Storytelling 101

Telling stories, a seemingly easy task, is much more than just saying “once upon a time.” It’s about making an experience come to life for others, connecting, and essentially putting the listener in your shoes with the hopes of a laugh, a cry or any other reaction. There are a multitude of layers to everything, even something as simple as a story. While there’s no real right or wrong, there are probably a few things everyone could do to improve their storytelling.

The basics

The first step to becoming a better storyteller is knowing your audience; if you’re able to connect with them, you’re able to captivate them.

“You could tell the same story to three different groups of people, and you’d probably have to tell it a little differently each time, depending on your audience,” says North Salem resident Jason Kadlec, a writer for Teddy’s Friends, a cartoon that helps teach kids life lessons.

But, because everyone is different and people absorb information in different ways, knowing your audience doesn’t mean knowing their likes and dislikes; it’s about understanding how they listen and comprehend information. 

“There are four types of people sitting in front of you,” says Carlo Pellegrini, creative director, producer and ringmaster for Westchester Circus Arts. “There are people who are action-oriented, so you have to engage them with your body and movement. There are the contemplative people who only think in bullet point form, so when you present on a slide or overhead projector, make sure that you include bullet points to keep them  engaged. Then there are the amiable people—the ones who like to help other people get things done. You engage them by talking about acts of service to others, no matter what the topic is. And finally, there are the creative people who need to hear really crazy ideas. They love animation and visuals, and those keep them engaged because they are off-the-charts creative and will get bored very quickly.”

The essentials

Once you know how to tell a story to your audience, whether you’re speaking to a single person or 100 people, you should keep it entertaining. And the best way to do that is with a bit of humor. It helps the listener really want to listen, which, in turn, helps you as the storyteller. And when the audience is engaged, you can get your point across. 

“If I’m telling a funny story, then I usually set it up with something like, ‘Oh, my gosh, I have something to tell you,’” says Kadlec. “Or, I’ll say, ‘Wait ‘till you hear this one.’ Or, ‘You wouldn’t believe what happened to me today.’ This way, they know a story is coming and not necessarily a dialogue. And then, at the end, they get the punchline, which opens up a discussion.”

And, importantly, don’t forget to be yourself.

“People love authenticity,” says Kadlec. “Being real with people is the secret to storytelling. You have to really lay it all out there.”

Of course, you also have to read the room. Pay attention to how your story is being received and go from there. If they’re looking away or looking down, they might be bored. And if you’re not sure, just ask. 

“You can ask them, point blank, ‘Does that make sense?’” Kadlec suggests. “Or, you can ask, ‘Do you understand?’ Or even, ‘Do you see what I’m saying?’ If they say it doesn’t make sense, you can follow up with, ‘Where did I lose you?’ and then return to that point and go slower. It’s about honing in on that person.” 

Another key thing to remember is to make sure you always “listen to the listening.”

“You’re telling a story to evoke something, but it’s a lot of give and take. You need to pay attention to what they are saying in response. Are they following you or talking about something completely different? Or are they are not saying anything at all?”

Building a structure

The two most important parts of a story are the beginning and the end. The opening hooks the listener, and the closing leaves them with something to think about. While the middle of the story is, of course, important, the beginning and end are what typically make the greatest impact. Each part of the story should have a point, and the three parts—beginning, middle and end—must each serve some sort of purpose.

A good story will also have a plot, theme, characters, tone, point of view, conflict, etc. This will help structure the story and engage the listener.

Furthermore, the shorter, the better. People get bored quickly, so getting to the point in a timely manner is salient. That’s not to say that you shouldn’t include all the details you need, but people can fill in the blanks for many things, so the details shouldn’t be excruciating.

“Everybody has a short attention span,” says Pellegrini. “Everybody has a busy life. So the privilege of telling a story means you’re taking three to five minutes out of someone’s day. It really doesn’t need to be more than that.”

And although brevity is important, it doesn’t have to pair with vagueness; keeping something short and leaving the listener not entirely informed are two completely different things.

Saving your most important point for the perfect moment is also critical. It should be done once you have everyone’s attention, but when there’s still more to share. 

Avoid oversharing or making it too personal

Going along with brevity, don’t overshare. And not just in the sense that you shouldn’t have too many details, but also in the sense that it needs to be relatable. If the experience is something that’s too centralized on you, it won’t land as well.

“Quite frankly, the story should not be about yourself, but a story that the listener can relate to,” says Kadlec. “If you have to make the story about yourself with a quick relatable personal story, make it quick, brief and interesting, and make sure it ties into the story or you will bore the listener to death.”

Additionally, there shouldn’t be too much going on. It should be easy for the listener to follow—if they’re confused, they may zone out. Only include the most significant aspects of the story you’re sharing, and it will make your story a lot easier to understand.

“They’re only going to remember two things that you say,” says Pelligrini. “You can present 40 points, but no one will remember more than two or three points, so keep it short and sweet.”

Practice makes…better

Have you ever heard the saying “practice makes perfect?” Well, there’s no “perfect” way to tell a story, but you certainly can get better, and practice will help. There are many ways you can practice—mock-storytelling sessions and mirror work are two good examples.

“You should start by simply communicating with other people—it could be your neighbor, your parents, your friends, your family, your kids,” Kadlec recommends. “Communication is an art and a science. The art is when you embellish the story, and the science is the timing and tone. The more you communicate, the more you’ll improve your ability to tell stories.”

Along with this, practice in front of a mirror, and particularly practice looking people in the eye. It’s a powerful way to make a personal connection and hold the listener’s attention. 

“When you’re talking to somebody, you can focus in on one eyeball,” says Kadlec. “Just stare at that one eyeball. It even helps when you’re telling a story to a group; focus on one person and one eyeball. And then you move on to the next person and the next eyeball. When you’re talking to people like that, the whole audience gets it.”

And above all else, keep practicing and keep telling stories.

“The most important thing in life is to be able to speak your mind,” says Pellegrini. 

This article was published in the July/August 2024 edition of Connect to Northern Westchester.