Comfort vs. Change on Tech Teams

Note: I wrote this a few months ago, but am just publishing now. These “recent events” seem like they happened a lifetime ago, but I still think this point is relevant.

At the end of the day, human beings are satisfiers, not optimizers. Or at least this is what we say in my house when I point out that there has been a large pot soaking in the sink for three days, or we’re opening the window next to the overflowing garbage can, or stepping over piles of laundry on the way to the bathroom. We all have situations where we would rather live with something mildly inconvenient rather than change it.

I’m not a psychologist, but I can tell you that the human beings I know are motivated by discomfort. We’re hermit crabs who happily inhabit our tiny shells and don’t think to trade them in until we’re feeling our lungs constrict and the sand rubbing against our skin. I remember taking a great deal of comfort in this metaphor a few years ago when I finally walked away from a church (and as it turned out an entire religious tradition) that wasn’t fully welcoming to the people I cared about. If we’re uncomfortable, it means that we’re growing.

I have been thinking a lot lately about the kinds of people I work with best. I made a list of some of my all-time favorite coworkers, clients, and teammates, and do you know what nearly all of them had in common? They were all trying to make things better. They weren’t always negative, but they were continually willing to speak up when something wasn’t working. I was reminded of my teammate on my last project who kept pointing out issues with our development processes that saved us a lot of time and effort, or my coworker at a former job who bravely raised her hand during an all-hands company meeting to ask why they didn’t promote any women this year. I genuinely love working with people who aren’t satisfied with the status quo, because they challenge me, make me feel safe when I vent my own frustrations, and are quick to offer a “me too” when things aren’t always going well.

But trying to be an optimizer in a room full of satisfiers is risky business. The tech industry is full of people (most often cisgender white men) who are really comfortable with things the way they are. Sometimes those of us who speak up get silenced, sidelined, or retaliated against. We talk a big game about weekly retrospectives, iterative processes, and continual improvement, but at the end of the day, the core power structures remain unchanged.

In my experience, there’s a certain kind of person who shows up to every meeting. He continually plays the devil’s advocate, questions change, and often says things like “everything seems all right to me, so I’m not sure what the issue is here”. He’s comfortable with things the way they are — either because he made them that way, or he has been doing it the same way for years. Even if he means well and isn’t intentionally trying to harm anyone else, he is my least favorite teammate. Why? Because intentionally or otherwise — he is centering his own feelings and experiences above those of everyone else, particularly those of marginalized people who may be experiencing things differently than he is.

I think this is why some of the recent Basecamp pronouncements struck a chord with so many—it was clearly written by someone who has never needed to advocate for his own right to sit at the table. He has never needed to start a committee to advocate for more time with his children, inclusive medical benefits, or fewer microaggressions at work. He can focus on the work that brings him money and influence and trust that the Head of People can advocate on his behalf and stand up for his interests, as they always have. When employees start DE&I committees, give feedback to leadership, advocate for their right to be decision-makers at the company, and have bad reactions to major policy changes that are announced on social media before they are ever discussed internally, it makes him uncomfortable. And to someone who isn’t used to being uncomfortable, this discomfort is treated as something to be avoided at all costs rather than as an invitation to grow. Doubling down after backlash is a predictable reaction from someone comfortable for far too long.

When we’re not all learning and growing together, asking questions, and advocating for the needs of people other than ourselves, this is where our cultures break down, both on companies and teams. As others have said better than I can, the founders of Basecamp and any other like-minded tech companies have a choice. They can own their past decisions and respond to this discomfort by shedding their shells of intellectual superiority and allowing themselves to grow, or they can continue to double down.

As a member of the tech community, I sincerely hope that we do not have to keep choosing between keeping our jobs and working to enrich men who are satisfied with a status quo that benefits them. For those of you who are out there doing the good work—keep speaking the truth, holding leaders accountable, and advocating for change.