We all can be socially awkward, but introverts doubly so. Here are some tips to learn the art of smalltalk...
First, you need to engage the target of your smalltalk
The Initial Engagement: Connect and handshake
Start with a quick story about yourself, that your target can related to, then ask for reciprocity. If you have heard of Philipp Humm's "storyselling", this is a "connection story". It should be based on your recent experience, followed by "what about you?"
EX:"I used to play tennis at semi-pro, but recently I picked up the racket again and I can barely get the ball over the net. What about you? Got any sports that you can't let go even though you're not good at it?"
Once you got the target talking, you can do the name and handshake.
Listen, Wait to Respond, Ask for Clarification and/or Paraphrase Back
When the target starts talking, listen carefully. You're trying engage him/her to talk some more.
When target finishes talking, do NOT start talking just to fill the silence. Take a few seconds to think about what you are going to say. Don't take too long though. 3-5 seconds at most. This makes you look more deliberate, and emphasizes that you've been paying attention.
Asking for clarification, as well as paraphrase their point back to them proves that you were actively listening. Establish dialog.
Keep it Small and Light, Using Context and and Structure
Smalltalk is no place to bring up politics or religion. Keep the subject light, and talk "small" (or "brief" and "concise"). Not sure what to say? Answer the following 3 questions: "What? So What? Now what?"
EX: "American football, huh? Never felt I had any talent for it. But those footballer get to hang out with all the cheerleaders, at least back then. Was it same for your school too? Wonder what happened to them?"
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