Ask Questions That Give The Other Person Somewhere To Go

A good question widens the road rather than narrowing it.

Some questions leave the other person a lot of room and some leave them almost none. Asking whether someone had a good weekend leaves a gap the size of one word. Asking what they got up to leaves a paragraph. The difference is not depth or cleverness, it is how many honest answers the question permits. A question with one obvious correct reply is a form of politeness, not an invitation. If you find that conversations keep stalling after your questions, the problem is usually not the person answering. It is that you handed them a slot with only one shape.

The other thing a good question does is let the person choose the subject. Something like asking what has been keeping someone busy, or what they have been enjoying lately, or how a thing they mentioned earlier turned out, transfers the steering wheel. They will pick a topic they actually have something to say about, which is far more reliable than you guessing. Questions that are too specific do the opposite: they make the other person work to fit their real life into your assumption. If you assume they had a restful weekend and they spent it in a hospital waiting room, they now have to correct you before they can answer.

Beware the question that is really a statement waiting to be delivered. Most people can feel when they are being set up so that the asker can arrive with a prepared opinion, and it makes them careful. The test is simple: would you be genuinely interested in an answer that goes somewhere you did not expect? If not, you are not asking, you are cueing. Real questions carry a small risk, because the answer might take the conversation somewhere you cannot control. That risk is the entire point. Conversations only go anywhere interesting when at least one person is willing to be taken somewhere.