Stop Boring Your Friends and Get Better At Storytelling


Storytelling is an essential skill in today’s world. From big journalistic articles about world-changing events to smaller updates to your friends about what you did over the weekend, we consume and tell stories on a daily basis. Being able to tell a good yarn will help you communicate effectively with your peers and employees, opening doors for you that can lead to new opportunities.

The catch, of course, is that storytelling can be difficult if you don’t know what you’re doing. The ultimate failure of a story is boredom: a non-reaction that is so non-plussed people won’t even bother to summon the energy to say “HEY, stop talking! You’re wasting my time!” 

The good news is that there are surefire ways to avoid telling boring stories, and they’re all contained in this awesome class from Keith Yamashita, founder and chairman of SYPartners. He’s consulted countless CEOs on how to use better stories to be better leaders, and although his class is catered specifically to business leadership concepts, there are plenty of helpful insights to make any story you tell less snooze-worthy. 

Below, we talk about the three questions you need to ask yourself about your story to make sure it’s on the right track.

1) What type of story are you telling?

Stories can be boring if they have no focus; if you’re not focused on your story, how can you expect your listeners to not yawn half way through? Avoid this by going in knowing what type of story you’re telling. Keith outlines four categories that your story could fit into depending on what you’re trying to accomplish. 

Story of Me

If it’s a casual story to your friends about something that happened on the weekend, you’re probably going to be telling a story of me. A story of me involves highlighting your personal journey as you’ve experienced it: what you went through, how it affected you, what you learned about yourself, etc. Telling this type of story well will require you to open up about your own struggles and realizations, so be ready to get get personal!

Story of Our Company (or a group)

Maybe instead of a personal story, you’re telling a story about a group of people and what they achieved or experienced. A good example of this would be a story about your group of friends and the mischief you got into when you tried to sneak into a second screening of the Matrix, or the struggles your design team went through to arrive at the perfect user experience for the latest version of your app, or about your high school sports team winning a championship despite being the underdog. These may overlap with a story of me, so be sure to focus on whether your story reflects the experience of the group as a whole or you as an individual.

Story of an Idea

As Keith mentions in his class, Steve Jobs is a great example of a master storyteller that focuses primarily on ideas. Before the release of the iPod, for instance, it was simply a story about a device that has a thousand songs and fits in your pocket. Consumers captivated by that idea made the iPod a huge success when it released. A story of an idea doesn’t have to be about a product though. Politicians could be considered storytellers that focus on ideas about how the country could look with them in office. On the other hand, architects could sell an idea of what a building might look like through blueprints and models. Whatever idea you choose, be sure to make it the main subject or hero of the story instead of yourself.

Story of Results

When you want to communicate how your actions have impacted the world, a story of results is what you’re after. In this case, you’ll want to take the hard evidence of your work, whether it be a marketing project or a surgical procedure, and communicate what it means in a way that is widely understood by your audience. TED Talks are great examples of these stories: speakers will often take complicated data and translate it into more digestible stories for a broader audience.

To get the full scoop on how to tell your story, check out Keith Yamashita’s class on Skillshare!Take keith’s class

2) What components are going to make up your story?

An unstructured story is a bad story, and if your audience can’t follow your story, then you might as well not tell it. To help you navigate, there are structural components of story that are universal and will help you fill in the details that make your story unique. By using these components Keith highlights, you’ll be able to tell a fluid narrative that fits into a format people are familiar with and keep them engaged from beginning to end.

Here are some of the bigger components of story you’ll want to think about using:

“Once upon a time”

Almost everyone is familiar with this trademark fairy tale opening. Of course, you don’t have to literally say that line every time you start a story, but mechanically, what that line does is help you set the scene that your story takes place in. It establishes an important context from which your audience can understand the story that follows. Without acknowledging the world where your story takes place, the audience may be without a key piece of information and might receive your story differently than you intended. Imagine Star Wars without “A long time ago in a galaxy far, far away…”!

Great characters

A crucial piece of any story is the players in it. When you’re telling your story, be sure to think about how the characters help push the plot, or story events, forward and what they add. Faceless names don’t make people lean forward in their seats, they need to be unique, even if it’s a short anecdote that helps you establish what type of person a character is (“this is the kind of person that would do x, y, and z”). Establishing a clear hero and villain of the story is always helpful, too; when those opposing forces are set up, you can then work in ancillary characters that color your story and make it interesting.

Challenging situations

Without a challenge, there’s no conflict, no drama, and no lesson learned: all components that Keith lists as important to consider in your story. Your characters could be the funniest, most interesting people that have ever been imagined, but if they just go about their day, taking care of everything they need to without obstacle, then go right to sleep at night because they’re feeling accomplished, we learn nothing about their true character and wind up leaving unsatisfied.

“Happily ever after”

If you’ve ever listened to someone tell a story and listen as a silence hangs in the air after they finish it, and, even worse, felt an urge to jump in and say “and then you found $20?” to defuse the awkwardness, this is likely because there was no “happily ever after” moment. What Keith means by this is having a true ending that ties off the story neatly with a moral, an answer to why it matters in the world or to humanity. Without this final bookend, your audience will be left on the precipice of an ending, unsure of what to make of the ten minutes you just had them wholly engaged in.

Is there an archetype that fits your story?

A story archetype is a structure of a story that has been used so frequently throughout human history that it’s developed a reliable pattern. When telling your story, you can use these different patterns to your advantage and craft a reliably engaging story, filling in your own unique aspects while sticking to the familiarity of the archetype. They work because they’re stories that everyone knows and has probably even experienced themselves in their own lives.

Here are a few examples of the archetypes Keith discusses:

Coming of Age


“After years of learning and growing, you’ve reached a milestone. You know who you are. You are strong, experienced, and confident. You’re ready to take on whatever comes next.” This is the story you tell when you want to communicate a sense of experience or strength to your listeners. You could tell a story about how you finally learned how to do long division, or when you finally realize your true potential as a sandwich artist at Subway, for example. Everyone grows up and learns from their mistakes they made in the past, so by using the coming of age archetype, you’re able to tap into that shared experience and craft a story that will resonate.

True as it Ever Was

“Your purpose and values have endured throughout the years. The world has evolved and you’ve changed with it, but your core beliefs have remained intact. They guide everything you do.” Want to communicate that an unwavering belief is the best way to achieve greatness? This archetype is the one to go with. Weave a yarn that shows how your commitment to paying your workers a good wage, even through economic downturns, has lead to your company succeeding in ways you never thought possible. It will establish you as a port in the storm of distractions, fads, and misdirection and win the trust of your audience.


“You’ve always had a clear objective and you’ve pursued it relentlessly. Over time, you’ve summoned your talent and passion to turn your vision into reality. Through twists and turns, you’ve maintained your focus, and you will never let it go.” Probably one of the more common archetypes you’ll see in pop culture, quest stories will help you communicate your persistence, passion, and dedication to achieving a milestone. Make yourself into Indiana Jones: dodging spears, discovering (and losing) treasure, whipping bad guys, and taking on whatever challenges you face as you strive for the ultimate prize.

This is just the tip of the iceberg, and if you’re really serious about starting to communicate through stories more effectively, I’d highly recommend checking out Keith’s full class Storytelling for Leaders: How to Craft Stories That Matter on Skillshare. You’ll be winning hearts and minds in no time.

Written By

Ethan Mantel

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