Earlier quoted context omitted.
Depends on how high up the ladder the management is you're talking to. Your line manager may be interested in a technical issue / improvement and understand its value without further explanation -- for instance, we're using a brute force algorithm that takes exponential time to foo the bar in the Baz module. It's got test coverage and the problem has a known logarithmic solution, so we could rewrite that in a week to…
Exactly. The other piece I've seen is being able to handle "I want Foo by X". It's easy to take on the engineer mindset and say "Sorry, that's not possible. The whizbangs alone would take more than that time!", but what do you do when they simply repeat "I want Foo by X"?. Picture the various Star Trek series where the engineer would say it'd take 5 hours to fix something and the captain retorts "you have 2". It's re…
One tactic I can suggest (if your manager isn't a totally unreasonable cartoon tyrant) is to simply be explicit about it and ask "can you explain more about why you need Foo?" and then "what's driving the deadline of X?" Understanding the business case is generally necessary - though not always sufficient - for coming up with an alternative solution.
I suspect that part of the gap between people who are and are not good at this is how well apprised they are of the general conditions, initiatives in other departments/teams, and short-term strategic goals of the company.
Some of that is on the person who may or may not put in the effort to remain informed; and some of that is on the company's management that may do a good or a poor job of communicating those things proactively between departments/teams and from senior management down to junior management and line workers.