Improve Your Storytelling With Inside Jokes And Good Questions

In any conversation, there is a high point. There might be multiple memorable points, but by definition, one part is the best and highest.

This can take many different forms. You can share a big laugh. You can both get emotional and cry. You share a strong perspective on an issue that no one else does. You witness something either horrifying or hilarious together. You both struggle not to laugh when you observe something. You finish each other’s sentences. Most of the time, if you do it correctly, your stories become high points because of the emotional impact and pure intrigue you can use them to create. This makes it easy because you are planting the seed of connection for you to harvest later.

Coincidentally, calling back to this high point later is what a deconstructed inside joke looks like. Therefore, to easily create an inside joke, all you have to do is refer to the high point later in the conversation. Take note of it and put it in your pocket for use in the near future. Don’t let it go sour like month-old milk that you’re afraid to throw away because of the smell. Assuming that you told a good story or elicited a good story earlier in the conversation, all you need to do is refer to it in the context of your current topic.

For example, you told a story about your favorite kind of dog earlier in the conversation. There was a high point about comparing yourself to a wiener dog because your shape makes it unavoidable.

Now your current topic of conversation is fashion, personal style and different types of jackets. How do you call back to the wiener dog high point by referring to it in the context of jackets? “Yeah, unfortunately, I can’t wear that type of jacket because I’m mostly similar to the wiener dog, remember?”

Bring up the first topic, hopefully the topic of your story, and then use it in the current subject. You are repeating the old topic in a new context, and this tends to be better received, even if it wasn’t funny the first time. And the best part is that you can keep doing this with the same thing to create an even stronger unique bond (inside joke!).

Listen for something funny or notable that you would classify as a conversational high point. Keep it in your pocket. Wait like a cheetah in the tall grass of the savannah to see a different context or topic you can repeat it in. And then unleash it.

Here’s another example.

Prior conversational high point: a story about hating parking lots.

Current topic of conversation: the weather.

Callback: Yeah, the rain will definitely be welcome when we can’t find parking spots within ten blocks of our apartment.

And here’s one more:

Prior conversational high point: a story about loving donuts.

Current topic of conversation: hating work.

Callback: Well what if your office provided free donuts? How many would you need to change your opinion of work?

In the same way an orchestra conductor can hit the same high musical motif through different arrangements and songs, you can keep referring to this conversation high point. Voila, you’ve just created an inside joke from thin air.

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 (an underrated skill in conversation and life in general)? Well, it’s just a matter of how you ask for other’s stories. There are ways to make people gab for hours, and approaches where people will feel compelled to give a terse one-word answer.

For instance, 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 onto the reporters. It’s not a situation conducive to good stories, or even answers.

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.

Reporters provide the athletes with detail, context, and boundaries 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 an excuse that obscures the fact we aren’t making it easy for them. They might not be giving you much, but you also might be asking them the wrong questions, which is leading them to provide 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 reveal 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. These answers are often too boring and routine for people to care. They will still respond to your questions but in a very literal way, and the level of engagement won’t be there. Peppering people with shallow questions puts them 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 looking 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 encouraging them to narrate the series of events that made their day great or not. And your query can’t really be covered 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 derive from the conversation. 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 coworker 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, the person probably doesn’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 high point and don’t be afraid to show that you’re engaged.

One quick tip to show that you’re involved and even willing to add to the conversation is something I call pinning the tail on the donkey. There is probably a better name for it, but it will suffice for the time being. 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. In essence, you are taking the impact that someone wants to convey, and you are amplifying it. You are assisting them in their own storytelling—they want to extract a specific reaction from you, and you are going above and beyond with the tail.

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. Here’s an example:

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 hone 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.

Sabrina’s story: “After I ate lunch, I ran into the president of my company and he said he remembered me because of the great ideas I had at the last meeting!”

Tail: “Just like you were winning a beauty pageant!”

This story was about how Sabrina felt flattered and hopeful, and so the concept of a beauty pageant amplifies these emotions. Get into the habit of assisting other people’s stories. It’s easy, witty, and extremely appealing because you are helping them out.