How to Fail At Casual Conversation

Casual conversation. The life blood of relationships big and small. When you boil down what it means to be ‘social’, most of it is really just casual conversation.

It’s important, if you’re good at it life is good. But there is a duality to it that most people miss; the more you try to control casual conversation, the more likely you are to lose the other person.

Across all settings — business meetings / social gatherings / close relationships / etc. — there is one major way to fail at a casual conversation: not creating enough space for others to engage.

When a conversation isn’t going well, consider that it might not be that ppl don't care what you have to say, instead perhaps they aren’t getting the opportunity to contribute.

This is something I’ve felt many times. When I’m excited about a topic, it's easy to feel like I need to get everything out at once. There's this underlying fear that if I pause, I risk the other person losing interest or changing the subject. But ironically, that's exactly why they disconnect. The moment you turn a dialogue into a monologue, you've lost them.

On the other hand, the best casual conversations I’ve had you can feel it, there is back n’ forth between both parties, there is balance. Like the closer you are to a 50/50 speaking split, the better.

We're all self-absorbed in our nature. As soon as a question forms in our mind, we start to forget what the speaker is saying and fixate on the smart thing we're about to say. It's like being in fourth grade when your teacher tells you to lower your hand and write down your question instead of interrupting.

Failure to create conversational space happens everywhere:

• Introductory sales calls

• Internal team meetings

• Investor pitches

• Happy hours (where someone corners you with their life story)

• Dinner tables & cocktail parties

The art of being a good conversationalist isn't about having profound things to say—it's about guiding the conversation in ways that let the other person feel like an active participant. It's a bit like dancing. If one person leads too aggressively, the other doesn't have fun and starts looking for the exit.

It's about being an empathetic speaker who leaves room for pause. And it's about being an active listener. (The surprising truth is that learning to listen well actually makes you a better speaker).

What to do if someone is over-talking? Sometimes in conversations, it can feel like you're being held hostage by someone who won't stop talking. There are polite ways to interject:

• "That's interesting—can we explore that point a bit more?"

• "I'm curious about something you mentioned earlier..."

• "Before we move on, I'd like to understand better about..."

I've noticed podcasters like Tim Ferriss and Lex Fridman do this exceptionally well. They guide conversations without dominating them. They create space for their guests while still maintaining structure. If you are looking for real-world examples, listed to them.

The paradox of great conversation is that to be truly heard, you need to speak less. The most memorable and effective communicators aren't those who say the most—they're the ones who create space for everyone to feel engaged.

Next time you find yourself in an important conversation, try this: after making a point, pause. Ask a question. Create a gap that invites the other person in. You'll be surprised how much more they remember what you said when you let them participate in getting there.

Peace,
Ramsey