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10 Simple Storytelling Skills for Business Storytellers

So, when I was 30, I spent 4 months wandering about Africa with a band of vagabonds (OK, backpackers, on a Bedford truck). 3 months in, we spent a few weeks in the gorgeous country of Malawi, on the shores of Lake Victoria.

One day we happened upon a thrilling event in village life. Something more interesting than our group arriving in an African village? We had to check it out.

On the red clay expanse normally used for fast moving soccer games and the weekly market, someone had set up a “pop up” stage. A breathless audience had gathered, we could feel their excitement.

It turned out to be a kind of play, performed by travelling players. The action unfolded with the boisterousness of a kindergarten pantomime. The audience response was HUGE, with cat calling, applause, singing, clapping, movement and loads of laughter.

The Africans were entranced for the full hour or so of the show. We stood at the back, and whilst we couldn’t follow the dialogue, the plot was not beyond us. Mostly we marveled in the face of the joy and enthusiasm.

A small brightly coloured box of washing powder was the hero of the piece – the entertainment was sponsored by Procter & Gamble. This was all an elaborate way of communicating brand benefits using the ancient tradition of storytelling.

Storytelling has emerged as a key marketing skill for the 21st century.

This is particularly true for entrepreneurs following an Authority Branding strategy. We need to position our value with absolute clarity.  (A few precise words.) But we also need to connect with a broad audience, (generally a whole bunch more words, whether spoken, written or presented).

Why are stories so effective in marketing?

Our brains are hardwired to respond to stories. Stories trigger the older part of the brain, the limbic system, which responds to patterns and images. For thousands of generations stories (parables) have been assembled, told and recalled by pre-literate societies. They were the number one tool for passing on history, education, culture, ethics and warnings. Plus, of course, stories can persuade us to change (or buy).

  • Stories grab and hold attention and stir our emotions.
  • They activate multiple areas of the brain and this engagement improves the “stickiness” of information.
  • Telling insightful, vulnerable, engaging or funny stories puts people at ease.
  • They accelerate know, like and trust and prime our audience for our offer.

So, there are solid business reasons as an entrepreneur to master storytelling.

Also, I want to get better at stories.

I’m not “naturally” good at them, I don’t come from a “stories round the dinner table” family tradition. I’d love to be like my friend Nicola, who can hold a room spellbound as she recounts the story of a late night séance with ghostly visitors when she lived on the island of Jersey.

I want to be able to weave intimate, visceral moments into my writing like Cheryl Strayed in Tiny Beautiful Things. And have these emotionally intense moments land as universal truths

I want to be able to create compelling characters and narrative arc like Malcolm Gladwell. (He does this with all the panache of a best selling fiction writer). He is the master at moving seamlessly from complex data to story to sticky concepts.

Or hone my ability to sniff out the kind of fine detail that lands like a punch in the gut, like Australian non ficiton writer Peter FitzSimons.

My goal for this post is simple. I want to get better at writing stories, but how?

I’ve read 5 books on the topic and have started writing everyday.  So, I decided to be more forensic and investigate the skills of story telling. Because I’ve enjoyed the research so much, I thought I’d share what I’ve found.

This is not a definitive post and some of the areas overlap with others. It doesn’t have the tidy kind of framework I’d usually design.  It is micro rather than macro.

I looked at the “petticoats” of the work of my non fiction storytelling heroes. (I’m the kind of person who reverse engineers things that impress me to figure out how the magic happened).

So I took another look at the work of Cheryl, Malcolm, Peter, Brene (Brown), Liz (Gilbert), Nancy (Duarte), the Stephens of Freakonomics and a bunch of TED talks to see what I could learn.

Then, I went back and found non fiction stories that have stayed with me and re-read them in an effort to understand why they moved me.

A few common themes emerged:


1. Tell your story with a shape

“There are only 2 or 3 human stories, and they go on repeating themselves as fiercely as if they had never happened before”.

Willa Cather

Memorable plots have a common shape.

I learned this for the first time 20 years ago and it is one of those things that once you know it, you see it everywhere, speeches, parables, non fiction, TV and screen writing, short stories, novels and even songs.

There are a number of models, but for the purpose of storytelling for business owners; here is one I distilled:

  • We meet someone and learn something of their life
  • They encounter some kind of roadblock that challenges them or hardship that threatens them (and these may continue to build).
  • The generally face their darkest hour, which acts as a catalyst.
  • They have to change or fight, generally with help. (Breakdown before the breakthrough might be a good way of thinking about it)
  • Redemption, growth, changed future
  • Then transition to the content

When it comes to structure, the giant upon whose shoulders we all stand is Joseph Campbell, who used the structure of myths to define the epic Hero’s Journey.

I want this piece to be like an artist’s palette for business story telling. I want hone in on skills that you could immediately deploy, rather than take a deep dive into structure.

But what to do with the information on story structure that I found?

From the Hero’s Journey (which you can absorb in 5 minutes, 5 days or 5 months), to ancient story telling structure for corporate leaders, to Nancy Duarte’s fabulous TED talk about inspiring people with what it possible…… If I include it, I’ll have accidentally written another 13,000 word post like Authority Branding.

So, I’ve compiled those models onto a pdf you can download at the end (no opt in).  So if you want to learn more about structure, I recommend that.

Your key take out is this:    Fictional stories have shape, which can be mimic’d when you are presenting information ……Like the marketing discipline of positioning –  storytelling is about what happens in the minds (and hearts) of your readers and listeners.

2. You Don’t Have to Start at the Start

One of the most interesting ways to tell a story is to find a non linear structure.   When you are telling a story your opening should be a pattern interrupt – something startling that arrests your audience immediately.  Generally this is the highest point of drama in the story.

“I was woken from a deep sleep by a noise in the other room, I sat straight up and came face to face with an intruder standing at the end of my bed holding 2 of my bags”.

(This happened to me).    Hopefully this would grab your attention – (I think that is likely if you are a female that lives alone).  I would return to an earlier point in the story to set the context and colour in with detail.  

It was New Year’s Eve and because I had a view of the fireworks I’d had a small party (and a few extra drinks).  It was stifling hot so my loungeroom window was wide open (which it NEVER was) and there was a tap underneath which created a ladder for an intruder.  Who knew?

So start with a dramatic high / darkest hour, loop back to the start and continue with the story through to the point you are demonstrating.  Then add the redemption.

Let’s look at the next overall theme, which is effective use of detail:



Specificity in story telling doesn’t bog the story down, rather, the delicious detail invites us to join the story by enabling your listener to paint a “mind picture”.

I’ve noticed detail used in 3 main ways; character, setting and sense activation.

2: Use detail to bring characters to life:.

Use characters in your stories (even if you are the character) and describe what is remarkable about your characters so the reader can picture them and bring them alive.

Malcolm Gladwell took non fiction writing by storm by incorporating fiction like storytelling techniques. Character is one of the things he does so well, see this example from his New Yorker piece “True Colors”.

Shirley dressed in deep oranges and deep reds and creamy beiges and royal hues. She wore purple suede and aqua silk, and was the kind of person who might take a couture jacket home and embroider some new detail on it. Once, in the days when she had her own advertising agency, she was on her way to Memphis to make a presentation to Maybelline and her taxi broke down in the middle of the expressway.   She jumped out and flagged down a Pepsi-Cola truck, and the truck driver told her he had picked her up because he’d never seen anyone quite like her before. “Shirley would wear three outfits, all at once, and each one of them would look great,”*

Could you draw a picture of Shirley now?

* This is from “True Colors – Hair dye and the Hidden History of Postwar America, about the first women copywriters.

The best known character development frameworks are the archetypes, which were based on mythology and proposed by Carl Jung. As a corporate strategist, I was particularly influenced by the work of Carol Pearson who built on Jung’s work. She draws the parallel between ancient archetypes and brands in her seminal work Awaken the Heroes Within.

In this post, I’m concentrating on the “micro” picture of storytelling, and as archetypes are a topic of their own, I’ve linked to an overview of the archetypes below.

So how do we learn to add colour and meaning to our stories?

4:  Use detail to paint a picture and pull people into the moment.

Create a sense of time and place in your writing.

I’ve been learning this from the excellent story telling in the narrative podcast “Start Up”. A recent episode set the scene like this:

“It started in a grocery store in Vancouver, Canada. It’s a little shop with hardwood floors and high ceilings. The kind of place with regulars, who stop in to buy the same things every week”

Another example …. The champion Australian Rules footballer Jimmy Bartel (the epitome of Australian masculinity) recently wrote a searing article about growing up with an abusive father. Unfortunately, this is an all too common story, but the specifics of Jimmy’s account pulls us right into the moment.

Jimmy was only 4 years old when this incident took place.

“There was one occasion though that still sits vividly in my memory. I remember where I was, how the house was set up, where I was standing. I remember Mum being on the floor in the hallway; he had repeatedly hit her, and she was trying to crawl away from him. I remember Olivia (eldest sister, 10) trying to push him away from Mum, and he physically threw her against the wall, like a rag doll, which is hard to comprehend. … My other sister, Emma, ran and hid under the bed. I tried to get in between him and Mum, and I was the next to get thrown, into an old-fashioned bureau. He belted Mum one more time before he left. That was a major turning point in my life”. *

Jimmy’s use of positioning and place puts us in that hallway with the terrified four year old boy. Detail adds authenticity to the account and invites us to live through that horror. He doesn’t need to tell us how he felt, we can imagine it all too well. Because he has painted this picture so clearly, the emotional intensity of the scene is a take out, not an input.

* From Jimmy’s interview with the Herald Sun, the full article is referenced below.

5:  Search for a unique or fine detail that will make the story “stick”

In “Made to Stick”, Chip and Dan Heath studied what we know as “urban myths”, stories that get passed around.  Amongst the things urban myths have in common are surprise twists that are memorable for their uniqueness.

Peter FitzSimons talks of seeking what he calls “SSS” (sounds, sights, smells) and hunting for the kinds of detail that awaken a sensate response …. Here is an example he gave on a recent podcast.

Scott of the Antarctic had reached the South Pole and was on his way back to base. He and his men were a mere 11 miles from safety when hit by a catastrophic blizzard. The tent was found by the search party six months later with all 3 men deceased.

It is clear that the other 2 men died first and Scott has respectfully laid them out and closed their eyes. Scott is found half in and half out of his sleeping bag and frozen under Scott’s hand is his journal.   His last words appear on the final page, most likely written very close to the time of his death.

“Whoever finds this journal get it to my wife Kathleen Scott of 23 Killborough Lane, West London”.   There is a final amendment. The word wife was crossed out and replaced with the word WIDOW.

Whoa …. a breathtaking detail … …. (Or is that just me?)



The next area I noticed was the use of truth and emotion for more impactful storytelling.  This is how your messages will land powerfully.

6:  Segue intimate stories into universal truth

At first glance it’s a paradox, but great storytellers know that the more personal and intimate your storytelling, the more universally it may resonate.

Anyone who has read Cheryl Strayed’s seminal book Tiny Beautiful Things will know she is the master of this. This book is a collection from her (then anonymous) advice column, Dear Sugar, for Rumpus (circa 2010).   She leads many of her responses with deeply personal stories which use empathy as the bridge to address the writer’s issue.

In one of the most acclaimed columns a woman who’s had a devastating miscarriage asks Dear Sugar how to get unstuck.

Cheryl begins with the story of her job as a youth advocate with girls from challenging backgrounds who were abused and mistreated. She tried so hard to “fix” things for them, but in the end concluded that the only way to truly help people is to help them help themselves. Here she transitions from her story to the plight of the grieving letter writer, saying, “healing is entirely up to you. How are you going to change your life? Because no-one can do it for you”.

From an intimate personal story she bridges to a universal truth – as Cheryl reflected on the Longform podcast:

“the truth that runs like a river beneath it is the universal truth that we all are responsible for our lives, we will all suffer, and we all need to find light in that darkness, strength in that weakness …”

Cheryl urges all writers (and speakers) to dive deeper …. “when you speak in the truest most intimate voice about your life you are speaking in the universal voice”

I linked to this story below, it is truly a masterpiece. And you might notice something in your eye as you read it.

7:  Connect with Vulnerability

I’m sure many of you are familiar with the groundbreaking work of social scientist Dr Brene Brown. Brown also speaks of how you can truly help people:

“Rarely can any response make something better — what makes something better is connection”.

And the best conduits of all?

Empathy and vulnerability – opening up about difficulties. Brown writes in her seminal book Daring Greatly:

“Vulnerability isn’t good or bad. … Vulnerability is the core of all emotions and feelings. To feel is to be vulnerable. To believe vulnerability is weakness is to believe that feeling is weakness”.

Presenting an idealized version of ourselves creates separation from others and can make us appear to lack empathy.  Surprisingly, people are more likely to remember and respect us for our struggles as for our achievements.

My first business was a catastrophe. One year down the track I was broken, homeless and owed so much money that I couldn’t imagine paying it off in 10 years. I moved back in with my parents (and yes, I acknowledge I was fortunate to have this option).

Once I was back in the street where I grew up, the pain intensified so much that I hid indoors in case I saw the neighbours on the street. The thought of facing people who had known me since childhood and been told of my “high flying” career – to find me back where I started at 41 years of age – filled me with paralyzing dread.

I couldn’t express how I was feeling to anyone.

Some time later, I started revealing scraps of information to strangers. The most surprising thing happened. No one called me stupid or shunned me.

People were kind, they said things like “most people never even try something like that, so good on you” or “good will come from this, you’ll see”.   Admitting to difficulties allows people to open up about their own struggles.

I’m now very grateful for the whole experience. It made me an empathetic person who can see behind the mask. It made me realize nothing is ever as good or bad as it seems.

Whilst vulnerability accelerates connection, it shouldn’t be at the expense of credibility. Choose vulnerable sharing that doesn’t create doubts about your ability to deliver results in your area of authority.

I can be vulnerable about tech difficulties (because, Lord knows, I find tech challenging), social media or failing to get traction with a new business model but it would undermine all credibility to admit to a poorly positioned Brand.


8: Curiosity, suspense and open loops

We humans are strange and sensitive creatures …. there are a number of psychological traits that can be harnessed to punch up your stories.

The first is curiosity. Human beings are endlessly curious, especially about experiences or challenges that are outside of their realm.

This is why stories about winning against the odds or surviving hardships are compelling. In a story of danger or difficulty we put ourselves into the action and wonder how we would survive it.

Another trait accounts for our addiction to suspense and inability to resist a cliffhanger is related to an effect observed by Russian psychologist Bluma Zeignarik in 1927. The Zeignarik effect observed that the human mind is intrigued by, and therefore remembers better, that which is incomplete.

This is the reason many marketers open with a question, then leave it unanswered and continue on another path before looping back to the question.

I still remember a sales video Dane Maxwell created for The Foundation that opened with “What is the one, single most important thing for businesses to have to be successful …….”

(Dane had an answer, and it was an excellent answer too, you’ll have to ask me in the comments what it was)

Would you like to know how I turned my failing business around with one new marketing strategy?

This is the reason soap operas create cliffhangers between ad breaks, episodes and seasons. Also, the reason people hate spoilers and reality shows film 3 endings so the truth doesn’t get out.

Open loops are a great technique to use in your stories and sales writing.   Practice by using questions that remain initially unanswered or starting down a track and switching.  Watch what comedians do in story telling. .

9. Seed and bloom – the story telling method that works great in sales

A related psychological trait is what Peter FitzSimons calls “Seed and Bloom”. He improves his story telling by priming (foreshadowing) a critical element or detail earlier in the story so it lands with greater impact in the timeline. Particularly if he knows he has a killer anecdote, he seeds a character or part of the event earlier in the narrative.

He’s a non fiction writer making great use of a fiction writer’s palette. Novels play with this often, particularly with foreshadowing and future pacing; “of course this was the decision that cost me everything, but I wasn’t to know that until much later”.

“Keep them wanting more”. Priming is something that magic, comedy and sales writing have in common. They use a structure that teases, builds anticipation and delays the reveal or surprise.

Learning to seed is a great technique for sales conversations and persuasive writing, because it has a conversational, “incidental” feel.

Sales trainer Catherine Hawkin has this great description of seeding, in this case she is talking about it being utilized in a content webinar with a pitch at the end.

Seeding is the art of dropping a casual mention of something that you offer. The idea is that it piques interest and curiosity in your client. And what’s so nice about it is that you don’t need to do anything else or labour the point. You just trust that if the ground is fertile the seed will grow on its own. Then when you are ready to introduce your offer at a later time the client is much more open to listening to you.

You can use a seed within a story to boost your credibility, “when I was presenting to the board of the Commonwealth Bank ….”

I’m a bit resistant to the notion of “selling”, I find it more enjoyable for all concerned to “tell” rather than “sell”, and I’ve found seeding an excellent tool.

And finally, the art of transition between story telling and moving people to action or embedding a message.

10. Using Story as a Trojan Horse for Learning

One important thing to master is the transition between your story and your offer, and it takes some practice.

Again, let’s turn to the work of the master.  In the Tipping Point, Malcolm Gladwell examines the 3 pre-conditions for a viral event to occur – they are all led by people.   The first type is “the Connector”, and once again he leads with character, in the form of Lois, the woman who “knows everyone”.  He tells some amazing stories of Lois’s kindness, her interest in everyone and ability to put people together.  But it seems like pure story.

Then he breaks down what Lois is doing:  “First, she reaches out to someone outside her world … then, equally importantly, that person responds to her …. … she has no snobbery … She has some instinct that helps her relate to the people she meets …. she likes everyone … she sees possibility”

Highlighting Lois’s traits in this way transitions back to the “skills” and brings the notion of a “Connector” alive.  Writing out the skills makes them able to be replicated and learned.

I learned this technique from Cindy Tonkin in her Presentation Mastery course.  She calls it Story / Point / Benefit.

So first, telling your Story, with context, exposition, detail and climax.

Point is the transition across to what you want to happen:

“The reason I’m telling you this ….  the thing I learned from this ….. what this situation has in common with what I’m here to tell you ….  what this demonstrates is ……”

You need the transition to connect the dots and you need to link the memorability of the story with the information you want to embed or the action you want them to take becomes the Benefit to them.

If you miss this step they may remember the story but they won’t remember the lesson.

Here is an example of a post that is masterful at connecting with story and leading back to content:

Thanks for your attention, there are sources below and I’ve got an upgrade post which helps you find stories to tell.

[thrive_leads id=’1959′]


Sources:  Additional reading:

PDF Download of Story Structure and Shape – includes various story models and the Hero’s Journey.

Character Archetypes (from Carol Pearson) Awakening the Heroes Within – Archetypes 101

Nancy Duarte – The Secret Structure of Great Talks

Jimmy Bartel – Speaks About Domestic Violence

Cheryl Strayed, Tiny Beautiful Things and this letter that was referred to: – http://therumpus.net/2010/07/dear-sugar-the-rumpus-advice-column-44-how-you-get-unstuck/

Podcast Interview with Peter FitzSimons on Mia Freedman’s  “No Filter”

Malcolm Gladwell – True Colors – http://gladwell.com/true-colors/

 Adam Grant on What Makes Malcolm Gladwell Fascinating

Start Up Podcast by Gimlet Media Pirate Needs Pirate

My own “vulnerability story” about the rollercoaster of my first business, Social Life:

Seeding:   http://catherinewatkin.com/blog/seeding-your-secret-weapon-for-non-pushy-sales/

Seeding:  http://theinvisibleclose.com/articles/simple-seeding-secrets/

Great examples of entertaining storytelling can be found on the TV Show “Would I Lie to You”.