It is human nature there is one universal in conversation; everyone likes to talk about themselves. The secret to eliciting good conversation is to know when to talk and more importantly when to listen. It is impossible to listen during an awkward silence. Asking the right questions is the shortest path toward engaging conversation. As you ask the right question you illicit a response that strikes at an emotional core for you conversation partner. Additionally by selecting the question you have the ability to steer the conversation in a direction you will find engaging.
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I was no chief and never had been, but because I had been more deeply wronged than others, this honor was conferred upon me, and I resolved to prove worthy of the trust. - Geronimo