The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
I saw in your career journey, it said that you're an occasional manager.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
And you seem like someone who really enjoys the technical aspects of things.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
So how did you decide to occasionally dip into management?
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
Yeah, there's another piece that you wrote I thought was really good about leading by example.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
And you actually say it's bad to lead by example, but there's a quote in there.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
It says, modern tech workers can be an anti-authoritarian bunch at the best of times.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
Let's say you're a tech lead or tech lead manager or manager.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
How do you strike that balance so you don't lose credibility as a tech lead?
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
Influence without authority is huge.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
And I think there's, I mean, even big companies like Meta, they technically don't have titles.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
Everyone's just a software engineer.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
Is that also how Convex is run?
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
On the topic of tech leadership, I mean, in that article, I mentioned, you know, the title was don't lead by example.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
And I think that kind of might be confusing for people.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
Can you explain why you think you shouldn't lead by example?
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
That slider you mentioned, what if you give someone accountability and they blow it?
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
Do they go back down the slider to where you start micromanaging?
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
You mentioned, because you were the most senior engineer at Dropbox at some point, that you had to mentor other very senior engineers.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
And when I think about mentoring a junior engineer, it's relatively straightforward patterns.
The Peterman Pod
Dropbox’s Former Most Senior Eng: Building Great Systems and Advice for the AI Era | James Cowling
But when I think about, let's say I need to mentor a senior staff engineer, maybe even a principal engineer,