What led you to move into managing developers?

The move from engineer to manager is an important decision and one that many struggle with. I also struggled with it. I was working at Yahoo! In the early 2000’s and served as a team lead on a project to replatform the frontend of HotJobs (acquired by Yahoo in 2002). I found the work to be very demanding — as a team lead, you are essentially working two jobs: engineer and manager. Thankfully, I survived that project.

Moving forward from the project it was evident to me that I could not play this dual role long-term and I would have to make a choice. I was highly enjoying my work as an engineer, maintaining C++ bindings to Yahoo’s search engine (ysearch), creating and maintaining PHP extensions. I also enjoyed the higher level view that leading a small group provided. Upon reflection, I decided that the opportunity to lead efforts larger than ones that I could code by myself was more exciting and scalable than writing code full-time. I’ve thought back to that moment many times and sometimes regretted it, but on balance, I feel I made the right decision for myself. This is a very personal decision, and different paths are right for different people.

Why did you choose to come to Squarespace? 

When I was on the job search that culminated in accepting a role as Engineering Director at Squarespace, I had 5 must-haves that I used to determine which opportunities I would seriously consider. They were (in no particular order):

• A job that would challenge me technically

• A job that needed doing. In other words, I didn’t want to have anyone make up a role just to have a place to put me once hired

• A business that actually improves people’s lives

• A culture that matched with my core values (growth mindset, servant leadership, cooperative leadership)

• Competitive compensation

Squarespace turned out to be the right choice for me. I’m happy to report nearly two years later that all 5 of the must-haves remain true for me.

What does ‘engineering culture’ mean to you, and what does success look like when building one?

Engineering culture is a favorite topic of mine, and one I’ve written about before. Culture is the combination of the customs, arts, social institutions and achievements of a particular group. For me, if the mission statement of the company is the interface for a company’s operations, the culture is its implementing class. Culture is the codification of what constitutes belonging in a group, and as an empathetic leader, I look at it as the key to job satisfaction for engineers. Hence, it is critically important to get right.

In a successful culture, key knowledge of customs and practices such as how decisions are made and the level of technical standards expected from an individual or team is well known, communicated, and can be interrogated in public. In other words, it “open sources” the organization, making it clear how a person can contribute to it.

The more that people can spend their time intentionally and focus on their core role, the stronger the culture is.

One of the most common questions interview candidates ask is what Squarespace’s approach to Diversity, Equity & Inclusion (DEI) is. You made the fantastic point that “you will not succeed at DEI if your goal is to feel comfortable” — are there any stories or examples you can share about your learnings from this?

Most accomplishments in software engineering have their roots in the intersection of computer science education, industry and macrosocial trends, and can be empirically stated. Google’s Project Aristotle extended empirical analysis to the realm of teams of people, and determined five key factors that can be used to measure a team’s efficacy:

1. Psychological safety - “If I make a mistake on our team, it is not held against me.”

2. Dependability - “When my teammates say they’ll do something, they follow through with it.”

3. Structure and Clarity - “Our team has an effective decision-making process.”

4. Meaning - “The work I do for our team is meaningful to me.”

5. Impact - “I understand how our team’s work contributes to the organization’s goals.”

What is most interesting to me is not the factors themselves, which I agree are useful areas to focus on to improve team efficacy. It is in how you get from where you are, to that desired end. You might think, as I did once, that the key to success is to recruit people to represent differing perspectives, find the “lowest common denominator” (the things everyone in the group agrees with), and make those the basis for the team’s cohesion.

If you do that, which I have done, you will see that you end up with a team that can get along, but doesn’t try to learn or celebrate the differences between team members, and instead focuses on the few things that are in common amongst the whole group. This leads to people not bringing their whole selves to work, and ultimately nullifies the diversity of perspectives that you worked so hard to achieve.

My eyes were opened after taking an IDI (Intercultural Development Inventory). I realized that I had been focusing on diversity, but not equity or inclusion, and that I had a lot of work to do. I spent a lot of time soul-searching and examining everything I do as a leader and manager of groups to see where I could be more inclusive, and am better for having done so. I’ve learned that DEI is a never ending journey, but I am convinced that I’m on the right road. 

A note on comfort — as a cisgender white heterosexual male, I am part of a group that is predominantly included in situations. This journey has shown me that one of the biggest impediments to improving true inclusion and equity is “white comfort”, the notion that a white person’s need for comfort in all situations trumps the need for inclusion and equity by underrepresented groups. It is my belief that the only way to make progress is to start by accepting that you will be uncomfortable.

For those leaders looking to improve their awareness, take a moment to reflect on when you felt excluded in a work setting. If you are a senior leader, you might not feel excluded much anymore, but chances are that you did once, and it is likely that at least someone on your team feels that way now. Ask yourself, can you tell who feels excluded? Think about the last time you were looking to give someone a big promotion or a career growth opportunity. Did you consider all available candidates? Or did you choose someone who looks like you, is part of the same work in-group, or lives near you? I would also recommend you take an IDI — it is eye-opening.

What techniques have you learned to balance a busy work schedule with your family life?

I have also written about this. :-)

My answer to this question has varied wildly during the pandemic, however the two main keys are still the same. First, your success in balancing work with non-work depends greatly on the level to which your non-work activities are important to you. For me, my family is very important and deserving of my time. Second, you need to create a real boundary between work and non-work. If you do not, no one will do it for you.

The pandemic has pushed work into our homes, and for those who have never worked remotely, the adjustment is significant. Beyond needing to create the work/life boundary, many of us have had to face health challenges and the stress of the world. To those facing hardships right now, I hope that you and your family are well and in good health — COVID-19 is not kind.

The two techniques that have helped me the most, and have been the most resilient help have been to start my day by thinking about, writing down and executing on my MIT, or Most Important Thing. Determining my MIT on a given day is just a matter of sitting quietly and thinking about the 1-3 things that, if I accomplish them that day, would constitute a successful day. I do this with my wife most mornings, and we keep each other honest about our level of success with each day’s MITs.

The other technique is to physically separate from work at the end of each workday. In my house, I have a monitor that I connect my work laptop to during the day. Then at the end of the day, I turn off the laptop and plug in the Mac Mini I have for personal/home use. This makes it easier when I inevitably think of that “one more thing” to do after work. I have whiteboard wallpaper on the wall next to my desk, and if I have a thought, I’ll write it there with a dry erase marker, and come back to it the next morning.

What is your experience with burnout? 

Burnout is a serious problem, and is exacerbated by the pandemic. The WHO defines it as an occupational phenomenon which:

...relates to stress, often work stress, that is chronic and unsuccessfully managed, and is characterized by feelings of energy depletion/exhaustion; increased mental distance from the job e.g. cynicism; and reduced professional efficacy.

I experience it in waves, and the predominant symptom for me is a feeling that there is so much to do, but no point in trying to do any of it because I don’t see how it could be successful.

However you experience burnout, it is vitally important to a) admit it, and b) make a plan to deal with it. You might think that your projects can’t be successful, but if you focus inward on a plan to deal with the burnout, you might surprise yourself with some new energy, once you have engaged in enough self-care.

I hit up against burnout a few times this summer. The most recent time was in the past month. I admitted it and worked with my manager to find areas of my work where I could divest without causing much harm. I also scheduled myself a vacation. This might work for you — I’d recommend trying it if you are feeling burned out. 

As you’ve been promoted, how have you dealt with the increasing expectations and scope of your work?  

The Peter Principle is a management concept which observes that people in a hierarchy tend to rise to their “maximum level of incompetence”. On its face, it would seem to be an indictment of the promotion processes at companies. It goes hand in hand with imposter syndrome, defined as a psychological pattern in which an individual doubts their skills, talents, or accomplishments and has a persistent internalized fear of being exposed as a “fraud”.

I try to do my job to the best of my ability, and that is how I derive satisfaction from the work. When imposter syndrome strikes, I try to remind myself a) it is just in my head, and b) everyone gets it. Having spent time studying and writing career leveling documentation at a few companies, I have learned that career progression happens differently for every person, and it is not the case that people grow in all competencies (which we articulate internally as: knowledge, scope, autonomy, communication and delivering impact) at the same rate. Also, I recognize that all roles within the industry have a range and are part of a continuum. So, when I am promoted to a new level, am I incompetent at that level? Mostly likely yes — but that’s only a problem if you don’t continue growing. If you continue to grow, you will be more “competent” at the role every day, leading to your next promotion (and your next encounter with incompetency)!

Playing competitive 9-ball has been a hobby of mine for many years. Many a weekend, before a tournament began, looking around the room I would say to myself “How could I possibly win? Look at how many talented players are in the field!” Then, after I had spent many months practicing and improving my game, I entered the next tournament. This time, I looked around and said “There are all these great players here. I’m a great player too. So why couldn’t it be me?” I happened to win that tournament, and was considered as a favorite to win tournaments from then on.

What made the difference? Was it all of the hours spent practicing, lowering the sense of imposter syndrome? Was it realizing that all of the other players were also feeling some imposter syndrome? Or was it all in my head the whole time? I’ll leave that exercise for the reader.