November 4, 2018 When I was applying to college some years ago, one of my teachers asked me if I thought I would regret not applying to more prestigious schools, making the observation that it's not whether the professors will be good--professors are good everywhere--but the quality of the student body. Would I learn from my peers? I hadn't thought of that conversation in a decade, but it floated up through the layers of memory recently when someone asked why I originally joined Stripe.
October 14, 2018 I was recently reflecting on a strange experience I had when leading Uber's SRE team, which was being asked by an senior engineer on the mobile development team to prioritize setting up and managing their mobile test clusters. At the time, most of my attention was focused on how we could clarify better interfaces around the services we provided, eventually ending with a service cookbook, but as I reflect on it now, what comes to mind is something else entirely: how frequently teams and organizations make resourcing decisions that at least initially come across as entirely implausible.
September 26, 2018 A peculiar challenge of management is trying to invest in someone's career development when they themselves are uncertain about their goals. As a manager, you may have more experience and more access to opportunities within the company, but that represents a small slice of their career possibilities. Our schooling often rewards us for being methodical, linear thinkers, but that approach is less effective outside the intentionally constrained possibility spaces.
September 23, 2018 Some years back, I was sitting in a room with my manager, our CTO and a crisis. An engineer on my team had mishandled two alerts, which had cascaded into plausibly the worst production incident the company had experienced to date. There were three root causes: alert fatigue, a lack of velocity context for out-of-diskspace alerts, and relying on a centralized database with little support for vertical scaling. At that moment, though, we were no longer talking about root causes. We were discussing whether to fire the oncall engineer, and I was saying no.
September 23, 2018 At an early job, I worked with a coworker whose philosophy was "If you don't ask for it, you'll never get it", which culminated in continuous escalations to management for exceptional treatment. This approach was pretty far from my intuition of how a well run organization should work, and it grated on my belief that consistency is a precondition of fairness.