Business Storytelling: How to Tell a Great Story

Business storytelling can make a message easier to understand, remember and repeat. But including a story does not automatically make communication more engaging.

Many workplace stories become long explanations of what happened. They contain details, characters and a sequence of events, but listeners are left wondering why the experience was shared or how it connects to the larger message.

Effective business storytelling is different.

Strong business storytelling has a clear point. It includes details that help listeners enter the experience, and it creates a response that supports the communicator’s broader objective.

This excerpt from Sally Williamson’s third book explores what SW&A learned by watching people business storytelling, listening to audience reactions and identifying the common gaps that prevent potentially meaningful experiences from becoming memorable business storytelling.

Chapter 14: Telling Great Stories (an excerpt from Sally Williamson’s third book)

Listeners like stories in a business context because it helps them remember and repeat ideas. But when we asked people we surveyed about stories, they told us that they don’t hear stories often and, when they do, they don’t repeat them because the stories aren’t relevant or don’t align with the topic. They thought stories would be more memorable if they were more relatable and if the presenter was a better storyteller.

In order to solve for those expectations, we formed focus groups to watch and listen to people telling stories. Our goal was to observe how people tell stories so that we could identify commonalities and develop best practices. But what we found communicators had in common were the mistakes they make, not what they do well. The takeaways from these sessions validated a lot of what people had told us in our third-party survey.

• “The stories themselves aren’t always interesting.”
• “Many storytellers aren’t great at delivery.”
• “Listeners get frustrated trying to figure out the point of a disjointed or rambling narrative.”

In short, our most consistent takeaway was that many people find it hard to tell a story well.

We also asked focus group participants about stories they hear in business settings. Here’s what they said:

• “We tell stories about our brand; not about our people.”
• “Stories that I hear and repeat hit me emotionally, not logically.”
• “We talk about stories, but we don’t use them.”
• “One in a hundred stories that I hear are worth repeating. But when I hear a good one, I use it over and over again.”

In the focus groups, we also tested whether participants could remember and retell a story.

One participant used a personal story to illustrate to a group of new hires that they were joining a great company. Here’s Craig’s story:

Five years ago, I’d been out of work for almost a year. My search for an IT management job took longer than I thought, and it was stressful on me and on my family. We were so grateful when I was offered a job here, and I started working in early November. I didn’t have my confidence back yet, so I was concerned when I was called into my manager’s office after just three weeks. Unbeknownst to me, each department here has a tradition of giving away a holiday turkey, and my manager had selected me. He seemed to know that my family had been going through a tough time, and it was a wonderful gift. That’s when I knew this is a company that cares about its people. You’ve made the right decision to work here.

The participants’ feedback? They wanted more emotion. They wanted to feel a personal connection to Craig’s stress level before landing a job.

Here’s how I retold the story:

I know as you sit here, you are a little unsure of what it will be like to work here. I can tell you that in short order, you’ll realize that you haven’t just accepted a job, you’ve joined a family.

That’s certainly how I felt five years ago. I was an IT manager who’d been let go from another company during downsizing. I had a solid skill set and thought it would be pretty easy to find another position. I was wrong. I was out of work for almost a year. If any of you have been through this, you know how hard it is being out of work that long. I’d passed the point of stressed out. I was beginning to genuinely worry about how I’d take care of my family.

It was a huge relief to be offered a role here and to get started in early November. Things were still a little stressful; we’d fallen behind on some bills and I was still playing catch up. But we had a way forward and I hoped the situation would improve by the new year. I didn’t talk about this with my new coworkers, but I always carried that weight with me. Three weeks later when I was summoned to my manager’s office, I could feel my stress neurons firing. Surely I hadn’t messed up already. What could he want?

Well. Unbeknownst to me at that time, the company’s tradition is to give away a turkey to someone in every department, and my manager thought it might make a difference for me that year. Boy, was he right! We were living week to week. Thanksgiving wasn’t even on my radar. That simple act of kindness was a big gesture to my family. The fact that my manager had noticed something was off and wanted to support me—that was a powerful signal to me that this company is an extended family. So the message I want you to hear today is: welcome to the family!

I asked the group again after my version and found that the group remembered the emotion in the story and connected with it more.

We continued the exercise of listening to stories and then I repeated each story. Each time we asked for observations based on the storyteller’s version and mine. Here are some of the groups’ observations:

• The story took longer when I told it, but it didn’t feel long.
• The people and circumstances were more relatable.
• My story seemed to include the listeners.
• My version of the story expressed more emotion.

As we worked with each group to rework their stories, we found three key elements that many of their stories were missing:

Business Storytelling – A Point: Many of the initial stories told in the focus groups left participants thinking, “So what? Why did you just tell me about that?” This matched what we learned from our survey participants as well. Listeners often feel that most stories don’t have a point or any direction at all. This is something most people have experienced at some point. Speakers fail to tell a story well because they get too bogged down in details or they add elements to a story that really aren’t relevant to the takeaway.

When we asked the focus group participants about the flow of their stories, we found that many of them were simply relating the events as the details came back to them. They had little structure in mind. That lack of structure is precisely what leads to rambling and disjointedness.

Business Storytelling – Listener Interest: Some of the stories did have a point, but either they were boring or the storyteller failed to make the audience feel like a part of the experience.

We then worked to retell the stories with more texture, more detail. Listeners in the focus groups confirmed that the details made a significant difference in what they remembered.

The storytellers were surprised at this. In my retellings, the added context came from questions we asked the storytellers after they had initially told their stories. It wasn’t new information; they just hadn’t included that level of detail in their stories because they didn’t perceive the need for it. This ties back to the risk associated with telling stories. Most speakers don’t know how much detail is too much or too little, or what kinds of details make a story interesting. When I retold some of the stories, I added texture by focusing on things we wanted the listener to relate to in the story.

It was another important proof point that stories can take a while to tell. Several of our storytellers were worried about this. They weren’t giving themselves permission to embellish the story enough to make it interesting.

Business Storytelling – Listener Response: Few stories actually drew a response from the listeners. While people were willing to listen, they didn’t have comments or questions afterward, unless to ask for clarification or because they had missed the point. The listeners didn’t give reactions, share similar experiences or seem impacted by the stories.

Our observation was that storytellers were simply sharing experiences and not working to make the experience matter to the listeners. If stories are told well, they are the elements of a presentation that will be remembered and repeated, because listeners relate to them. But the stories told in our focus groups weren’t accomplishing this.

In response to what we learned from these focus groups, we now had insights on common gaps in storytelling. But, we still wanted to capture best practices and see if there were commonalities in people who tell stories well.

So, we continued our research by asking companies to introduce us to their best storytellers. And the most common response we got was a blank stare. This seemed to have something to do with the aura that people attach to great storytellers and the lack of compelling communicators in company cultures. The term “storyteller” is loaded. People expect a master communicator, an entertainer. So we changed our question. We began asking for the people who bring ideas to life and who seem to put context around their thoughts. We compiled a list of storytellers from a number of companies and interviewed them to test the mechanics of storytelling we’d hypothesized.

Our earlier research had shown that people who tell stories find it easy. This new round of interviews reaffirmed this.

Many of the storytellers we interviewed had been telling stories for so long that their approach was more habitual than intentional. We had to dissect their habits to get at the principles that made their storytelling effective.

So with the challenges identified in focus groups and the habits we observed in good storytellers, we were able to identify three principles that are universal to good storytellers…

Excerpt Ends.

Business Storytelling: Why Business Stories Are Difficult to Tell Well

Most people know when they have heard a strong story. They may not know how to create one themselves.

When we remember an experience, the details often return in the order we recall them. That is not always the order an audience needs to hear them.

The storyteller knows the people, context and eventual outcome. The audience does not. When important context is missing, listeners struggle to understand the significance of the moment. When every remembered detail is included, the point becomes difficult to find.

Business storytelling requires selection. The communicator must decide what the listener needs to know, what will create interest and what can be left out.

That judgment separates a story from a simple account of events.

Business Storytelling: What Listeners Expect from a Business Story

Listeners expect a story to lead somewhere.

They want to understand why the experience matters and how it connects to the idea being discussed. They also want enough detail to imagine the situation and recognize something relevant in it.

A useful business story should help listeners:

• Understand an idea
• See why the idea matters
• Relate the experience to something familiar
• Remember the central message
• Consider a different perspective
• Recognize what should happen next

The story does not need to be dramatic. It needs to be relevant.

A small moment can create significant impact when it illustrates a larger truth that matters to the audience.

Business Storytelling: The Difference Between a Story and an Example

Leaders often introduce an example as a story.

An example explains or proves a point. It may describe a situation and its outcome in only a few sentences.

A story allows listeners to experience the point. It introduces people, creates context and develops enough tension or uncertainty to make the outcome meaningful.

Both are useful. The choice depends on the communication objective.

Use an example when the audience needs quick evidence or clarification. Use a story when the audience needs to feel the significance of the idea, remember it or see the situation from another person’s perspective.

Business Storytelling: How to Choose the Right Story for a Business Message

Do not begin by asking, “What story do I want to tell?”

Begin with the message and the audience.

Ask what listeners need to understand, believe or do. Then identify an experience that helps them reach that point.

The right story should:

• Support the central message
• Reflect something relevant to the audience
• Contain a moment of change, discovery or decision
• Be appropriate for the setting
• Reveal something that facts alone cannot communicate
• Lead naturally into the next idea or action

A compelling personal experience can still be the wrong story if the audience cannot see its relevance through business storytelling.

Business Storytelling: Create a Clear Point

Every business story needs a reason for being told.

The point should be clear to the storyteller before the story begins. If the communicator cannot explain the takeaway in one sentence, the story will probably include too many directions.

The point is not necessarily a moral announced at the end. It is the central insight the details are designed to support.

A leader might use a story to illustrate:

• Why a strategic change is necessary
• How a customer experiences the organization
• What a company value looks like in practice
• Why a team should approach a problem differently
• What was learned from a setback
• How one employee created an unexpected impact

The clearer the point, the easier it becomes to choose the right details.

Business Storytelling: Build Listener Interest

Interest comes from relevance, tension and texture.

Listeners need to understand what was at stake. They want to know what the person in the story wanted, what stood in the way and why the outcome mattered.

Texture includes the details that make the experience easier to picture. It may involve a reaction, a specific setting, a moment of uncertainty or a line of dialogue.

The goal is not to embellish by inventing facts. It is to select truthful details that help listeners enter the experience.

Too little detail makes a story feel distant. Too much detail slows the story and hides the point.

Business Storytelling: Create a Meaningful Listener Response

A business story should do more than receive polite attention.

The response might be emotional, intellectual or behavioral. Listeners may recognize themselves in the experience, reconsider an assumption or become more willing to support a recommendation.

Before telling the story, ask:

• What do I want listeners to feel?
• What do I want them to understand differently?
• What conversation should the story create?
• What should they remember?
• What action should become easier afterward?

These questions help connect the story to the broader communication objective.

Business Storytelling: Common Business Storytelling Mistakes

Business Storytelling: Beginning Without Knowing the Point

The storyteller starts with an experience and hopes the meaning becomes clear along the way. The audience receives a sequence of events without a useful destination.

Business Storytelling: Including Every Detail

Not every accurate detail is relevant. Extra information creates length without creating interest.

Business Storytelling: Removing Too Much Emotion

Business communicators sometimes strip stories of anything personal because they want to sound professional. The result may be accurate but difficult to remember.

Business Storytelling: Making the Story About the Speaker

A personal story should still serve the listener. The experience matters because of what it helps the audience understand, not simply because it happened to the communicator.

Business Storytelling: Failing to Connect Back to the Message

Even a good story can feel misplaced if the leader does not help listeners connect it to the idea, decision or outcome under discussion.

Business Storytelling: Questions to Ask Before Telling a Story

Use these questions to prepare:

Business Storytelling: Point

• Why am I telling this story?
• What should the audience understand?
• Can I state the takeaway clearly?

Business Storytelling: Listener

• Why will this experience matter to this audience?
• What context do listeners need?
• What might they relate to?

Business Storytelling: Details

• Which details create understanding or interest?
• Which details can be removed?
• Is there a clear moment of change?

Business Storytelling: Response

• What should listeners feel, think or do?
• How will I connect the story to the larger message?
• What should happen immediately after the story?

To learn more about our three principles of good storytellers and business storytelling pre-order your copy of Storylines & Storytelling. Or, you can learn more about our Connecting Stories to Storylines program that introduces and coaches the fundamentals of a compelling storyline and a memorable story.