Questions to Progress a Conversation: These questions help the conversation along by relating to what you have been talking about and taking it to a greater depth. The question should be easy to answer, include everyone and not cause offense to anyone. Some examples would be: If talking about sport: 1. What did you think of their last game? This is particularly useful when you have established a mutual liking fora sport with the person that you are talking to. Perhaps you have even discovered that you both support the same team.