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- Listen. Listening is a very difficult skill few master. Do not be thinking about what you're going to say while they are talking. Genuinely listen. Let the conversation slow down. It's okay to take a few seconds after they've finished talking to form your sentence. Ask them to expand on some of the things they brought up. Take note of the most important things, especially the most emotional things, and ask about them.
- Speak more slowly. Take your time when you are talking.
- Threading. In any given sentence there will be several topics that are potential topics of conversation. "Yesterday I went to a show with Joanne." The three possible topics in that sentence are — yesterday, the show, and Joanne. You can ask more about the day yesterday leading up to the show. You can ask about Joanne — how they met, what their relationship is, etc. You could ask about the show. In order of emotional impact, the best threads appear to be — "the show," "Joanne," and "yesterday." Along each thread, you can identify additional connecting points to your own life that let you relate to the story.
- Avoid questions and favor statements whenever possible. If you say "How was your day?" you are putting all of the responsibility on the other person to provide the value in the conversation. This isn't necessarily bad, but it could be better. You want to be creating value and energy, not consuming it. "You look like you had fun today." You are making an observation. The observation itself can be talked about, or the reason they look like they had fun can be talked about.
- If you ask a question, try to provide more value with the question than you are consuming. This is a principle in improv comedy. If you say to your scene partner "Where were you?" they have to invent a story to entertain the audience, and you have provided nothing except pressure. If you ask "Were you wrestling in the barn again?" your scene partner now has something specific to work with. If you're going to ask a question, make it specific and something easy to extrapolate on — "What is it about music that makes you so passionate?"
- People like to talk about themselves. Generally speaking, if you can get a person talking about how awesome they are, and if you agree with their awesomeness and appreciate them for what they want to be appreciated for in a genuine way, they will like talking to you.
- Develop your breadth of knowledge in your free time. Look into stuff you don't know anything about. Listen to music you don't listen to. Try things that you haven't tried. You will develop stories and have a lot more topics to bring up in your conversations.