Why can't they just...? Revisited

(This is an updated version of a post I first wrote in 2017. Given everything happening in tech today, it felt worth dusting off.) The question “Why can’t they just…” has been a common refrain I’ve heard throughout my career. “Why can’t they just X” is, at its core, a great question—“why can’t they just find spending cuts elsewhere?” or “why can’t they just tell us what the technical strategy is?” or “why can’t they just tell engineers to write more tests?”—these are all valid questions that come from a place of deep concern. I hear this from all sides of the same challenge. Let’s use AI mandates as an example: Engineer: “Why can’t they [senior leaders] just let us keep using the tools that we already know and are frankly more productive with?” and “Why can’t they [managers] see that just because they’re finding manager work more productive with these tools, it doesn’t feel the same way with engineering work?” Manager: “Why can’t they [senior leaders] understand that mandates don’t…