Dan Na's personal blog. Lessons from the technical leadership track.
The last ~12 months have been a whirlwind. Working at a smaller company during an aggressive growth phase has run the gamut of emotions - exciting and overwhelming, stressful and joyful. But I’ve received what I was optimizing for in spades, and it’s been satisfying to get back into the details, challenge the limits of my comfort zones and push forward in the midst of collective aspiration.
I have a lot of career conversations (interviews, reports, chats with people asking for advice) and the single clarifying question I’ve grown to center the discussion around is this:
I left Squarespace at the beginning of July, which brought my tenure to roughly 7 years and 8 months. Life has been a whirlwind since then - a house move, a new job, the persistent chaos of young kids - so I haven’t had much time to slow down and write about my time there.
The two defining characteristics of the coworkers I enjoy working with most are ownership and urgency.
An unexpected source of management inspiration I’ve mentioned more than several times recently: “have you seen the ending to the movie 8 Mile?”
Over the last several years I’ve had the opportunity to mentor several newer managers, and it’s one of the most rewarding aspects of my role. On a purely tactical basis I think scaling manager capability is the best (only?) mechanism to scale my own capacity, but beyond that I know personally how rudderless the job can feel without help. The internal feeling of underperformance as an IC isn’t…
Say an engineering team wants to change the behavior of other engineering teams, and for a very good, big-picture reason. This happens often on horizontal platform teams or at wider architectural scope. I’ve been in a lot of conversations around goals of this type: encouraging better test coverage, considerations of web performance/accessibility, adopting a different coding paradigm (e.g.…
I was interviewed on an engineering management podcast! Listen to it on the web via managingmanagers.tech or on Spotify!
One side effect of leading the International engineering effort for so many years is exposure to executives, given the strength of International’s growth and revenue impact. And as the cross-functional team has grown, so have the number of initiatives that ultimately fall within the remit of an executive stakeholder. Consequently one of my recurring meetings for the last several years is…
I was recently inspired by this fantastic point about delivering “balanced” feedback from Randall Stutman. I offer a lightly edited transcript (for coherency) below, but it’s a better experience to watch the clip directly on YouTube via The Knowledge Project:
In the early 2000s there was a trope in the programming community about “a friend with an app idea” 1: It’s interesting that I don’t hear about this happening at all anymore. I assume it’s because coding feels significantly more democratized/accessible than it was then, and the “someone has already built an app for that” factor is so high now.
I was recently asked for advice about 1:1s:
Scott Galloway has an interesting take on the two types of effective leaders (starts at 26:14):
Tyler Cowen, economist and prolific blogger/podcaster/internet thinker, frequently poses a question to his podcast guests:
It’s a weird time in the tech industry, and if you’ve been in the industry long enough you’ve likely experienced an economic downturn or a company under financial crisis. Consequently there have been a few moments in my career where I’ve heard leaders plead with engineering teams to “act with urgency.”