One Simple Habit To Crush Any Conversation: From CEOs To The Girl In The Bar

Today, we’re going to completely strike from the face of the earth an uncomfortable 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 cares 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, engaging 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 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.


P.S.  If you liked this topic, I’m writing a book that is going even deeper into the actionable steps you can take to get next level charisma. Click here if you want more info.


  • D Giovanni Harmon 2 months ago Reply

    I do something very similar. Whenever someone asks my age or what I do, I always have the same response. I won’t answer the question directly. I say, ” When we first meet someone we tend to ask a few questions, How old are you? What do you do? Where are you from? We ask because we think that these questions will give us an idea as to who this person is. But we all have preconceived ideas, we have stereotypes that we put on people. I don’t usually fit into the pictures that people have in their heads. I prefer a person to get to know me, my personality and then make their decisions about who I am.” This almost always leads into talking about our values and how we see ourselves and others. Of course I do have ways to answer the questions that tend to come up, ie. job, hobbies, favorite band, song, book, etc. My answers are not the boring answers that most people give. Leil Lowndes has great books on communication if anyone is intersested.

    • M 1 month ago Reply

      Sounds like you’re dodging the question, like you’re ashamed of how old you are or are unemployed.

      Not everything is for magical value sharing. Sometimes you just gotta get information out.

  • Josh 2 months ago Reply

    Nice post Charlie. For a while I was annoyed by the question “Where are you from?” and thought that the solution was to say “I’m from Rhodesia.” or “I’m from Peru.” This either made me feel bad for deceiving people, or it made people not trust me because I lied to them within 15 seconds of knowing them.

    Recently I started saying something like this, “Well I was born in California, but I consider Brazil my home now. Brazil just has something special about it that I haven’t been able to find in any of the other places I’ve lived.”

    • Charlie 2 months ago Reply

      Perks of being an ex-pat: you have a great answer to this question by default :-)

  • Quisinoh 2 months ago Reply

    Uh, this was lifted practically word-for-word from the book “How to Talk to Anyone” by Leil Lowndes, including the example of Columbus, Ohio….you could at least give her credit…

    • Charlie 2 months ago Reply

      I recently read the book, but honestly wasn’t thinking of it when I wrote this and the advice I give is very different from hers. I’ve been teaching my clients the habit I describe in the post for a long time and have gotten more questions on it in the last few weeks, which is what inspired the post. You’re probably right about the words “Columbus, Ohio” slipping in there subconsciously

      I will say, if I remember it correctly, she recommends remembering a fact about where you’re from. That might extend conversation, but what actually allows you to connect with people is the values part.

      • Derp 2 months ago Reply

        You acknowledge this is the comments but you still haven’t cited where you paraphrased and haven’t added a bibliography. Stop being a plagiarizing scumbag and fix it.

        • Charlie 2 months ago Reply

          Here is a link to the book How to Talk to Anyone by Leil Lowndes.

          I’m not citing it because I didn’t plagiarize it and I didn’t paraphrase it. Go reread the chapter that discusses “where are you from.” I just did. Her advice to improve your answer is “Learn some engaging facts about your hometown that conversational partners can comment on.” She recommends starting at the chamber of commerce and talking about your home city’s history.

          This is fundamentally different advice than talking about your values and answering “why” instead of “where.”

        • Corey 1 month ago Reply

          Perhaps you are familiar with Albert Einstein Derp. or maybe not. If so, you may remember the quote “To steal from one is plagiarism. To steal from many is research.” Charlie, you, me and everyone else on the planet who has access to internet or books has been inspired at various points in our lives by the ideas/theories/writing of others, and we often combine them to form our own ideas/theories/writings on the world, based on the lens through which we see it, which is in large part determined by the influences we’ve had along the way. Charlie has read extensively on the topic of self-help and self-improvement, and thus his own ideas are a conglomeration of the best of what he has come across and his own ideas for how people can make themselves better. If you asked me, that wold make him the opposite of a scumbag, or certainly of someone who berates another individual on a public website for an imagined offense without having ever met them. So maybe you should ponder that, “derp.” Or should I say Twerp?

  • john 2 months ago Reply

    What if the journey isn’t all that interesting? For example, I left my home state for college. So my ‘why’ is fairly mundane, except for the actual school I chose (but it seems like a bit of a stretch to answer this question with ‘why I chose this school’.

    • Charlie 2 months ago Reply

      Definitely not a stretch. A stretch is to try and run a conversation off boring facts. So you could say something like, “I’m from X state, but I wanted to come to Y college, because I love the style of life here/the program the offer is what I love doing.”

      It’s totally appropriate to answer why this school (Assuming you do it in 2-3 sentences and don’t ramble). You’re doing the person you’re speaking with a favor. They don’t know what to say, which is why they asked you “Where are you from?” in the first place. You’re helping them move the conversation towards the good stuff.

  • Phil Drolet 2 months ago Reply

    Charlie, that was an excellent post. It’s so simple… yet so overlooked. I did the 2 exercises and I’m pumped to share my values more explicitly when meeting new people. Cheers!

    • Charlie 2 months ago Reply

      Glad you liked it, Phil! And hope to meet you in person soon so I can hear those values for myself :-)

  • tydus 2 months ago Reply

    yeah thanks charlie for all the nice insight, sometimes i think directly telling others about my values are good too as in it gives a clearer information to the others. like example, “i’m adventurous and i like to travel to alot of places” and “i’m usually caring and i usually like to take care of all my friends”

    • Charlie 2 months ago Reply

      Yeah, the one thing I would add is that it also helps to cite examples

  • Will Legend 1 month ago Reply

    Great post. Not only does revealing more about yourself provide the other person a launching pad to ask you questions, but it also shows them that you have interest in learning more about each other. It’s more genuine than a typical, mechanical, 3-word response.

  • Della Nova 1 month ago Reply

    I’m struggling with this exercise because my answers don’t relate to my values. My living in Michigan has nothing to do with my values, it’s only because I was born here.

    • Charlie 1 month ago Reply

      Great point you raise. The way I see it there are two potential situations you’re in:

      1) You decided to stay. In which case get in touch with the reasons you’ve decided to stay, potentially family, friends, etc
      2) You are just floating through life. You’re not making the most important decisions, but are a passive participant in your life. In this case it is going to be difficult to be charismatic. The recommendation I would give is to actually pick where you live and what you do. You have to live by your values before you can share them.

  • Dave 1 month ago Reply

    Great article Charlie! Followed the exercise and look forward to seeing how people respond to my new answers. I’ve always considered those questions a bit of a social experiment and change my answers all the time.

    Your advice to the commenters is excellent as well! Keep up the great work!

  • Sean B 1 month ago Reply

    Nice post, Charlie. This is real, genuine stuff–learning about yourself, how to articulate your values to others and improving conversational skills all in one exercise. Thanks for this!


  • Anita 1 month ago Reply

    This is definitely my favorite post thus far! Not only did it open the door for interesting conversations but it also helped me identify people whom I knew I would and wouldn’t get along with based on how they carried on the conversation. Thanks for the articles and I can’t wait to read more!

  • LudvigSunstrom 30 weeks ago Reply

    Hey Charlie,

    Just saw you over at SJ’s site and came here.

    I like the strategy. Good idea on being short and succinct, and getting them to invest more into the conversation by asking questions. Like you said, I think it’s a good idea to let them ask for more.

    Interesting site you’ve got.

    • Charlie 30 weeks ago Reply

      Thanks Ludvig! Looks like you have something very cool over at SGM yourself :-)

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