Culture

Originally published on September 20, 2022 I was lucky. One of my first real gigs was at a startup that actually understood agile—not just the part where you stand around at 9:30 reciting what you did yesterday. No, I mean real agile. The founder believed in it. Not just the words, but the mindset. And in 2007, that made them look a little unhinged. Estimates in points instead of hours? Delivering small, usable increments? Developers writing tests on purpose? Teams interviewing and hiring their own teammates? It was weird. It was new. And it worked. ...

Originally published on August 26, 2022 In my last post, I described the arc most software companies follow—from chaotic startup to process-heavy bureaucracy. If you missed it, check it out here: An Evolution of a Software Company. Spoiler: there’s a pendulum, and it swings hard. Today, we’re talking about what happens next—and how to stop the pendulum from turning your team into a JIRA-powered approval queue. From Chaos to Control By the time the dust settles, you’ve landed in a company that’s seen one too many outages and decided that the cure is process. Lots of it. ...

Originally published on August 15, 2022 Let’s start with a story. It’s one you’ve probably lived through in some form, if you’ve spent more than ten minutes in the software industry. The Origin Story (and Its Inevitable Sequel) A company forms. There’s an idea, a goal, a dream. Usually it involves building the next great thing—a widget, a platform, a barely differentiated SaaS for onboarding PDFs. The founding team is small and experienced. They might be well-compensated, but more often they’re paid in the warm, fuzzy promise of equity. ...