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.
September 4, 2018 Many effective leaders I've worked with have the uncanny knack for working on leverage problems. In some problem domains, the product management skillset is extraordinarily effective for identifying useful problems, but systems thinking is the most universally useful toolkit I've found.