Storytelling is made up of simple elements that drive people to act, laugh, feel compassion and relate to others (even buy your products or services, or hire you). It’s knowing how to hit the sweet spot of elements to achieve an effective story that entertains and informs. Not too long, not too short. Enough detail, but not too much. Kinda like porridge, not too hot or too cold, but just right!
The reality is that everyone has a story to tell, but not everyone is a natural-born storyteller.
And even if you master telling stories, what stories do you tell?
It’s not as scary when you have a guide to help you through the process, and that’s where this blog comes in. I promise, because I have seen it manifest in my life, that it will get easier to tease out your stories once you know how to tell them and where to find them.
Storytelling is an art form, and with practice you can make storytelling a great new skill to help showcase your expertise through your experiences.
In my book, Ditch the Act, I discuss how sharing your stories are crucial to building your personal brand. And if you want to get hired or run a successful business, having a strong personal brand is key. To make this whole storytelling process easy, I have a gift for you. It is my Storytelling Worksheet that breaks down step by step what to do, including prompts to tease out the stories you can tell. I’ve linked it here for your reference.
When I was asked to speak at the 2020 Caribbean Future Summit, I chose to focus on how to harness the stories in your life to persuade people to hire you. You can listen to my talk, or read my article to learn the key principles behind creating stories that stick. This information is not only useful for those seeking jobs, but for startups that want to grow or for mid- to large-sized companies looking for talent.
Experience leads to expertise
Let me tell you a story. I had an awesome childhood with a family who loved me, yet I was often picked on for having freckles, or made to feel like an outsider. This bullying was a small part of my story, but it is an important one. Being picked on in elementary school really shaped who I am, especially in how I dealt with it.
Being an outsider was tough. It was even worse for me because I had difficulty sharing how I felt. Actually, it’s still something that I struggle with today because I often internalize all my feelings and try to be macho or tough, pretending like things don’t really affect me, when they really do.
I have one vivid memory of young me standing in line on the playground, eagerly waiting to be chosen for a basketball game. Standing as tall as I could to make myself stand out more, I desperately wanted someone to pick me for their team.
I watched the team captains go, “You, you, you.” I’d just stand there, watching everyone else beside me happily get chosen. I kept waiting, and, of course, was picked last.
Before other games, sometimes I wouldn’t even be picked to play at all.
That’s pretty defeating—actually humiliating—and when that happens enough times, you just stop doing certain things.
I remember being super sad and eventually just giving up, not even trying to get involved in the games. I’d try to convince myself that basketball was just a stupid game and that those people were stupid, but on the inside I was still sad.
My Mom is pretty perceptive, and she knew something was wrong. She eventually pried what was happening out of me. Being the problem solver that she is, she looked at me and told me that if the other kids were letting me play in their game, then we were going to Sport Chalet to get my own basketball.
I’m now in Sport Chalet, and I’ll never forget this moment. There was a white Michael Jordan limited edition basketball, and I just had to have it. With my new basketball—my key to acceptance—I remember bringing it to school, excited until I realized that basketballs don’t fit into backpacks. I found myself literally carrying around this white ball, and everybody was just staring at me. But I had no idea what to do with it.
Recess came and it was my time to shine. I announced to everybody, but no one in particular, “I’ve got a ball, who wants to play?”
I was waiting for someone to respond with “Yes!”
I did get a response but not the response I wanted.
They already had a ball.
That was the first time that I learned that having a ball doesn’t necessarily get you in the game. I had an expectation that my basketball was the key, but unfortunately, it did not unlock the door to acceptance.
Now, why am I telling you this story? Because it is a real experience that shaped me at a young age. As an adult, I understand that having “things” won’t get you in the “game.”
Here are some examples:
- Just because you have a Twitter account does not mean that people will interact with you.
- Just because you have a cellphone that shoots video does not mean that the videos will make themselves.
- Just because you are on a team does not mean that you will get along with your teammates.
- Just because you enroll in a class does not mean that you will learn.
- Just because you publish a blog does not mean that people will read or share it.
Telling you that story showcases my experience and the lessons learned. I can tell this story from the stage during a keynote, to a prospective client, or as the basis for an entire blog.
The lesson that having a “ball” won’t necessarily get you in the “game,” has far and wide implications, and is a great way to showcase my ability to not assume things will be easy. It is a real-life story that highlights how I move on from adversity and live my life as a wiser person.
This story can translate to showcase your expertise and skills. Recall the general examples above, and see how they can become more personalized.
- As of writing this article, I have tweeted over 52,000 times. Part of my success on Twitter is knowing that I have to be actively involved to spark engagement.
- I use my cellphone, iPad, and/or GoPro to make videos. It has taken years to learn how to do it, including learning how to edit and publish them. It’s a skill I am always improving.
- I have been on teams that don’t work out. In fact, I had the courage to leave my last company because the relationship with my ex-business partner was toxic. I understand that partnerships take work, and that sometimes they just don’t work out.
- Even though I teach at the University of California, Irvine, and Cal State Fullerton, I still take classes, attend workshops, and am always learning. I know that the time I put in will result in new skills and knowledge. Check out my YouTube video for helpful tips to keep learning daily.
- I know that by publishing this piece, I will still need to share and promote it to get people to read it. (If you like this blog, you can help me by sharing it to your network and across social media!)
This simple childhood story can help people understand my entrepreneurial spirit, my drive, my skills, my motivations, and ultimately my expertise.
Let’s dive in a little more to understand what makes a good story.
No guts, no story
When you are able to recognize and tell stories from your past, you can unlock the superpower of storytelling.
And did you notice how the story was not about a time in elementary school where something awesome happened? It was a story rooted in not being accepted, in my sadness, in my being left out of the game. It might seem hard to share these stores, but it helps people connect to moments in their lives.
By sharing your personal life challenges, it gives people a chance to see themselves in your story. When you read my story of not being picked for a basketball game, did it make you think of a similar story in your life? I’ll bet it did, and made you think that perhaps I am not so different from you after all. Sure, we have different stories, but the feelings or results are the same. This creates a connection between our stories, leading to common ground.
If you dissect my whole story, you’ll see that the good, bad, and the ugly all combine to become my unique life experience. We all have our own experiences, and that’s what makes us unique.
But did you know that with experience also comes expertise?
Let’s explore how sharing your experience will help you showcase your expertise.
Getting hired: give employers what they are looking for
Do you think people hire you for your experience or your expertise?
Remember, your experience is everything that’s happened to you. Your expertise is what people say you’re really good at. Do people hire you for your experience or expertise?
Decide on your answer… and say it to yourself.
Is that your “Final answer?” Haha, just kidding.
But I’m all seriousness, my final answer is that I truly believe people hire you for your “experience,” not necessarily your “expertise.”
The nice thing is, that when you focus on your experience, you don’t have to worry about being an expert to get hired. It’s time to get comfortable with the idea that we’ve all failed and have experience that stems from failure. By constructing your backstory to acknowledge your failures, while showcasing the lessons learned, you are showing your authentic self. Let that sink in for a minute.
The interview is everything, so leverage the power of your story
One thing to know about interviewers in general is that they aren’t necessarily looking for candidates who tick every box of nice-to-haves. Yes, they are looking for your leadership, problem-solving and teamwork skills. But they’re also looking to hire human beings who have real-world experience.
The interview is where you can share your stories. You are more than your resume, and the interview is how someone can hear your unique experience and decide if you’re a fit.
In the interview, they will ask you questions. I challenge you, instead of rushing through your job titles and reporting the tasks and skills you picked up over your career as your answer, to do something different. Tap into the power of your story.
Answer the question with, “Let me tell you a story…” Then share a story from your past, like my story of not being picked for the team. After telling it in a compelling way with all of the key elements, say, “and the reason I am telling you this is because…” And then fill in the lesson or lessons learned, how it makes you look at life, business, or leadership in a new way. This is how you can show your skills, rather than tell them.
Be prepared with stories that highlight experiences when you weren’t so stellar at the skills they ask about. Then say, “Because of that experience, I have learned x, y, and z, and this is how it has shaped my skills to this point.” These stories have hidden in them all of your skills and expertise, which is why, at the end of the day, storytelling is your greatest asset.
Now that you know the power of your stories, let’s focus on how to tell them.
The essential components of a story
To tell a story, you need to know/remember and share the following elements:
- Who was involved? (The characters)
- Where did it take place? (The setting)
- What happened? (The mood)
- When did it take place? (The insights)
- Why did that happen? (The motivations)
- How did you feel? (Lessons learned)
Storytime: The not so shipshape engine
Here’s one of my recent stories as an example. Look for these elements as I tell it.
Cyn and I own a 34-foot 1977 Cal sailboat; her name is BINGO (And yes, we love our floaties!).
After each summer I make sure to get regular maintenance done on the boat so that she is shipshape. Many sailors know how to work on their own engines. Unfortunately, I’m not one of them. My only mechanical experience was a semester of auto shop in high school, and I never got the engine to start. In fact, that whole experience at an early age made me intimidated by engines. To be totally honest, engines scare me. I’ve always been happy to hire professional diesel mechanics to work on my engines.
This past winter my mechanic informed me that there was more maintenance than usual, which resulted in a few months of work and more than a few thousand dollars in labor and parts. But as you may have heard, “B-O-A-T” often stands for “bring on another thousand.” A good boat is a safe boat, so that’s why maintenance is so important. When summer came around and we took our first cruise of the season for Memorial Day, I was expecting zero issues. The reality is that there’s not always wind, and on this particular crossing that was the case. So we fired up the engine and put-putted our way to Catalina Island. All seemed good till I heard an odd noise. A high pitched squeal that didn’t sound good. I looked at the temperature gauge, and it was moving in the wrong direction. I rushed to remove the panels to investigate the engine compartment, and the first thing I saw was smoke. Not good! I yelled out for Cyn to cut the power, and I had no idea what was wrong. Then I remember smelling the diesel fuel. At that point, I knew things were bad. We sailed the rest of the way and sailed back, being very gentle on the engine to get her back in the slip.
The first thing I did was call my mechanic, Martin, and ask him to come down and investigate what went wrong. It was early June 2020, and the pandemic was in full swing. Donning masks and keeping socially distant, we fired up the engine and investigated the issues. Sure enough it was overheating, and diesel fuel was spilling all over the place!
Martin took a long pause, then proceeded to tell me that I needed to rebuild the fuel injection pump, have my heat exchanger overhauled and replace the thermostat. Apparently the work that he had done prior was on other parts of the engine that needed help. Swallowing the lump in my throat, knowing that this would be more work and more money, I said, “OK if it needs to happen, then let’s do it. Summer is here! When can you start?” Martin took another long pause and then said that due to the pandemic and being backlogged, it would be close to five months until he could fit me into his schedule. Since it was June, that meant he wouldn’t be able to even start working on the boat until after summer. I tried not to get angry, as that wouldn’t serve any purpose, and it had taken me a long time to find a mechanic who I could depend on. Then I heard myself say, “Do you think I could fix it myself?”
He looked at me, smirked, and asked did I have the engine manual?
I said yes, I did, and he said, “Sure, I think you can figure it out.”
And right then and there I decided to take on my biggest fear: fixing the engine. Over the next few months I spent countless hours watching YouTube videos referring to my 1977 manual, asking friends, texting my mechanic, and visiting the Marine Hardware Store so many times they knew me by name.
I took the engine apart, got all the pieces serviced, and somehow figured out how to put it all back together. I did have a few nuts and bolts left over and I’m still not sure where they go, but long story short, I fixed everything that needed to be fixed and got the engine back to good health. If you want to see the drama unfold, of me trying to fix my engine, you can see my documentation of the process through this Tweet Storm.
Now why am I telling you the story? It’s because this experience of being essentially forced to take on a project that has always intimidated me, has given me the confidence to take on other things in my life that seem insurmountable. Big projects that I’ve always wanted to do but never thought that I could do myself, I now look at in a different way. I know that with enough time, YouTube videos, tools, and patience, I can figure it out.
Having my mechanic be too busy to help me fix my engine was one of the best things that happened to me this year. And the best part is that I have a new passion for diesel engines. I still watch videos, read books, and on any given weekend you can find me likely tinkering around trying to learn more about the engine, how it works, and how I can keep the 40-year-old chunk of rusty metal running properly.
And side story, we had to cancel our wedding this year due to COVID-19, but ended up eloping on our sailboat to Catalina Island. And if I had not taken on the project, our dream wedding would have never happened! You can see BINGO in the picture below; she got us to the island safe and sound, and it’s where we spent our honeymoon, too! Imagine if I had not taken on the challenge of the engine that scared me.
If I were in an interview for a job, and the interviewer asked me a question about examples of projects that I’ve recently taken on, I could answer by saying, “Let me tell you a story.” Then telling the story of having to fix my own diesel engine in my sailboat could be the perfect way to showcase the fact that I can take on projects that are intimidating. That I’m willing to research and find solutions to problems. That I’m a fast learner, am resourceful, and take on challenges as opportunities to learn. These traits are what the interviewer is trying to learn about me, and I can deliver a story that encapsulates my own personal experience to showcase the value that I can bring to the job I’m interviewing for.
When you read that story, did you notice the elements of a good story?
- Where did it take place? (On my sailboat)
- What happened? (Engine not working right and the mechanic was backlogged, decided to fix myself)
- When did it take place? (Close to summer this past year)
- Why did that happen? (We wanted to use the sailboat during the summer)
- How did you feel? (I learned not only about my engine, but also not to let big projects intimidate me)
It does not matter in which order you include your elements, but they are all necessary for the person hearing your story to stay engaged and understand the story. Did you also notice moments that stimulated a physiological response with visuals, audio, movement, or smell? Sure you did!
What challenge have you faced during this pandemic, or at any other point in your life? What is the story? And what did you learn? How did it make you the person you are today? Collect these stories and be ready to share them, and stand out from the crowd of others interviewing for the position that you want!
What not to do
Just like I worked on my own engine, you can work on improving your storytelling.
Here are the things you might be doing that are taking away from the power of your story.
Your story suffers when…
- You do not give enough information
- You give too much information
- You report it instead of reliving it. (Reliving is more powerful than reporting because it allows people to imagine they are there with you.)
Do you know how I improve my storytelling skills? Learn and practice! I will always be working on my storytelling skills. It is how I can most effectively connect with others.
One of my favorite things to do is connect with other storytellers and swap stories! And I love doing that via podcasts, so naturally I invite good storytellers on my podcasts. Here are a few episodes with some of the best storytellers I know!
- Park Howell featured me on his Business of Story Podcast.
- Josh Linkner and Vinh Giang were recent guests on my World of Speakers Podcast.
- Dan Bennett was a guest on my 3-1-3 Challenge Podcast.
My mom always told me, “Ryan, if you want to be the best, you need to learn from the best.” So I always try to seek out and connect with great storytellers, and you should too!
Don’t get scared, get prepared
Why have I been telling you all of this? It’s because stories will get you hired. People don’t hire you. They hire you for your experience.
Your goal should be finding the backstories of how you have acquired specific skills that are relevant to your field. And they won’t all be fun, happy, or stories where everything worked out to plan. Oftentimes, the biggest learning experiences come from the biggest mistakes.
Don’t discredit the value of your past. There is a treasure trove of stories that helped make you who you are. But you might not think so. You might be thinking to yourself…
Below I picked some prompts that are included in my Storytelling Worksheet. Read a few of them, and think of the first story that comes to mind. Do it for a few of the prompts and you will quickly see how many stories you have to tell.
- What did you see as a child that affected your life?
- What did you want to be when you grew up and why?
- What is one thing that your parents did that made you realize they truly loved you?
- Can you describe the first time you got in trouble as a child?
- What was the first embarrassing moment that you can remember?
- What was your most memorable moment in elementary school?
- What was your first day of school like?
- What inspires you to continually improve and become the best version of you?
- Can you walk us through what your biggest failure to date felt like?
- What was the most unusual adventure you went on when you traveled?
Now pick one of your stories, and let’s see how to develop it!
Follow my step-by-step storytelling process
Step 1. Set the scene and tease out the details.
Start your story at the beginning. What was the first moment like? Did the memory start with a phone call, or did you bump into someone on the subway? Start there. Then work to re-create the environment, giving background details, like the year, day of the week, time of day, what you first noticed about the person, etc. Stories are made in the details. Laying out the who, what, when, where, why, and how creates context.
TIP: Give yourself permission to think. Your memory will do the heavy lifting for you. As long as a question sparks your internal thoughts, the memory will reappear. Try to recollect what you saw, tasted, heard, felt, smelled, and thought. Start to describe the story.
Step 2. Uncover the issues.
A good story should expose some sort of conflict or obstacle. You don’t have to hit people over the head with it; let the story unfold on its own.
Step 3. Lead up to the action.
Build your story to a point where a climactic action takes place. This could be a conversation or a turning point; it could be funny, exciting, or intense. This will set your story up for the action.
Step 4. Work through the problems.
Your story is shared from your perspective. You may recall the conflict happening quickly, but it is imperative for you to draw out the details. Share how you felt in the moment, and give your reader a play-by-play of what happened.
Step 5. Close it out.
The end of a story does not need to have a happy ending—it just needs to end. Sometimes, the ending comes with a lesson and an opportunity for growth. What matters is that you share the outcome of the conflict. Use dialogue between people and explain how the parties seemed to react in different ways.
Step 6. Name your story.
Now that you have completed your story, what does your story reveal? Take the central idea of your story and name your content accordingly. Headlines for stories should tell the readers or viewers what they will get out of the story. Does the story answer a specific question? Or does it provide insight into what to do in a particular situation? Or does it express how you felt after an incident or event? If you need help figuring out how to title your story, use a tool that tracks how many times articles have been shared on the web, like BuzzSumo, to see what the most popular stories are, and use those as a baseline for how to structure your headlines.
Step 7. Share your story.
Be brave, be bold, and consider sharing your story as a form of content, like a blog or a video.
If you are not ready to share publicly, that is OK. Take these prompts and share your story with a friend. If that is too much, write your story down, record it on an audio device, or make a video and don’t share it with anyone. Maybe scribble the outline on a piece of paper, or use a whiteboard to map it out. Do what works for you.
The best way to get better at storytelling is to tell more stories. So now is a great time to get started.
In conclusion, you have two choices
When it comes to creating content and building your brand, I tell people that they have two choices. You can do it yourself, or you can get help.
I know you all have great stories! But, if finding, creating, and sharing your stories is something you struggle with, maybe I can help. Building a personal brand is really sharing your story with the world, and doing it in an authentic way is sharing more than just the shiny stuff. Feel free to email me at email@example.com to learn about how I might be able to help! And if you’re not ready, then I suggest you subscribe to my “3 Things Newsletter” that gives you something to LISTEN to, WATCH, and SEE.
Till next time, see you online, and more specifically, ryan.online.
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