“As human beings, we make sense of our experiences through stories.” — @McKeeStory in @HarvardBiz 
I just finished reading Exhalations by Ted Chiang, a collection of short stories. One of them, “The Truth of Fact, the Truth of Feeling” was about how a person remembers their past, and how that story about ourselves can change depending on how we view ourselves. For example, an inside joke I have with a racquetball buddy is that I’m undefeated in all the years of playing against him. The joke is that because I can’t recognize my own failures, I automatically forget when I lose… and therefore I remember myself as undefeated!
But, what does storytelling have to do with positivity and productivity?
When I think of storytellers, the image that comes to mind is someone that’s the life of the party, regaling a crowd with an amusing story, or perhaps a dinner host or a preacher or a parent tucking their child into bed. What all these storytellers have in common is that they control the conversation and they are influencing.
“Good storytellers are not necessarily good leaders, but they do share certain traits. Both are self-aware and both are skeptics who realize that all people — and institutions — wear masks. Compelling stories can be found behind those masks.” 
Here’s what we’ll cover to unlock the hidden skill of storytelling:
- Basics of Better Stories
- Find Your Own Voice
- Tell a More Compelling Story
- Stop the ‘Companyspeak’
- Stories in a Fast Paced World
- Advanced Techniques for Better Stories
1 — Basics of Better Stories
Aaron Sorkin, who wrote the West Wing, A Few Good Men, Moneyball, and The Social Network, has a MasterClass that teaches screenwriting. Below are a few of his advice, which I’ve adapted for use on emails. Because let’s face it, we do A LOT of storytelling in emails and we can do better.
“Get to the end of your first draft before you even begin to rewrite it.” For your email, lay out the “bones” of your email before you go back and do rewrites. I’ve noticed recently when I write emails at work, I start in the middle. I write the body of the email, and then I go back to the intro and closing.
“Connect your characters to their intentions and obstacles.” For your email, make sure it has enough background and context to make sense. Make sure it clearly describes the problem and what your point is. In other words, make it worthwhile to read. For me, if I finish watching a movie and by the end of it I don’t know why it mattered, that movie just wasted the last 2 hours of my life. (Cough cough, Infinite starring Mark Walhberg.)
“Show the audience what they want — not who they are.” This is next level advice right here. When I write an email to someone, I clearly know their position and what I’m asking them to do. The next level advice is to understand what they personally want. For example, maybe Joe from Accounting makes sure the correct funds are applied to the correct projects. But maybe Joe wants to make sure they are done early so he’s not up against his financial deadlines. Help him help you.
For more on emails, check out my Uncommon Rules for Email.
2 — Find Your Own Voice
When I think of Jeff Bezoz, the impression I get is a very self-centered person focused on his personal accomplishments and wealth. (Bezoz was supposed to be the first billionaire in space, but good ole’ Richard Branson made a last minute change to beat him to it, taking off on July 11.) But when I think of Chadwick Boseman, someone who had colon cancer, “kept his condition private, continuing to act while also extensively supporting cancer charities until his death in 2020 from the illness,” I have a very positive impression of the guy.
The thesis is that what we choose to tell the world actually reveals the truth about ourselves. For everyday people like us, that means the stories we choose to tell and the questions we ask (yeah, you better be asking questions and not just talking about yourself) are insights into who we are and what we value.
Neil Gaiman, author of Sandman, Stardust and Caroline, teaches in his MasterClass:
“Finding your voice — Your writer’s voice is what makes it possible for someone to pick up a page of text and recognize that you wrote it.”
When it comes to telling stories, what’s your style? What’s your worldview (i.e. how you make sense of the world)? Much like the worldbuilding that occurs in the Harry Potter or Marvel universe, each story adds depth and reveals how things really work. So, you need to understand how you think the world works, to identify where you may have blindspots.
“Developing a worldview as a writer takes time and self-exploration. Sit in a quiet room and visualize a picture of your life in your head. Think of what’s important to you. Your north star. That’ll be the center of the portrait.” — @bryanjcollins about @SalmanRushdie
Storytelling is key if you want to move people. So if you’re looking to make a positive impact and to be more productive, learn how to move as many people as you can in the direction you want. Understand how your worldview compares to your audience’s. Then use your story to move everybody towards your north star.
3 — Tell a More Compelling Story
Malcolm Gladwell, author of bestsellers Blink, Outliers, and The Tipping Point, is an expert at taking complex, big ideas, and distilling them into understandable, relatable terms by using powerful stories.
Isn’t that what we all want — convey to others our point in a way that’s relatable?! Yet, we most likely fall flat in a number of ways. For me, I get too rambly because inside that main point, I also want to also make a billion additional sub-points. Or sometimes I’m trying to be so efficient with my communication, that I leave out the ‘why.’
“Telling a compelling story is how you build credibility for yourself and your ideas. It’s how you inspire an audience and lead an organization. Whether you need to win over a colleague, a team, an executive, a recruiter, or an entire conference audience, effective storytelling is key.” — @jboogie in @HarvardBiz 
Let’s get some pro-tips from Gladwell, where on MasterClass he teaches writing: 
“Life is very limiting if you are unable to empathize with the experiences of others. Writing, at its best, is about transcending one’s own experience of life. It’s an empathetic act.”
I’m an engineer by education, so I’m used to communicating in factual, data driven ways… which can get quite boring. But when it comes to inspiring people, I try to communicate with compassion, putting myself in the shoes of others, and extrapolating what I think is going on in their head and saying something that’ll catch their attention. The trick is — even in dry, data-driven situations, strive to understand the audience’s emotion and aim to be empathetic. (Or telepathic, if you’re that good.)
“Don’t interview a source looking to “find” anything interesting in what they have to say. Effective interviewing is all about convincing them to find themselves interesting — and you’ll hear gold.”
Final thought, when you’re having a conversation with someone, ask questions that make the other person feel great about what they’re talking about. If you can make the other person feel special, then the entire conversation transcends into something special.
4 — Stop the ‘Companyspeak’
“When executives need to persuade an audience, most try to build a case with facts, statistics, and some quotes from authorities. In other words, they resort to “companyspeak,” the tools of rhetoric they have been trained to use.” — @McKeeStory in @HarvardBiz 
At work, I’ve been complimented over the years for my ability to communicate in simple terms. People have told me that they appreciate how I can break down complex concepts into digestible, relatable terms. To be honest, it always surprised me. I’m not the smartest guy (I know, I know, the stories we tell ourselves, but that’s another topic for another day), therefore, I figure if I can understand it, then I should be able to “parrot” back what I think is going on and add my own thoughts.
And then there are analogies, something that I’m horrible at. But, when it comes to relating to others, I find analogies and stories are critical to conveying a point with a punch. Even if my analogy or story fails, it’ll at least create some laughter at how bad it is!
Malcolm Gladwell, famous writer with eccentric hair, gives this piece of advice:
“Go through the same story again and highlight or underline the story’s “candy.” What parts of the story is most captivating — what could you tweet from this story to make it clickable? What did you learn that really stuck with you? How did the author include this “candy” and in what format?” — @Gladwell in @MasterClass 
What’s the “candy” in your story? What’s the point you’re trying to make in that story? Practice makes perfect, so keep telling stories, keep reading your audience to see if you’re connecting, and then adjust next time.
5 — Stories in a Fast Paced World
Holy cow it’s a fast paced world! Zero inbox is impossible to keep up with (and nor should you). Social media feeds have infinite scrolling. Our poor brains are in overdrive from the moment we wake up.
So, when it comes to connecting with others and inspiring them, the window of opportunity to do that is tiny. People’s attention spans are just too short these days. Our options are to either talk faster or hope our story is so gripping, it holds their attention.
“Leaders gain trust and teach people what’s important to them by telling stories. But these days there’s so much to attend to — now! — coming at us so fast. You might be tempted to let slide your soft skills, like how to tell a useful story. Just get to the point and move on to the next thing on the list. No time for fluff.” — @HR_STU @HarvardBiz 
Maybe it’s romanticizing, but I really love the image of sitting around a firepit with friends, drink in hand, and listening to great stories. Or perhaps it’s a scene from a movie where the hero gives a stirring speech before heading off to battle. Why can’t we achieve this level of memorableness in our daily life?
“For even as the digital age compels us to develop ever-increasing capacities for a switch-your-focus-but-remain-present state of mind, as a leader you still have to be able to convey a narrative that resonates with your people and inspires them to move with you in the right direction.”
Two tips in this fast paced world:
- Tell them what you’re going to say, say it, then tell them what you just said. This works especially well in work settings, when you’re presenting to an audience. Just don’t forget to use stories as much as possible to make it even more memorable.
- Surprise the audience. Try talking with a slower cadence, for suspenseful effect. Open with a joke or a humorous story. For example, I just emailed a very high-level executive to coordinate an upcoming speaking event, and he replied back with what looked like a serious response but was in fact a joke about how he procrastinates until the last moment, panics, and then completes a task. Hilarious.
6 — Advanced Techniques for Better Stories
One of the best pieces of advice I ever received about how to give great speeches is that I have permission to tell the story how I want to tell it.
For example, imagine I’m telling you a story about how I found a copy of the very first Batman comic book at a garage sale. (I didn’t, but I imagine it all the time.) All you need to know is that I’m there at the garage sale, rifling through a stack of seemingly worthless comics and magazines, when I stumble across the first Batman comic book. At that moment, the clouds parted and a ray of sunlight bathed me in its warmth. And I knew it was destined to be part of my life.
Now imagine if I told that story in detail and in chronological order. How I drove up the driveway, how there were old lamps on the left and a broken lawn mower on my right. That explains why the grass was absurdly tall. That there was a dog laying on the garage floor… WHO CARES.
Telling stories is how we connect with others, and as a leader, it’s how you motivate people. In our quest to be more positive and productive, telling the most powerful story possible helps us make an impact and save time.
Here are some powerful tips to elevate your storytelling game:
Know what you want your audience to leave with. Once you know your objective, “create a clear vision of the story you want to lay out. A vision is a projection of yourself into the future. Unlike a goal, a vision doesn’t have a clear finish line. A vision is big, bold, audacious — an ideal to aim for, not a box to check.” 
Add a personal story when giving a report or presentation. “This weekend I was thinking about this presentation when I remembered … [insert a personal story.]” Don’t be afraid to buck the norm and throw in your personal style, such as your sense of humor.
Go ahead and exaggerate. You might disagree with me on this, since it implies being disingenuous or perhaps lying. But consider this, the point of a story is to convey a point to the audience. As long as the intention is positive and to benefit the audience (not self-serving), then exaggerating a story is ok because it helps the audience understand and remember the story.
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- Storytelling Can Make or Break Your Leadership by Jeff Gothelf
- How to Curate Your Digital Persona by Ben Dattner and Tomas Chamorro-Premuzic
- Disrupt Your Own Narrative by Michael Gervais
- Storytelling That Moves People by Robert McKee and Bronwyn Fryer
- How a 2-Minute Story Helps You Lead by Stewart D. Friedman
- Neil Gaiman Masterclass Review: Can He Teach You The Art Of Storytelling? by Bryan Collins
- Is the Aaron Sorkin Masterclass on Screenwriting Worth It? By Carson Reed
- Malcolm Gladwell’s MasterClass wasn’t what I expected (MasterClass Review 2020)
- Malcolm Gladwell Masterclass Review 2021: Will It Make You A Better Writer? By John Wolcott
- Salman Rushdie Masterclass Review: Can He Teach You About Storytelling? by Yaseen Sadan
- 15 Minutes Of Storytelling Could Boost Productivity By 23% by Esther Choy