How to Tell Your Story

UPDATED: July 11, 2023
PUBLISHED: October 22, 2018

We were in the minivan. I was 12 years old, traveling north with my family down rural Minnesota roads on the way to our small lake cabin for the weekend.

The scene in the van always looked the same. My father drove and listened to the Twins or Vikings game on the radio, my mother read her book and complained about having to read over the sound of the game. I, too, read from my seat in the middle row. My younger brother sat in the back, listening to a Beach Boys cassette tape, and my younger sister slept next to him. Every drive, for five hours, it was the same; each of us keeping quietly to ourselves.

But on this particular trip, our relative silence was broken by spontaneous bursts of laughter from my brother.

It was annoying at first, as noise emitting from little brothers tends to be. And then it was confusing; what was suddenly so funny about “Help Me Rhonda”?

The mystery was quickly solved when I realized he wasn’t listening to the Beach Boys but rather a tape my mother had checked out of the library—a storytelling tape.

On the cassette were 10 or so stories, told live by different storytellers at the National Storytelling Festival. As an older sister, it was my job to be disinterested in whatever my little brother was doing, but this simply couldn’t be ignored. His laughter was so genuine that we all wanted a piece of it. My mom made my brother remove the tape from his Walkman, my dad reluctantly turned off the game, and we played the tape from the beginning for the whole van to hear.

Though we varied in age, experiences and road-trip agendas, we were all equally captivated. We laughed until we cried for all of Side A and most of Side B until we arrived at the cabin. We were the most united I ever remember.

All it took were a few stories.

That was one of a handful of vivid memories from my childhood when I witnessed and experienced the grip a story can have on an individual, the glue it can become for a group.

Several years later, I entered and won a national storytelling competition. The grand prize was the opportunity to tell a story at the very festival where that road-trip cassette tape was recorded. So I traveled with my mother to the National Storytelling Festival in Jonesborough, Tennessee, where every October people from all over flood a no-stoplight town and gather under enormous tents to hear stories from master tellers.

The tellers aren’t there to sell a product or promote an agenda, but rather to connect the people who squeeze into those tents by the thousands. I watched and listened as the tellers’ stories mesmerized the crowd and had the distinct sense that the impact of storytelling went beyond what meets the eye.

When the festival concluded, my mother and I traveled back to the airport together. She looked at me and said, “You could do this, you know. You could be a professional storyteller.” I scoffed at her and rolled my eyes, as is teenage custom. “Oh yeah. I’m going to tell stories for the rest of my life. Sure.”

And though she now likely feels the urge to say, “I told you so” to me on a daily basis, I like to think we were both right because, yes, since that moment, stories have been my life; they are what I do, they are what I know, they are how I earn my income and how I make my difference.

However, the storytelling I do has very little to do with my stories and everything to do with helping you tell yours.

And that is why I am here. As a reader of SUCCESS, you surely have goals similar to those storytellers who came into our minivan so many years ago, and you want break down the barriers that stand between you and your goals. You want to compel your customers or colleagues to turn off whatever is distracting them and pay attention to you. You want to engage people in real, meaningful ways such that you’ll be remembered long after the interaction is complete.

Just as my family came together in the van during that drive to the cabin, so do stories unite teams, connect customers to brands, and close the gaps that divide us.

When Storytelling Works Best

I once received an email from a woman who used storytelling to great success and wanted to tell me about it. It was a special occasion and she had desperately been trying to secure reservations at a restaurant that was impossible to get into. She thought she had tried everything, but after hearing me present about the power a story can have, she decided to try one last time to get a table. So she called the restaurant and asked to speak to the manager, this time telling him the story about what they were celebrating and why the restaurant was so special to them. “And we got the reservation!”

I tell you this not because I think your most pressing need is getting a table at a local hotspot, but rather to illustrate that when you feel like you’ve tried everything, the thing you’ve likely missed is the story. Whether you are struggling to get someone to understand what is truly at stake, or you are trying to compel someone to do something or choose you, storytelling is valuable in all types of scenarios.

Storytelling and Sales

If you are in business, it’s likely you are suffering from a little known, but alarmingly common plight that plagues entrepreneurs and companies across the globe. I call it TTT Syndrome. TTT stands for “Through the Trees.” You know how difficult it can be to see the whole forest (the big picture) when you’re focused on each individual tree (the day to day of your business).

It is your job to be obsessed with the finite details of your work—to know every last metric, to eat, sleep and dream the features of your product or service, and to never stop telling the world about it. However, as you become increasingly more entrenched in the details, it’s easy to forget the bigger picture and, more importantly, to communicate what that bigger picture means for others.

Several years ago, I was on a conference call with a potential dream client. She asked all the tough questions, and I was feeling pretty good about myself for having the answers to all of them. I told her everything she needed to know about the program and the product, the deliverables, and why I was qualified for the job. As I hung up the phone, I had no doubt that I’d nailed it. I half expected her to send me an email right away to confirm that I had the job.

But that email didn’t come. Several days passed and still nothing, so I followed up with a breezy message—something about looking forward to the possibility of working together, and was there anything else she needed? I tried to bury any hint of desperation in my upbeat tone. To my delight, she wrote back! But to my dismay, she simply said, “I just need something… more…”

What was she even talking about? I’d given her everything—every detail of every last tree I was growing in my small business forest. After a moment of panic, it came to me. I didn’t give her the thing she needed most: a story. One of another client and what hiring me meant for their success. A story about results.

I’ll be honest. It’s not always comfortable to tell these kinds of stories. In an effort to not sound braggy, it’s easier to stick with the facts. However, in those moments when everything “makes sense” and they are still not saying yes, it’s because logic is only part of the equation. Emotion is the other, more important part—the part that compels them to say yes, instead of convincing them to.

So I wrote back. This time, instead of talking about more trees, I told her a story about a recent phone call I had with a woman who had seen me speak. She said my message transformed her work by solving a problem her team had been struggling with for a long time. I typed up that story and then read and reread my email before hitting send. Five minutes later, I got a response: “Let’s do this.”

If ever you are trying to sell—whether it’s a product, a service or an idea—and your message keeps falling flat, it’s possible you are suffering from TTT Syndrome. Take a step back from the features, benefits, data, metrics and whatever else rolls around in your brain all day, and look at the forest you’ve built. Tell the story of the value you’ve created and the difference you make.

Storytelling and Leadership

Storytelling isn’t only about making sales. It’s a key to great leadership, too. The best leaders are great communicators who captivate people. The most captivating communications are stories. If you have your sights set on leading the masses—or even a small team—fast track those goals by telling better stories, more often.

Think about the people whose advice you took, whose paths you emulated, whose guidance you accepted. Think about the people who have influenced you. Think about the people you have followed and why. It’s likely story had something to do with it. Here’s why:

  1. Storytelling establishes credibility.

A requirement of leadership is trust—faith that you are qualified to lead people in the direction they want to go.

How do you establish that credibility? How do you let your potential followers know you’re the leader they need? You could tell them your title and how long you’ve had said title and hope they’re impressed. You could give them a list of accomplishments and hope they’re impressed. Or, you could tell them a story about what you did to earn that title or what you’ve done while you’ve had that title and know they’ll not only be impressed, but invested, too.

Here’s where wannabe leaders often go wrong. When trying to establish their credibility, they think a conversation focused on quantity trumps one focused on quality. They opt for a list of many accomplishments instead of diving deep into the importance of one success.

If ever you are in the position where you need someone to understand that you are the man or woman for the job, by all means, share the laundry list of your relevant skills and credentials, but do it after you tell a story that highlights the one that is most important. The most powerful way to establish your professional credibility with a group of followers, be they employees, clients or potential customers, is to share one story of you implementing your expertise. One well-told story will accomplish much more than a list of services.

Are you a turnaround specialist for struggling companies? Tell the story of a particular, distressed client and the relief they felt when you showed them how to turn it around. Are you a real estate agent specializing in the luxury condominium market? Tell the story of one seller, one buyer and the one killer sale that was a win-win for both.

The best leaders are those who understand that the power of their leadership is not in the title they hold, but in the stories that happened to earn that title. Telling those stories in a strategic way will get you the respect you deserve.

  1. Storytelling enables controlled vulnerability.

In today’s business landscape, being authentic and vulnerable is so important. And not just because in the age of social media, the world wants to know your story the moment you achieve a position of leadership, but because if you don’t tell your story, someone else will… and you might not like their version.

So, who are you? What are you about? Can people trust you? Whether they know it or not, your followers will remain restless until their questions are answered and their concerns are mitigated. Your effectiveness as a leader is entirely dependent on how quickly and thoroughly you can satisfy these demands.

Fortunately, storytelling gives you the perfect platform for delivering the vulnerability and authenticity people crave, while at the same time maintaining control of the messaging. Whether the story is inherently positive in nature or deals with sensitive information, a well-crafted, well-placed, well-told story can help any leader navigate disclosure.

Storytelling Beyond Business

There’s a meme about doing anything creative that I found several years ago. It goes in order from “This is amazing!” to…

This is tricky.
This is crap.
I am crap .
This might be OK.
This is amazing.

Anyone who works for themselves can likely relate. I sometimes cycle through this series of statements multiple times in a day. It’s exhausting! And those middle few phases—the ones where you second guess yourself—are sometimes hard to snap out of. Although storytelling has obvious implications in business or relationships with other people, I believe the most important stories you can ever tell are the ones you tell yourself.

In those dark moments, do you have a story ready? A story of a time you made a difference in your customer’s life? A story of a time someone believed in you? A story of a time a spouse, or child, or friend or family member stopped you and told you how great you are, how proud they are, or how much your work matters?

There are a million different places you can use stories to your advantage, but none of them matter if you don’t have your own story straight.

Finding Your Story

So you may be asking how you can get started harnessing the power of stories in your business or career. The first point is to understand what a story really is. I’ll give you three main points.

  1. A story must have identifiable characters. For your message to be a story, there must be a character your audience can identify with and care about. Most often it’s a person—it could even be an animal—but it is definitely not a company or product.
  2. A story must include emotion. A recitation of events will not make a compelling story. Include emotions to draw your audience in.
  3. A story must include a moment. Statements like, “We’ve always been committed to excellence,” have their place in business. However, for your message to be an effective story, choose one moment when that excellence was exemplified.

There is more to consider, but that should be enough to get you started. So now you’re ready to be a better storyteller. You know why stories work and what to avoid… now what?

To begin the process of story-fying your messages, think first about the message you’re trying to deliver. Clarity of message is critical to the effective use of storytelling in business. It’s the difference between the “Let’s do this!” answer and the “Why did you just waste my time?” brow furrow.

Once your message is clear, think back on your life and business experience and look for moments that show this message in action.

If it’s a sales message, you may need to find a story about a time your product made a difference for someone. If it’s a story for your team or to help establish yourself as a leader, look for moments in your life when you exemplified leadership qualities. Keep in mind, anything is fair game! Some of the best business stories I’ve heard weren’t actually about business at all, but rather stories from the teller’s personal life.

Remember, people want to do business with people. The moments you choose will become stories that will connect you in ways flow charts and compensation plans can’t.

It’s like the story I told you at the beginning of this article. I don’t know if you grew up in Northern Minnesota or were the oldest of three kids or what sports teams your dad liked. I don’t even know if you’ve ever even been on a road trip. But I’m pretty sure you could imagine me there, in that van, as if you were there yourself. And in that moment, as you were listening to a story about the power of story… you were actually experiencing the power of story.

And it’s my hope that the next time the stakes are highest, you break down the barriers and bridge the gaps because you chose to tell a story.

This article originally appeared in the Winter 2018 issue of SUCCESS magazine.

Kindra Hall

Kindra Hall is the bestselling author of Stories That Stick and a sought-after keynote speaker. She is the president of Steller Collective, a marketing agency focused on the power of storytelling to overcome communication challenges.