Captivating Stories

Captivating is a pretty strong word, and as such, it’s probably something that we want to strive for in our interactions.

When we think of a captivating person, what kind of mental image comes to mind? If you were to choose a picture for a “captivating person” in a dictionary, what would the person be? What is this person expressing, how are they acting, and what are you watching them do?

More often than not, this person is going to look like they are on a stage or pulpit gesticulating grandly and expressively, with an emotion-filled face. And I would also bet that this person is in the middle of weaving an engrossing tale that captivates his or her audience. Indeed, if you think about it, it seems that only with storytelling can we mesmerize and charm others into hanging on to our every word.

Okay, that’s up for debate, but determining whether or not that is true is not the aim of this chapter. No one can deny that storytelling is an important element of memorable conversations and discussions that you want to have. The question is always how to capture this elusive skill and make it your own. Therefore, in this chapter, I want to present a few perspectives on how you can use storytelling in your everyday conversations and even small talk.

It’s helpful to first take the mystique away from the whole concept of storytelling. What is storytelling? It’s just telling someone about something that happened. That’s all. Of course, there are better and worse ways to do this, but at the core, storytelling is just talking about the past in a way that makes people pay attention. The first part we have no problem with—we’ve all described our pasts, and we all have great experiences worthy of being told—but the second part is typically the challenge. With that in mind, let’s see how we can get better at storytelling.

A Life of Stories

To get better at stories, we have to begin to recognize them in our daily lives. No, seriously. We don’t think of our lives as being very interesting on a day-to-day basis, but we do quite a bit more than we realize. It’s not that every day you are engaging in a massive protest that you can tell your kids about, or you were chased by a wiener dog down a dark alley whereupon a man dressed as a parrot saved you by tackling the dog. These stories are self-evident and don’t need any organization or special way of telling them to make an impact.

We have to draw from our daily lives, and believe me, there is plenty to draw from. It’s just a matter of seeing the mini-stories that are inherent in our everyday existence. What is the definition of a mini-story in this context?

“So what do you do?”

“I’m a marketing executive.”

Well, not that. That’s going to get a reply of "Oh, cool. I’m going to the bathroom now, goodbye.” Let’s try again.

“So what do you do?”

“I’m a marketing executive. I deal mostly with clients. Just last week we had a crazy client that threatened to send his bodyguards to our office! I definitely wish I dealt more with the creative side.”

There we go. This will probably garner a stronger response than wanting to escape to the bathroom, such as “Oh my God! Did he actually send them? TELL ME MORE.”

That’s a mini-story. It’s answering questions (or spontaneously sharing) briefly using the elements of a story—an action that occurs to a subject with some sort of conclusion. As you can see above, a brief mini-story will create exponentially more conversation and interest than any answer to the question, “What do you do?” All you needed was three sentences. Try reading it out loud—it takes less than ten seconds, and you’ve jam-packed it with enough information to be interesting to anyone.

What’s great about mini-stories is you can also create these before a conversation, so you can have compelling anecdotes at hand in response to very common and widespread questions. The main benefit to creating mini-stories ahead of time is to be able to avoid one-word answers that you may be accustomed to using. This can give a sense of confidence going in, because you’ve prepared for what will come.

When you break down the context surrounding a mini-story, they become much simpler. Shoot for three sentences that can answer some of the most common conversation topics that will arise.

1. Your occupation (if you have a job that is unusual or nebulous, make sure you have a layman’s description of your job that people can relate to)

2. Your week

3. Your upcoming weekend

4. Your hometown

5. Your hobbies and so on.

When you are using a mini-story to answer a question, make sure to first acknowledge the question that was asked. But then, realizing that you have something far more interesting to say, you can jump into the mini-story, which should be able to stand by itself.

“How was your weekend?”

“It was fine. I watched four Star Wars movies.”

“Okay, I’m going to go talk to someone else now.”

Let’s try again.

“How was your weekend?”

“It was fine, but did I tell you about what happened last Friday? A dog wearing a tuxedo walked into my office and he peed on everything.”

“Wait. Tell me more.”

Using mini-stories allows you to avoid the tired back of forth of “Good, how about you” you’ll find in everyday small talk. That’s the first step to being captivating.

It might help to reframe mini-stories this way: when people make small talk with you and ask any of the classic small-talk questions, they aren’t truly interested in the answers to those questions. They want to hear something interesting, so give it to them.

This is an important point to repeat: when we ask how someone’s weekend was, or what people’s travel plans are, we usually aren’t that interested in the literal answer. We’ve already talked about how you should disclose and divulge more about yourself in an effort to find more similarities, and now you can see another benefit of offering more.

Not only that, mini-stories are an inside view to the way you think and feel. They give clues to your mindset, personality, and emotional leanings. Learning about those aspects is the first step in allowing anyone to relate and feel connected to you, so it’s imperative that you learn how to take any question and expand it to your advantage. It will also encourage them to reciprocate.

Mini-stories also underscore the importance of providing more details, as mentioned in an earlier chapter, and avoiding one-word answers. Details offer a three-dimensional description of you and your life. That automatically makes people more interested and invested because they are already painting a mental picture in their minds and visualizing everything.

Details also give people more to connect to, think about, and attach themselves to. With more details, there is a substantially higher likelihood that people will find something funny, interesting, in common, poignant, curious, and worthy of comment in what you have to say.

Detail and specificity put people into a particular place and time. This allows them to imagine exactly what’s happening and start caring about it. Think about why it’s so easy to get sucked into a movie. We experience enormous sensory stimulation and almost can’t escape all of the visual and auditory detail, which is designed to make us invested. Detailed stories and conversations are inviting others to share a mental movie with you.

Beyond giving flavor to your conversation and storytelling, and giving the other person something to ask about, details are important because they elicit emotional engagement. Details remind people of their own lives and memories and make them feel more drawn to whatever is presenting them. Details can compel others to laugh, feel mad, feel sad, or feel surprise. They can control moods and emotions.

If you include details about specific songs that played during your high school dances, it’s likely that someone will have memories attached to those songs and become more emotionally interested in your story. Share details about all the figurative nooks and crannies, because that’s what makes you interesting on an emotional level.