Leigh Howes shares some great ideas on how to get more context out of your conversations. If you get the context right, you can respond in the best way.
A simple technique to achieve this is to swap out a closed question for an open one.
Think of questions that start with what, where, who, when, and how. These kinds of open questions allow you to find out more about someone and understand their wants and needs. It will also provide key information that you can then respond to.