Subtly Charismatic: Humor And Misdirection

To put it simply, misdirection is when you say one thing and then proceed with an immediate opposite. For example, “It’s a secret, but let me tell you immediately,” or, “That show is great, except for everyone in it.” It’s not rolling-in-the-aisles funny, but it definitely captures attention, and gives conversation a kind of light playfulness that most people will be happy to call wit.

It seems confusing, but what you are doing is breaking a sentence into two parts.

You’re stating something in the first part, then contradicting it immediately in the second. People won’t immediately be sure of what you mean, and part of the humor comes from this introduced confusion. You have both positive and negative, or vice versa, in the same sentence.

The second part of the sentence is the element that people will react to, while the first part is typically the setup. The second is your true sentiment on the topic.

This formula is the secret to the humor in such lines as George Jessel’s, “The human brain is a wonderful organ. It starts to work as soon as you are born and doesn’t stop until you get up to deliver a speech.” Douglas Adams also used it when he said, “I love deadlines. I like the whooshing sound they make as they fly by.” Here’s another example: “I love dogs, but I hate seeing, hearing, and touching them,” or, “This juice is awesome. Did it come from the garbage disposal?”

There’s just such an appealing zing to statements like this. You can probably agree that they work, but why do they work?

Most of us try to be polite to people. We use euphemisms frequently, and we don’t say what we really feel. The first part of a misdirecting statement is what people expect—politeness. It’s you following the same old tired expected script. But then surprise! You contradict yourself and give them a dose of reality, which sets up a humorous contrast since you have deviated from what most people expect and would say themselves. As you might have observed, ironic similes also make use of misdirection to derive comedic effect. The whole effect is to send a powerful message that you don’t take yourself, or the topic at hand, all that seriously. Done right, misdirection can be amazingly charming and funny—it’s a way to break the rules that works so well because you appear to be using the rules at first.

Last but not least, misdirection is simply a funny way to express your feelings on something. If you really feel X about a topic, then use misdirection! “Opposite of X, but actually X,” will almost always be received far better than “Gosh, I hate X.”

Sarcasm is a way for people to say things without saying them, and is the most common way we use misdirection.

Think about how Chandler Bing from the television show Friends talks. If he says something is wonderful, he says it’s wonnnnderful in a tone that immediately lets you know that he thinks the opposite.

Sarcasm functions like a social cue—both are ways to express something without having to explicitly say it. In that way, it’s a great device for handling uncomfortable topics or pointing out the elephant in the room without directly offending people (or pointing). It allows us to walk a tightrope, as long as we don’t fall into the pit of passive-aggressiveness.

At some level, most of us can appreciate sarcasm because we know what is being accomplished. It can even be the basis for your own personal brand of humor. Standup comics often use it to great effect.

Chances are, you are already using sarcasm regularly without being fully aware of it. Sarcasm is mostly used as friendly banter with a friend or acquaintance with whom you are comfortable saying something negative. For example, consider that you’ve committed a minor gaffe at work, for example forgetting to return a borrowed file before it’s due. If a close colleague teases you about it, you may reply with a sarcastic, “Oh yes, this is scandalous! This would for sure be in the headlines tomorrow!” But if it’s your strict boss who sternly calls you out on it, you would not be likely to make a sarcastic announcement in response.

Sarcasm is usually used to poke fun at someone or something and is heavily context and audience dependent. If you are around somebody who enjoys wit and has a sarcastic sense of humor, it will be quite welcome. Sarcasm is also dynamite when used to make a playful jab at yourself—the irony is how it can have the effect of making you seem supremely confident, self-aware and intelligent. Someone might say, “Oh no, I think I’ve lost that twenty dollars I was holding on to . . .” and you quickly jump in with, “Oh no! What an idiot. I would never do something so thoughtless. When I lose money, I make sure I lose the whole wallet and everything with it.”

But around others who don’t share the same sense of humor, are less secure, or don’t like you, it’s too easy for them to interpret your attempts at sarcastic humor as a full-fledged insult. That’s not what you’re aiming for here. They might just think that you are an insulting jackass, or they’re more inclined to listen to the first part of the misdirection than the second.

Using misdirection in the wrong context will cause people to think you lack empathy or, worse, get your jollies from hurting other people’s feelings. There will be others who simply won’t get the sarcasm, no matter how obvious you make it. They won’t be insulted, just very confused. You’ll want to avoid both outcomes. The only way to do that is to make sure you “know your audience” and start small, judge the reaction you’ve had, and go from there. If other people happily use sarcasm themselves, it’s probably a sign that they’ll appreciate yours.

Choose the correct context and sarcasm can make you more likeable and charming. It also makes you look intelligent and witty. In some social circles, appropriate levels of sarcasm are not only welcomed, but required—think of it as a refreshing antidote to humble bragging or complaining.

Now that you have a clearer idea about the proper context of sarcasm, the next step is to articulate the elements to make sure you don’t just insult people left and right in your attempts at building rapport. If your annoying coworker understood sarcasm better, they might be as funny as they think they are.

For the most part, sarcasm is saying the opposite of (1) an objective fact, (2) a subjective emotion, or (3) thought.

It makes a contradictory statement about a situation to either emphasize or downplay its effect.

Objective fact: Bob plays Tetris at work constantly.

Sarcastic statement: Bob, you are the busiest man I know.

Subjective emotion or thought: It is hilarious that Bob plays Tetris at work constantly.

Sarcastic statement: Bob deserves a medal for worker of the year.

Here’s another one.

Objective fact: There is a surprising amount of traffic lately.

Sarcastic statement: What are we going to do when we get to our destination super early?

Subjective emotion or thought: I hate traffic so much.

Sarcastic statement: This traffic is the best part of my day.

That’s the first and most common use of sarcasm. Now let’s lay out a framework for different types of sarcasm and exactly when and how you can use it. You’ll be surprised how formulaic and methodical you can get with this, and subsequently with humor.

When someone says or does something very obvious, you respond by saying something equally obvious.

Bob: "That road is very long.”

You: "You are very observant."

Bob: "It's so hot today!”

You: "I see you're a meteorologist in training.”

Poor Bob: "This menu is huge!”

You: “Glad to see you’ve learned to read!”

The next application of sarcasm is when something good or bad happens. You say something about how that good or bad event reflects on the other person.

If it's good, you say that it reflects badly on them; if it's bad, you say it reflects well on them.

Bob: "I dropped my coffee mug.”

You: “You've always been so graceful."

Bob: "I got an F on my math test."

You: "Now I know who to call when my calculator breaks."

You observe Poor Bob dropping a cup of coffee and state "You would make a great baseball catcher. Great hands!"

Proper delivery is crucial for sarcasm. This can mean the difference between people laughing at your sarcastic joke, or thinking that you're serious in your sentiment and branding you an overall jerk. Also keep in mind that sarcasm is perhaps the most overused technique to create humor. Use it sparingly, but effectively.

You have to make it clear that you're being sarcastic and give others a sign indicating so. Otherwise, people will feel uncomfortable at the uncertainty. Are you just being mean, or are you trying to be funny?

The most common way to do this is with a combination of a deadpan vocal tone and a wry smile or smirk. With deadpan delivery, you don't laugh while you're saying it; you appear completely serious. Then, you break into a smile to alleviate the tension and clue others in to your true intention. If paired with a genuinely nonsensical or over-the-top statement, people will put two and two together and see what you’ve done.

Now that you know when to deliver sarcastic remarks, it’s also important to learn about how to receive them and be a good audience. Let’s pretend that you are Poor Bob from earlier and insert a reply for him.

Bob: "That road is very long.”

You: "You are very observant."

Bob: “You know it. I’m like an eagle.”

Bob: "It's so hot today!”

You: "I see you're a meteorologist in training.”

Bob: “I can feel it in my bones. It’s my destiny.”

Poor Bob: "This menu is huge!”

You: “Glad to see you’ve learned to read!”

Redeemed Bob: “I can also count to ten.”

You need to amplify their statement and what they are implying. Does this look familiar? It’s a self-deprecating remark + a witty comeback! If you can volley back a sarcastic comment without even blinking, the humor is basically guaranteed. You’ll appear sharp and quick, as well as confident enough to not be flustered by an off-color remark. In fact, you signal that you’re game for some witty banter, and are happy to have a bit of fun in the conversation.

When you respond to sarcasm this way, it creates a greater bond. And just as important, you don’t come off as a bad sport or someone who can’t take a joke. Everybody is comfortable, and you create a funny situation and potential for greater banter. This is how so many long-standing in-jokes get their start in life. If you can remember one of these witty remarks and call back to it later in the conversation, congratulations, you now have a shared conversational history with the other person—and that can be a very powerful thing.

However, there is a downside when dealing with sarcasm. A lot of people who rely on sarcastic humor, pretty much on an automatic basis, are actually masking passive-aggressive personalities. They're constantly using sarcasm as a defense mechanism to hide their true feelings. They use sarcasm to pass off their otherwise negative emotions. They might be doing this to you, so it’s important to know how to sidestep their subconsciously vicious attacks.

In such cases, responding with sarcasm will only encourage them. It indicates that misusing sarcasm in that way is acceptable. If you find someone being overly sarcastic with you in ways that are passive-aggressive, approach them and politely convey that their sarcasm feels hostile, even if they didn’t intend it to be so. With sarcasm, it’s all about intention. Are you laughing at or with someone? Who is the butt of the joke, if anyone?

Next, we have irony. Irony is a type of humor that is very close to sarcasm, and often confused with it.

Here’s the official definition from Dictionary.com, just because it’s something that people can struggle with nailing down: “the expression of one’s meaning by using language that normally signifies the opposite, typically for humorous or emphatic effect.”

This is different from sarcasm in a few ways. First, irony is generally about situations and incidents, not about people. Something happens which is the opposite of what you expected. When you’re presented with an irony, like a fire station burning down, it will quite obviously be ironic, and not sarcastic. However, sarcasm is usually more derogatory in nature. You’re saying things you don’t mean. The definition of sarcasm is “the use of irony to mock or convey contempt.” Thus, you can see how saying, “You are very observant,” when someone says, “This road is very long,” is sarcasm, not irony, because of the element of mockery inherent in the former remark. (Naturally, you’ll be using sarcasm not to insult or convey contempt, but to create humor, which will hopefully build rapport and connection.)

Ironic humor is when something that is the exact opposite of what you might expect occurs. Another way to define irony is when you say something but mean the exact opposite of what you expect.

In other words, the words that come from your mouth are the opposite of the emotion you are feeling. If you’re starving, an ironic statement might be something like, “I’m so full I need to unbuckle my belt. It’s like Thanksgiving in July.”

Ironic humor draws its power from contrasts. There is a contrast between literal truth and perceived truth. In many cases, ironic humor stems from frustration or disappointment with our ideals. The way we imagine the world should be produces comedy when it clashes with how the world actually is.

Ironic humor is usually used to make a funny point about something or to point something out. For example, when you see a big a sign that says, “No signs allowed,” that’s ironic humor. The sign bans signs but is itself a sign. The expectation that the sign ensures there will be no signs in the vicinity failed.

Another example is when you see a car with a logo on the door saying, “Municipal Traffic Reduction Committee,” and the car, along with everybody else, is stuck in two hours of bumper-to-bumper traffic. There is a profound ironic comedy there, as you would expect the traffic management planning committee would do a better job so they wouldn’t be stuck in traffic themselves. It’s like someone ordering a diet soda after they’ve just ordered three double cheeseburgers and fries or someone else crashing into a “thank you for not speeding” sign.

Irony is all about finding contrast and drawing some interesting and creative judgment out of it. As the examples indicate, ironic humor is more a matter of observation than one of spontaneity or creativity. You’re more likely to find and point out things that are ironic than come up with something that is.

Ironic humor, on the other hand, is when you intentionally imply the opposite meaning of what you say. When we think about how to use irony conversationally, what we’re really asking is what ways can we convey two messages at one time? So, your boss tells everyone to attend a meeting to discuss some issues with people being tardy to work and you slyly quip, “Sorry, Bev, is it all right if I’m ten minutes late?” with a big cheesy smile. (This, of course, depends on whether Bev is likely to find this funny or not . . .)

The Power of Improv

Let’s turn our attention to a group of people who have made good banter and wit their business: improvisers and stand-up comedians.

The Rule of Improv Comedy: Great improv is a result of the creativity in spontaneous situations, and set agendas and outlines put a very low ceiling on that.

Improv comedy performances are, guess what, improvised!

The performers may occasionally work with a set theme that has been decided on beforehand, but there will always be large portions of an improv performance that involve taking direction from the crowd or audience. They can’t predict what a crowd will give them to work with, so it’s out of necessity that they can’t have a strict agenda or outline.

That’s part of the fun in attending an improv performance: you feel that you are a part of the outcome and have contributed to the show.

Obviously, these are situations where the performers have to think on their feet as quickly as possible, so they don’t get tongue-tied and silent while everyone in the room is waiting. But overall, we have the perfect arena where we can watch spontaneity, curiosity, and good humor play out.

As an improv performer, you have to process what was said to you, try to project where you want the scene to go, and then predict what others might also say in response. And you have to do it all knowing that your plans might need to completely change when the other players switch things up. You have to read people’s body language, try to determine if there is any ulterior message, and actively provide detail that other people can work with.

Improv comedy is collaborative in nature, but it’s impossible to know what your teammates are thinking. In a split second, you need to perform a full analysis of the entire scene and spit out words that will enhance the most important aspects of it. Oh, and you’re in front of a crowd of people, and there is a team of people on stage waiting on your response.

That might be the very definition of thinking on your feet (or hell on earth, if you’re prone to anxiety!).

How does all of this make you a better conversationalist?

Recall that improv performances and conversations have the exact same goal—a flowing, entertaining interaction. If we look at some of the ways that improv performers are able to think fast and approach this unpredictability, we’ll be able to improve our conversation skills immensely. Without trying too hard!

Don’t Hold on Too Tightly

The first step, without a doubt, is to let go of any preconceived notion of how and where you want your conversation to go. Be “outcome independent.” Professional improv players are able to create a fluid, dynamic, and witty interplay with their audience members because they are flexible and open to any possibility and direction. They are not stubborn or rigid—they understand that conversations emerge from the collaboration of the group and cannot be predicted or controlled too closely.

Yes, it can definitely be scary to go into a conversation with a completely blank slate, so to speak, especially if you are the type to plan and scheme. But planning and scheming has probably not gotten you too far in social conversations, so it’s time to open up and let go of the talking points or agendas you want to take into your conversations with you.

Don’t worry. I won’t let you enter conversations unprepared—you just won’t be using set agendas. By the way, when I mention set agendas, I mean goals, talking points, or objectives that people want to achieve or gain from a conversation. Your conversational resume? Sure. Your HPM and SBR tools? Absolutely. But these are temporary training wheels, and they’re there to help natural conversation, not replace it.

When you talk to other people, the focus of the conversation should be about the conversation. Each conversation is its own animal, with its own inherent flow and natural rhythm. It should not be about you or what you are trying to get out of the other person or people. It shouldn’t be forced to resemble a great conversation you’ve had before or some idea of how you think perfect conversations go. Why restrict yourself that way?

The moment other people are able to perceive your agenda, guess what happens? They will shut you out. You become somebody worthy of suspicion and skepticism. If you are trying to sell something, it makes it all that much harder once people feel that you have an ulterior motive. It’s difficult to overcome the feeling that someone wants something from you. The same goes if you’re trying to impress someone, to convince them of something, to get them to do this or that, to force them to pay attention to you. People want to feel like conversations are natural, fun, and something they do because they want to. Nobody wants to feel manipulated, right?

If you are approaching a conversation with an agenda, even an unconscious one, first it becomes exceedingly clear that you are only waiting for your turn to speak, and not actually listening to people. You aren’t present and you aren’t listening.

People might say something to you, and you might not even acknowledge their statement and just continue along with yours. You are telling them that you don’t care about where the conversation is naturally heading—your agenda is more important. Others will notice your patterns sooner than you think. What are they getting out of a conversation like that?

Second, agendas leave people unready to adapt. Unless you are going to drop a speech on an audience, things will never go exactly as you plan.

When you create an agenda, you memorize it and become reliant on it. The more often that happens, the more uncomfortable we are with the unpredictability of thinking on our feet. You are essentially acting form fear—or reacting. What happens when you deviate and can’t find a good place to step back into your agenda? You’re left utterly unprepared for the rest of the interaction because of your reliance on what you’ve planned. You’re no longer alive and authentic. You’re like an actor on a stage who’s forgotten their lines.

This is why it is extremely important to constantly listen to other people and acknowledge them. You might even go with their agenda. That’s okay, because your goal here is to build rapport, and that will do it. Not holding on too tightly to an agenda sems scary until you realize that an agenda only gives you the illusion of control. That once you abandon it and just be in the moment, the real interesting stuff happens!

People can sometimes fall back on agendas or fixed plans out of fear or lack of confidence. They want to avoid that embarrassing moment when they’re tongue-tied and awkward, unable to think of what to say next. But actually, it’s those very moments that keep a conversation alive and interesting. And really, what’s so wrong with finding yourself in an unexpected situation? Is it really the end of the world if you are not perfectly in control?

If you can trust yourself a little and surrender to the conversation rather than try to steer it, you give yourself opportunities to learn to become comfortable with that crucial moment, when all eyes are on you and it’s time to say something. At the very least, don’t underestimate the power of self-deprecating humor or a little disarming honesty:

Person A tells a witty joke, and you laugh, but suddenly feel at a loss for words and can’t think of an equally funny thing to say. So, you shrug and say what you’re really thinking: “You know, that’s exactly the kind of brilliant joke that I could come up with, but you’ll have to wait until three a.m. tomorrow morning for me to suddenly think of it…” In other words, you’ve made a witty joke… about not being able to make a witty joke. Congratulations, you’ve thought on your feet!

On the other hand, conversation is not about performance. If you can’t think of anything to say, it’s also a valid move to just pass the ball to someone else. Keep it going, whether all you do is ask a question, reiterate what’s just happened, or use something unexpected to put the limelight back on someone else.

Learn to Make Quick Connections

Let people feel that the conversation is a two-way street. It actually becomes a two-way street when you stop, listen, and interrupt your own thoughts for theirs.

Up to this point in the chapter, we’ve discussed the negatives of over-preparing for conversations and coming in with outlines of what you want to discuss. Being able to rely solely on your ability to improvise is incredibly important, but just as frightening for some. So, how can we increase our capacity for quick thought?

There’s no way other than through intentional practice. No, no rehearsing a script or churning out lines. But practice.

The first method is to turn on your favorite quick-witted television show with your remote in hand, because you’ll be pausing constantly. For example, 30 Rock, Gilmore Girls, or even Saturday Night Live. These are all good shows to use because there is a lot of witty banter, and direct and indirect jokes. They have the type of dialogue we want to be able to create ourselves. (Actually, for our purposes, you don’t even need to watch a show you find particularly funny. It’s still useful just to watch how those jokes unfold, and how energy moves between the players).

Now, pretend that you are one of the characters on the screen. It doesn’t matter who you are, as long as they have a lot of interaction with other characters. Then, when other characters reply to your character on screen, pause the show and construct your own reply. Play the show again and compare your responses. What do you notice? This is going to train your ability to think through different circumstances and come up with responses.

It’s not going to be easy at first. You’ll probably be blank a lot of the time and not know what to say. However, if you can do this for at least fifteen minutes a day for a week, you’ll eventually become quicker with your replies. It’ll start to feel more comfortable, even second nature. You can also practice this exercise with podcasts and radio interviews. What you’re doing is putting yourself in a position to think quickly. You can then hear what your character or avatar actually said, and you can get immediate feedback on what you could have said given the circumstances. You get to do all this at your own pace, and with the gift of being able to pause the conversation. Every piece of feedback is going to help hone your ability to come up with wit in record time.

The second method is to play free association with words and phrases. Free association is when you hear a word, then you come up with another word that the first word makes you think of. The second word can be anything, and the goal is to do this instantaneously.

For example, cat:dog, dog:puppy, puppy:paws, paws:fur, fur:allergies, allergies:medicine, medicine:nurses, nurses:doctors, doctors:plastic surgeon, plastic surgeon:fake lips, and so on. That was a free association word chain that began simply with the word cat.

How do you train this? Pick a word at random from a dictionary, and list out fifteen words in a free association word chain as quickly as possible. Then, do it again and again—verbally, because that will require the quickest thinking. The trick here is not to try too hard. Don’t think about it, literally just say what pops into your head, without censorship or mulling over it.

After you grow more comfortable with random free association with words, you can take the next step and choose two random words from a dictionary and pretend they are the name of a company. Then, create a short story about what that company does, as quickly as possible.

For example, the two random words you pick are: bottle, Africa. The short story I would construct about a company named “Africa Bottle” is that they import African homemade liquors. Sure, you’ll probably come up with a few doozies as you practice this, but keep your judgment at bay—your only goal is to practice being swift and relaxed making associations.

The final step of this set of free association exercises is to choose five random words from the dictionary and make up a story that involves all of the words, as quickly as possible. Let’s say you choose hiccup, elevator, heat, president, and fern. Then you quickly envisage a skit where the president once got overheated in an elevator in Hawaii and thus developed hiccups, which meant he had to postpone his media conference for ten minutes while one of the aides attempted to scare him again and again behind some fern bushes in the lobby. By showing him his latest approval ratings. In a way, this is not dissimilar from what you did with the R part of SBR, or the M part of HPM.

Again, these exercises train you to think quickly and be creative, so it’s imperative that you do these exercises at “full speed,” so you don’t have the time to step in and start second-guessing yourself. They’ll be tough, and at first, your responses might be terrible. But imagine how big the difference will be between your first day and your tenth day, for example. That’s the power of free association, and practice.

If you also care to analyze the similarities between free association and conversation, you might find that they are virtually the same. In conversation, you’ll reply to someone on a topic, a slightly related topic, or a new topic. That’s exactly the type of thought process that free association takes. In a sense, you are training yourself to come up with conversation topics quickly. In another sense, you are training yourself to trust these first impulses and not self-censor—you may be surprised, in other words, at just how creative you can be when you simply get out of your own way!

The third method is to come up with a simple structure for yourself when you’re backed into a corner. For example, an easy response structure you can use for just about anything is to (1) restate what was said, (2) state an emotion, and (3) ask a question.

Here’s how that looks in practice:

“So, then I punched him in the face and all was well.”

 “You punched him in the face? That must have been satisfying. How did it feel after?”

“Did you like the coffee?”

“Did I like the coffee? Well, I’m in a great mood now, so I guess I did. What kind was it?”

“I hear the zoos here are amazing.”

“The zoos are amazing? That would make me so happy to see one. Do you want to go tomorrow?”

It’s an easy template that allows you to respond to anything, even if your mind is blank, because it literally tells you what to say. So, relax; even if you’re in the pickliest of pickles, getting out of it can often be as simple as that. Skip a beat and don’t sweat it—you’ll be witty on the next one.

Have a Little Faith

What really makes confident people feel confident? So much of the beauty in our lives is unplanned. This occurs because we are able to step outside of the boxes and limits in our heads and explore things we wouldn’t have otherwise. And what results is often amazing. Confidence could be called the belief in this truth.

Over-planning and preparing is like a straitjacket for your conversation and rapport. The irony is that holding things with lightness takes far less effort than trying to force and control them, and always leads to better results. In a way, it’s about committing to having better conversations rather than becoming a better conversationalist—once you get your ego out of the picture, you can actually start to let things flow. But you have to take that first step, and that takes trust.

When you remove the possibility of spontaneity from your conversations, you might feel like you are safe from spectacular failure, but you also limit the potential of how high your conversation can soar. In other words, it’s safe but boring.

The most memorable moments do not typically come because somebody planned them that way. In fact, it’s usually the opposite.

Here’s a quick thought experiment that will bolster your sense of confidence in the face of unpredictability. Hopefully it will help you realize that you don’t need an agenda, and that your worst-case scenario is not really that bad.

Pick five topics that you know absolutely nothing about. Bring them up one by one with a friend. Commit to talking about each topic for at least five minutes. See the various angles and routes you can go to make a topic interesting. Grasp for straws on how to keep a dialogue going. Notably, see how you can relate it to other topics, and see how easy it is to get side-tracked onto something else. There’s not much to fear, is there? You might convince yourself of something interesting: that the content of a conversation is only secondary, and your attitude and energy play a much, much bigger role.

The 1:1:1 Method of Storytelling

On the theme of simplifying storytelling, we’ve been talking about how we can use a mini story in many ways. You may be wondering what the difference is between a mini story and a full-fledged story.

To me, not much. As I mentioned, many people like to complicate storytelling as if they were composing an impromptu Greek tragedy. Does there have to be an introduction, middle, struggle, then resolution? You may have read that great stories are about X, Y, and Z; that you need a beginning, middle, and ending; that you should use as much descriptive detail as possible; or how important pauses are. That’s one way of doing it, but certainly not the easiest or most practical.

My method of storytelling in conversation is to prioritize the discussion afterward—similar to what you saw with the fallback stories in an earlier chapter. This means that the story itself doesn’t need to be that in-depth or long. It can and should contain specific details that people can relate to and latch on to, but it doesn’t need to have parts or stages. It can be mini by nature. That’s why it’s called the 1:1:1 method.

It stands for a story that (1) has one action, (2) can be summed up in one sentence, and (3) evokes one primary emotion in the listener. You can see why they’re short and snappy. They also tend to make sure that you know your point before starting and have a very low chance of verbally wandering for minutes and alienating your listeners.

For a story to consist of one action means only one thing is happening. The story is about one occurrence. It should be direct and straightforward. Anything else just confuses the point and makes you liable to ramble.

A story should be able to be summed up in one sentence because, otherwise, you are trying to convey too much. This step actually takes practice, because you are forced to think about which aspects matter and which don’t add anything to your action. It’s a skill to be able to distill your thoughts into one sentence and still be thorough—often, you won’t realize what you want to say unless you can do this.

Finally, a story should focus on one primary emotion to be evoked in the listener. And you should be able to name it! Keep in mind that evoking an emotion ensures that your story actually has a point, and it will color what details you carefully choose to emphasize that emotion. For our purposes here, there really aren’t that many emotions you might want to evoke in others from a story. You might have humor, shock, awe, envy, happiness, anger, or annoyance. Those are the majority of reasons we relate our experiences to others.

Keep in mind that it’s just my method for conveying my experiences to others. Whether people hear two sentences about a dog attack or they hear ten sentences doesn’t change the impact of the story. The reason I abbreviate stories is so the conversation can move forward and we can then focus on the listener’s impact and reaction. So what does this so-called story sound like?

“I was attacked by a dog and I was so frightened I nearly wet my pants.” It’s one sentence, there is one action, and the bit about wetting the pants is to emphasize the fact that the emotion you want to convey is fear and shock.

You could include more detail about the dog and the circumstances, but chances are people are going to ask about that immediately, so let them guide what they want to hear about your story. Invite them to participate! Very few people want to sit and listen to a monologue, most of which is told poorly and in a scattered manner. Therefore, keep the essentials but cut your story short, and let the conversation continue as a shared experience rather than you monopolizing the airspace. Make it a shared experience rather than all about you.

The 1:1:1 method can be summed up as starting a story as close to the end as possible. Most stories end before they get to the end, in terms of impact on the listener, their attention span, and the energy that you have to tell it. In other words, many stories tend to drone on because people try to adhere to these rules or because they simply lose the plot and are trying to find it again through talking. Above all else, a long preamble is not necessary. What’s important is that people pay attention, care, and will react in some (preferably) emotional manner.

Ask for Stories

Most of the focus with stories is usually on telling them—but what about soliciting them from others and allowing them to feel as good as you do when a story lands well? What about stepping aside and giving other people the spotlight? Well, it’s just a matter of how you ask for them.

When you watch sports, one of the most illogical parts is the post-game or post-match interview. These athletes are still caught in the throes of adrenaline, out of breath, and occasionally drip sweat on to the reporters.

Yet when you are watching a broadcaster interview an athlete, does anything odd strike you about the questions they ask? The interviewers are put into an impossible situation and usually walk away with decent soundbites—at the very least, not audio disasters. Their duty is to elicit a coherent answer from someone who is mentally incoherent at the moment. How do they do that?

They’ll ask questions like: “So tell me about that moment in the second quarter. What did you feel about it and how did the coach turn it around then?” as opposed to: “How’d you guys win?” or: “How did you turn this match around, come back, and pull out all the stops to grab the victory at the very end?” as opposed to: “How was the comeback?”

The key? They ask for a story rather than an answer. They phrase their inquiry in a way that can only be answered with a story, in fact.

Detail, context, and boundaries are given for the athletes to set them up to talk as much as possible instead of providing a breathless one-word answer. It’s almost as if they provide the athletes with an outline of what they want to hear and how they can proceed. They make it easy for them to tell a story and simply engage. It’s like if someone asks you a question but, in the question, tells you exactly what they want to hear as hints.

Sometimes we think we are doing the heavy lifting in a conversation and the other party isn’t giving us much to work with. But that’s a massive cop-out. They might not be giving you much, but you also might be asking them the wrong questions, which is making them give you terrible responses. In fact, if you think you are shouldering the burden, you are definitely asking the wrong questions.

Conversation can be much more pleasant for everyone involved if you provide fertile ground for people to work in. Don’t set the other person up to fail and be a poor conversationalist; that will only make you invest and care less and cause the conversation to die out.

When people ask me low-effort, vague questions, I know they probably aren’t interested in the answer. They’re just filling the time and silence. To create win-win conversations and better circumstances for all, ask for stories the way the sports broadcasters do. Ask questions in a way that makes people want to share.

Stories are personal, emotional, and compelling. There is a thought process and narrative that necessarily exists. They are what show your personality and are how you can learn about someone. They show people’s emotions and how they think. Last but not least, they show what you care about.

Compare this with simply asking for closed-ended answers. Answers are often too boring and routine for people to care. They will still answer your questions but in a very literal way, and the level of engagement won’t be there. Peppering people with shallow questions puts people in a position to fail conversationally.

It’s the difference between asking, “What was the best part of your day so far? Tell me how you got that parking space so close!” instead of just, “How are you?”

When you ask somebody the second question, you’re asking for a quick, uninvolved answer. You’re being lazy and either don’t care about their answer or want them to carry the conversational burden. When you ask somebody one of the first two questions, you’re inviting them to tell a specific story about their day. You are inviting them to narrate the series of events that made their day great or not. And it can’t really be answered with a one-word answer.

Another example is “What is the most exciting part of your job? How does it feel to make a difference like that?” instead of simply asking them the generic “What do you do?” When you only ask somebody what they do for a living, you know exactly how the rest of the conversation will go: “Oh, I do X. What about you?”

A final example is: “How did you feel about your weekend? What was the best part? It was so nice outside,” instead of just: “How was your weekend?”

Prompting others for stories instead of simple answers gives them a chance to speak in such a way that they feel emotionally invested. This increases the sense of meaning they get from the conversation you’re having with them. It also makes them feel you are genuinely interested in hearing their answer because your question doesn’t sound generic.

Consider the following guidelines when asking a question:

1. Ask for a story

2. Be broad but with specific directions or prompts

3. Ask about feelings and emotions

4. Give the other person a direction to expand their answer into, and give them multiple prompts, hints, and possibilities

5. If all else fails, directly ask “Tell me the story about . . .”

Imagine that you want the other person to inform your curiosity. Other examples include the following:

1. “Tell me about the time you . . .” versus “How was that?”

2. “Did you like that . . .” versus “How was it?”

3. “You look focused. What happened in your morning . . .” versus “How are you?”

Let’s think about what happens when you elicit (and provide) personal stories instead of the old, tired automatic replies.

You say hello to your co-worker on Monday morning and you ask how his weekend was. At this point, you have cataloged what you will say in case he asks you the same. Remember, they probably don’t care about the actual answer (“good” or “okay”), but they would like to hear something interesting. But you never get the chance, because you ask him “How was your weekend? Tell me about the most interesting part—I know you didn’t just watch a movie at home!”

He opens up and begins to tell you about his Saturday night when he separately and involuntarily visited a strip joint, a funeral, and a child’s birthday party. That’s a conversation that can take off and get interesting, and you’ve successfully bypassed the unnecessary and boring small talk that plagues so many of us.

Most people love talking about themselves. Use this fact to your advantage. Once someone takes your cue and starts sharing a story, make sure you are aware of how you’re responding to that person through your facial expressions, gestures, body language, and other nonverbal signals. Since there is always at least one exciting thing in any story, focus on that exciting point and don’t be afraid to show that you’re engaged.

One quick tip to show that you’re engaged and even willing to add is something I call pinning the tail on the donkey. There is probably a better name for it, but my vocabulary was severely lacking at the time. The donkey is the story from someone else, while the tail is your addition to it. It allows you to feel like you’re contributing, it makes other people know you’re listening, and it turns into something you’ve created together.

People will actually love you for it because, when you do this, your mindset becomes focused on assisting people’s stories and letting them have the floor.

Bob’s story: “I went to the bank and tripped and spilled all my cash, making it rain inadvertently.”

Tail: “Did you think you were Scrooge McDuck for a second?”

When you make a tail, try to home in on the primary emotion the story was conveying, then add a comment that amplifies it. The story was about how Bob felt rich, and Scrooge McDuck is a duck who swims in pools of gold doubloons, so it adds to the story and doesn’t steal Bob’s thunder. Get into the habit of assisting other people’s stories. It’s easy, witty, and extremely likable because you are helping them out.

Conversational diversity

Hypotheticals

A hypothetical is a classic conversational diversification tactic. Okay, that’s a fancy term for what really amounts to, “Hey, what would you do if . . .” and “What do you think about . . .”

But here’s what happens when you throw a hypothetical into your conversation. You inject exponentially the amount of variability and unpredictability possible because it’s likely something your conversation partner has never considered, and the hypothetical you pose will be something that has no clear or correct answer. Instead, something hopefully exciting comes out of it and you get to discuss something that would never have come up otherwise.

Use hypotheticals to see how people react and how their minds work. You’ll learn something about them from how they answer, and you can treat the hypothetical itself like an inkblot test—how they answer probably says something about them. In the end, wherever it goes will probably be more interesting than an interview!

The easiest way to make a conversation awkward or to introduce dead space is to ask questions that can easily be answered by a simple yes or no. Open-ended questions allow for creativity. They allow people to dig into their memory banks, come up with random associations, or otherwise trigger their imagination. With that said, your hypothetical question should be challenging enough so that the recipient actually needs to be a bit creative in answering the question.

The secret to hypotheticals is to make them appear spontaneous. Ask for their opinion on something out of curiosity. You don’t want to come off as contrived or like you’re reading from a script. That’s going to make you look ingenuous. And you don’t want to seem as if you have some sort of agenda.

Adding a one- to two-sentence backstory as to why this thought “spontaneously” popped into your mind tends to help.

Finally, keep in mind that when you use these, you must also have an answer prepared for the hypothetical you ask. You can step in with your answer while they are formulating theirs—and you should have thought about this answer beforehand so you can be prepared and rehearse it. Don’t be in a situation where you don’t know the answer to your own hypothetical. You don’t need a definitive answer, but you at least need a stance or opinion. There’s nothing worse than your conversation partner saying, “I don’t know,” and you also saying, “I don’t know.” Nothing else will fill that space besides awkward silence.

Here are some examples of hypothetical questions you can toss into your conversations like a grenade. It’s a good rule of thumb to have a few prepared and up your sleeve for when you sense you are falling into some type of routine or pattern.

Type #1: What would you do if . . .

Example: What would you do if the waiter from lunch screamed at you to give him a bigger tip?

Type #2: Would you rather have this or that?

Example: Would you rather be four inches shorter or sixteen inches taller?

Type #3: My friend just did/said this . . . What would you have done?

Example: My friend just called out his boss for working too much. Can you imagine that? What would you have done?

Type #4: What if you were in this situation . . .?

Example: What if your co-worker was stealing your food from the fridge every day? How would you handle that?

Type #5: Which of the following . . .?

Example: Which do you think is better: super cold winters or hot summers?

Type #6: Who do you think . . .?

Example: Which of us do you think got the best grades in school? Or the worst?

Think Out Loud

This is a rather simplistic way of phrasing it, but thinking out loud can introduce quite a bit of conversational diversity. We filter ourselves far too much, and while it’s called for sometimes, it doesn’t always help.

If we just voice our inner monologue about what we’re thinking about during our day, this can be quite an icebreaker. Share your thoughts about your surroundings or what you observe around you. Share what you are doing, what you are seeing, what you are thinking, and what you are wondering. Thinking out loud can also just be voicing your feelings, such as, “I’m so happy with the sunshine right now,” or, “I can’t believe the coffee here is so expensive!”

This will lead to a more open flow of communication. Others will feel less guarded around you and that can lead to a higher level a mutual comfort. It’s also bound to be more interesting than filling the silence with a question that no one cares about.

Just say what’s on your mind and you are inviting others to speak, but it’s not a demand.

The added benefit is you’ll probably end up being that person who says what everyone is thinking but is afraid to say. Maybe they’re just shy or want to seem polite. Whatever it is, they are thinking it, but they feel it’s not proper to voice their thoughts aloud. If you become that person who is the first to say what everyone is thinking, you break the ice.

People will feel they can trust you and be comfortable around you because you actually have the guts to say what they wanted to say. At least you’ll bring up some common ground that others can comment on.

Summary

• Lightness, humor and playfulness are the life blood of good conversation, and there are ways to develop them for yourself.

• One quick technique is misdirection, where a statement has two parts: the first is expected and ordinary, the second contradicts it with unexpected and comedic results. Sarcasm can be powerful but is best when directed at yourself and used with those you are more familiar with. Ironic humor is similar to sarcasm, but more focused on the observation of the contrast between the expected and the actual.

• The world of improv has a lot to teach us about good conversational chemistry. One improv rule is not to hold on to any outcome too tightly, and be ready to follow the emerging flow of the conversation.

• Another rule is to rely on quick connections to make sure you always have something to say. This can be practiced by free associating one, two, or five words. Good improv is about having faith in the conversation’s direction, and your ability to be okay with where it goes.

• The 1:1:1 method of storytelling is a mini story technique that relies on one action, summarized in one sentence, that evokes one main emotion in the listener. This keeps your stories engaging, short, and effective. Alternatively, you can ask for other people’s stories.

• Conversational diversity is about having as many different tools in your toolkit as possible. Hypothetical questions are one such tool. These kinds of “what if . . .?” questions inject some excitement, creativity, and unpredictability, while showing something interesting about the person giving the answer.

• Finally, thinking out loud can be a way to turn monologues into dialogues. If we speak freely and without self-censoring, we break the ice, share ourselves honestly, and invite (rather than demand) others to join us.