Insight questions can only be asked after you develop situation awareness. They are necessarily local and unique to the situation. When you are faced with a difficult situation, you will start as a prisoner of the unanswerable/too expensive formulaic questions, and your first job is to break out. The reason the weird “right questions” work is that they expose cracks in your default, formulaic mental model. By attacking those cracks, you force the useless default mental model to collapse, creating room for a new one.