How to...

10 Ways to Have a Better Conversation

What’s worse than small talk? Bad small talk.

What’s better than both of those? Genuine conversation.


In a time where text communication reigns supreme, it’s more important than ever to nurture the skill of exchanging words with another human being.

Since starting my podcast, I’ve been forced to flex this muscle and become increasingly aware of what it takes to get into a comfortable verbal space with another person, whether it’s a long-time friend or someone I’m meeting for the first time.

To have better conversations, you’ll want to keep three things in mind:


Clarity  –  Learning  –  Connection

Clarity: You’re sharing information in a clear and effective way.

Learning: You’re asking questions, you’re listening, you’re present, and you’re curious.

Connection: You genuinely care about getting to know someone. From greeting someone warmly and exchanging pleasantries all the way to in-depth convos about the psyche.


Keep those concepts in mind and use the following tactics to step your conversational prowess up a notch:


1. You’re already talking to a friend.*

This is the mental framework you should embrace when attempting to build rapport with new humans. Greet people like they’re an old friend and throw them a warm smile. Beam a little light in their direction. You’re sending them cues that you’re approachable and that they can feel comfortable talking to you.

*Unless they’re clearly an ax murderer.

2. Read all the things.

Books, news articles, blog posts. Read something everyday and not just about things you already enjoy. Read about things you know nothing about. Seek out a variety of subjects to make yourself well-rounded and revel in amazement at the bits of knowledge you’ll be able to access when drawn into an active conversation. You’re providing yourself with a huge well of information to draw on so that you can hold your ground with all kinds of people and contribute in a meaningful way.

Not to mention, looking at well-constructed sentences enables you to instinctively create them for yourself. Think of the wonders this will do for your conversational confidence.

3. Listen to podcasts.

Podcasts are an amazing way to expose yourself to good conversation. Find some popular ones that focus on multiple subjects. Seek out conversations with scientists, comedians, political analysts, normal people, etc. You’ll find that you’re enhancing your own dialogue skills through osmosis.

Need somewhere to start? Try: “The Joe Rogan Experience”, “Under the Skin with Russell Brand”, and “The Tim Ferriss Show”.

4. People enjoy polite and pleasant.

Ask people how they’re doing. Say “Good morning”. Tell people to “have a nice day” or a “good night”. Remember that whole “smiling” thing we talked about? Do that.

Bring up something from the last time you talked: “Hey, Jim. How’s the model airplane coming?” Ya know, totally normal stuff like that.

Even in the quick exchanges, you’re cultivating a foundation of friendly encounters that increase the potential of reaching a deeper level of communication with them in the future.

5. Don’t make it weird.

Not all conversations were meant to continue. When a conversation is clearly not going anywhere, or one or more of you is uncomfortable, you can still exit the conversation with a quick politeness. Smile and excuse yourself at the first available moment. Casual and a cool cucumber. That’s you all over.

If you’re focused on making a good impression, don’t swear until they swear.

Are they barely making eye contact and their body language is closed? They’re not into talking anymore for whatever reason and your time is better spent elsewhere. Let them be.

Are they inquisitive and making good eye contact? They’re engaged. Look at you, being all magnetic.

Stepping away from a dying conversation ensures that you don’t end up being perceived as annoying or awkward (even if you feel that way sometimes).

6. Be curious and live some life.

How many times do we see people day in and day out and then come to realize that they were actually born in Bolivia? Well, probably not too often (unless you’re reading this in Bolivia right now). But, if we’re not careful, we can know people for years and not know some of the most fascinating things about them…because we never thought to ask.


Pro Tip from “How to Talk to Anyone: 92 Little Tricks for Big Success in Relationships” by Leil Lowndes:

Stop asking people: “What do you do?” Replace it with, “How do you spend most of your time?” Some people dread being asked what they do for a living because they don’t enjoy it or it’s the last thing they want to talk about. You’ve given them the choice to talk work or talk hobbies. Above all, you’ve asked them a question that communicated that you see them as more than just their job.


Now that we’re more curious about other people…what if we elevated our curiosity about life in general? Sometimes, we forget that we have the power to make ourselves more interesting.

Expose yourself to new activities, places, and hobbies. Partake in the occasional random mini adventure. You won’t love everything you try, but I bet all those experiences will turn themselves into good stories.

7. Observe, imbibe, and savor.

Stuck in the small talk cycle? Jazz it up by using your surroundings as chat fodder. Look for interesting people in the area, compliment something they’re wearing, explore the environment with your senses.

Steer clear of the weather, unless you’re in an actual weather event. Most people instinctually feel that the conversation is losing momentum once people start mentioning things like the unusual cloud coverage or the fact that you’re both living in the same atmosphere and experiencing the same temperatures. It’s the first chapter in: “Small Talk for Beginners.”

Take advantage of the built-in social material if you’re eating and/or drinking with people: comment on the food, ask them their favorite type of wine, mention another great restaurant you know of in the neighborhood, ask them if they’ve been there, tell them about the time you ate escargot in New York at 3am (true story).

You’re gathering information so that you can fluidly find a path to a new topic.

8. Be concise and embrace vocabulary.

Don’t use a thousand words when twenty will suffice. Keeping it short and sweet gives your words more impact and will allow your listener to more readily retain the thought/idea.

Synonyms are your friend. With so many words to use, why would you limit yourself?

Ex: “Nice”. How often do we use that word? Try replacing it with one of these today: pleasant, likable, agreeable, personable, congenial, amiable, affable, genial, friendly, charming, delightful, engaging.

Having a strong vocabulary isn’t about throwing “fancy” words around in places they have no business being or trying to look smarter than other people.  Using the word “indubitably” instead of “absolutely” is gonna make you look like you’re trying too hard in most circles. Instead, just sprinkle them in here and there and let those well-chosen words take the place of lengthy descriptions.

Speaking with a certain amount of eloquence will turn a lively conversation into a scintillating one in no time.

9. Remove judgment, bragging, and assumption.

You’re not going to agree with or like every person you come across. That’s a given. But, as long as they’re not a raging bigot or generally hateful individual, take the opportunity to learn about their perspective. Disagreement needn’t breed hostility.

Ex: Avoid phrases like, “You’re crazy. I would never do that.” That’s a convo shutdown. Change it to, “Oh wow, you’re brave to have done that. I would have been too nervous.” Look at you, sounding all kinds of open-minded.

If someone tells you about an accomplishment of theirs, don’t take this as an invitation to one-up them. Acknowledge their accomplishment before making it about yourself.

Did you just realize you’ve been talking about yourself for too long? Just smile and say, “But, how about you? What have you been up to?” Re-engage them with a question and demonstrate that you’re not just there to bounce words off of their face.

Have an assumption about someone? Acknowledge that train of thought and then leave it in the station while you set out to look past your first impression. Many people aren’t what they initially portray themselves to be.

10. LISTEN.

The ultimate influencer in better conversation. Listen with interest and be in the moment rather than planning your next sentence before they’ve finished theirs. Only then will your responses be able to lead the interaction into an honest and worthwhile place. More importantly, people can tell when you’re actually listening and they’ll take mental note that they enjoy speaking with you.


Instead of always existing on the shallowest surface of distracted small talk, see what happens when you truly engage and work towards being an enjoyable conversation partner.

The difference will turn arguments into discussions, casual interaction into potential opportunity, and acquaintances into friends.

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If you like this post: share it with your friends, check out another one, or listen to my podcast “We’re All Human with Courtney Diamond”.

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