> I think re-planning is a failure when nothing is learned from previous assumptions not being correct

This is the exact problem, and why it is so extremely difficult to communicate about the subject.

Another way to say "learn from previous [failures]" is "bureaucracy". We did something wrong last time, so we need a rule about that failure.

It SHOULD NOT be seen as failure, we SHOULD NOT add bureaucracy, simple rules CAN NOT fix the issue.

What should happen: Line managers and developers should be able to communicate about what they are learning as they do the work of software engineering. Developers should be able to re-plan their approach to problem solutions.

This simply will not work if there is not strong trust between upper management/[the money] and the engineering/execution side of the organization.

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The meta-problem is that you have to see things go wrong many times in many ways before you really understand what is going on, and by that point ... well everything gets very tiresome.