Mastering Conversation

I have to say I’ve been dissatisfied with the current self-help information on communication. Much of the material I have read focuses on how to become a more empathetic listener, problem solver or better transfer information. Very little focus is put on what is probably the most common form of communication, the conversation.

Learning empathetic listening skills and effective communication of your ideas is great for when you need to understand and relate, especially in high intensity situations. Unfortunately, most of the time you talk with others it isn’t to find solutions to a mutual problem or to gain a deep understanding but simply to relate or entertain.

People don’t judge you so much for who you are as they judge you for how you communicate yourself. And most of this marketing is done through conversation. If your conversation skills are poor you will appear boring, humorless and unlikable. Conversational masters make friends easily and others genuinely enjoy spending time with them.

Seeing as your social life depends on you being a great conversationalist, what can you do to improve your own skills and become the person everyone wants to be around?

Conversation Isn’t About Content

Here is the first rule of conversation: It isn’t about content. A lot of people falsely assume that conversation is more what you are talking about. This is wrong. Conversation is a lot more about how you communicate than what.

I’ve had fantastic conversations with people that were about something completely trivial and unimportant. My first impressions about people were often based on similar discussions. People don’t have most conversations to get information but simply to interact with other human beings. It is about entertainment and subtly proving you are a person worth being around.

There is an old quote I like, “Who you are screams so loudly I can’t hear what you are saying.” This is a great example of what I am talking about. Conversations aren’t so much about the content about your speech but really what that speech says about you. Are you interesting? Funny? Important? Likable?

I come from a family of conversationalists so I know the difference between sharing a great talk with someone and struggling to keep on a boring interaction. When I talk with someone who shares this skill we can talk about anything and make it interesting and great. With other people they can have great material but still come off wooden and dull.

People Don’t Care About You

Unless of course, you are interesting. One of the worst mistakes someone can make when having a conversation is the belief that people have any real interest in the events of your life unless they make great conversation. Ever have dinner with your spouse or friend and ask, “How was your day?” That sentence alone indicates you are struggling for material.

People don’t want to find out about you from what you explicitly say. Telling everyone you are a banker who likes to golf and take long walks on the beach doesn’t say much about you. But if you have a conversation about how you eat crackers and you make them laugh you will speak volumes about your personality.

I think this is often a big problem when people first meet in a more formal context like at a wedding, party or for a date. They ask questions like, “What do you do for a living?” or, “Where did you grow up?” or my personal favorite, “What do you do for fun?” Although these questions can trigger interesting conversations the actual information gleaned from them doesn’t make a noticeable impression.

The Three Skills of Conversation

In my opinion there are three major skills that come with being a master conversationalist. Skill in these three areas makes the difference between someone who can leave a great impression, magnetize people and form friends. By now I hope you realize that these skills rarely have much to do with what you say as opposed to your personality and who you are.

Be Funny and Interesting

The first part about being great at conversations is to simply be both funny and interesting. If you are humorless and dry people will quickly forget you and likely form a neutral to negative impression about you. Without interest you appear very mono-dimensional and boring. If you lack one category you can make up by including more of the other, but a lack of both will kill conversations.

Humor is an incredibly complex skill that can’t be learned overnight. It takes a lot of practice until you can figure out the natural timing and flow of a joke. Once this rhythm sets in, it will become part of your personality. Practice makes perfect.

If you aren’t naturally funny the best way to start is to simply start asking yourself, “What is funny about this?” Generally the reason most people aren’t funny is simply that they think of something funny but fail to effectively verbalize. Keep trying and eventually the timing will set in.

If you have trouble thinking of funny things to say, read some jokes and try to work them into your conversations. Using scripted humor isn’t as good as genuine humor but it can be good training material until you get your funny bone.

Interest comes from having an interesting life. You can be interesting by telling stories (which I’ll mention later) or by simply being quick to bring up an interesting fact. Interest is similar to humor whenever people discover something they didn’t expect.

A favorite piece I do when conversation gets dull is to ask this question: If I fold a piece of regular paper in half fifty times, how thick would it be? By asking this question and getting answers (most are usually within the range of six inches to a few feet) you can astound people with the actual answer. A piece of paper folded on itself fifty times will be approximately the distance between the earth and the sun in thickness. (.1(mm) * 2^50)

Why is being funny and interesting important? Shouldn’t people like you for who you really are? The answer is because people rely far more on conversation than a resume to determine who you are deep down. I recently heard a statement which I thought to be incredibly true: “You tell one joke and it was a funny joke, you tell ten and you are a funny person.” People will judge you based on conversation skills so get over it and start practicing.

Tell Stories

The second skill in being a great conversationalist is to know how to tell a great story. Being funny an interesting is great but when you can only pull off one liners you won’t create the intensity of interest you want. People relate all things through metaphor and story and becoming a great storyteller is critical to creating a connection.

So how do you tell a great story? Being a great storyteller is incredibly complicated so if you end up getting “uh-huh’s” from people after boring them into the ground with your mediocre tale, it is going to take a lot of work. But the basics of good stories is fairly simple and by practicing them you can hone the finer details of your conversational craft.

Rule One: Know Where You are Going

A story is told simply to provide context for one or a sequence of interesting points. Don’t tell a story just to tell it. You need to have an interesting point to make it worthwhile. If your story has a couple of interesting points, better, but it needs to have at least one. When someone asks you how your day was, you’d better respond with something more than the summary of your itinerary.

Rule Two: End With a Bang

Your most interesting point should be the last thing you say in your story. Saying an interesting point followed by a bunch of boring ones reduces the impact of your story. So if the main point of your story was that you met Tom Hanks in the produce aisle of your grocery store, don’t keep talking about what type of lettuce you eventually settled upon.

Rule Three: Keep it Short or Keep it Interesting

If your story only has one really interesting point, keep it short. People will stop paying attention if you spend fifteen minutes to provide only one interesting point. If your story needs to be longer, pace it out with humor or interesting points to keep the attention sustained up until your final point.

Rule Four: Keep it Personal

People prefer stories about people they know. Try to only use stories that somehow involve you. Just because a friend has an excellent story doesn’t mean it is worth retelling to people who never met her. Conversational stories are interesting because they form a window into your life from an intriguing context. Even fantastic stories that are unrelated to you or the person you’re talking to will appear noticeably dryer. This is a common mistake by people who don’t realize that I (or any other human being) don’t care about people I’ve never met before.

Rule Five: Don’t Grasp for Stories

In an effort to get a conversation going a lot of people start grasping for stories to tell. Questions like, “How was your weekend?” are a perfect example of story grasping. You should have enough material that questions like that are a last resort. These statements should be used out of kindness but you should always have a great story as back up if the person can’t think of one.

Rule Six: Practice Your Stories

A story can be told more than once. I have many stories, anecdotes and humorous topics from which I know people react favorably to. Whenever the conversation needs it I simply use one that I haven’t used with this group of people before. The more you tell a story the better you get the natural timing and emphasis. Just don’t reuse the same story with the same people.

Watch the Tempo

The third skill to understand when mastering conversations is to understand the natural tempo and rhythm. Each communication you have will have a natural flow of ideas at a certain relative speed. This also relates to how fast the switch-offs between speakers are and the amount of pauses.

If people are having a very fast conversation, don’t break out a slow building fifteen minute story with just a few points of interest or they will be dying to interrupt you the entire time. Don’t bother speaking if you can’t capture attention, and people aren’t paying attention when they have their own story to tell.

If you don’t have an incredibly valuable story for a fast conversation it is probably best to stick with interesting or funny quips instead. Slower paced conversations, however, can make use of a long story which can then provide fuel to speed up the tempo.

Conversational rhythm is of critical importance when you are trying to enter a conversation, particularly with strangers. Starting out with a long story isn’t nearly as effective as offering a quip. Once you integrate yourself into a conversation you can start offering longer stories to fill the space.

Often people don’t go and meet people because they aren’t sure what to say. The key is simply to throw a small comment. Small quips are like asking for an invitation and if they get a response you can easily work your way into even the most high energy conversations. When your humor and interest skills become worked into the deepest levels of your personality you can enter just about any conversation smoothly.

Communication is largely about conversation and when you begin to understand this you will improve your relationships. Ultimately it breaks down to improving your ability to use humor, interest and tell captivating stories. Watching the tempo is critical so you can smoothly insert your conversational skills and join any conversation you want. Have fun conversing!

  • Stanley Kubasek

    I also think mastering conversation is one of life’s greatest and most useful skills. Great article.

  • Scott Young

    Thanks Stanley.

  • Gary

    Well said Scott! Human beings judge based on what they perceive than what really is…

    Thanks! I’ve Learnt a great deal from you!


  • Eric

    Hi I read your entries on conversation. I have been told that the pace of conversing with people is slow. I take sales over the telephone for a living and direly need to know of ways on how I can speed up my pace.
    I really would appreciate your help if you could give it. Thanks in advance.


  • Scott Young


    Generally talking too fast is more of a problem than talking too slowly, although I could see how telephone sales differ. I can’t offer you any real suggestions other than practice. I’ve always had to try and slow my conversational pace rather than accelerate it, so I can’t offer more advice.

  • Mike Miho

    I am very impressed with your candid remarks on such a pervasive yet under-analyzed topic. Do you make any suggestions for further reading? I have an affinity for studying communication, especially interpersonal, and haven’t found a text that specifically covers effective tactics and strategy in the “art of conversation”.

  • Scott Young

    I haven’t seen that much on conversational skills, but there are many available books on communication and dealing with people. None to recommend for you, but do an amazon search and read what sounds interesting.

  • Fred

    What if you don’t have any interesting stories to tell ?

  • Scott Young


    Is that really true? Everyone has interesting stories, you just need to have the skill at telling them and the confidence to believe other people will want to hear them — and they do.

  • Eddie

    Hey Scott! Great article and great advice! I have one question though. What should our stories with interesting points be about and how should we go about in telling them?

  • Scott Young


    Preferably try to use stories from your own life, but people will listen to just about any story if it is entertaining.

  • Elaine

    Wow, are you really 18? I thought you were 20 or 30 because you know so much about ‘mastering’ a conversation. It’s a good article. I’m just 17 and I don’t completely think I can speak as interestingly as other people I know. Scott, what’s your advice for people who have a low voice? I sort of find it hard to join a conversation because I’m a bit soft-spoken. Do people have to be vivacious?

  • Ed

    i have the same questions as Elaine. Do u have any advice for them?

  • Scott Young

    Elaine and Ed,

    Work on projecting your voice. This is a bit complicated to explain over a blog comment, but if you are having trouble being heard, you want to project. Projecting your voice means letting your voice resonate on the entire column of air in your lungs instead of just the throat.

    Ask yourself how you would need to talk differently if you were addressing a crowd without a microphone and not yell. Chances are you would project your voice.

    Hope that helps, it is a lot easier to explain in person.

  • Emmanuel

    Hi scott
    Iam from a foreign country and I noticed people react a little different to people with accents. Do you think there’s a way I could project myself in a way that actually creates equal attention.

  • Scott Young


    What you see as a weakness could very well be your strength. As long as you can be properly understood, an accent can often give you some uniqueness that demands more attention, not less.

  • Mike


    I really appreciated this article because, as you pointed out, there really isn’t much in the self-help world on the simple topic of what to say in a conversation and how to say it. However, I’m with Fred on this one–some of us just can’t seem to find any interesting stories in our lives. Things happen, sure, but they don’t happen in an interesting, unusual, or noteworthy way… there’s no ‘bang’ or punchline at the end… it’s just one thing after another. I guess either we really are boring people or we’re somehow not picking up on the story potential in our lives. Do you have any advice for this situation?

  • Scott Young


    I think the problem could be two things:

    1) You aren’t practiced at storytelling
    2) You haven’t sorted your experiences to fit into stories.

    Being a good storyteller helps. Go to Toastmasters and take up some speaking classes and you can improve your ability to weave together a narrative.

    But beyond that you need to start recognizing life experiences as stories. I don’t have grand stories in my life, but there are some interesting anecdotes. I’ve told stories about how I’ve been stuck in an elevator or met someone new.

    Lower your standards, don’t aim for perfection and practice.


  • conrad

    an article that keeps on giving (written in 06… now reading in 07!)
    thanks… filled in some gaps of my knowedge base! very much needed
    are you going to write anything else that will expand on this topic? Im sure many people will love it! *i know i would*

    Thanks again!

  • Scott Young


    Search the site for Stories, I’ve since written two on the subject of telling stories (an important part of conversation)

    Otherwise, I also wrote an article at the HowTo on small talk:

  • max night

    I am the silent type, so this doesnt help me except to convey information that has an actual importance…

  • Wendy

    My interest lies in the clues in a conversation (conversation markers perhaps?) that tell the speaker it is time to become the listener. I have a relative who seems to lecture as he doesn’t or perhaps won’t recognize when the listener is ready to share or comment. Is there anything available that helps a ranter or lecturer to heed when he is losing or has lost his audience. Being forceful in interrupting only incurs his anger. Any suggestions?

  • graham

    “Everyone who is honest is interesting. — Stefan Sagmeister”

    I appreciate your analysis, Scott, but I generally disagree with your insistence that “conversation” is about delivery, rather than informational or empathic exchange.

    Sounds to me more like you are describing how to entertain an audience in a captivating one-way performance, rather than actually facilitate a two (or more) way conversational exchange of ideas. I didn’t read much mention of why other people are necessary.

    If you’ve ever spent a sober night among drinking friends, I’m sure you can appreciate the difference. Little is as intolerable as someone who attempts – and systematically fails – at your rules above, with the insistent conviction that everything they say is absolutely fascinating to everyone.

    Maybe you’re right, and most people really do just usually want to emote and feel good together… There’s definitely skill in facilitating that, and being “likable” in general… But let’s not confuse it for “conversing”.

    I can’t help but feel you are courting delusion a bit here with the rationalization that people judge you by how you speak, not by what you say… This may be most true during a first encounter, but beyond that, if you don’t have something to offer besides a slick smile and some stock stories, those new friends won’t stick around very long.

    How many times have you met someone who appeared to be very interesting and charming in the first few moments of your encounter, only to realize seconds or minutes later than they’ve told this same story 100 times? It’s vaguely insulting to realize they are treating you exactly like every other person they’ve tried the line on, and a probable sign that this person is not willing or doesn’t actually know how to empathetically connect. I appreciate the effort, but you’ll get much further by simply having the courage and self-confidence to be yourself, listen carefully, and respond genuinely with something of what you really feel. Not *everything* – “tact” is certainly another skill – but I am convinced measured honesty will get you miles ahead of the guy who appears to have his audience in stitches. People leave the party saying, “Ya, that guy was funny…”, but it’s YOU they phone to get to know more, because you had something honest to say about them. Test it and see if I’m right on that.

    If you really want to learn how to talk to people, you must put yourself in situations where you have to. It’s a delicate dance of give and take that can’t be captured in words. Like learning an instrument, it’s just about practice, practice, practice.

    I appreciate your systematic breakdown, but it reminds me a little of the many “seduction” schools of thought that have been popularized recently – Interesting as a psychological study, but potentially dangerous to your integrity in practice… Beware the entrapment of your own ego when playing that game…

    In 7 Habits of Highly Effective People, Stephen Covey highlights the difference between “Personality” versus “Character” ethics. He criticized “personality ethic” as falling victim to the gimmicky sort of sales techniques that often dominate in seedy business success seminars. They are effective in the short term because anyone can learn them, and they do work – in the short term.

    I recommend playing a long-term game with everyone you meet. It’s really only your personal integrity and character that can carry that relationship past that first superficial step. Leaving a great impression, magnetizing people, and form friends works at first… But trying to get ahead in the first five minutes for short term approval could cost you a lifelong relationship.

    Real communication is about empathy, and the exchange of ideas. That requires a lot of patience, humility, insight, and a genuine interest in others. Framing your context to make it interesting is always important, but you shouldn’t need to seduce others as your audience just to get yourself heard. You basically get what you give – if you’re really having a conversation, there is no need – only that joy of sharing something that makes us uniquely human.

  • Scott Young


    Interesting analysis, but I have two points:

    1) Conversation, at least not always, is not about the exchange of information.

    Communicating information is just a partial reason. More importantly, I’d say people have conversations to connect with other people. This is what I meant by “presentation over ideas”. People don’t really care about what you say, they care about you. They want to connect with a person, not with ideas.

    Storytelling, is one way to improve the art of saying what isn’t said. I don’t suggest that you rely on scripts of stories. However, practicing your ability to tell stories helps you find what is most important to people, especially in a casual setting.

    2) Socializing is like dancing.

    Conversation is like dancing, there are people better at it than others. Ultimately, the people who dance with their own style and freely are going to do better than the people worried about how they dance. But practicing certain established dances will improve your natural dancing ability.

    If you’re completely left-footed when it comes to conversation, sometimes it helps to go through the mechanics of what goes into a conversation. But, like a dance, only you can give it life and personality.


  • Leesa

    I agree with graham althou I do like ur twist on it scott. Listen we are all having a coversation via blogging. So u all rock and keep up the good work people.

  • Anish

    Scott, i liked your blog. Thanks. Now,i am well read n humorous but who failed in getting content to build conversations as you adviced.what worked for me was changing myself into a person with a confident outlook. Earlier, my time was wasted fighting insecurities about how the other person will accept what i say. Now, i dont care. Any content is a playground for my expressiveness. Thanks.

  • Matthew

    This article/blog is dead on. The things described here are what I’ve just naturally discovered on my own.

  • Steve

    I’m getting 3/4s of the way to the sun.

  • gabe

    confidence or no self confidence i don’t see why that’s so important. Yes, to get people to notice you, but if that person your talking is somebody who actually is halfway smart and not a complete asshole they will realize that maybe your a little anitsocial am i right? There are ways to use this, but I don’t see where this will get you. Don’t you think it would feel just an overall bettter feeling if you make one friend just by being normal instead of changing the way you look at things?

    This is sorta of like living by society and living by how society dictates you shouldn’t it be the other way around, be an individualists and do whatever you want, and say whatever you feel like saying. I don’t think your article was wrong or bad or giving people bad advice because i think there are people who can use this and it will help them in their overall lifestyle

    and as for the communicating to someone better to people i think this can be a way to get to know people and then show them who you really are so i agree with you

    c i just want to say one thing I have a real example of a a couple of friends of mine. SO there is this person a man who is witty smart funny good timing basically the epitamy of what you described, he has self confidence, and there is this other guy who is funny but in his own way he a little shy, honest with people, doesn’t communicate well, you get the picture… They both have there good qualities and bad and they both like the same girl…now the girl is extremely truthful,, who do you think she would like?

  • Vincent Ng

    While I think a lot of self help books don’t focus on small talk, it’s because our society seems to devalue it as if it’s not important. But the truth is you’re right, small talk is important and the reason I believe is because it allows us to build trust slowly.

    And small talk with the right person can become very interesting, while at the same time having boring conversations can be a drain, and it’s no fun in all honesty. However, people do need to work on all areas of conversation, but especially storytelling since it’s pretty much the fundamental communication method of our society. We need to be a society of great storytellers again.

  • rowan

    Scott, your the man..the best conversations I’v ever had are not information based at all and believe me I’v got some information 🙂 Sometime I make people cry laughing with the simplest things ever!

  • elliot

    Hello Scott,

    I’ve read your article and it’s very interesting, but I have a few question.

    I am a pretty introverted person so I have a hard time expressing my genuine self around people and I often blank and have absolutely nothing to say, even around my closest friends. What is an example of a conversation starter that doesn’t seem so desperate like “how was your weekend”, and that could lead to a good conversation filled with personal experiences and interesting stories?

    How can I improve my social skills (especially small talk) in order to meet new people?

    Thank you! 🙂

  • john

    have a same problems like elliot… any good suggestion related to some book?

  • Derrek

    Do you have any posts or ideas on improving critical thinking?