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  • Writer's pictureDillan Taylor

A simple tip for better conversations

I’ve been connecting with strangers, coaching people, and staying in touch with friends for years. Here’s what I’ve learned about great conversations.

First and foremost, people love to feel important or interesting. It’s a basic human need—to feel like we matter and that people care about us.

That’s why we’d much rather talk to someone who asks us questions than someone who just talks about themselves. We all know people who only share their stories, their opinions, or their knowledge. Being asked zero questions can feel like we’re just being talked at. No matter how captivating or funny they are, eventually we want them to show some curiosity.

In coaching there are three types of listening: level 1, level 2, and level 3.

Level 1: listening through your lens

ex: “That reminds me of the time I did that. It was crazy!”

Level 2: listening through the other person’s lens

ex: “That’s crazy because you typically love doing stuff like that!”

Level 3: recognizing another person’s energy

ex: “You feel more excited than normal. What’s going on?”

When we converse with someone who only uses level 1 listening, we want to shoot ourselves. There’s no back and forth, no collaboration.

Want good conversations? Ask questions. Want great conversations? Ask follow-up questions.

Asking someone what they do for a living is common. Asking them why they chose that line of work, what they love and hate about it, and if they’d still be doing it if they had $1,000,000…most people don’t get asked those questions.

Follow-up questions make people explore and tell us more about their values, personalities, and decisions.

But all this doesn’t mean level 1 listening is bad. In fact, it’s necessary. Which brings me to the second principle of great conversations.

People want to feel a connection.

So while they’re powerful, don’t only ask questions. That turns a conversation into an interview. Some amount of self-sharing and inserting is needed.

What then, is the balance? Try this simple trick.

The 2-for-1 rule.

Ask two questions. Share one thing. Repeat.

If the conversation doesn’t seem to be flowing and they’re not asking any questions in return, take the lead. Ask a question. Then ask a follow-up question. Then share something about yourself.

This ensures that the other person knows we’re interested in them but also connects the dots between them and us.


  1. “How was your New Years?”

  2. “Sweet! How do you typically like to party or celebrate?”

  3. “Yeah, I feel the same. My ideal weekend is a cabin in the woods with a dog and a book.”

Obviously, this doesn’t have to be followed like a script. But the idea is to ask more questions and to connect with the person we’re talking to.


  1. Ask more follow-up questions.

  2. Still share your own experiences, ideas, and knowledge.

  3. Use the 2-for-1 rule: ask two questions, share one thing, repeat.


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