Establishing Routines for Remote Work Success

Read more about Cate Huston in “How to Build and Strengthen Distributed Engineering Teams.”

Cate Huston is the Head of Developer Experience at Automattic, where her team is responsible for hiring, onboarding, and retaining some of the best software engineers in the world. In this episode, Cate talks with Matt about what kinds of people thrive on distributed engineering teams, and how team leads can keep their engineers happy, productive, and connected to their colleagues. 

The full episode transcript is below.

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MATT MULLENWEG: There are all sorts of approaches to distributed work. Some people work from home or at a café in their neighborhood. Others are digital nomads. I’m Matt Mullenweg, the CEO of Automattic and co-founder of WordPress, and I travel around 300 days out of the year. I appreciate that I get to spend time with my family in Texas, but I love life on the road too, and being able to hang out with friends and colleagues all over the world, and meet WordPress users wherever they might be. One of the nice things about running a fully-distributed company is that even the CEO gets to be just as remote as everyone else. 

Today’s guest is Cate Huston, who is a true digital nomad. All she needs is a cup of tea and a place to set up her laptop and she’s ready to go. Her home base is the city of Cork, in Ireland, but you’re just as likely to find her in any other corner of the globe.

Just because Cate is always moving doesn’t mean she has trouble staying connected. Her role at Automattic requires her to be in close contact with her team, and it’s her job to help make sure that all of her fellow engineers stay connected, too. 

After leading several engineering teams at places like Google and others, Cate became the Head of Developer Experience at Automattic, a team responsible for helping all our engineers at Automattic stay engaged, productive, and professionally fulfilled. 

I knew we had to talk to Cate on this podcast because she lives out the distributed model so fully. She also has a comprehensive point of view on what kinds of engineers excel in distributed environments, and how companies can create the conditions that help engineers thrive.

Alrighty, let’s get started with Cate. 

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MATT: Hello Cate, thanks for joining today.

CATE HUSTON: Hi Matt. I’m ready for a one-on-one.

MATT: [laughs] Ahh I forgot to tell you we’re recording it. 

CATE: [laughs] You should warn people about these things.

MATT: For the audience, can you catch us up a little bit on some of your experience that led you to Automattic?

CATE: I worked at Google as a software developer and then spent a year roaming the world and doing my own thing, and then joined a startup and was a questionably-legal migrant in Colombia for a while, and then that startup kind of imploded. And around that time, you sent me a GIF of a raccoon being adorable and I was like, “Okay, he can be my new boss.”

MATT: [laughs] You joined to lead the Mobile Team at Automattic.

CATE: Yeah.

MATT: But that has grown. So talk a little bit about that. 

CATE: I joined towards the end of 2017 to lead the Mobile team, which was amazing. And then after about 18 months I went on rotation to the Jetpack Engineering team, which was also super interesting because, as you know, I’ve been using Jetpack for a long time too. But when that came to an end it was clear that I was more needed elsewhere. So I didn’t back to the Mobile team, and I got to work with you, and rolling out Gutenberg. And now I lead our Developer Experience team. So we work to support our entire developer organization, and that includes owning the engineering-hiring process. 

MATT: What is developer experience at Automattic? I’ve heard of user experience but what does developer experience mean?

CATE: I mean: “What does it mean to be a developer at Automattic, what are the challenges of development at Automattic, what are the challenges of development in a distributed, remote context, how can developers learn from other developers, how can they have the support that they need to chart out their own career path?”

We have a lot of autonomy at Automattic, which I think is amazing, but that autonomy can be a bit overwhelming. So can we turn it for people [from] “Write your own MadLib,” into “Choose your own adventure,” [giving] people that kind of support. Also a critical part of the developer experience is the hiring experience going through into the onboarding experience. So how do we give people in our hiring process a good experience so that they can see if this is the right fit for them and we can see if they are the right fit for us, and how do we carry that through into them joining their team and becoming successful?

So one of the ways that we think about developer experience is — our engineering organization is quite big and we’re only so many people. So what we talk about is, “How do we find the pivot points for individuals in teams so that we can be present at those pivot points and try and make them accelerants where possible?” An example of that is when the team gets a new lead, that’s a pivot point. So we want to be there supporting that new lead, bringing them into the kind of support that we have for dev leads, helping them develop and iterate on their process so that that new lead can take that team to new levels. 

MATT: There are probably some engineers listening right now who would love to be hired at Automattic or another distributed company. What advice would you give to them?

CATE: The first thing I would say is, “Be patient, because I think all distributed hiring processes take a little longer.” I think people feel — I don’t know if it’s true — that they get a stronger signal in a day of face-to-face interviews but I think people feel like they have a stronger signal in a day of face-to-face interviews. 

And distributed companies, you can’t tell really if someone doesn’t show up to work. I mean, you can eventually tell, but it’s much easier to disappear. The level of trust required is much higher. And so there is a portion of the process that is earning that trust. We really believe that people can be successful and we’re looking to make people successful. There is no “prove it again” after you get hired. I think that’s really important.

So the first thing is patience and just understanding that the processes take longer. The other thing is that these jobs tend to be more competitive, especially for more specialist roles. There’s not always as many of them as you might want. So you want to craft what you’re doing a little better. Tell a good story in your cover letter, get excited about that company specifically, not just remote work in general. I’m sure all remote companies get a lot of the kind of applications that we get, which is like “Yeah, I just want a remote job so that I can travel around the world.” And it’s like, “Okay, it’s cool to travel around the world, I do it, you do it, but it’s not easy to do that on top of a full time job.”

MATT: So what’s the key for maintaining high performance, as you do, in all these far-flung locations?

CATE: I get pretty rigid about certain things. Like breakfast, I’m very rigid about. So every morning there’s breakfast and then I – 

MATT: That’s very British.

CATE: [laughs] Very British. British being rigid or breakfast being important?

MATT: I think breakfast.

CATE: [laughs] So I try and carve my day into two four-hour blocks. And I just don’t expect to do anything fun during the week, so I do my tourist-ing on the weekends. I really just go and spend a month in a place and try to live there. And honestly I live like that most of the time. When I’m in Cork, because I live in Cork, I try to do things on the weekend, get away from the computer, go out and see things. So if I’m doing that in a different place, it’s fine.

I have my certain needs, which are pretty minimal, like breakfast and some form of exercise and that’s it. And so I just orient myself on “This is breakfast and here is a place to work, there is tea, and this is how I’m going to get regular exercise,” and then, honestly, that’s fine, that’s all I need. 

I’ve probably paired down these needs over time. I don’t know if I started that way, and it is quite hard if you need more stuff. I think sometimes people want peace and quiet, for example, or they need more social contact or whatever, and things that take more time to build, but for me, a laptop, a pair of headphones, a good amount of tea, everything’s fine.

MATT: When you’re hiring engineers, what are you looking for as part of this process besides obviously some base technical-level skill?

CATE: Probably two really big things. One is the ability to work with the kind of code base that we have. WordPress has been around for a long time, there’s probably still code you wrote floating around in it, and that’s quite hard. Not everybody has the experience, the desire to work with truly legacy code. 

And it is a very complex system. It’s not just about technical capability but it’s also being able to grok the complexity of what we had. And this is something that we saw in the mobile apps as well. We would have people on trial for that. There would be three networking stacks because the mobile apps have to speak to WordPress.com, they have to speak to Jetpack, and they have to speak to every other WordPress site too via XML-RPC. 

There’s just a huge amount of complexity that comes with that. And if somebody has not worked on something that is really complex before then they’re going to have quite a bad time with that. And we want to see how they can adapt to that complexity, how they can work with it, and how they can deliver things. 

The second thing that we pay a lot of attention to is how well do people respond to feedback. We are not really hiring people just for what they’re capable of today, but we see it as a long-term commitment. These people, we want them to stay with us for a long time, right? So we’re also hiring them for their growth and the growth that we believe that they can do. And the best predictor of that is that they respond well to feedback. So if we give people feedback and they take it and multiply it and do a lot better, then we feel way more excited about hiring those people than the people who take the feedback and they’re okay with it. And then of course the people who don’t take the feedback well at all, we reject them.

MATT: How have you grown in learning how to take feedback well?

CATE: The first thing is working on self-awareness. When people are not self-aware, you can’t really connect with them because you are always being indirected by their ego. And so developing your self-awareness is super important, something that I work a lot on.

MATT: What does it mean to be self-aware and how do you develop that?

CATE: Do you tell stories about yourself? Do you have things about yourself that you really need to believe are true but might not be?

MATT: What’s an example?

CATE: Some people want to be seen as really nice or really caring, for example, but they might not be very caring. And so they’ll talk a lot about how caring they are but they’re actually not. And so this gap between the way that somebody talks about themselves and their actions will show you this gap in self-awareness.

MATT: How do you cultivate self-awareness?

CATE: Just disabuse yourself of all your illusions. 

MATT: You make it sound easy.

CATE: No, it’s horrible, it’s a lot of therapy and coaching and just being willing to confront the pieces of yourself where you know you’re not as good as you would like to be. Second thing, broadening your perspective, being more open to possibilities outside your worldview. So reading fiction is demonstrated to make people more empathetic, but then reading a broader variety of fiction written by people who are not like you can also broaden your self-awareness. Cultivating a broader network of people, making sure that you’re connected to diverse voices and people who are not like you. And then traveling outside your comfort zone. We talk about the digital bubbles we live in, but a lot of us also live in physical bubbles. And for me, I spent a lot of time living in Medellin, and existing in my third language was a profound exercise in human limitation and empathy.

MATT: Totally. I’d also say you can travel outside your comfort zone without leaving your city.

CATE: One hundred percent.

MATT: There’s probably parts of your city or places that you haven’t been to, buildings you haven’t gone into, places of worship, neighborhoods, stores, barbershops, that can be a journey as well.

CATE: Totally. I am right now in a part of Cork that I had never been to before today. I did not know it was here. So shedding defensiveness, you know? I think people’s first reaction to feedback is to be defensive. It creates conflict, it means you don’t really learn what’s happening, and it shuts the conversation down or it makes the conversation about your feelings rather than what this person is trying to tell you.

Something my coach always tells me is “get curious.” So learning to be — if something makes you uncomfortable not to shut down but to lean into it and to ask questions and really try and understand it is super helpful. Something that people do here is offer context. So people give you feedback and what you give them back is context. And to a certain extent that’s fair enough but too much context is just a polite way to defend yourself. 

MATT: Someone says, “You need to improve X, Y, and Z.” And you say, “Well this and that and this was going on.” Is that what you mean by context?

CATE: Yes, or maybe like, “Oh, you know, I didn’t like how you responded to X.” And then it’s like, “Okay, but for context this set of things was happening.” It’s not really helpful. It’s also getting ahead of that, right? If you say, “Cate, you’re missing your goals.” And I say, “Now let me give all the reasons why this is hard,” that’s not a healthy conversation between us. Right? 

So I’m always trying to get ahead of that with you and be like, “Okay this is where we’re at, this is what’s going on, this is what I’m worried about, this is what I need your help with,” so that you know that you’re not finding problems and giving to me because I know my own problems, and I am on top of them, and I’m telling you what’s going on and what I need from you, so that you should know that you can trust me.

MATT: Got it.

CATE: Asking for advice is also very helpful in self-awareness. Often people are afraid to give feedback because they don’t want to upset you and they are particularly unwilling to give you feedback if they think you’re doing a good job. It’s like, “No, no, no you’re good, you’re good.” But they might have some advice for you.

MATT: So just changing the word you’re using can change how people respond?

CATE: Totally. We have all these negative connotations about feedback, but feedback is really just your own being-in-the-world and being-at-work, for example, being reflected back to you. And it’s neutral really, or it should be. When I’m writing feedback for somebody, the question that I will ask them when I give it to them is, “Did you feel seen when you read this, did you feel like I see everything that you’re doing that’s great and everything that you’re capable of, and how you can do better?”

MATT: Something I try to remind myself, especially when I’m receiving feedback that might be tough, is that good feedback, and by good I mean it’s thoughtful, is a gift — feedback is a gift. And when you receive that you can use it well or you can use it poorly. And I love what you said around getting curious. That is a nice way to reframe something that might be challenging. 

CATE: Yes. If somebody cares about you enough to tell you that they think you should do better then it means that they believe that you could do better.

MATT: What else is on the list?

CATE: There’s two more. The other one is stop giving advice. [laughter]

MATT: That seems incompatible with receiving advice.

CATE: Most people are way too willing to just give advice without context and often without even understanding what someone is trying to achieve. Declaring a moratorium on advice can at least make us pause and ask questions and get context and reflect back to someone what they’re saying to you. 

And the last one is to own up. If you can admit what’s not going well then it’s much less scary for people to talk about the details of how that didn’t go well or what’s not going well. So again you can just make it easier for people to give you information that you wouldn’t otherwise get. 

So my team doubled in size recently. I put up a post on our P2 and I was like, “Okay, so our team has doubled in size and clearly my job is going to change too, and these are the ways where I currently see myself not doing as well, and what do you think? What do you need from me?” And I asked these structured questions to get feedback around what’s the most useful thing that I do for you or what do you think I should stop doing. 

And I got all this amazing input from my team. And if I hadn’t just straight-up admitted it in public, maybe they would be in private being like, “Ohh, Cate seems really frazzled, I don’t know what I can expect from her, I guess I understand that the team is bigger now…” But they might be afraid to tell me what they were experiencing. Whereas instead, putting it out there and having that conversation together made it a team change and a — My job is just the piece of how our team works and we are all deciding and designing that together.

MATT: I know you’re passionate about engineering management. One area where engineers do this a lot is in code review.

CATE: Right.

MATT: Pull requests, etcetera. So what do you see there and what are you working on or want Automattic to work on there?

CATE: I think code review is a core function of a healthy engineering team. Code review done well is such a powerful collaboration tool because both people, or anybody involved in the code review, is learning what the person who wrote the code did, the questions the other person asked, and the reviewer asked. It’s a structured way to have a conversation about the task itself and also the long-term [project] of the code base.

MATT: What else makes a great engineering culture?

CATE: Something that we used to talk about on the mobile team was that a senior engineer makes the whole team better, but we don’t want to be prescriptive about how people made the team better. That was up to them. There were options, but that was the expectation for everyone on the team. It’s like, you come in, you’re an experienced engineer, we expect you to be making the whole team better in some way, and what that looks like is up to you. 

That captures my aspiration for a great engineering culture because one, it suggests that everybody is additive and two, it suggests that everybody is allowed to be unique. And three, it suggests that everybody has the autonomy and the support to operate from a place of strength.

MATT: How much of this is specific to being distributed? How much of this was true when you were at Google versus what might be different now in a distributed company like Automattic?

CATE: The thing I think about distributed is that it makes the things that are hard explicitly hard. I don’t think it really changes anything.

MATT: Tell me more about that.

CATE: You might say that getting a team to be coherent and inclusive and what have you, is just intrinsically hard. And if you are collocated, then you might say, “Oh no, my team is very coherent, we have lunch together everyday, and we do stand-up together every morning, and every so often we do some group activity together. Our team is very good.” 

Whereas if you’re distributed you’ll be much more intentional about it. You’ll say, “Okay, well now I have a new team, and I want that team to be coherent, so how do I make it coherent? How do I make sure that the team understands what their mandate is? How do I make sure they understand what their priorities are? So how do we really maximize the value of a meetup so that people come away the most aligned that they can be?”

MATT: I think it’s helpful for us to be very real on this and talk about the downsides of distributed as well as some of the upsides, which we cover pretty extensively. So to be real and candid about Automattic, what do you think are our biggest challenges and weak points right now?

CATE: I think that we have not always done a great job of hiring and onboarding senior leadership especially into the distributed context. Sometimes we hire people who see distributed as a thing that needs to be mitigated or worked around, rather than a thing that you work with. I don’t think we’re delivering particularly well right now. I don’t think we’re shipping enough and I don’t think we’re shipping enough user value. 

MATT: Totally.

CATE: And I think we’ve evolved our org chart in ways that have been more disruptive than we realize, and have created a lot of gaps that it’s not clear how we should fill or if we’re going to fill. The way that I think about org charts is that they’re really just our chosen optimization, and we can choose what it is, but we have to manage it. 

And I think the thing about a distributed context is that sometimes you can choose your new optimization but if you don’t do the change management it’s not always as obvious what’s going on. Like if you’re in an office and morale is low, you feel it. But in a distributed context it feels different.

MATT: Cate, those are definitely some good challenges. One that has been on my mind recently is I’ve noticed a lot of negativity in some of the teams and some of the feedback. What are your thoughts on that and where does it come from? What can you do to address it?

CATE: I think people get increasingly negative when they don’t feel heard and when they don’t feel hopeful. And so I have spent a lot of time listening to people be negative, and have them not see the value of things that I’m doing. Hearing them out has always been really important and some people will never come around, and some people just need to feel like they’re heard, and to get some of the context that they may be missing, and to have a reason to hope.

In one of my Quartz articles I wrote about how, in any kind of period of change, the people who struggle most are the low performers and the high performers. And the low performers struggle for very obvious reasons, like, change is difficult for them because it’s potentially threatening. They know they’re not amazing. And so for those people, often you can make change good for them, because hopefully you can help them level up. I don’t believe anybody thinks, “Oh I want to be mediocre at work today.”

But then for the high performers, the things that they struggle with, is that they have found a way to succeed in the system as it is, and so any change seems unnecessary to them because really, the problem is that other people haven’t figured it out the way they have. And so those are people where — they’re to some extent right and to some extent wrong. And so helping them have the context, see the empathy, experience the empathy and see some reason for the change and helping them see a sense of improvement is really, really important, because you need to bring those people with you. 

If your high performers are not bought into what you’re doing, then other people won’t be bought into what you’re doing either. So you spend a lot of time, or I personally have spent a lot of time on the high performers who are like, ‘Yeah but really other people just need to be better.” It’s like, “Well, yeah, they do, and so we’re going to help them be better now by doing these things,” and eventually they’ve seen the value of it. And that has generally brought me a disproportionate amount of credibility with other people on the team. 

MATT: Who might distributed work be excluding that might be more included in an office environment?

CATE: Extroverts. Offices give people a certain amount of structure and community, and in the absence of that you have to create your own, and not everybody can or wants to. Work is really just one part of life. When you talk about distributed work, that’s great, there’s all these things that we can do. But when I onboard people into a distributed context, especially for developers, they don’t tend to struggle with the work aspect of it. 

But what they do struggle with is the life aspect, especially people who have not worked in a distributed context before, or a remote context. They struggle to give themselves the structure in their day. They can start work whenever and so they do, and then they finish work at 2:00 in the morning. And at some point, some people are genuinely nocturnal and — fair play, but most people are not actually nocturnal. And starting your day at 4:00 in the afternoon and working until 2:00 in the morning is maybe not that good for you. It’s normally quite bad for your social life unless you are friends mainly with bats. 

So there’s a bunch of knock-on effects to that, which affects your social life, it affects their life-life, it affects their health, because they’re not getting enough sunlight, exercise, what have you. So as someone’s manager, I care about them as a human being, but I’m not their mom. And so that can be quite hard because often it affects their personal well-being more than it affects their work, but it will ultimately affect their work too.

MATT: How can managers encourage inclusion, especially when they might have people across normal categories that we talk about, but also across countries and everything?

CATE: You have to be explicit and talk about it and measure it. In all our reporting on hiring, you will find the same words, which is “Diversity is more than gender, and gender is not binary.” But this is what we can measure and so we measure it, but then we do almost nothing that is just targeted at women. We just use it as a metric and as an indicator of diversity. And we talk about it very explicitly, constantly. 

And I think being explicit like that is really, really helpful. I think being very vocal that it matters — in tech now, I feel like we have talked about diversity maybe too much, inclusion — not enough. And now if you’re not saying, “Oh inclusion is very important,” then you’re clearly a terrible person. So we’re all saying inclusion is really important, but what are we doing?

And then the final thing is building that human connection and checking in with people. I think there are a lot of things that we miss when we don’t see people in person, and you have to notice when people are quiet. And that actually is something that requires a lot more attention.

MATT: Cate Huston, thank you so much for sharing both the good and the bad about distributed work. I think there’s a lot of wisdom in the things we’ve covered.

CATE: Thank you, Matt. I appreciate you.

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MATT: That was Cate Huston. You can follow her on Twitter at @ C-A-T-E-H-S-T-N.

I mentioned earlier that there are different approaches to distributed work. And that’s not just true for travel habits. People with different personality types prefer different levels of socialization, communication styles, and leadership styles. Some managers love to have lots of meetings and others would rather keep things moving in the Slack channel. This diversity of styles can make Cate’s job challenging, and as a leader of distributed teams, it can make mine pretty challenging too. 

But I also think this is one of the things that makes the distributed model so exciting. It’s easier for us to meet people where they’re at and give them a custom work experience that suits their personal style. This ideally makes for happier employees and better work. 

Next time on the Distributed podcast, we’ll be talking to author Scott Berkun, who once worked at Automattic and wrote a book about the experience called The Year Without Pants. I’m going to talk to him about his time as our first Team Lead, and about how the distributed-work landscape has changed in the last seven years. 

Thanks so much for joining us and see you next time.