When we worked together, my friend Don Peppers used to sometimes say that I reminded him of George Ball, Under Secretary of State to President Lyndon Baines Johnson in the 1960s. Ball was always asking questions about the policy of escalation in Vietnam. Johnson usually listened carefully to Ball, appreciated his questions, and then ignored him.
I took this as a compliment, with full knowledge that it was not entirely intended that way.
Asking the right questions is never easy, because most people ask the wrong questions. This is not because they are dumb or naive. It is because the right questions often lead to more time, energy, and resources than seem to be available.
For this reason, the “most logical” short-term course of action is often to stick with the wrong questions. But such easy questions—and answers—will lead you into a box. They are the reason why seemingly successful companies fade into obscurity, and successful professionals “suddenly” find themselves out of a job.