The Daily Challenge: Dinner Conversation - An Art Worth Mastering


Make every dinner conversation an interesting one. 


Master Communicator.

Time to Read: 4 mins

Holiday dinners. Often they're enjoyable, but sometimes they're a bit like a science experiment: putting a variety of completely different individuals at the same dinner table and expecting the conversation to go well. 

Whether you're stoked for your upcoming holiday dinners or completely dreading it, one thing is certain: there will be conversation. 

Conversation by itself isn't so bad. But what about when you find yourself sitting next to someone who seemingly has nothing in common with you? How can you help get the conversation to an interesting level? We're talking beyond "what do you do for work"? 

Be curious, ask smart questions, and know your audience. 

Step 1. Listen. It's not uncommon to get distracted by the commotion of a holiday party, but while you're in a conversation - do your best to truly be in it. (Check out more on the 4 steps of active listening). 

  • What is this person saying? 

  • How do they feel about the topic? Excited? Happy? Nervous?

  • Is this really the topic they want to talk about? Or do they seem bored?

  • Do you understand the context or do you need to ask clarifying questions to make progress here?

Step 2. Ask questions...and then ask more. Rather than turning the conversation back to yourself, consider asking a few thoughtful questions. By digging deeper into a topic will help you learn more about your audience and drive the conversation beyond surface level.

Here are a few follow up questions that can drive any conversation further:

  • Tell me more about that? 

  • How did you feel about that? 

  • Would you do it again the same way? Or would you change something?

  • I'm not familiar with the subject, can you explain it further? 

  • What factors caused you to make that choice (or choose that direction)? 

  • Was that experience typical for you or new?

  • If I wanted to learn more about that, where would I go? 

Step 3. Know your audience and modify your delivery to align with their interests. Just like with all public speaking, knowing your audience is critical. Now that you've had a chance to learn more about the interests of your conversation partner, use this to practice adapting your public speaking skills. How can you keep the conversation interesting for them when they start asking you questions? 

Pro Tip: Remember what you've heard. Chances are high that you'll bump into this person at the next holiday dinner (or at least at some point in the future). You'll get bonus points for remembering the conversation. Repeating the main points back as you hear them, asking questions, and summarizing the topic are all ways to lock this conversation into memory

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