Telling Compelling Stories Isn’t Complicated — Here are 3 ways to tell a your story so that it connects.
By now, we’ve all heard the advice that storytelling is pretty useful. Stories seem to function as some sort of social panacea.
They help sell, they build leadership, they create romantic attraction, entertain, engage, and generally make you seem like a cool person. They do everything.
But how do you do it?
While storytelling is one of those things that can be developed over the course of a lifetime, learning to tell a compelling story doesn’t have to become your life’s work. With these 3 simple strategies and a little practice you can learn to tell stories that build genuine connection in no time.
#1 Determine Your Purpose
As with any endeavor, it will be more effective if you begin with the end in mind. Know why you are telling the story before you even think about the story. This will help you to better frame out the story as you move through the rest of the story-telling process. Knowing your why involves two key considerations, the story itself and the context of the telling.
Why this story?
First, consider why the story is important to you. What is the “moral” of your story? As we will explore in the next section, all stories basically follow one very simple arc and revolve around some key transformation. What is the transformation that is on display in this story?
A key thing to remember is that the main reason stories work is that the listener comes to identify with one or more of the characters in the story and can imagine themselves sharing the experience. We “play” along with the story teller.
Stories have universal appeal, the better your story connects with the collective unconscious, the easier it will be for your listener to take their personal meaning from it.
Did you learn something? Did you overcome some challenge? Did you get the better of someone or some situation? Did you grow in some meaningful way? All of these questions will help guide you to the point of your story before you even begin crafting it.
Why tell it now?
Second, as you prepare to tell a story consider the immediate context. This can help you to both select the proper story for the situation, and tailor the story to the listeners of your story.
Some situations will be easier than others when you are tailoring your story. Speeches and presentations let you dictate the context to a large extent, while interpersonal and social stories require careful connection to the conversational thread.
Good conversations happen in a natural flow as different people make their contributions. If you don’t connect your story clearly to the greater conversation, it can be a bit jarring. It might seem like you are hijacking the conversation.
To avoid the perception of conversational hijack, be sure to connect with the conversation. Once you’ve done the prep work to understand the “moral” of your story, you can use that to connect with what was just being said.
For example, I have a story about how I got pulled over on my motorcycle and had a really transformational experience that changed the way that I related to police, the law, and my motorcycle.
This story can be naturally told from conversational threads related to motorcycles, police, trouble, tickets, the law, speeding, or even personal change. If any of these topics come up, it might be an opportunity to tell that story.
As you begin to craft your stories, take the time to connect them with the universal consciousness and your immediate context and you will start to notice that people are really leaning in to your narratives.
#2 Understand the Arc
This is one of the simplest and yet most effective parts of good story telling. You’ve probably learned about story arcs at one point or another in your life. In creative writing, there are plenty of frameworks designed to help people craft better stories. You can really go down a rabbit hole in studying the different elements of plot, for instance.
I like to keep things simple, though, so I will share with you a basic structure that you can use to frame out your stories. Since my earliest study of storytelling was about myth, I like to think of them as paradise, cataclysm, and reconciliation.
Paradise
Paradise is the starting point of a story. Everything is normal, just fine, or perfect. The beginning of the story happens before all the trouble starts. This is where you will introduce characters and lay out any relevant context for your story.
Note: sometimes, stories don’t start in the paradise phase, starting after the cataclysm instead. When this happens, there will usually be some revealing of what happened earlier. Aristotle called this beginning in medias res, or in the middle of things.
Cataclysm
Cataclysm can be thought of as the reason that there is a story at all. Something happens that interrupts the paradise that was existing. This might be some malevolent force or antagonistic person, some important event, or even something unusual.
Stories don’t need to be about an epic battle to be interesting. The cataclysm is just something that creates a question in the listener. Most jokes, for example, use some quirky event to create the cataclysm. A duck walks into a bar… Creating questions is one way to keeps listeners engaged throughout the story.
Reconciliation
Reconciliation is the conclusion. It’s the happy ending (or the tragic one, depending on the story). This is where they fundamental question created by the cataclysm is answered. The listener or reader is left with a sense that things have resolved. Maybe a hero defeats an opponent, or maybe it’s a simple perspective shift that creates the resolution.
Whatever the method of resolution, it directly relates to the moral of the story determined in the prep work above. If the point is to make people laugh, the resolution is the punchline. If it’s to illustrate a point, this will be where the point becomes clear. Without a reconciliation, it’s not a story, it’s a chronology.
Example
One day, I was out raking leaves (paradise), when my rake got caught in a root and broke (cataclysm). So, I went on YouTube and learned about rake repair and repaired my rake. Now, I have a rake that is better than new because I truly understand it (reconciliation).
Ok, obviously that story isn’t very interesting. It’s light on emotional connection and has very little moral-of-the-story. It does, however, lay out the same archetypal story structure of every story. Ever. Here’s one you might be more familiar with:
Thomas Anderson was living a normal life (paradise) when he met Morpheus and learned that humanity was enslaved by machines (cataclysm). Then he learned kung fu and a bunch of other stuff to become The One and defeat the machines on their own turf (reconciliation).
Every story that you’ve ever heard has involved some version of these three phases, and if you want your stories to connect well, they should too.
#3 Connect Emotionally
Now that you’ve determined what happens in your story (the arc) and why it’s happening (the moral), it’s time to add some flavor with details. Effective stories develop tension, and what better way to develop tension than by plumbing the depths of the human psyche?
Remember, part of why stories work is because of their universal appeal. People identify with the characters as they move through their struggles. By developing the details of the story, you give the listener more to connect with in their own experience. Notice how much time movies spend on developing the experience of the characters.
So how do you do this in your stories?
As you develop your stories notice what emotions are present for the characters. Are they angry, frustrated, confused, afraid, or excited? We all attach our own experiences to those words, so emphasizing the emotion will bring it up for the listener.
If you are a character in the story, consider not only which emotions you were feeling, but also what you were saying to yourself that emphasized those emotions. For example, consider the following.
I was so freaked out: I thought he was he was going to arrest me on the spot. What would happen to my insurance? How much was this ticket gonna be?
Listing thoughts like these helps the listener connect with their own emotional experience of the story. We’ve all experienced stress like that. Maybe not exactly like that (the cataclysm in that particular story was me being an idiot 
), but we’ve all been freaked out. Flesh out the details to provide the listener with emotional hooks grab on to.
Workshop: Prepare Your Own Story
When I was first learning about interpersonal skills I worried that if I rehearsed my stories that it would somehow be inauthentic. I should just be able to fire them off with no practice, right? They should just come up naturally.
This isn’t true for any other skill, so why would it be different about storytelling? If you want to improve your own storytelling, it takes practice. Once you develop the story, you can improvise the delivery and connect with the conversation.
To improve your own stories, you can follow this 5-part workshop process:
Choose a story
You probably already have a few of these moderately prepared. If you can’t you think of any stories from your life, here are a few questions to use as prompts:
What was the biggest perspective shift you’ve ever experienced?
What’s the most scared you’ve ever been?
What’s your most embarrassing moment?
What’s one lesson you learned the hard way?
Discover the moral(s).
Why is this story important to you, and why should it be important to your listener? If you chose a story based on one of the prompts above, that’s a great start. Remember that most stories can have multiple points though.
Do a little brainstorming to think of lessons that could be taken away from the story. Maybe there are principles that are illustrated. Maybe it’s just a sheer emotional experience that you are going for with the story. That’s fine too. For our purposes, the moral is just the reason you are telling the story.
Recognize the arc
Every story has the 3 parts discussed above. What was life like before the story (paradise)? What happened that changed that (cataclysm)? Finally, what resolved the questions/dilemma/challenges that happened as a result of the cataclysm (reconciliation)?
Connect emotionally
What aspects setting, characters, or speech (internal or external) can be used to emphasize the tension in the story. What emotions are there and how can you emphasize those emotions for the listener?
Practice on your own
While it might feel a bit silly to practice stories in front of a mirror, this is a great way to become a more fluent storyteller. Do you think actors and professional speakers only practice their stories in front of an audience? Of course not. And they are the professional story tellers.
Practice telling your story first to yourself. Listen while you tell it, and even record yourself telling the story and listen afterward. You will see opportunities for improvement. That’s how practice works.
As you practice, you’ll start to notice these components of well-told stories all around you. Doing things well doesn’t happen by accident and storytelling is no different. Pretty soon you’ll have a few stories that you can tell masterfully to others. You’ll love the way it creates connection!
