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How To Spark Interesting Conversations

Nate Anglin
2 min readJan 7, 2021

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Most conversations are dreadful.

They start with the same questions, like, “how are you? What’s the weather like? What did you do today?”

By the second sentence, you want to crawl out of the room.

Being a better conversationalist is about sparking exciting conversations.

It’s why David Sedaris has a rule for writing better stories; ask better questions.

But not just better questions, more interesting questions.

“If you ask more interesting questions, you’ll get more interesting answers.”

Here are a few ideas:

If you could only speak one word today, what would you say?

If you could lock up one person in a mental institution, who would it be?

What book have you recently read and got lost in?

You don’t want the conversation to get stuck on a boring topic or a topic you know little about, which is why you need to practice free association.

Just because someone mentions NASCAR doesn’t mean you’re stuck with that subject.

When you use free association, you train your brain to think outside of the box.

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Nate Anglin
Nate Anglin

Written by Nate Anglin

Small Biz Investor, CEO, & helping others improve their performance, profit, & potential w/out sacrificing what’s most important. www.nateanglin.com/newsletter

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