I don't know anything about your organization.
But my take is that this isn't a quality that you see in healthy organizations. We're human. We can't see the future. In the best of cases, we ingest as much information as we can find and we use that to make the best decision we can. And, truly, the best of cases never happens, but even if they did: New information is discovered. The Environment develops and changes. And that change has to respond with internal change as well.
One of the phrases I've heard people in my organization say is something along the lines of "are we sure this is the right decision?" or "how can we be sure this is the best path forward?" That's a mindset I'm trying to move people away from. The better question is "how are we accounting for a need to change in the future?" If you view a system as "X", then changing "X" becomes very hard. If you view a system as "X+Y+Z", then you can ask "how can we change Y to V without throwing away all the work we did on X and Z?" And then, in 12 months when you have X+V+Z, maybe you want to change X to W. And so on. That's continual improvement and true agility.
Its damn hard; in both implementation and changing mindsets from the "we want this perfect thing from day 1" to "its alright if it isn't perfect; its more important that we can easily change it." And, actually the hardest part is convincing people that this Is Not Optional; the most productive, highest performing organizations on the planet are the ones who know how to do this, and they'll eat your lunch if you're not ready. Maybe in 6 months, maybe in 50 years, but it'll happen.
It might help if I told you something about my organization. I'm in University IT. We're not building a product, the product is the education, and we merely support that with technology (the students, the research, and the administrative efforts.)
That's part of the problem, to be honest, is that the organization will not rise or fail due to the tireless efforts or minor failings of IT. We like to shoot for perfect, we want to do the best thing, but unfortunately if it's a choice between making a decision that leadership sees as a little shaky or uncertain, versus maybe making a more conservative choice that doesn't have as many bells and whistles, but that we're sure we can live with for a long time, they'll have us go the conservative route every time, so we can get this one important thing off of our plate and get back to the central focal business of the University.
I appreciate the way you're decomposing the issue, because I think you're right about all of this. The problem all this time has been, (and I've started to recognize it more and more)
1. we propose Kubernetes, knowing that it solves a lot of problems for us, right out of the box. X is Kubernetes.
2. Leadership asks "what problem does X solve" looking for the big show-stopper answer that says "well obviously, we have to solve that. We'll make it a priority!"
3. For each "well obviously" the honest answer is, "X doesn't really solve that without additionally Y and Z."
We don't even really truly get to the point in the conversation where we're worried about picking the wrong X. It's in the back of everyone's head, who has done any research on Kubernetes. There are so many flavors to choose from, how do we even know that Y and Z will work when we get there, if we start with X first?
Fortunately I think the glacial tides are turning, but they don't call it an "institutional pace" for no good reason.