I recently had the chance to have a video call with Cate Huston, the author of The Engineering Leader, one of my favorite books of 2024.

I covered my impressions from the book in a previous post¹. Today, we're learning more about the author and her journey. In the interview, we will cover four main areas:

1. Cate's Leadership Journey

2. Her long-standing relationship with writing

3. Diversity and Inclusion

4. Some perspectives on the open-source drama going on in the WP community

If there are questions you wish I'd asked Cate in our chat, don't forget to add them to the comments section and we'll get them answered!

#1 Your leadership journey

Q: Can you briefly introduce yourself to those who might not know about you?

I’m a Senior Engineering Director at DuckDuckGo, focused on Native Applications, and author of The Engineering Leader.

Q: Like most of us, you started as a software engineer before moving on to leading teams and organizations. What was the primary motivation for moving to leadership? How did that happen?

I dropped out of grad school and went to work for Google, but after nearly four years at Google, I wasn’t sure I wanted to keep working in tech. I took a year off and spent it on my own projects, writing a lot, giving talks, and working on a passion project - an image processing app - I reconnected with what I loved about programming. To make some money, I was doing screening interviews for tech companies. Basically being a professional interviewer! It was interesting doing so many interviews, it was a way for me to really work on my clarity of feedback and meeting people where they were at and helping them do as well as they could.

As I started thinking about what was next, a friend of mine was looking to hire an engineering manager, and he asked if I’d be open to moving to Colombia. Anyone who knows me can guess that the answer was “of course,” so I went through the interviews, and that was my first job as an engineering manager.

That job lasted less than a year—the company wasn’t really going anywhere and eventually shut down. But I really liked my team, and I had time to learn the basics of engineering management. Some of the harder things, like doing a layoff, were still the worst days of my professional career. 

As that startup was imploding, Mullenweg pinged me and asked if I'd be interested in working for Automattic. I’d been a long-time WordPress user, so the answer was—again—of course!

Q: Was it a conscious decision to continue on the manager's track, or was it more about going with the flow based on what was being offered to you at that moment?

I wasn’t completely sure what I wanted, but I was definitely open to going back to a dev role. Practically, I hadn’t been writing a lot of code, so I figured I would let the management hiring processes I was in play out and then figure out what to do and potentially start studying to do technical interviews again. In the end, I had two offers, and I picked the option that didn’t have me moving to the US right as the 2016 election was called (great decision, Past-Cate). And that was it!

Early in my career, I really wanted to make it to Staff Engineer. But obviously, that isn’t how it worked out. For me, I really think the director role is where I thrive. An EM is busy with the team, managing ICs, and paying attention to team delivery and process. I find that up a level you have more space for working on things that personally I find more interesting, like technical strategy and organisational design - I really think organisational design has a lot in common with system design, you have to figure out your pieces and how they interoperate. I’m okay as a line manager, I like it fine - when I switched from Automattic to DuckDuckGo I was kinda back there, with a way smaller team than I was used to. But I do enjoy it more when I have a broader scope and more time for strategy. Hence, a bit over 4 years later, the number of people I’m responsible for is ~10x what it was when I joined, and I feel my time and responsibilities align more with my strengths and interests.

Q: Let's explore your view on the role of Directors more. One way to put it is that while an Engineering Manager focuses mainly on people, processes, and execution, a Director needs to be deeply involved in technology and technology strategy specifically. Is that what makes you like this role in particular? And what are some of its challenges?

You need to understand what the teams are doing if you want to do a good job, whether as an EM or a director. However, as a director with more teams and more scope, you need to understand their work more at a systems level than a detail level, as in, it’s more important to be able to draw an architecture diagram than commit code. You need to understand how that work fits into the business's goals and have a longer-term view of how that will evolve over time.

And yes, I think this is my sweet spot: the scope is big enough that I have interesting problems to work on but not so big that I carry the issues of the entire organization on my shoulders. I think at a director level, assuming your own stuff is in order, you have the remit to look outside for other problems you’re interested in, but you’re not on the hook for all of them. You get to choose — or at least negotiate! 

One challenge is finding the right balance between being present with the team and giving them space to be autonomous and come up with solutions.

For instance, with my team, after I re-orged it to put in a leadership structure (we split from one big Native Apps team to platform teams), I went through a period where I really was less visible to make sure the new leaders could be effective. I wasn't absent but I was less involved with the team's discussions. I still felt accountable for outcomes but needed to approach that in a way that wouldn't undermine the new leadership structure.

Then, recently, I took a leadership course that made me realize that I might have been a bit too much behind the scenes. It pushed me to be more visible and weigh in on things in public more rather than staying behind the scenes. I think it's fine to become more engaged now. The leaders have had over a year to establish their authority - they’re no longer new! I don’t need to be as careful not to undermine them. The course was a good reminder for me that sometimes we pick a course of action rationally, but we also need to think about changing things, even if they are not obviously broken; just because the decision was good at a time doesn’t mean it’s good forever.

Q: At your level, how do you get a sense of the distribution of competence and skills across the organization? How do you keep a map of who the best talents are versus those who require support?

I generally try to have a sense of it, but I'm open to being wrong. I’m not part of the day-to-day, and people do change over time. Mostly I ask questions and share observations, such as I've noticed this lately; can you explain why that is happening?

The organization I work in is very text-based, so it's easier to figure certain things out. I do think that when you have been doing this for long enough, you develop a degree of intuition.

This has happened to me lately with one of the teams I'm responsible for. I have been having some vibes for a while—making observations and asking questions—but it took time until I could articulate the issue and align with the person responsible for the team. There was a process of going from awareness of the visible symptoms of the problem to figuring out the core of it and labeling the actual issue that needed to be addressed.

Q: What was the most challenging part of the leadership transition?

I was so lonely. So lonely.  Especially given that I was the only engineering manager in a small company. I ended up creating the Engineering Manager Slack group to cope with the situation. This is also why I keep repeating that your work BFF (Best Friend Forever) is the most important person. Someone who will check you on genuinely hard decisions, the person you can talk to when you are having a bad day.

It’s essential to have someone you can turn to. Otherwise, who are you going to talk to? Your partner? I don't necessarily want difficult feedback from my partner at lunchtime when I’m annoyed at work or in the evening when I want to disconnect.

Having somebody who can tell you I see it, and this is what I think you can do better is a fundamental form of support for any engineering leader.

I try to do the same for my direct reports, but obviously, I could be the cause of their troubles or frustrations. I want to be able to push them and know that they have the broad base support they need to work things out. I try to get them all to have a coach.

#2 On Writing

Q: When did writing become essential to your personal and professional life? What has been the primary motivation for you to get started on this journey?

I think when I was in grad school, another lonely place, I started blogging just to be able to post things more regularly and quickly than an academic paper.

There have been times during my career when I wrote less regularly, but this habit has stayed with me ever since. It helps me process things. I need to take some emotional distance from what happened and what I learned before sharing it with the internet. I also need to make my thinking more clear if I want it to be understood by others.

I was writing for Quartz for a while, where I had a fantastic editor (Heather Landy) who helped me improve my writing. I learned to delete things I liked but didn’t add to the overall arc or message! I do love the freedom you have when writing for your own blog, though: some things will be popular, and some things will not, and they're not necessarily the ones you expected. One of my most popular posts from a couple of years back was initially rejected by Quartz. I was glad of the feedback and also glad I published it anyway.

Q: When did you start flirting with the idea of writing a book? What has been the primary motivation behind it?

I started thinking about it sometime in 2019 but put it aside. Then, at the end of 2021, I had the DRI Your Career series that struck a chord with people, and I started seeing the arc of the book. So, in 2022, I was proving to myself that I could write a book, and in 2023, the book deal became a reality. I was lucky with O'Reilly. An editor, Melissa, reached out to me after I posted on Mastodon that I wanted to write a book, and she helped me build the confidence I needed to finish the book proposal I’d been sitting on for a year. Once the proposal was accepted, I got editing and writing, that was 2023. 

And now, in 2024, I'm in the post-book phase. I'm trying to blog again, slowly building back the habit. Writing a book was so different; I couldn’t write a book and blog at the same time. Also, there are only so many hours in the day/week when I’m not working at my day job! Now I’m trying to switch gears and go back to being more of a blogger again!

Q: How did you develop the main idea for The Engineering Leader? One might think that there are already plenty of books on the topic. What was the main selling point you successfully used to get O'Reilly Media to accept your book proposal?

I think the selling point was this idea of self-management. Often in my career, I didn’t feel like I had much of a manager, and this is something I’ve heard from many others. I wrote the book for other people in that situation. I hoped the book would give people a way to answer the question: If you don't feel you have a manager supporting you, what do you do? I wanted to share the message that you are not powerless even if you feel alone. You have a lot more power than you think.

Q: I found something about your book's style particularly effective. It's funny while still discussing serious topics. Can you tell me more about that?

On the one hand, I liked the idea of writing the funniest engineering leadership book. But another reason is that if you can make people look at things differently, you can help them take new approaches. 

Humor does just that: disarming people so that they can look at something differently. For instance, the word process is kinda loaded, so instead, I talk about penguins. It allows me to make the point that people react to processes differently because of what they expect them to be, without bringing in all the baggage from the word “process” from the get-go. I do feel like this is a bit of a marmite section, though. Some people really loved it, but I did get feedback before publishing that it was too weird! I’m glad I kept it in!

Often, conflicts arise from people having completely different views on the same situation. One of the things you learn in coaching is how to take somebody through having their own completely different view on their situation. It’s a valuable tool. Generally, if you can zoom out (or in!) to another perspective, you’ll at least learn something.

Q: What book do you think is still missing in the broad discipline of engineering leadership? What book would you love for someone else to write one day?

I think the missing book is determining and delivering technical strategy. 

#3 Diversity and Inclusion

Q: You often take the angle of Diversity and Inclusion in your writing. What are some of the actions you've seen as the most effective in your career in building a solid culture of inclusivity beyond fancy HR slides?

I like to call those instances of performative DEI diversity as performance art. It’s about putting on a show rather than effecting change. The two types of actions that I've seen as effective in this space are sponsorship and allyship.

Sponsorship is finding people that don't look like you and lifting them up. This is hard to do because you have to lend your reputation to somebody else. When we talk about sponsorship, we often focus on the need for it but downplay how hard it is to earn.

If you are willing to sponsor someone you believe might deserve it, you need to figure out your gradient, advocate for smaller things, see how they go, and progressively escalate.

The second thing is Allyship. As a woman, I don't want always to be the person who has to explain why something is sexist or otherwise disrespectful. Similarly, people of color shouldn't always be the ones having to explain why some comments or behaviors are racist.

There is a massive tax on under-indexed people, as they have to bear not only the cost of what happens to them but also the additional burden of explaining to others why that was problematic.

If we can take that tax away from people, while it doesn't change what happened, it can help them feel supported and recover faster from whatever happened.

One approach you can take if you're from the privileged group – typically white men – is to speak for yourself and not on behalf of the victim of the situation. You can say I am not comfortable with those types of remarks because I find them sexist/racist/whatever. That is a good way to shift the focus of attention towards your own feelings - rather than saying something like, let’s not make sexist comments in front of Jane - which 1) positions Jane as the problem rather than the comments 2) suggests that Jane needs protecting and 3) implies that it would be okay to make those comments if she wasn’t there. If it’s not okay to make comments in front of you, own that.

#4 Open Source Drama

Q: Given that you worked at Automattic, I guess you might have some opinions on the ongoing WP drama. What are your thoughts on the situation?

In economics there is this concept of public good, which is something that benefits both the individual and the society at large. Education is the most common example we use to represent that.

We talked a lot about writing, and for me, blogging has been very much for the public good. It's been good for me as the author, and hopefully, it benefited some people reading it.

The same goes for Open Source. It benefits the people who work on it, and of course, it benefits society as a whole. I think we're at a stage of capitalism where the dominant approach is becoming to take the public good and exploit it. I think this is a problem. 

It’s not just OSS. I don’t love it as a writer how companies are using AI to scoop up everything I write and then regurgitate it badly without citing me. There’s no benefit to me from this, and when I started trying to blog again, it was something I really struggled with.

In the period of zero interest rates, some companies spent a ton of money on OSS, and now they're trying to tighten up the bottom line. There are other OSS arguments going on, about relicensing etc. I think the core of the argument is about the responsibilities of companies built on OSS to maintain the public good, not just exploit it. Then, there is a soap opera’s worth of drama around it that I’m staying well away from!

If we want to have open-source software in 10-20 years, we have to think about how we're treating it today. We also have to think about other things we might want in the future, like clean air and a vibrant Internet. If we keep just exploiting everything, we'll end up with a desolate wasteland filled with bots talking to each other. The Nasdaq might be very high, but that's not the world I want to live in!

It's been great talking to Cate, and I hope you all enjoyed reading it as much as I enjoyed having the conversation with her.

If there are questions you'd like to ask Cate, please post them in the comments section. And if you want to know more about her and follow her work, here is where you can do it:

• https://cate.blog/

• https://hachyderm.io/@cate

• Catehstn.bsky.social

• https://www.linkedin.com/in/catehuston/

If you found this valuable

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You'll find my review in this article

📚 Books I read in September 2024: The Good, The Great and the Meh Sergio Visinoni · Oct 9 Read full story