Learning to Swim in a Very Large Pool

These were the early days of learning how teams operate at scale, how influence is built through action rather than position, and how leadership often shows up before the title ever does.

Over the weekend, my dad came over for breakfast with my mom. They had just returned from a three-week tour of the southeast of the United States in their RV, and we hadn’t really seen each other since they left. This Saturday, they came over for breakfast, and as we sat around the kitchen table while my kids were still asleep, we started talking about how the trip went and about all the other things that had happened since they were gone. One thing led to another, and I mentioned to my dad that I had to go to Southpoint Mall to replace my glasses. One of the lenses had somehow gotten scratched, and I was hoping that the warranty was still valid—it wasn’t.

My dad, already retired and having nothing else to do, volunteered to come with me to the mall. So after breakfast, we dropped off my mom at their place, and we went together. As it usually happens, my dad and I started talking about life in general, and what my plans were for the future. Inevitably, our conversations always turn to my work and how things are going. Since I’ve been at the same place for 14-plus years now, it’s hard not to talk about work and to try to stay away from some of the “perennial” issues with my dad. Not because I don’t want to talk about whatever is bothering me at work, but mostly because it was the weekend and, since I hadn’t really seen him for quite some time, I didn’t feel like treating our trip to the mall as a trip to a psychologist.

Between going to the mall, ordering a new pair of glasses, and stopping by Dick’s Sporting Goods to buy a new volleyball for my kid, we had a pretty good chat. He gave me some really interesting advice, but one thing in particular stood out, which I think is a story on its own. Suffice it to say, he surprised me because most of the time my dad has always cautioned me to be careful with my words and actions and to try not to rock the boat too much because, you know, I’ve always been so impulsive.

This time around it was quite the opposite, and he was very supportive. It felt good to hear my dad basically not telling me to slow things down, but instead to make sure that I was taking good care of myself and not letting myself fall into a pattern where people might adjust their decisions based on what’s happening at work—or out of fear of what the job market looks like.

Anyhow, like I said, that’s a story for another time. I got back home after dropping him off and sat down with my wife, and we talked a little more about my trip with my dad and the things we discussed. Coincidentally, we’ve been talking a lot about work lately. My wife has just switched to a new job after many years striving to be recognized for what she does, and now she’s playing a primary role in this new position. I’ve been talking about what’s going on at work too—some of the things that still drive me, and some of the things that sometimes bother me to the point where I wake up at 4:00 in the morning, which is never a good sign. And I started reminiscing about the 14 years I’ve been at my current employer.

I remember when I was first interviewed, back in the fall of 2011. The person who would eventually become my manager was calling me from California, where he lived, and after the initial interview he recommended me for the next round. A few days later I took the morning off to go to the main office in Raleigh to be interviewed by a bunch of people. I remember very clearly walking in and leaving the interview feeling pretty confident that I had gotten the job.

I believe that not only my experience from the previous five and a half years automating tests with Python and learning everything there was to learn about Linux and system administration, but also my many years of involvement in the open-source community, paid off big time. There were moments in the interview process where I could feel people were excited to talk to me just because they had read or followed my blog posts or had used some of the code I had written or maintained. It felt pretty good being in that position. Sure enough, a couple of days later, I got the offer to join the company, and I’ve been here ever since.

One of the first challenges I encountered when I started my job at “The New Place” was that not only was my manager still in California and not physically around, but the person assigned to be my mentor—a Principal Software Engineer (one level higher than me)—wouldn’t be around either; he was taking a month to work remotely. So there I was, showing up at the main office and not really knowing where to go or who to talk to. While I did feel lost and overwhelmed at times, maybe because of my many years working at a startup, I had learned that when you find yourself in a situation like that, you either swim or sink. Swimming, I did, and I started paddling really fast. Whenever I needed something, I went looking for the right person or asked around to see who could help me.

Back then, the company had grown so large that they didn’t even have a desk waiting for me. They did provide me with a computer, but there was nowhere for me to sit. It was funny—I had to camp out at the desks of people who didn’t show up that day. I did that for about a week, carrying around the computer, connecting it to monitors, and then taking it all apart and putting it in a closet so that the next day I could do it all again. Eventually, they found me a desk, but it wasn’t near my teammates.

The overall team was pretty large, and I believe that by the time I joined there were about 80 engineers reporting to the manager in California. The new desk was waaaaay on the other side of the building from where everyone else working on our project sat.

In order to meet my coworkers and start getting to know them, I had to walk across the building, which actually created an opportunity that maybe wouldn’t have been available to me otherwise. I got to meet people from other departments and who worked on different areas as I made my daily walk from one corner of the building to the other. I learned a lot during those days, and I asked a ton of questions—which probably means I annoyed the hell out of a lot of people—but I think it was a great learning experience.

I remember the first time I had to join our daily stand-up call. I gathered around a speakerphone with ten other engineers in the local office while seventy more dialed in from all over the world. I don’t know if you’ve ever done a stand-up call, but typically you’re given a minute to briefly describe:

What you accomplished the day before
What your plans are for the day
Whether you need help or are blocked on anything

Round and round you go until everyone has spoken. Now imagine doing this with eighty people, some of whom worked on completely different projects. Add unreliable internet and phone connections, and it was utter chaos. It was impossible not to zone out until it was your turn to speak.

The worst part of waiting an hour for your name to be called was listening to people try to solve problems over the phone—things that could have been handled over IRC (no Slack back then). There was no one stepping in to tell them to take it offline. Those one-hour calls easily turned into bike-shedding or long discussions that could have been an email or an IRC chat.

It was interesting that even then I felt strongly about what good looked like and how things could be improved, and I never really refrained from sharing my opinions with my manager. I have to give him credit—he was very patient and put up with me and all my suggestions. I was the first person to go up to him and show how that one-hour call could have been a regular 15-minute call if he had only the leads from each group run stand-ups with their teams separately and then report back during a scrum-of-scrums. I gave him a ton of ideas and probably annoyed the hell out of him for a long time, but eventually he recognized that I wasn’t the kind of person who would just sit there, sling code, and follow orders.

It didn’t take long before he asked for my opinion on a conundrum he had. On one hand, he had a principal engineer who aspired to be more than just a principal but didn’t want to manage people. On the other hand, he needed “boots on the ground” to help with career development and managerial tasks that were becoming harder to handle from California. He noticed the positive influence I was already having with the team and stakeholders, and my tendency to be a go-getter who always tried to do what was best for the team and the project. So he offered me the opportunity to become an associate manager, the entry-level management role at the company.

Back then, I didn’t really know better, but I did know there were many things I wanted to do professionally. Things I believed the manager title could help me achieve—or at least pave the way toward. Could I use my approach to influence not only the people above me but also the direction of the organization? Would my manager allow me to continue making suggestions and perhaps change how software engineering testing was done at the company? These thoughts were all going through my mind as I discussed the opportunity with my wife one evening. And since we had just purchased a house, paying the mortgage and keeping my family safe and well-fed weighed heavily on me. I went to my manager the next day and said yes.

One of the first things I had to adjust to as a manager was handling the fact that people who used to come to me and chat about anything—or sometimes complain about leadership—now reported to me. Would they still feel comfortable having those conversations now that I was no longer “one of them”? That was something I had never experienced before, and I was curious and eager to see how it would go. More importantly, because of the relationships I had already built, I also knew where the problem areas were. I knew who wasn’t doing their job well.

Would I be able to fix those problems and have the difficult conversations required to change performance? Little did I know that not one, not two, but three opportunities to deal with exactly that would come up within a week of becoming an associate manager.