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!


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