Maybe it's just a natural part of getting older, as habits and perspectives become more ingrained over the course of time.

In my experience, the people who won't ask "why" aren't simply "older." They're the in-between. Young people ask "why." But also older people, maybe 50+.

My experience has been that it's the project managers and their overlords in the 25-49 range that seem to think they know everything and everyone else is unclued.

The young ask "why" because they're curious and want to learn. The old as "why" because they want to understand what's behind decisions. And managers hate explaining themselves.

For internal or contracted apps, there is usually a well-defined customer. There may be other stakeholders, too, but that first one is the key.

If the problem is getting them (or their representative, and not a dev side proxy, engaged, well, that's the problem you need to fix.)

“Agile” methodologies that try to sidestep this, e.g., by designating a IT org proxy are broken in the same way as “Marxist” methodologies that try to sidestep the requirement for mature capitalist development and proletarian class consciousness, e.g., via an privileged revolutionary vanguard.

> Product owners are a poor proxy at best but at least they're a definitive throat to choke when things go awry.

That's pretty much exactly what is not needed.

> Being told for the 20th engagement in a row that the right people for a conversation about a feature can't spare the time to be in the the room to workshop it or provide meaningful feedback (so why are you paying $300/hr for my time?) is de-motivating.

Sure, and if that is happening often then prioritization isn't fitting business priorities, even if it is fitting what business says are their priorities.