I never wanted to be fully remote. As an engineer, I recognized that the ability to work from home was there once the high-speed internet became ubiquitous and most company services were accessible via VPN. Going heads down for most of the day on challenging code was incredible. However, I needed the in-person interaction to get code reviews, feedback on designs, and to stay connected to my team. “Maker time” (dedicated time to focus and stay in a flow state) was key.

After I moved into management, I had less interest in being remote. My ability to quickly connect with my team members and peers, get everyone in a room and discuss issues, and connect easily trumped my desire to avoid the commute. Plus, I didn’t need “maker time” nearly as much anymore; “manager time” (collaboration and discussion primarily) worked great at the office. 

I interviewed for a fully remote role in 2015 but didn’t want to be a manager and only see my team face-to-face a handful of times each year. And then 2020 came around. By then, I had been managing teams in Tokyo and Seattle and only seeing them a few times per year (although I had leaders in each location who saw them much more often, of course.) Like everyone else, I was thrown into fully remote management. I still think it’s less ideal for managers and a boon for engineers, which is why I particularly like a version of hybrid that allows everyone flexibility to come in when it’s convenient for them. However, we’re all still figuring this out and probably will be for another decade.

In-person collaboration

As we get closer to launching the stealth startup, the team has been increasing the face-to-face time. Even working side by side for half the day the other day, I realized several topics I hadn’t discussed with the team. A few minutes later, those were put to bed. It was a good reminder that the speed & seriousness of conversation should be directly proportional to the fidelity of the conversation. 

• If you want to go fast, get the smallest group of people necessary into a synchronous conversation on the topic.
• A face-to-face conversation is best if the material you’re discussing is sensitive (performance management, for example).
• Email can be an excellent medium if you can wait more than a day for the answer.
• If you are blocked by something and need a reply today but not immediately, instant messaging/Slack/SMS works well.

Work → Social

Concerning work-from-home, the cat is out of the bag in the long term. Aside from highly regulated industries (security, finance, etc.), for those of us in tech, we will have some work-from-home component to our jobs for the foreseeable future. And honestly, it’s good. The balance of picking up my kids from school, enjoying lunch with my wife, and (thinking about) working out has generally been a good addition. 

While I enjoyed the work relationships I built over the last 20 years, ultimately, we were never much more than “work friends” in most cases. I knew about their kids, birthdays (sometimes), and vacations, but for most of them, the main thing that brought us together was work. Occasionally, I’d make a longer-term friendship around another shared interest (Broadway, baseball, board games, our kids/spouses, etc.). But that was rare.

Since COVID sent us all to work from home in 2020, I’ve leaned more toward my “non-work friends.” We already had friends in our neighborhood, through our church, and through shared activities (primarily kids’ sports). It’s been challenging to make this transition, but the reward of having friends who supported me in the layoff and transition to a fractional CTO has been incredible.

Fun