Business storytelling… knowing when to quit

Yamini Naidu Business storyteller

“After all, tomorrow is another day.” In the end of the blockbuster, Gone with the Wind, this is what southern belle Scarlett O’Hara (played by Vivien Leigh) says after Rhett Butler (played by Clark Gable) walks out on her with the parting shot: ‘Frankly, my dear, I don’t give a damn!”

Her entire response is ‘I’ll go home. And I’ll think of some way to get him back. After all… tomorrow is another day.’

Everyone remembers or knows that famous last line―brimming with potential, an ending that leaves an audience wanting more. Author Margaret Mitchell understood the power of ending at the right point, even though the novel is 1,037 pages long!

Storytelling in a novel is like swimming in the ocean―you have all the time and place in the world. However, business storytelling is like swimming in a bathtub. It has to be tight and short. One way to be concise with your business storytelling is knowing when to end. Ideally, your ending should be only one line or two short lines.

An ending leaves your audience with a message without banging them over the head with it. You imply, suggest or invite, never dictate what your audience should get from your story. In business storytelling, your ending should leave your audience wanting more.

Business storytelling mindset for success

Yamini Naidu Business storyteller

Christopher McDougall was a desperate man. He was about to embark on a gruelling challenge of a lifetime in a 50-mile race through some of the world’s toughest terrain. He had heard about the Tarahumara tribe, or ‘running people,’ a reclusive tribe who lived in the canyons of northern Mexico.

The Tarahumara tribe are renowned for this activity, often running 200 miles in one session without a rest! Despite this superhuman talent, they don’t suffer from running injuries.

Intrigued, McDougall set out to track them down and discover their secrets. Despite their reputation, they were welcoming of him and shared their secrets, which he describes in his book, Born to Run.

McDougall says that the lesson from the Tarahumara was simple: learn to love to run. The Tarahumara people have a mindset and culture based on the belief that running is an essential human skill. It is hard to be a part of the Tarahumara and not enjoy running. It’s seen as a necessity that makes them who they are as a people.

McDougall also reminds us that this running passion is not exclusive to the Tarahumara. As children, most of us run around in play with wild abandon, enjoying the freedom. However, a lot of us disconnect from this as adults.

I was immediately struck by a similar experience my clients have with storytelling. As children, we love stories―listening to them, reading them and even coming up with our own. But, sadly, as professionals in the business world, we tend to disconnect from storytelling as a valid tool. The biggest successes my clients have had with business storytelling is when they have embraced it as a mindset, often challenging one another by saying, ‘What are some of the stories we are going to share?’ And this is across contexts. Could be for a pitch, an important client meeting, a team briefing or even a corridor conversation.

A few years ago, I was featured in BOSS Magazine, along with some of my clients from Nab, Ericsson and Accenture. The then Managing Director of Accenture, Jack Percy, is quoted as saying ‘Storytelling doubled our revenue.’ The key reason was that their organisation embraced a business storytelling mindset.

How to use business storytelling like a pro

Recently, I completed a stand-up comedy course at the School of hard knock knocks (I know!) No plans for a career change, just professional development that feeds into my speaking.

The first thing our instructor said was, ‘All comedy starts with writing.’ You could have heard a pin drop in the room. None of us ever thought that comedy starts with writing! Jerry Seinfeld writes a joke every day. He says that, at the start of every year, he hangs up a large year-at-a-glance calendar on his wall. Every day, when he writes a joke, he marks a red “X” over that day. Eventually, he creates a chain of red Xs. He says the idea is to never break that chain.

Storytelling is no different―it all starts with writing your story down. The trick is to write like you speak so your story isn’t stilted. Writing your story down forces you to think, and disciplines you to keep your story short and stick to a structure (beginning, middle and end). It sounds simple, but is a powerful step that separates amateurs (who try to wing it) from the pros. Also, once you have written your story down, you can then continue to tweak it and make improvements.

The other business storytelling technique that separates the pros from the amateurs is pros use personal stories to land a business message. Personal stories immediately engage a business audience. Yet, for a storyteller, personal stories in business take skill and confidence. It is often challenging to find the right personal story that serves our purpose and our audience. We feel vulnerable when we share personal stories, yet we know instinctively that they pack a punch. Personal stories in business are pressure tests on our risk capacity. They feel risky but, with the right business storytelling training, are not. And, as in life, the greater the risk, the greater the reward. The pros know the power of business storytelling rests with personal stories.

Finally, pros make it all seem so effortless. When they share a story, it is like they are sharing it for the first time ever, even though we know this not to be true. So, what’s their secret? We had the opportunity to interview who we were told was a natural storyteller―John Stewart, then CEO of National Australia Bank. When we asked him, he laughed and replied ‘My most ad-libbed stories have been practiced for hours in front of the mirror.’ Just like in every other field (e.g., sports, music, public speaking, etc.), all pros practice. They practice, and then they practice some more.

So to be a pro at business storytelling: write your stories down, use personal stories and practice.

Why ‘A Dalmatian ate my burrito’ holds the secret to brilliant business storytelling?

“A dog ate my lunch,” my client Jen recently tweeted. She then replaced it with, “A Dalmatian ate my burrito,” and Twitter immediately exploded! People loved it. Why?

What separated those two tweets and transformed “ho hum” into “ha ha?” The magic happened when she was specific―a Dalmatian (not just any dog) and a burrito (not just a generic lunch).

Being specific is the key to good business storytelling. Relating a specific moment in time, a specific event, a specific person. There―have I said the word “specific” enough times?

This sounds easy but is a stumbling block for many professionals when using business storytelling. We are often good with the abstract and the general. Yet, for your story to resonate, it has to be concrete and specific.

JFK, the president of America in the 1960s, nailed this when he said: “We want to put a man on the moon and bring him safely back to earth by the end of the decade.” Very concrete and specific. Dan and Chip Heath, in their bestseller, Made to Stick ponder what JFK would have said if he were a modern-day CEO. They think he probably would have said, “Through strategically targeted aerospace initiatives and team-centered innovation…” (abstract and general).

Being specific, like the tweet above creates emotion (makes people feel something) and sensory data (paints a picture). People can visualize images in their mind’s eye centered around what you are saying. Being specific is the key to business storytelling success.

Business storytelling success secrets for presentations

Leaders often ask me, “How do we use business storytelling effectively in our presentations?” Smart, successful professionals know that stories can make your presentations memorable. Here are my top business storytelling techniques for presentations.

It is important that every story you relate links to a message. Otherwise, you are wasting your audience’s time by being self-indulgent. Your stories are there to help your audience connect and remember your messages, so use your stories purposefully.

There is a humor drought in most organizations. In fact, in any other context, a drought of this magnitude would be declared a global emergency. If you want your business storytelling to rock your next presentation, make sure some of your stories are funny. Watch any TED talk by Ken Robinson, who is a storytelling master. Even the most serious story should incorporate at least one funny line.

Magic happens when you share a purposeful, funny story that is also personal. This is a trifecta. The holy grail of business storytelling.

There is a scene from The Matrix, a 1999 science fiction film, in which Neo (Keanu Reeves) points to a helicopter and asks Trinity, “Can you fly that thing?” She replies, “Not yet.” Then she calls Tank and says, “Tank, I need a pilot program for a B-212 helicopter,” and he uploads it into her brain!

Isn’t this every presenter’s dream? Where your presentation is so good that people immediately get it and remember it? While we don’t have a Tanks program, using business storytelling well is our best bet yet. Stories are like Velcro for your audience’s brain.

What are some business storytelling techniques?

Leaders new to business storytelling often struggle with mastering techniques essential for success. Here are my top 5 business storytelling techniques that will turn a business storytelling apprentice into a master.

Clarity on purpose

The most important business storytelling technique is to be clear on the purpose/message of your story. When you are in the pub or sharing stories with your friends and family, the stories don’t really have to have a purpose. In your personal life, people are more forgiving. However, for your stories to succeed in business, they must be purposeful–this helps your stories land on a message. Having a clear purpose also helps you, as a storyteller, find and share the right story. Purpose is like the foundation block of your storytelling. Get this right, and your story is set up for success.

Does it serve the room?

At a recent networking event, I met an entrepreneur who had set up a new business. When I quizzed him on his target audience, he replied, “Anyone with a pulse, really!” In storytelling, that is a sure-fire way to fail. Every story has to be carefully designed with an audience in mind. Is it going to be for your customers, your channel partners or your suppliers? How does your story serve them? None of this is easy to do, but this business storytelling technique guarantees that your story will resonate with your audience.

Sharp and short

Legend has it that Ernest Hemingway won a bet by writing the six-word story, “For sale: baby shoes. Never worn.” Poignant.

In business storytelling, short and sharp is best. Perhaps not six words, but a rule of thumb is that most of your stories should be under two minutes long. This time frame ensures you are punchy, and your audience stays with you for the whole duration. Importantly this lets you dodge the terrible curse of diminishing returns, which is when, after a point in time, the more you put into something, the less you get back. By keeping your stories short, you maximise their impact. This sounds contradictory, but would you rather leave people wanting more or wondering when you will be done?


A powerful business storytelling technique is to use personal stories to land a business message. It sounds counterintuitive as the field is called business storytelling, so we feel compelled to use stories about business. But nothing could be farther from the truth. Conversely, in this realm, the personal packs a punch. The minute you share a story that starts with growing up on a farm, or being on a holiday in Canada, your audience is hooked. They are intrigued and want to know what happens next. Business stories about business are boring and predictable―a death knell for any storyteller. So go personal and reap rich rewards.


There is, unfortunately, an earnestness that has seized the whole business-storytelling world. The gravitas common in company announcements, meetings and presentations is now seeping into storytelling. With the exception of some stories that will merit a level of seriousness, the most important thing we can do is to have fun with storytelling. Share stories that you enjoy telling and that are meaningful to you. We once heard a CEO squirm his way through a story about his childhood. It was very uncomfortable for the audience, and it later turned out that he had been persuaded to share the story by a well-meaning advisor.

There’s an ancient Hopi Indian proverb that says “He who tells the stories, rules the world.” So, are you ready to rule your world?

What is business storytelling?

Business storytelling is storytelling with a purpose and for results. Let’s look at an example.

Two salesmen were sent to Africa in the 1900s to see if there was any opportunity for selling shoes. They wrote telegrams back to Manchester, one of them writing, “Situation hopeless. Stop. They don’t wear shoes.” And the other one wrote, “Glorious opportunity. They don’t have any shoes yet.”

This story, shared by Benjamin Zander at the start of his TED talk, had the audience roaring with laughter. Zander links this to his message. There’s a similar situation in the classical music world, because there are some people who think that classical music is dying. Yet, there are some of us who think you ain’t seen nothing yet. He is passionate about classical music, but knows most of his audience will probably roll their eyes at the mention of this genre. So he uses the most powerful tool in the book, storytelling.

This is an example of business storytelling that is purposeful (links to his message), tailored around an audience and delivers Zander results. The surprising thing about business storytelling is that your stories do not have to be about business! That would be boring. Business storytelling, whether it involves parables like this one or personal stories, is about engaging people’s hearts and emotions.

Business storytelling–I already do this

Recently, I was presenting on the power of business storytelling at a professional services firm. I had been brought in with the brief that the team members needed to humanise their content. Clients had been complaining about drowning in data and not feeling a connection to the solutions. The professional services team members were even accused of being ‘robotic’ in their client interactions.

In my presentations, I demonstrated why storytelling is important and got participants to experience the power of storytelling and explore the missing piece in their practice (it’s high energy, fun and practical). At the end of this presentation, one of the audience members said, ‘We already do this. We have always shared stories about our work, our war stories.’

My jaw almost hit the ground! Here is what is happening when leaders think they already use storytelling:

  • Leaders who use storytelling tend to be an anomaly; they are the exception rather than the rule. If you, as a leader, are using stories that are brilliant, you cannot make the assumption that this is happening across the board in your company (especially based on what clients are saying).
  • The word ‘story’ is a very loose label. Often, leaders think they are sharing stories when they might be sharing case studies or a series of facts. Labelling something a story does not make it one!
  • War stories or stories about how we do things can frankly be boring for your clients. These are not tailored around your audience and their needs, so they are not invested in these stories. I call this asymmetrical storytelling, where the audience doesn’t see the story the same way as the narrator.
  • Even if you are using storytelling in business, there is always room for improvement. Are our stories short, purposeful, crafted for an audience? Is there impact in their delivery? Are we measuring our ROIs and building our library of stories?
  • Finally, to answer this, I want to share my model:
    in terms of storytelling, some people are amateurs. They have no idea how to use storytelling. Some people are apprentices, and they have just started learning. With proper skills, training and practice, some people become masters. They influence and have impact with their stories. These are like black belts in karate. Finally, you have story artists. Think Brene Brown or Ken Robinson; they are the like the Karate Dans. Interestingly, in Karate and storytelling, even the Dans never stop learning.



Inspire Artist
Influence Master
In training Apprentice
Insipid Amateur

Business storytelling―how to segue into a story

Imagine if you walked into a business meeting where no one knew you and immediately launched into your content without shaking hands or introducing yourself. This abrupt start won’t set you up for success. In the business world, handshakes and introductions are rapport-building ways we connect before we get down to business.

Similarly, when using business storytelling, leaders I work with grapple with how to launch into a story. Sentences like ‘Let me tell you a story’ feel amateur and may send the wrong message to your audience. What leaders need when using business storytelling are story segues.

Christine Nixon, when she was Chief Commissioner of Victoria Police, was masterful at this. She would share a PowerPoint slide that was dense with strategy points and then say, ‘For example, just yesterday, I was taking to a farmer named John in Gippsland…’ and then proceed to tell John’s story. Phrases like ‘for example’ or ‘to illustrate the point’ are good examples of segues. I also use ‘I would like to share…’ and then share the story.

You want segues that are authentic to how you normally speak, so they don’t sound forced or contrived. You also need to have a few segue sentences up your sleeve for variety. So, over to you, what are some story segues that will help your business storytelling shine?

Business storytelling – I’m afraid it won’t work

One of the biggest challenges leaders face when using business storytelling is the fear that it won’t work. When we tell a personal story, we feel vulnerable, and the stakes are high, thereby creating pressure points around success. We seldom apply this same pressure test to data that we might use! (That’s just a sideways rant  🙂 )

Fear of failing might be a way of sabotaging our use of storytelling altogether. Is this an easy cop-out? What if it doesn’t work? This is the standard bogeyman that every stand-up comedian faces every day.

One lesson we can borrow from them is that they always test their material. With business storytelling, we can test our stories with friends, family members and even a supportive colleague before using it at that important pitch.

But, for me, important work to ensure success happens before the testing stage itself. When we draft a story, we always draft it with a purpose and audience in mind. Answering the question, ‘How does this serve my audience?’ helps us stay on track with our stories. I cannot emphasise enough how important it is to keep your stories short. This works for both you and your audience.

When you deliver a story, you are often greeted by silence.
As leaders, we might misinterpret this silence and react with ‘OMG, it didn’t work.’ In business storytelling, silence is the equivalent of a standing ovation at the end of a performance. Silence means your audience is thinking about what you have said, and you can use the silence to sit back and savour the sweet taste of success.

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