibly similar to the people that were already there. This was like this high dimensionality vectors that had a whole bunch of characteristics about one person's code history versus the people who were working there, and it matched them. 

And what you were usually looking for was people who would fit in the code base or people who would be like someone else on the team, because that's often how we hire. We want another senior front-end engineer who looks like Janet because she's really great. And by the time it came for the companies to actually run the people through the interview process, and we were doing this with hundreds of companies so the sample size wasn't small. They extremely rarely ended up hiring the people who objectively showed to be the best fit for their code bases or for the people they were hiring. Because there's so many human biases that we have that at the end of the day... And when we run through the interview process, we pick every person... In... We throw in every person, but a different set of biases. All right? And I think, most of the time, none of us are even aware what our biases are.

I recently had somebody who was telling me oh, I really appreciate they went to this school or that they showed up wearing a shirt with a collar. Two things to me that had absolutely zero I didn't even think about it. And somebody else said, oh, their age. And I'm like, I've worked with them for three years, I don't know what their age is, right? And I for sure have my own biases, but they're not obvious to me, but other people's biases are obvious to me when they're so different to my own. And so I really wonder if and this is maybe a much broader topic and probably for a whole episode. If at all, we're just any good at hiring. We're somewhere probably within a spectrum of random. I don't know.

Alexandra: Yeah. I think anyone who says they're good at hiring is lying. It's a gamble. 'Cause people can also be amazing at interviewing and awesome to talk to and do really well on code tests and all that stuff. But you have no real way of telling how they're gonna do on the job. 'Cause the job is so different from any interview process. It's about how you collaborate with engineers and other teams, how you deal with long projects, how you collaborate and give code review, feedback. There's just so much to it that you can get signals for, based on the interview. But, how you present yourself in an hour or two has no impact on how you're actually gonna be to deal with over months and years. Yeah.

Jason: I agree entirely. I think that basically we're at a random stage for hiring, and I think people will argue differently. But here's what I do think too, is that we confuse hiring as, as well as remote and in person, at different stages, because the type of person you're gonna hire for a five-person start-up out of the gate, likely looks different than a Microsoft size person you're gonna be optimizing for different sets of traits. Even though you're saying we would like them to have each of these traits at each one of these stages. The depth at which they're going to have maybe one of those is going to be slightly different, so. You know, GitHub as an example the first five people likely look very different than last in the 2500 range. 

And yet they all worked at GitHub at various times. And it makes it very difficult, one, because most people don't have the intent- intentionality of saying, what are we hiring for? Who are we hiring for? What are the traits we want out of these people? That's usually the first. They say we need to go hire five engineers. Five engineers that... Of what type of, who are doing what, who we want to slope grow into, that sort of thing. And then the other is, I find that most people tend to be really poor, again at interviewing because what they're looking for is they're just pattern matching. They're like, I liked this about them. Which is literally the worst measure you could possibly do. I like a lot of people that I'm never gonna wanna work with, and I dislike a lot of people who I think would be actually excellent at their jobs. So, you have to... You have to understand the balance of these things.

Eiso: Jason, I'm gonna throw a question at you and I'll throw the same to you, Alexandra. Today it's invest, before it was... It was hire. But I'm gonna ask you for both contexts. If you think someone's very good at what they do, and you don't like them, would you hire them or invest in them? 

Jason: So This obviously depends. I say this is kinda like a Travis Kalanick or Trevor Milton stage type of thing, or Adam Newman. If I dislike them and I think that they're an awful human who is going to go do things that are over lines, no, I won't. But if I dislike them because of their Twitter personality or something else that I think is different than mine, but it doesn't fall into the caustic range, then I likely would. Because the job is not to find a thousand people that I ultimately wanna hang out with and have a beer, which is why . I hate that test. The test is not would I wanna have a beer with them. The test is, ultimately, is this company going to be better off? Are people around the table going to learn more from this person? Are people going to remember the influence from all these people? Are they gonna make us a better place?

And yes, there, there is some element of, quote unquote, dislike that comes into that. But generally speaking, if you... You're a thousand people, there are going to be many people in your organization who are excellent at their jobs that you dislike and you're never going to be able to find a set of a thousand people that all thousand people like. That is... That is impossible to go do. Already, we already know that there is going to subsets of people that we do enjoy hanging out with or not hanging out with, et cetera, et cetera. But then there are going to be people who you are okay professionally interacting with, and then you're never going to have another interaction with them. It's going to be through a PR, it's gonna be through something else. So yeah. I would. Now, again, it depends. Because and now roles also become critically important too. Would I hire a VP who is unlikeable? Just completely unlikable by everybody in the organization or by the majority set of people? Maybe. If the subset of people who I absolutely care enjoy this person's interaction.

Let's say that, I have an engineering organization of 100 people, and the 20 best performers absolutely love working with this style of person or this person's personality. And we have a whole bunch of people who are under performers or whatever. I'm not optimizing for the 80, I'm optimizing for that 20 in this scenario because of what that organization needs for whatever reason. And again this is a super nuanced topic, but the point being, it's not straightforward and that to me is one of the most critical things you can get... You should remove from your organization.

Alexandra: I totally agree. The only thing I would add to that is I really like hiring people who specifically don't necessarily mesh with my personality. 'Cause it's... Or we work well together, but complement each other. Hiring for skills that you don't have is always a good thing to do, but I also think that hiring people who don't have the same way of thinking as you and approach things from a very different perspective is really great. I love working with our CTO Sam because we are total opposites where he's thinking so strongly about technology and code and, like, how to do things like that. And I'm thinking product, people, process. And it's like we'll have different opinions of the same thing, but that kind of conflict is really good 'cause that leads to the best decisions happening. I love hiring for that kind of conflict. 

Jason: This is the most important topic for me. And I've had this conversation with every boss that I've had for the last 10 years, and I've had this conversation with my partners now at Redpoint and stuff, which is the "how are we gonna fight conversation". Because the point is, we're going to disagree over stuff. And, I happen to like my partners at Redpoint. And in the past, there... I've had bosses who I've not liked at all, and I've had subordinates who reported to me or team members and stuff who I did not. But we had the conversation about how we're gonna fight. And you can get through this if you understand that dynamic. But it also tells you a lot about a person eventually if you realize what that interaction is going to be, and I can tell you almost... This is like the closest I can possibly get to a rule. The dirtier someone fights, the less likely I will... I should've hired them, and the more likely we will fire them. And also, if you have a boss who fights kinda dirty and kinda mean in that way, they're... That goes into the, I should not hire you. No matter how much I like you as a human, you are not a quality person. And that is as universal as a rule that I possibly will get to.

Eiso: I like it. We need to label that. We'll have to think of a name. But I think it's... I think it's a very good rule of thumb that universally will hold true. Alexandra, I know we're coming towards the end of the episode. Is there anything that you'd love to share with the engineering leaders that are listening to us as final words today?

Alexandra: Yeah, my go-to advice, which I always fall back on, and always have to relearn all the time, is to ask your team questions even if you think the answer is really obvious and you know it. Because I will... I will have the simplest question and it will seem like the most obvious answer, and before acting on it, I'll think I'm just gonna do a quick survey and run this by the team. And I'll send something out and everyone will have just absolutely totally different opinions than what I could've ever imagined. And it surprises me every single time for the smallest things. I'm always trying to get people to just ask your team as many questions as you can to really understand them and lead in a nice not democratic way necessarily, but just really be aware of what your team is thinking is super important. That's my final words of wisdom.

Eiso: I love those. I... Jason and I are smiling, for those who aren't watching it on video, because I think we both very much agree. 

Jason: 100%. Thank you.

VO: Thank you for listening to Developing Leadership. Make sure you subscribe to follow us on our journey to more meaningful engineering leadership. If you have any challenges or topics you would like us to explore in an upcoming episode, tweet or DM us @devleadership_ on Twitter. To learn more about data-enabled engineering and how metrics can help your teams and improve your processes, go to athenian.com. See you in two weeks for another episode of Developing Leadership

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