written on Wednesday, November 1, 2023
This year I decided that I want to share my most important learnings about engineering, teams and quite frankly personal mental health. My hope is that those who want to learn from me find it useful.
You can't make it 15 minutes on Twitter or elsewhere, without running into a post about a botched return to work implementation. You also can't make it for very long to hear about the San Francisco doom loop. These two topics relate in a quite deep way to me personally. This post is a reflection of working at Sentry for almost 10 years, a company primarily headquartered in San Francisco and how it is to work for it from a distance before and after Covid.
I'm a being that thrives in cities. In fact, I'm genuinely amazed every day how humans have managed to form societies where cities can function. But not only function, but function really well. They are quite remarkable because they greatly benefit of economies of scale. You can provide services in cities that would otherwise not be possible economically, because there are not enough people around that otherwise are in need of that service. As a friend of mine once described: cities are like small social experiments. Each city uniquely nurtures specific communities, each with their own values and ideas. Since forever I have been a software developer (amateur or otherwise), there was really only one city heralded as the city of technology: San Francisco. It has a profound impact on many of us, even if we don't live there.
It's not the city I want to live in, in many ways it's running the kind of social experiment with outcomes I'm not attracted to, but without doubt that experiment has an impact far beyond its borders. I'm in many ways a beneficiary of its existence.
Where cities shine is collaboration and meeting like-minded folks. Where I grew up, I was the only programmer in a tiny town. If you want to talk with others about your problems, the internet really was the only place. I took advantage of the opportunities that IRC, bulletin boards and mailing lists gave me. It allowed me to meet people that were otherwise outside of my reach.
My theory on what makes a successful company or project is collaboration and some shared, deeply rooted values. In some ways we sometimes do not quite know what our values are, we just “get them”. We get them because when we talk to each other we get subtle hints about being on the same page about a topic. Alongside that there is shared excitement about subtle, small details or things one could build. This kind of shared understanding can exist in a purely virtual form, but that can take years to foster. Finding like-minded people through the internet is what brought me to where I am today. Yet in many ways as I grew older I also realize how much harder this is. Compare this to meeting people in person. A day in person with another human being can replace a week of async online collaboration and a month of chipping away at a problem in isolation.
When I started working on / at Sentry, I already knew enough about David that I knew we're on the same page. On the other hand, I also knew that San Francisco wouldn't be the place for me. So if I wanted to work on Sentry, I also had to work hard to make remote work. The way I went into remote work for Sentry I was determined to figure out how to make the situation beneficial for everyone involved.
In early Sentry days I felt a lot of pressure on myself to make my remote work situation successful. And I loved that. It forced me to work towards finding the advantages in that situation. Initially this primarily meant better time zone coverage, but it also meant that I took customer calls in the early Sentry days to connect with European prospects. I managed to compensate for my remoteness in other ways. I also intentionally shifted my days to be closer to my US colleagues and eventually hired more folks around me.
Today there is an engineering office for Sentry in Vienna where I live. It's not a huge office, but I'm very proud of the accomplishments of the people working there. Vienna isn't a city known for its developer community, in fact it's probably not known for that much to begin with. So in many ways having an office here was a gamble. In a similar way to how I tried to find reasons for why my remote situation at Sentry works, I also approached the office in the same manner. What's the social experiment that Vienna is running, that aligns with the needs and desires for our company? Given that Vienna isn't an engineering hub, the talent pool is more restricted compared to San Francisco. On the other hand it also means that you can create an environment that focuses on retaining engineers. Vienna is a great city that enables pleasant commuting, is comparatively cheap, very international and great for cities. There is a genuine reason to work here. But the point is: both my own work situation as well as the office I approached with a certain level of anxiety that made me work for it.
And then Covid came.
And quite frankly with Covid a lot changed in fascinating ways. I will admit that I completely underestimated the impact that a Covid imposed remote work environment would have on us. And not just us, but quite a few folks around me as well. How was this possible? How could remote work, something I have been practicing for years all the sudden not work? How could this be so bad for a few months during Covid?
With the power of hindsight I think the biggest difference between before and after covid remote work, was how we all went into it and how much more extreme it was. I spent quite a bit of time talking with others who have made remote work and it comes down to the same: it's very intentional, and it involves understanding how to deal with the downsides. Covid remote work was nothing like this.
"With the onset of Covid, many individuals who previously had little experience with remote work suddenly found themselves working from home. Unlike earlier remote work scenarios where individuals made significant efforts to adapt, the pandemic brought about a shift in expectations. Folks rightfully began to demand better support for remote work from us. And it wasn't just us, I have heard similar stories from lots of others. In some situations people moved quite far outside the cities where they worked during Covid. In some cases that was unavoidable. When you have your partner and your kids at home 24/7, you might need a change in place. But even after things normalized, the offices were much more reclusive than before. The dynamics completely changed. There were fewer people in the office and collaboration between teams from different offices decreased.
This year, I engaged in numerous conversations with various individuals about the challenges posed by remote work and Covid. Probably not entirely surprisingly, very few mentioned any positive impact of Covid on work culture. Even more concerning is the negative perception of remote work in some areas. This has led to unexpected and stringent return-to-office policies, affecting even those who were originally working remotely prior to Covid as collateral damage.
One of the changes with Covid remote is that people work from home that previously were in the office. This even includes myself. This in practice easily ends up as a net negative unless you compensate in in some other way. We miss out on non-verbal communication, spontaneous hallway chats that can lead to resolution of current issues, and the casual office banter.
I don't think we can go back to pre-covid life, the world has changed. What I think we can do, is be more intentional about how we go into this hybrid work situation. I believe the biggest improvement from where we are to where we can be is reflecting actively on the downsides that remote works gives us. I love remote work, it gave me the ability to work with great people over the years which would otherwise be impossible for me to work with. Yet as you have seen, I'm painfully aware of the downsides that it brings. These downsides just need to be more directly addressed and I believe that sort of addressing only in parts comes from company and engineering management, it needs to come from everybody.
If you have a remote work force, one needs to find natural opportunities for people to meet face-to-face. Even if it's just annual get-togethers of managers. it's not the catered breakfast or office event that fixes this, it's the getting together with intention, the fostering meaningful interactions. Our hackweeks, for instance, have spurred incredible collaboration far more than any catered breakfast ever did. A focused six-week sprint with a clear but ambitious goal not only enhances engagement but also naturally encourages in-person meetings. I've found that our off-site meetings, which ironically felt like on-site for many, with a clear objective, have rejuvenated team morale more than any other initiative.
If you're an employee seeking remote work, it might be beneficial to adopt a pre-Covid mindset and present a compelling case for it. The most desirable companies are likely the ones that uphold rigorous standards for remote work going forward. Ensure you have a valid and convincing rationale for your remote work request.
If you are a small company, remote is almost natural. You have established trust, everybody knows everyone and it doesn't matter that much how you work. The office banter might as well be the one slack channel. But that just doesn't scale. That tightly coupled model stops scaling really, really quick. Today there is not one slack channel that has everybody at Sentry in. And it's not just that.
There is a lot a physical space gives you at scale: you see people's happiness and frustrations. You see their motivation or lack thereof. Working in a larger office is a shared experience. Everybody feeds off each other. We turn from individuals into a shared body. Sometimes good things happen, sometimes bad things happen. Sometimes people run into each other not just for work reasons but also because they undergo some other shared concern. We live in times of war and a climate crisis, and many of us have friends and families who are affected. You might not want to necessarily have these conversations at the work place, but you will see the despair in your fellow coworkers when you grab a coffee. You can reach out, you can talk, you can support. The best emoji game will not replace that kind of encounter.