One Simple Habit That’ll Make You Great At Conversations


Today, we’re going to completely strike from the face of the earth a pain in the ass experience we’ve ALL had….

I’m good in the first few minutes of conversation, but how do I keep a conversation going and keep the other person really interested? How do I stop it from stalling? How do I deal with silences?

Have you been there? Me too. You’re having a conversation with someone and it’s going great. Maybe it’s the CEO of the company you want a job at. Maybe it’s the beautiful girl you’re talking to at the bar. Suddenly conversation starts to stall and you’re thinking, “What do I say next??”

Today I’m going to teach you to cut those awkward pauses out at the root. No longer will you search for interesting things to say every 30 seconds! You’re going to have conversations that flow naturally and easily, regardless of who you’re talking to.

Here’s the deal: conversation doesn’t stall IMMEDIATELY. It usually lasts a few minutes, you get the basic stuff out, then twiddle your thumbs because neither of you has anything left to say. Or more accurately, because neither of you engaged the other enough to inspire further conversation. Then the CEO or the girl or whoever it is you’re talking to excuses themselves politely and finds someone else to speak with.

Bummer. But it didn’t have to end that way. Because you had a huge opportunity to really grab their attention. How? With this question, that comes up in almost every small talk chit chat conversation:

Where are you from?

And I would bet you answered something like this:

“New York.”
“Oklahoma, but I live in Philadelphia.”
“My parents are Korean, but I grew up in Florida.”

And that, my friend, is where you shot the conversation in the foot and left it to limp to its ignominious death. Don’t wanna do that? Soldier onward. The answer lies ahead.

Hint hint: You don’t need more questions.

You need to take those questions that are GUARANTEED to be asked in the first 5 minutes (like “Where are you from?”) and answer them in a way that makes the other person want to continue the conversation.

Take the “gimmes” and knock them out of the park

Let’s say you’re like me and your basic answer to, “Where are you from?” is “NYC.” The only shot someone can respond enthusiastically to “NYC,” is if they lived there, want to, or know someone who does. Luckily for me, a lot of people fit that criteria. But if they don’t, there is nothing left to say. And it only gets worse if you’re from Columbus, Ohio, or some place most people know nothing about.

(Sorry, Columbus – you know it’s true).

So give the person you’re talking with some conversational ammo they can use.


“Well I used to live in NYC, but now I live in Rio. I loved NYC, but the weather sucks for 8 months out of the year so I can’t do the outdoor stuff I like. And even more importantly the people in Rio have something that New Yorkers don’t, which is why I moved.”
Now you have interesting conversational threads for this person to pick up on.

How did you pick Brazil?
What kind of outdoor stuff do you like?
What is it about the people from Rio you like?
What is it that New Yorkers lacked?

All these are logical questions that people WILL ask. You hinted at something fascinating, but didn’t pull back the whole curtain. Their own psychology will make it near impossible for them not to ask more. And now they are solving the awkward silence problem for you

How to REALLY turn “Where are you from?” into a killer conversation

Obvious truth coming: no one really gives a shit where you are from.

It is a conversational crutch. They are being polite or hoping for a commonality. “You’re from Oklahaoma!? No way, I grew up there, too.”

Really, the only thing they care about is WHO YOU ARE. Who you are is not where you are from. And believe it or not, it isn’t what you do either.

It is WHY you do the things you do.

So if you’re from NYC, but currently live in Rio (like me), explain WHY you’ve chosen to live there. Take my previous example:

“Well I used to live in NYC, but now I live in Rio. I loved NYC, but the weather sucks for 8 months out of the year so I can’t do the outdoor stuff I like. And even more importantly the people in Rio have something that New Yorkers don’t, which is why I moved.”

90% of the time people will ask, “What do you like about Brazilians?”

…and NOW I get to reveal my values. This is where people get drawn into your world.

“New Yorkers are cool, but their priorities center around their career. Last year I got sick of it and visited Brazil. And it was immediately clear how some Brazilians–not all–were just so much more loving and alive. They smiled bigger, touched one another all the time, were incredibly loving and affectionate. I can’t stand people who are guarded. And while not all NYCers are one way and all Brazilians are another, I found more of that loving, friendly nature here so I had to move.”

Look at the values I included:

• Loving, friendly, open people
• Adventurous – I left NYC on a whim
• Freedom – I’ve set up my life so that I have the ability to live anywhere in the world

With those few sentences this person knows more pertinent information about me than they would if I read them my resume line by line. And chances are, while our biographies may not be similar, we can now connect on our shared values.

A note on oversharing

You’ll notice that in the above example, I don’t immediately overshare. I give a 2-3 line response to their initial question, and only dive deeper once they ask further questions. If they don’t ask, I don’t tell. I’m not trying to force feed them my worldview.
But they do ask 90% of the time, because I leave open loops. Conversational bait which prompts them to want to know more. Do the same. Because now…

We’re going to create your new, kickass responses

Yes, that’s right, it’s your turn We’re going to retrain your old habits so that when people ask you about yourself, you’re revealing values instead of boring ass facts.

This is going to help you across the board. It will help you turn a business meeting into a job offer. A chance encounter on the subway into a blossoming friendship. A stalling conversation at a bar into a second date. Every conversation improves when you reveal your values.

So to start, write out your values. You can use the ones I’ve listed as inspiration, but make sure the ones you write are true for YOU. Here are a few to get you started:

• Friendly
• Decent to all people
• Effusive in their happiness
• Funny
• Intelligent
• Non-judgmental

Write down at least 3. Seriously, do it. This is a waste of your time if you leave it as a theoretical exercise.

Take 5 minutes to boost the quality of every interaction you have.

So write at least 3 values you live your life by or want more of in your life. Got ‘em?

Cool. Now pick your top one. You’ll know it is important because it is the one you most want to find in other people. So if you NEED other people in your life to be adventurous, keep that one up top. Personally, I love people who are open-minded and live in contrarian ways, so I often talk about quitting my job to pursue my dreams. With girls that I might want to date, it is very important to me that they are affectionate, so I lead with that value.

Now, answer the following questions in a way that baits your listener to ask for more information AND reveals your primary value.

1. They’ll say: “Where are you from?” (convert this to “Why did you wind up where you are today?”)
2. They’ll say “What do you do?” (convert this to “Why do you spend your time doing what you do?”)

Now, get ‘er done!

Did you write down your answers?

If not, take the time. It will change the dynamic of every conversation and short circuit the awkward silences. You’ll wind up with more people that are interested in you because more people will know what you stand for.

Now you just have to work those more honest, revealing answers into conversation. You’ll have more engaged conversational partners. They’ll know what is important to you. And they’ll likely try to prove they have those traits as well. All from changing how you answer 2 common questions. Pretty neat. TC Mark

To create your dream life, check out Charlie’s upcoming book, Next Level Charisma.

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