Knowing how to tell a great story is something everyone can learn to do. Here's how to harness your inner storyteller and be the life of any conversation!

How to Tell a Great Story

Everyone has a storyteller inside them, and everyone has a story to tell. James Joyce once said he never met an uninteresting person. The difference between people who seem interesting and people who don’t is their ability to turn their experiences into compelling stories — which is why we make storytelling such a big part of our bootcamps.

It’s true that some people have more natural storytelling ability than others. But anyone can learn the craft of storytelling. That’s because storytelling, like so many other skills, is just a series of behaviors and principles you have to learn. With some attention and consistent practice, you can have people hanging on every word of your story — in bars and clubs, at professional networking events, and on dates.

In this piece, we’ll be talking about those key behaviors and principles to up your storytelling game.

Good storytellers inject emotion into their stories.

Two people can tell the exact same story with wildly different results. One captivates, while the other has the audience checking its watch. While we tend to look for exciting stories, the actual story material isn’t what separates a good story from a bad one. What makes the difference is the emotion the storyteller puts into their narrative.

For example, I’m a big fan (along with three million other people) of Dan Carlin’s Hardcore History podcast. Carlin makes history captivating by connecting historical moments with people and feelings, not just dates and events. You don’t just get a sense of what happened and when. You learn what people were thinking, what they were worried about, what emotions motivated them and drove them. Carlin creates empathy for real people, drawing the listener into his narrative.

Every story has an emotional core, and that emotional core is how the storyteller feels about the events they’re describing. Everything else is just window dressing. So think about how you felt when your story actually happened. What was motivating you? What troubled you? How did you feel about your surroundings? How do you feel now about what happened then? If you can express that, you can create connections with your listeners, and trust that they’ll be hanging on every word.

Structurally, you want to find opportunities in your story to weave your feelings and motivations into its events. Consistently return to your experience of what is happening in the narrative. The more emotion you can impart in your story, the better. This doesn’t always have to be deep or complex. In fact, taking a second to say something as simple as “I couldn’t believe it!” or “At this point, I was terrified” gives your story the emotional charge it needs to connect. You don’t have to go into great detail or be histrionic. You simply have to signpost your feelings and motivations, and share them authentically with the audience.

As the old saying goes, you have to be interested to be interesting. If you don’t care about your story, why will anyone else?

Good storytellers know their narrative.

You need emotion to make a story compelling. But every story is really just a sequence of events that need to be told in the right order. Extraneous information slows a story down and can have people wondering about the ultimate point. It’s like telling a joke: You don’t go on detours about what the chicken was doing for the last three weeks before it crossed the road. You tell only the parts that propel the joke forward. The same applies to storytelling.

So how do you know what’s essential to your story?

First, remember that every story starts before the main event. Why were you in the situation that you were in to begin with? What key information does the audience need to appreciate the rest of the story? That’s where the story begins. You need to tee up the story that you’re going to tell before you start telling it. This shouldn’t be your life story, but you should succinctly explain how you got into the situation you’re about to discuss.

Once you’ve done that, you need to think about the logical order in which you tell the story. That’s often — but not always — the important events of the story in the order they happened in. But sometimes it makes sense to back up a bit and fill the listener in on some piece of background information that wouldn’t have made sense at the beginning of the story. And while some small details that aren’t totally relevant to the story can be thrown in for emotional effect, you don’t want to get bogged down in irrelevant information.

Once you’ve got your skeleton, start thinking about what fills it in. Who else is involved in your story? What does the listener need to know to understand the other characters in your story? Fleshing out the other people in your story is one simple way to make the overall story more compelling and relatable. Even if the person listening can’t relate to you, they might be able to enter the story through another character.

While every story is different, most stories follow a general pattern. You start with the background, then tell the listener how the story started. This is the event that triggers the story to begin. The action should rise throughout until it reaches a dramatic peak — a point of no return — also known as the climax. You then drive from the climax to the final events of the story. After that, you can briefly discuss the consequences of the story. This is called the denouement, and it’s the bookend of the narrative.

Following this general pattern is crucial to being a good storyteller. Otherwise, you’ll find that most people, who have an intuitive sense of what makes a good story, will grow restless.

Above all, a narrative is always moving forward in some way, even when it takes a step back. The narrative is the sequence of events, but it’s also what creates the tension in the story. If emotion is what draws a listener in, the narrative is what keeps them wanting more. When you structure your narrative right, the listener will want to know what happens next.

Good storytellers create rapport.

The whole reason to tell a story isn’t to hear yourself speak. It’s to create a connection between you and the listener. That’s the magic of great storytelling. And like any kind of rapport-building exercise, there’s one simple rule in play: high risk, high reward; low risk, low reward.

Basically, the higher the level of self-disclosure in the story, the deeper the connection you’re going to make with your listeners. But there’s also the risk that you might expose too much and embarrass yourself. Alternately, you might come across too strong and alienate or even offend your listeners. Becoming a good storyteller is about mastering that trade-off over time.

Ultimately, that’s a calculated risk you’re going to have to make when you tell a personal story. But I’ve broken it down into three basic levels to help you get a feel for what you’re getting yourself into:

  • Light disclosure involves amusing anecdotes about yourself and the world around you. Light disclosure tends to be brief, with a clearly defined beginning, middle and end. This tends to be a quick little anecdote about something funny or interesting that happened to you in the course of your daily life.
  • Medium disclosure gets more serious, because it involves your beliefs, opinions and ideas about the world. This is a riskier proposition, because there’s someone out there who’s bound to be affected by your thoughts and feelings. Medium disclosure is best for after you have established some degree of rapport with your listeners. You need to feel reasonably safe that, even if they don’t agree, that they won’t be looking for the nearest exit.
  • Heavy disclosure is, as you might guess, the riskiest and most difficult kind of storytelling. This is where you begin sharing your fears, insecurities, failures and pain points with your listeners. There’s a two-fold risk with heavy disclosure. First, you might come across as needy or validation-seeking. Second, your listeners might laugh at you rather than with you. You want to save heavy disclosure for situations where you feel very safe sharing deeply personal and painful parts of your life. You also want your storytelling ability to match the level of disclosure, which is a matter of practice.

For the most part, when you’re out at a bar, business networking event or other place where you’re meeting new people, you’ll want to stick mostly to light self-disclosure with maybe a little bit of medium self-disclosure once you’ve started to make a connection. Heavy self-disclosure is either for people you already know very well, or people that you want to become trusted confidants and companions.

Rapport is ultimately what you want to achieve when you tell a story, so don’t gloss over thinking over this part. One of the most powerful reasons to tell a story is that it allows you to connect with several people all at once. Just how much do you want to connect? A good storyteller is aware of his level of disclosure and uses it skillfully.

Good storytellers practice their craft.

When it comes to telling stories, the more practice you get, the better you’re going to be. That might mean that you head off to a Toastmasters or join a storytelling group. It might mean that you practice your stories around your bedroom or record yourself for your own personal review. However you choose to practice, here are some pointers to getting the most out of the time you spend.

Start by listing out some of your favorite stories about yourself. These don’t have to be super detailed, just something to jog your memory, like “the linguine incident.” It’s good to have one or two bragworthy stories, but you don’t want all your identity stories to be chest-puffing braggadocio. That can be a real turn off when you’re talking to people, especially people you don’t know very well.

Pick one of your favorites and list the important elements of the story that jump into your head. Write them down in an order that makes sense. Now ask yourself how you got in the situation. There’s your backstory. That’s the skeleton of your identity story. Everything else is going to hang off of that.

Now practice telling the story without looking at your notes. You don’t want your story to seem canned or like you’re reading from a script. You want to write down the answers to the above questions, but that’s more for the purpose of getting your thoughts in order. Remember what I said earlier: This story is a bit like telling a joke. So you want to try telling it a few different ways, remembering the important parts, emphasizing different bits and playing around with your story to see what works and what doesn’t.

Finally, when you’re telling your story to an empty room, you want to pay attention to your tone of voice. Your tonality is going to do help the listener know when you’re responding emotionally or reaching a climax. Use your voice to communicate the feeling you want your listeners to experience.  You want to sound confident at all times — even when you’re being silly or vulnerable — because that’s what’s going to show your listeners that everything you’re telling them is totally true, no matter how strange or unreal it might sound. Always avoid vocal fry and uptalk. That’s never a good look on anyone.

It takes time and practice to become a good storyteller. Don’t shy away from putting in the reps. The process of learning how to be a good storyteller is just as fun (and even more rewarding) as telling the story itself. And when you do master the art, you’ll be amazed at how much easier it is to create emotional connections with the people around you — one of the most important skills we can master in life.

Lead image by João Gabriel da Fonseca

You may also be interested in ...