Shifting to 100% Remote Work With Sumbry

Transcript

George Miranda: Welcome to Page it to the Limit, a podcast where we explore what it takes to run software and production successfully. We cover leading practices used in the software industry to improve both system reliability and the lives of the people supporting those systems. I’m your host, George Miranda, @gmiranda23 on Twitter. Today we’re talking about a pretty timely topic for the software industry. The COVID-19 pandemic has forced us to make a shift into 100% remote work, many of us for the first time. The change to 100% remote work has mixed results, some people love it, but other people have found it to be a very jarring shift that’s difficult to adjust to. Even in companies that are the so-called digital natives, where working from home occasionally is the norm, many people now find themselves scrambling to cope with the change. Teams that were used to being in an office together to get things done are now working from home for the longest stretches of their careers. Learning how to make that adjustment under normal circumstances is tough, but it’s even tougher to do when you’re just starting to get to know a team because you were in the middle of onboarding when this pandemic hit, like our guest today. Distributed communication is one of the biggest challenges for remote teams, but that’s especially complicated when you’re not just learning new habits, but you’re also learning new people. So we’re here to talk about the lessons that we can all use to better work with and better understand our teams during this unprecedented and sudden shift that we’ve had into 100% remote work. We’re joined today by Sumbry, who recently joined Airbnb as head of reliability engineering. Sumbry, welcome to the show.

Sumbry: Thanks for having me, George.

George Miranda: Would you like to introduce yourself to the audience and tell us a little bit about who you are?

Sumbry: Of course. So my name is officially Donald Sumbry, but those that know me just call me by my last name, Sumbry. It’s been my handle for quite some time, longer than I can actually remember. I’m originally from Los Angeles, and for those of you that don’t know, me and George actually know each other from LA from many, many years ago and moved up to the Bay Area about 10 years ago. I originally started in the Bay Area to join Twilio, where I headed up the platform team there and got to do all kinds of cool stuff, especially leveraging AWS and working with a lot of the older school cloud technologies. I spent about four and a half years at Twilio and then moved to Uber, where I was basically running production engineering at Uber, and I did that for about four years as well. I tend to stick around at companies for a while when I join them. And just recently, I’ve now moved on to Airbnb, where as George mentioned, I’m heading up reliability engineering.

George Miranda: So we do know each other. And one of the reasons that I wanted to have you on the show was because we’ve chatted quite a bit about the ways that we work and some challenges that we’ve had. And one of the things I found really interesting is that this is the first time you’ve been working remotely for this long, meaning that you’re not going into an office. And so, I’ve been a remote worker for about eight years. For folks that don’t know, on the show I’m often called an extreme digital worker or remote worker. I’ve been doing the digital nomad thing for about two years and so I move around quite a bit. And Sumbry, what I thought was interesting was that you don’t move around a bit, but you have worked with a lot of globally-distributed teams. You’ve worked at companies like Uber and Twilio before coming to Airbnb. Those are really large names, not only in the Valley, but across the globe. You are dealing with teams all over the world, but you’ve never really worked from home for a significant stretch of time. So how about we start there? What is this shift to working from home and not going into an office been like?

Sumbry: The challenges with Airbnb are the fact that not all the teams that we actually worked with were global by default. We had the San Francisco first mentality. And so, this is just a big shift that had to change. An example that I use to express this point is take a video conference, with the San Francisco first mentality, most of the people on the video conference are in the same room. So when they’re talking and interacting with each other, there’s a natural ebb and flow to the conversation for folks in that room. But if you take one or two people and you add them as remote workers, what then happens is they always feel like they’re interrupting the flow of conversation anytime they try to interject. And so, by being SF first, that just meant that people in San Francisco or in the Bay Area had the loudest voice in meetings, then all of a sudden we just switched to everyone basically being remote all the time now. And it took a big cultural shift and it was really tough for people to get used to this in the beginning. And it’s interesting seeing the progression because what started out as people taking turns, interrupting each other and filling almost like we were using two way conversation just flowed into a more natural ebb and flow in the conversation as we got more and more used to this over the weeks. And so that’s just one example of having the break out of this SF Bay Area first mentality. I’m sure there’s lots of others as well.

George Miranda: You put a few things out there and you’re right. I do remember that stretch where you were working for yourself and you’re starting your own business and working from home, but the funny thing is that I don’t think I really think about that as your remote work experience, because you had to communicate mostly with yourself or a couple of other vendors, whereas I think the real challenge of working remotely is the thing that you mentioned. When there’s a center of gravity around a particular location, if you’re not there, it’s really easy to feel excluded. So this is great. I think we’re going to have some really good things to talk about. But one thing I wanted to start with is, one thing that we do here on the show is for whatever topic we’re discussing, we always start by debunking a popular myth or misconception about the thing that we’re talking about. So what myth do you want to debunk about working from home?

Sumbry: I have a few, but I’ll just start with one and I’ll work the others maybe into other parts of the conversation. And that big myth is that you should work from home in your pajamas, or you should not get dressed and basically take it easy. And I think that is 100% the wrong thing to do. I think it’s very easy to fall into that trap. So normally if you get up in the morning and you take a shower, and you get dressed and you go to work, working from home, you should still do those same things. Don’t get too comfortable not having that routine because it actually ends up making it tougher to be more productive because it’s all about routine. I think that’s one of the biggest ways that you can be successful. So I often tell people, “No, get up every day, shower, put on clothes, get dressed like you’re going into the office and then just go to your desk and work.”

George Miranda: I’ve said that for a long time and that’s always been my routine. And I have been that annoying person that’s always like, “Get dressed, go to work.” And not to get too personal, but I’ve actually had a little bit of a hard time these last few weeks with everything that’s been going on, and I became that person that stayed in my pajamas and my workdays suffered and just my overall wellbeing, that was the key signal where I realized, “Oh my God, something has really changed.” So I will say that different people handle it different ways. And my wife, for example, has no problem sitting in our bed, reaching over, grabbing her laptop and just typing away and getting her day started, and I can’t do that. So I think everybody needs their routine or their [crosstalk 00:08:26] so it takes different shapes and forms, but I 100% hear you. Dive into some of the things that I think we’re here to talk about a little bit more. So one of the things I thought was very interesting, like I alluded to in our introduction, was that you’re new to Airbnb. You’re just starting to get to know your teams, not just in an office, but now in this new dynamic. So let’s talk about that dynamic for a little bit. Is it easier to build relationships because you know that you’re eventually all going to be back in the same office? Do you think that this dynamic will go back to what it was? Do you see things being different? How do you feel about all the newness of the things that are happening?

Sumbry: So this is really interesting and I’ve made a couple of bets with some folks about what’s going to happen once things return to some semblance of normal. And to be honest, I actually don’t know what’s going to happen. The cynical part of me believes that we’ll just very quickly revert back to old habits, especially if you had this San Francisco first or barrier first mentality, I hope that does not happen. I hope a lot of what we’re doing now sticks, but as far as how it relates to onboarding, 100% agree. The challenge for me has been, I’m used to building these strong relationships when I first started a company and it’s a whole lot easier to do that in person than it is over video conference the first few times that you’re meeting folks. Generally, if I have a new manager or someone joining my team that’s going to be working in a remote location, we will actually fly them out to the central location for the company, and this happened at Uber and Twilio before that, where we’ll onboard them and have them meet a lot of folks in person first and then they will go back to their own local time zone and continue to build those relationships after the fact. And so, at Airbnb, I basically had four weeks to onboard and meet a lot of folks in person and then we started working from home, and we’re in our fifth or six week of that right now.

George Miranda: That’s a very common experience. I think whenever I have onboarded in a new company, creating that face-time is absolutely essential. And so, it’s not unusual, like you said, to go spend some time there, develop those relationships. And my last company before PagerDuty, I was actually spending about half of my time in San Francisco because I was working with a team that was not used to being remote at all. And so, I 100% hear you. I think it takes time, and especially not just as an individual contributor, I think not to divert the discussion, but when you get into more of a lead or a leadership role-

Sumbry: Correct.

George Miranda: … if there’s a center of gravity around leadership in a physical location, so much brainstorming happens in the hallway, or over lunch, or in ways that you are just excluded from if you’re remote. So how do you think that’s going to impact this shift now that all of leadership is distributed where you are?

Sumbry: So I actually just had a new manager that joined the team and that person joined just a few weeks ago, and so, all of their onboarding has been virtual. And so, it’s been really interesting seeing how they’re starting to come up to speed. I basically had to do a whole onboarding plan where they’re meeting everyone virtually, they’re meeting the team virtually, they haven’t met 90% of the team in person yet, and this is actually going to be a leader of the team. And so, it’s been interesting watching very experienced and then parodying that to my own experience as well. And it’s definitely been challenging. However, I think it’s developing a muscle that hopefully will continue to flex after this. And so, I have a funny story to actually tell about this because when I was at Uber, there was actually a person that I worked with that was overseas and I had never met this person in person for two years that I worked at Uber. We started out our interactions all over video conference and finally we actually met in person because that person flew out to do some in person work with the team. And as soon as I saw them, I thought that this was a very small and short stocky person, this person was like seven feet tall and was a giant, and [inaudible 00:12:54] and I just remember looking up and going, “Wow,” that just shaped so much of my perception of what that person was like and how I interacted with them and then seeing them in person changed that a bit. And so, it wasn’t really negative in any sense, it was just interesting that my perception changed a little bit. And so, I definitely was not intimidated interacting with that person over video conference. However, if that relationship had started and we started out by meeting in person, it might’ve actually changed the way we got to know each other a little bit. And so, from that point of view, I actually think it may end up being more beneficial having more and more folks start this by default because it removes some of that, if that makes sense.

George Miranda: It does make sense, and I think that’s interesting. That’s one of the things that people don’t talk about very often, which is when it comes to physical cues that you might get from being in the same room with someone, usually what we focus on is some of the nuance that’s lost or things that you might not pick up, but I think very many folks think about what sounds like in this case would have been an intimidating presence and how removing that allows you to more clearly see someone and establish a communication style that might’ve been hindered otherwise.

Sumbry: That’s correct, exactly.

George Miranda: I love that. So I think that leads to one of the things that I wanted to ask about, which is because you’ve managed globally distributed teams and you’ve had some interactions where that remote experience and the personal experience were so different, maybe let’s start by identifying where some of the overlap is. What are some of the challenges that you think you were better prepared for having managed globally distributed teams now that you’re just stuck at home and you’re not in an office?

Sumbry: So I mentioned one of these already, and I want to double down on this a little bit. And it’s this notion of just having a routine. When you’re working with a globally distributed team, you can’t just start randomly talking to folks in the hallway and resolve some critical decision by just walking to your next meeting, you have to plan everything. Every meeting is planned, every interaction is planned, because there’s no other way to coordinate. And so, on that level, that’s actually helped a lot going into this new working environment, this notion that you have to have all of this routine and not just your own personal routines, but actually the routines for the team as well too. And so, we actually just refer to these internally as team norms where we’ve taken what’s worked well for globally distributed teams and just made everyone do that. And so, what’s an example of a team norm. Well, the primary hours that we are all expected to be in front of a computer are maybe 10:00 AM Pacific to 5:00 PM Pacific. So we just set that norm and everyone will hang out in this chat or Slack channel, that’s another norm. And we will have two meetings every week during this time where we chat about these things, that’s another norm. And so, by having the globally distributed teams and already having some of those practices, applying those to all of the teams as well helped a lot in this. And we basically told all the engineering managers, “Hey, write a document with all your team norms in it, correctly set expectations and just develop this routine and this cadence,” and it’s actually helped quite a bit. So I was very happy that we were able to leverage that. And the interesting thing about my teams today are about half of the people on my teams are globally distributed and the other half are Bay Area centric. And so, we were able to take the lessons from the globally distributed half and apply those to everyone else. And I think that definitely helped. And in fact, some other teams that are outside org have started picking up on some of those lessons and copying some of the things that we’re doing and that’s great, that’s the best way to learn and adapt.

George Miranda: When I started at PagerDuty, my team was entirely based in the Bay Area, and as the team hired and expanded and grew over time, we became primarily remote. And one of the exercises that we did is we called it the rules of engagement and we documented what those expectations were. I’d like to see what I can share with those and maybe put a link to that in the show notes to help folks see what those things are like. But on that topic, one of the things I wanted to bring up is that, like I mentioned earlier, having been a remote worker and an extreme remote worker for so long, I’ve been a little baffled at how difficult it’s been for folks. And so, I wanted to get your perspective. I know that you have worked with global teams, but what are you seeing in your own teams? What are people having the hardest time with?

Sumbry: So you touched on this a little bit earlier, and this is a point of clarity that I want to double down on. And it’s funny, because in my mind, working from home and everybody being remote were conflated a little bit, they were the same thing. And I think the challenge with what’s going on right now is that we don’t just have a bunch of people working from home, we have a bunch of people working from home with their spouses who are also working from home, with their children who are also working from home. And so, it’s not just that we’ve changed one thing and everyone’s now working remotely, we’ve also just changed everyone’s households at the same time as well. And so, I even mentioned earlier about developing the routine. The challenge here is you’re not just developing your routine and the routine of your teams, but also of your household as well too and everything that comes with that. And so, that’s been the big thing that people have really been struggling with. And at one point we had to tell folks, “Look, I know we’re trying to set up these norms and whatnot, but some of you have families and children, and you’re figuring out how to make all this work, take the time to do that, take the time to figure that out.” Because it’s not easy if you find yourself in a situation where now you’re homeschooling all of your kids and you’re like, “I’m not qualified to be doing this, I got to figure this out and continue doing my day job at the same time.” And so, that’s been the really interesting thing is just seeing everyone adjust to that as well. I’ll share something personal here, even with me and my wife, my wife was not used to me being home all the time, and so she often will… When I go to work, I’m basically in back-to-back meetings all day, but to her, I’m like basically hanging out in the house, and so she’s always asking me to do things, and to do chores and things like that, and I’m like, “I’m not here, I’m working right now.” It’s setting that expectation. And I just think it’s taken everyone a while to get used to that and get used to these new rules of engagement, not just within your company, but also within your house as well.

George Miranda: It’s funny because there are things that are inevitable. And so, as you were speaking, one of the things that I was enormously thankful for is my dog is wearing a cone right now, the cone of shame. He has a paw injury and she is so sad when she has that cone on. And for the last half hour, I could just hear her whining in the background, and right now just going to knock on wood and make sure it doesn’t start. But that’s one of the things that I think we give a lot of attention to, which is when you’re working at home, there are disruptions that happen, like your dog might be whining, your spouse might be asking you to do a bunch of things that seem a little out of place or uncommon, but I would challenge folks and say, well, it’s unlike the disruption that you have when somebody is in your meeting room and they’re not clearing out and so your meeting starts late, or the office Wifi went out, or any number of other issues that we’re accustomed to in an office environment. But when they happen from home, it seems like, well, that’s a personal life thing, so that obviously is interfering with productivity and you’re not really doing your job. So let me ask you, in terms of productivity, how’s that going for you?

Sumbry: So interestingly enough, it’s a double edged sword. And I’ll talk about myself and then actually the team, because this is a really interesting question. From my own personal point of view, working from home, I’m a lot more productive, especially when I have to do creative things like put together presentations, or write documents or things like that, it’s 100 times easier to do work like that because I can focus, there’s not a lot of interruptions, I can mute Slack if I need to or things like that. And so, from that point of view, it’s gotten a lot easier. Where it’s gotten a lot more challenging is in the relationship building side of the house, it’s in getting to know folks and figuring out who the right people are to interact with, and how do I actually effectively get things done. Doing all of that navigation, I’ve gotten way less productive as a result, and it takes like 10 times as much effort. And so somehow, maybe this is all balancing itself out, definitely been able to focus more on the creative end, but on the communication and coordination point of view, I’m still getting a lot of stuff done, but it’s actually taking more effort to get the same amount of things done. And then if you actually look at the output of our teams, this is really interesting because we actually looked at the statistics for deployments once we started working from home and guess what happened?

George Miranda: You had more deployments?

Sumbry: More deployments. The deployment rate went up by about 20 to 30%.

George Miranda: Wow.

Sumbry: And we were shocked. We were like, “What the heck’s going on? Is this an anomaly?” The business is changing a little bit, so are people just shipping more things related to that? And it’s actually a combination of things, but we actually sent out a survey to a bunch of our engineers and managers to ask them exactly what was happening. And the interesting thing from the survey, the results that we got from the survey were that 70% of folks actually did say they felt more productive, but that same 70% actually felt like their energy levels were way lower as well. So we were getting more things done at the expense of more energy levels and effort, and so it was definitely very interesting.

George Miranda: I definitely feel that because I feel like when I have been lucky enough to be in a city where there is a local office, even though I’m a remote worker, in those situations, I have very much enjoyed having some time at home so I can focus and get things done. And then time where I go into the office to get some social face-time and talk to people, and in those moments I’ve had conversations in a hallway or across the desk exposing me to parts of the business I had no idea were even happening. And so, I think one of the things that we can do in this shift, or here’s what I’ve noticed with my teams, I do see that productivity still, but one of the things, and I don’t know if it’s because we’re all remote, or if it’s the pandemic, or a mix of all of the things that are happening, but especially right now, I think people are really hungry for that social connection, and whenever my team has made an opportunity to have a virtual happy hour or just have a meeting that ended early, we’re sticking around to talk to each other, to just have a little more social time. And so, it’s good because I feel like those connections continue to develop with my team. They’re not maybe as widespread with people that I don’t directly interface with, that I would have run into in the kitchen getting a cup of coffee, but I think those opportunities are there if we can maybe just find more ways to make those things occur. Does that make sense?

Sumbry: It does. And I will actually offer some things we tried to do exactly that, because I noticed very early on, and this wasn’t just true within my team, but across the company, is that because people weren’t used to doing those types of interactions over video conferencing, we had to force them a little bit. And I mentioned earlier, my team is split where half the people were globally distributed and the other half weren’t. And so, for the half that wasn’t, we had to actually do activities to help break that ice a little bit and get people used to that. And so, there’s a couple of that we did that were huge hits. One of them was we did a virtual talent show. I actually demonstrated deejaying. I was actually a DJ in a former life, and so I showed everyone how to actually do this for 10 minutes and played some songs and mixed some tracks together. We had another team member actually show off Beat Saber, which is this cool virtual reality game where you have light sabers and you slash these blocks to the beats of music. We had someone else singing and play guitar, and it was a really good icebreaker. The other really fun thing that we did is we actually did our own version of cribs. And so, everyone signed up for a slot and they actually would take their laptops around their house and they would show off their homes and their working areas. And we all figured sooner or later, we were all going to get used to seeing this stuff anyway, so we might as well just do it right off the bat. And it was really interesting because seeing people’s homes instantly changed the levels of interactions and familiarity I had with folks, I loved it, it was awesome.

George Miranda: That’s great, I love that idea. I feel like I would want to know that that tour is coming to clean up a little bit. If you gave me notice, I would love to do it. I think those are some really great tips, I love that. I think those are good, actionable ways that you can just create an opportunity to get a little bit more of that connection you might not otherwise. I got to say, this has been a really great conversation and I love that we are learning a lot more about remote work and distributed communication habits and ways to create that. I just want to call out, I think you actually have a lot to say about incident response. And there was one very notable occasion where I met you at Uber because we wanted to go out to happy hour. And I walked in, in the middle of one of the incidents that was happening for your team and I got to hear how your team was managing incidents, and I would love to sit down and talk with you a little bit more about that. However, we’re almost near time for the show. So before we go, there are two things that we ask every guest on this show. So number one, what is one thing that you wish you would’ve known sooner when it comes to running software and production?

Sumbry: So obviously, I’ve been doing this for quite a while. Definitely, one of the lessons that I learned that I actually wish not only I had learned sooner, that the industry would just really, really grok this right now is this notion that we keep adding more complexity to the things that we’re doing. We keep adding more and more layers of abstraction. We’ve got production environments, which are physical machines, running virtual machines, running containers, running service discovery and routing layers. And while we do get some bit of flexibility and functionality with this, that complexity comes at a cost and we have to always make sure we’re balancing the amount of complexity we’re actually introducing to our systems. I love new and shiny things, and especially earlier in my career, when I was younger, I loved playing around with the latest technologies and finding reasons to use things, but it did actually bite me in the butt quite a few times, and so now I’m a lot more thoughtful about making decisions like that. I know that if we introduce a line of code into production, it’s probably going to exist for years, and years, and years, and there’s a certain amount of support that comes with that. And so, just being very, very thoughtful about what we’re creating and the amount of technical debt that we’re doing in the process, definitely wish I would’ve known that sooner, definitely it’s stuck in my head now. And it’s just one of those things that I wish the general industry would adopt a little bit more.

George Miranda: There’s a viewpoint that simple systems have better uptime and it’s absolutely 100% true.

Sumbry: I agree.

George Miranda: The thing that we struggle with is that so many platforms now abstract so much of what’s happening underneath the trade-off. I don’t think things are getting any less complex anytime soon.

Sumbry: I agree.

George Miranda: But when you have increasing complexity, what’s important is you have to still be able to reason about what’s happening in the system and when you can no longer reason about it, that’s when you’re shot in the foot. So I love that, I think we should do a whole episode around that. Okay, and lastly, before we let you go, is there anything about running software and production that you’re glad that we did not ask you about?

Sumbry: I plead the fifth.

George Miranda: That’s very smart, most folks on the show actually don’t, that’s my sneaky way of trying to get you to answer a question that you don’t want to answer. [crosstalk 00:30:14] good job, I should have expected no less from you. Well, thanks Sumbry, I think that’s been a really good look at some things that we can do. So we’ll take a lot of those tips that you shared and put them in the show notes so that folks can refer to a few of the things that we talked about. So before we go, Sumbry, is there a way that our audience can reach out to you if they want to follow up with questions, or comments, or what should they reach out to you about?

Sumbry: So I’m pretty much Sumbry all over the place. So I’m @Sumbry at LinkedIn and Twitter, **Sumbry**@airbnb.com as well. You can reach out to me on any of those platforms. I always love to talk everything production engineering reliability, et cetera, and so happy to chat with anyone.

George Miranda: Awesome. Well, thank you very much, we’ll put that contact in the show notes as well. And thanks again for sharing some of your experience with us.

Sumbry: Thanks for having me, this was a a lot of fun.

George Miranda: And this is George Miranda wishing you [inaudible 00:31:13] day. That does it for another installment of Page it to the Limit. We’d like to thank our sponsor, PagerDuty, for making this podcast possible. Remember to subscribe to this podcast if you like what you’ve heard. You can find our show notes at pageittothelimit.com and you can reach us on Twitter @pageit2thelimit using the number two, that’s @pageit2thelimit and let us know what you think of the show. Thank you so much for joining us, and remember, uneventful days are beautiful days.