What somebody asks for and what they need are often two different objects, and the gap between them is where most misunderstandings live. A teenager asks for money and needs twenty minutes of undivided attention. A colleague asks for feedback and needs to be told the work is not a disaster.
Sensitivity means hearing both, and then usually answering the request anyway, because deciding you know better than someone about their own life is a fast route to being insufferable. Give the money. Then stay in the room a while longer than the transaction required.