I agree - the why skill is crucial and difficult. I won't claim to be any good at it (it's actually one of the things my current manager excels at intuiting an

I agree - the why skill is crucial and difficult. I won't claim to be any good at it (it's actually one of the things my current manager excels at intuiting and I want to learn from him). 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.