OKRs: Objectives, Key Results, and Corporate Cosplay

There’s a special kind of sigh that comes out when someone says, “We’re rolling out OKRs.” It’s not quite despair. Not quite sarcasm. It’s the sigh of someone who’s seen this play before—probably in Q1 of last year, and Q3 of the year before that. The costumes are different, but the script is the same. Let’s get this out of the way: OKRs—Objectives and Key Results—can be useful. They’re not inherently evil. But like many good ideas, they tend to die in the wild. Not because the framework is flawed, but because the way most companies implement them is. ...

May 22, 2025 · 5 min · The Cynical Developer

An Evolution of a Software Company

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. ...

May 15, 2025 · 3 min · The Cynical Developer