That definitely happens, but I wish had the displeasure of working at companies that were enamored with the solution they have, and couldn't be convinced to look again at the problem and see how it's changed since they originally solved it. As with most anything, the best approach is to somewhere in the middle, combining a love for the problem with a drive to repeatedly solve it. And one of the best tools for that seems to be dog-fooding, when the people in the company really want to use it for themselves.

What's ironic is that all that analysis is often framed as being responsible or strategic, when in reality it's risk avoidance dressed up as rigor

Oh man, I feel this.

Somewhat related, I've learned that when you're the one who ends up doing the thing, it's important to take advantage of that. Make decisions that benefit you where you have the flexibility.

This is an excellent piece about how doing something is better than just talking about it: https://www.joelonsoftware.com/2002/01/06/fire-and-motion/

you remove "managers" then simply rate of output goes up.

specially the middle managers i.e engineering managers, senior engineering manager, director of engineering duh duh

there's less coordination to do - to keep managers up to date.

the most functional software orgs out there - don't have managers

Output goes up until everything fails catastrophically

Which orgs did you have in mind?

That is OK if that fed into a decision to do another thing now because of <good reasons>.