August 27, 2024
The most successful speakers, creators, and leaders know how to tell insanely good stories.
And I wanted to do the same.
But when I started, I ran into three big problems:
To solve these, I interviewed 104 professional speakers, read 41 books on storytelling, and tried out a lot of unconventional ideas.
Through all of that, I developed a 5-step system on how to tell better stories than 99% of people.
As part of that system, you’ll discover
When I first started learning about storytelling, I had a moment that made me question the way storytelling is typically taught.
In 2020, I took an expensive storytelling course here in the Netherlands. They taught us about the Hero’s Journey.
The Hero’s Journey is a classic structure—a beautiful, 17-step formula used in almost every Hollywood movie, like Lord of the Rings or Star Wars.
I loved it. So, I decided to try it out at work.
I thought, “This is going to blow my client away. Once he hears my story, he’ll pull out his credit card on the spot.”
Well, it didn’t exactly go like that…
The next day, I was on a call with that client. I launched into my story. At first, he seemed interested, but as I went on, something strange happened.
He started looking away—more and more. It almost felt like he was embarrassed for me.
When I finally finished, he just said, “Ahh… well, thanks for sharing. We’ll be in touch, alright?” And that was the end of the call.
I sat there thinking, “What just happened? Where did I go wrong?”
The story was good! But I couldn’t figure it out.
Later, I called my sister to vent. She told me, “Philipp, your stories are too long and too dramatic. This isn’t a TED Talk. It’s a casual conversation.”
That’s when it hit me.
The structures they teach in most courses are perfect for big stages, but they’re almost useless for the stories we tell in everyday conversations—at work or with friends.
Those stories need to be short—around 1-2 minutes. And in 1-2 minutes, you can’t go through 17 steps of the Hero’s Journey.
Once I realized that, I started studying every structure I could find, pulling together the parts that worked. Eventually, I developed a structure that has completely changed my storytelling.
It’s a simple 4-step system I call C.A.R.T.:
Think of your story like a cart in a supermarket—it holds all the essential elements together. Or, if you’re like me and prefer to keep things simple, just remember: C.A.R.T. rhymes with “fart.” Easy to remember, right?
Let’s break it down:
Step 1: Context
First, set the scene with a little context. Where and when does the story take place? Who’s the main character, and what do they want?
Example:
“It was October 2023, and I was walking through Central Park in New York, taking photos for my mom’s upcoming birthday.”
That’s your context: Who, when, where, what. Boom. Done.
Keep it brief so you can quickly move to the more interesting parts of your story.
Step 2: Adversity
Next, introduce the adversity or challenge the main character faces. It could be a tough decision, a physical or emotional problem, or even another person—anything that creates tension.
Example:
“As I was heading home, I reached into my pocket and realized my phone was gone. I checked every pocket, searched my bag—nothing. Panic set in: ‘My phone has hundreds of photos for my mom on it. I haven’t backed them up. Weeks of work—gone.’”
Adversity is the heart of your story. Make sure to describe the struggle, what’s at stake, and how it affects the main character emotionally.
Step 3: Resolution
Now, show how the main character responds to the challenge. What actions do they take? How do they overcome the obstacle?
Example:
“At that moment, someone tapped me on the shoulder. I turned around—it was a jogger. He asked, ‘You seem like you’re looking for something. Lose your phone?’ Then, with a smile, he pulled my phone out of his pocket and handed it to me. I was so relieved I hugged him right there in the park.”
This part makes your story engaging, but your listeners still need to know why you’re telling it.
Step 4: Takeaway
Finally, share the takeaway. What did you learn from this experience? What’s the point of the story?
Example:
“What I learned from that experience is that there are good people out there who do the right thing, and also—it’s time to start backing up my phone!”
Be careful not to sound preachy. Avoid saying, “The moral of the story is…” or “You should…” Instead, go for something like, “What I learned…” It’s more subtle and less preachy.
This 4-step structure has given my stories a solid foundation. I use it every time, and it’s helped me tell better stories than 30% of people out there.
But as I continued to share more stories, I noticed something strange: some of them still weren’t landing.
I had this incredible structure—so why was I still losing people?
At first, I had no idea. But soon, I discovered the answer.
One day, I attended a free Storytelling Masterclass.
I didn’t expect much, but that single class transformed my approach to storytelling forever.
In the first few minutes, the speaker told a story about spilling coffee on his shirt.
It might sound boring, but the way he told it was extraordinary.
From the very beginning, he had me hooked.
I was on the edge of my seat, eager to see what would happen next.
It wasn’t because the story itself was compelling—spilling coffee isn’t that special.
It was the techniques he used that made it so engaging.
After that session, I was amazed and thought, “I need to learn these techniques. I need to understand exactly how he did that.”
For four years, I immersed myself in videos, books, and courses, trying to uncover what makes a story great.
After hundreds of pages of notes, I distilled it down to 20 key techniques used by the best storytellers.
Here‘s a link to the document with all 20 techniques.
Since we don’t have time to cover all of them in this article, I’ll focus on the three techniques I use most often.
Mastering these three storytelling techniques will help you tell better stories than 60% of people.
First Storytelling Technique: Raise Questions
As a storyteller, your job is to keep your audience wanting more.
You want them on the edge of their seats, eager to know what happens next.
One effective way to do this is by raising questions.
Example:
“Just as I was leaving the park, I realized something terrible. My heart started pounding. I emptied every pocket, searching frantically. Only to find out… It was gone.”
Each sentence here raises questions:
Great stories prompt questions in the audience’s mind.
So, think about how you can hint at interesting details that you’ll reveal later in your story.
You might say:
Build anticipation!
Second Storytelling Technique: Share the Thoughts
The best stories take us on an emotional journey.
One simple way to add emotion is by sharing the character’s thoughts.
What was the main character thinking at a crucial moment?
What were their hopes, fears, and concerns?
Example:
“I thought, ‘Shoot. Weeks of work, precious memories, and hundreds of photos—gone. My mom will be so disappointed. Why do I keep losing things?'”
When sharing thoughts, don’t try to sound overly sophisticated.
Be raw and unfiltered.
Now, let’s discuss the third technique.
Third Storytelling Technique: Share the Dialogue
Often, stories involve multiple characters.
Maybe someone helped you, annoyed you, or you had a significant conversation with them.
Including dialogue can bring your story to life.
Share the exact words spoken during those moments.
Example:
“Right then, I felt a tap on my shoulder. I turned around to see a jogger. He said, ‘Excuse me, are you looking for something?’
I replied, ‘Yes, I lost my phone with all my photos on it.’
He asked, ‘Is it an iPhone?’
I said, ‘Yes, it is.’
With a cheeky smile, he pulled my phone from his pocket.”
You can include a full conversation or just a key line from one character.
The key is to use concise and impactful language.
When I began using these three techniques, my storytelling improved dramatically.
I started sharing stories everywhere—at gatherings with friends, in work meetings, and even on stage.
People loved my stories.
But after a few weeks, I hit a problem.
I had run out of interesting stories. I had recycled my three main stories several times.
“How can I find more engaging stories?”
Initially, I thought I needed more adventurous experiences.
The real answer came to me only after discovering a particular book.
A book that has greatly helped me discover an abundance of stories is Storyworthy by Matthew Dicks.
It’s a fantastic book with many valuable insights, but two specific exercises have been instrumental in helping me find hundreds of stories.
1. Storytelling Exercise: First, Best, Last, Worst
This exercise helps me recall stories I had long forgotten.
Start by taking a piece of paper and drawing five columns.
In the first column, label it “Prompt.” In the next columns, write “First,” “Last,” “Best,” and “Worst.”
Then, fill in the prompts.
Prompts can be anything that triggers a memory, such as: Gift, Travel, Job, Teacher, Book, Trouble, Car, Hobby, Injury, Pet, and Kiss.
For example, if the prompt is “gift,” I ask myself:
At this stage, I just jot down one or two words to remind me of the story.
I repeat this process for each prompt.
Once I’ve completed several prompts, I review my entries and ask, “Do any of these memories stand out? Is there anything particularly entertaining, emotional, or interesting?”
If the answer is “Yes,” that’s a story worth exploring.
To save you time, I’ll include a template with my favorite prompts in the description.
“First, Last, Best, Worst” is a fun way to uncover stories from your past.
But there’s another exercise that helps you spot stories in the present—right when they occur.
2. Storytelling Exercise: Homework for Life
Homework for Life is an exercise designed to help you identify storyworthy moments every day.
Here’s how it works:
At the end of each day, ask yourself, “If I had to tell a story from today, what would it be?”
It doesn’t need to be a grand moment.
It can be an interesting conversation, a new realization, or even something that annoyed me.
Anything that touched me.
Once I identify that moment, I write down:
Example:
Today is August 6, and my storyworthy moment was “Feeling grateful after my 9km run through the park without knee pain.”
This is significant for me because I had to stop running for 7 years due to a knee injury.
That was my storyworthy moment.
What’s your storyworthy moment today?
Let me know in the comments. I’d love to hear about yours!
When I first started this exercise, my entries were quite mundane and vague.
One of my early entries was, “I really enjoyed the peanut butter sandwich today.”
But after a few weeks, I began to notice more and more meaningful moments.
Now, I have at least one super interesting moment each week that could turn into a great story.
If just 1 out of 7 moments per week is compelling, that’s 52 stories per year.
In 3 years, that’s 156 stories.
Isn’t that amazing?
To turn these moments into stories, I do some extra work.
I craft a story around each moment using the structure and techniques I’ve learned, then save it to my Story Bank.
A Story Bank is a central place where I capture, organize, and remember my stories.
What do I include in my Story Bank?
I keep it simple and track five things:
I prefer to save my stories in Notion for easy access while traveling.
But you can use any tool that works for you—Google Docs, Notion, or even a physical journal—as long as it’s convenient.
Here you’ll find a template for my Story Bank so you don’t have to spend an hour creating one yourself.
I started my Story Bank about four years ago, and I keep adding new stories as I discover them.
It takes a few minutes to capture each story, but it’s worth it.
I know I’ll be able to use these stories for years to come.
By using the structure we discussed, incorporating the techniques you’ve learned, and saving your stories to a Story Bank, you’ll be a better storyteller than 80% of people.
To reach the top 1% of storytellers, there are two more steps you need to take.
When I started practicing my stories, I initially rehearsed in front of a mirror, as that’s what most people recommend.
However, I quickly realized that this advice wasn’t very effective.
Why?
It’s unnatural to see yourself while speaking. All it did was make me self-conscious about how I looked.
I would think, “Do I always look this tired? Where did those wrinkles come from?”
Rehearsing in front of a mirror wasn’t helpful.
Instead, I found it much more effective to rehearse my stories out loud in my room.
I often use random objects in my room as my imaginary audience.
For instance, my water bottle represents one person in the audience, the photo frame another, and my dog a third.
I hold eye contact with each object for a few seconds before moving on to the next.
This technique has improved my ability to make deliberate eye contact.
I usually rehearse my stories 2-3 times before sharing them with an actual audience.
Rehearsing 2-3 times is enough to become comfortable with the story and to refine every detail.
After rehearsing, I share the story with someone I know to get feedback.
Initially, I asked friends and family if I could share my stories with them.
This worked well for a while.
However, after asking my best friend for the 7th time, I started to feel awkward.
I thought, “He’d probably prefer to do other things than listen to my stories every week.”
I considered hiring a storytelling coach but soon realized they were very expensive.
Good coaches cost at least $200 an hour, and excellent ones can charge thousands of dollars.
Then I discovered a game-changing solution: I hired an English language tutor.
But I didn’t use the tutor for English.
Instead, I used the tutor to work on my storytelling.
Platforms like preply.com or italki.com offer private English tutors for as little as $3 per hour.
In these one-hour sessions, I share 2-3 stories and ask the tutor for feedback.
Even though these tutors are not professional storytelling coaches, they can still provide valuable insights on how they felt about the story, where they lost interest, and how it impacted them emotionally.
After sharing 2-3 stories, I use the remaining time to improvise a few stories on the spot.
This approach is a fantastic hack.
Meeting with a tutor once a week for a few weeks has made a significant difference.
However, paying someone to listen to you has its limitations.
That’s why the last step is absolutely crucial.
Even though I knew how to tell stories, it took me a while to use them in everyday situations.
I often didn’t realize until hours later that I could have used a story in a particular moment.
This changed once I adopted a new habit.
Instead of waiting for the perfect opportunity to tell a big story, I started telling small stories in one specific situation: when someone asked me, “How are you?”
Previously, I would respond with simple answers like “Good, thanks” or “Yeah, great. The sun is finally out.”
Now, I share a tiny story.
Example:
If someone asks me today, “How are you?” I might respond like this:
“I’m good. Actually, I had a beautiful moment. After two weeks on the road, I walked into my apartment, flopped onto my couch, and let out a big sigh. I was so relieved to be back in my own space, with my routine and my coffee mug.
Anyway, what about you? When was the last time you returned from a big trip, and how was that for you?”
That’s it. Just a small story that reveals a bit more about me as a person.
When someone asks me “How are you?” I try to give a response that’s more interesting than just talking about the weather or traffic. This could include:
Remember Homework for Life?
You can use those storyworthy moments when someone asks, “How are you?”
You might wonder, “Isn’t it awkward to share a story about yourself when the other person didn’t explicitly ask for it?”
I initially found it awkward too.
But after years of sharing these small stories, I can tell you it’s worth it.
Not only will you improve as a storyteller, but you’ll also have more meaningful conversations with coworkers, friends, and even strangers.
That’s it! By following the 5 steps you’ve just learned, you’ll know how to tell better stories than 99% of people.
Today, we covered some storytelling techniques, but there are more to explore.
For additional insights, check out my book, The StorySelling Method, or read this next article in which I share my favorite storytelling techniques.
Enjoy!
Are you ready to transform your storytelling skills?
Discover how your storytelling skills score and uncover useful insights to help you become a charismatic storyteller:
