It does seem that you need EITHER a very particular combination of things for "Guess culture" to be more effective than "Ask culture", or you need a system that

It does seem that you need EITHER a very particular combination of things for "Guess culture" to be more effective than "Ask culture", or you need a system that is so irrevocably corrupted by its faulty incentive structures that it can't function as a bureaucracy without lots of plausible deniability. My boss at this point understands that he's often putting me in a double or triple bind, but is obligated to do so and is never going to get approval for not doing so; My attempts to acquire verbal directives as to priority are met with "figure it out" and a grin. But then he's also extremely forgiving about accountability, doesn't attempt to apply metrics, because he understands that I'm going to be working on it all day anyway. Sometimes the bureaucratic style, enforced from the top down, is "Ask for unreasonable things in order to attain reasonable outcomes". I do not work with life-critical systems, where this sort of thing absolutely would not fly.