Most people treat asking good questions as something you either have a knack for or you don't. Bob makes the case that it's actually a trainable habit, one built on slowing down long enough to catch a guess before it disguises itself as a real question. Along the way, he and Andrew revisit an old closing segment from the show's early days, the one where negotiating the question mattered more than answering it, and connect that memory back to the discipline architects rely on every time technical requirements and design instincts have to share the same decision.