Block reviews

Incoherent management, plans changing every three months, AI-obsessed leadership

After 2023, Square became...chaotic. Leadership (Jack Dorsey and his direct reports) made rash decisions without much consideration or explanation. They prided themselves on working "in the open" but in reality their shower thoughts became major company changes, which was distracting and immature. "Work about the work" (i.e., anything related to process, alignment, or collaboration) was villainized in favor of moving fast and breaking things. As a result, though we just made dumb decisions faster and ignored anything that felt messy. Spoiler: the messy things ALWAYS came back to bite us in a way worse way than if we just addressed it. Leadership also picked favorites and weren't shy about perpetuating that. The Golden Children could do no wrong and everyone else was stuck in a pattern of proving their ideas to deaf ears.