How to tell a compelling story: a step-by-step guide

Conventional sales wisdom says to expect four nos before you finally get a yes – or even just a partial yes. But that’s no way to prepare new salespeople during training. Rejection is painful, and condensing the experience to a single statistic will leave them unprepared.

But imagine if you told the story of your first successful sale: you left a nervous, genuine voicemail and got no answer. You called the person again, and they said no. You called a third time, and they said, “Not now.” The fourth time, they asked a few questions but said no to a demo. Finally, on the fifth call, they agreed to a sales demo.

For even more compelling storytelling (and a laugh), you might mention that they stood you up and it took three more calls. This is a slight twist on expectations that underscores your point.

Knowing how to tell a story instead of reeling off a statistic helps your trainees:

  • know they are not alone,
  • internalize that success happens but won’t be immediate,
  • see the importance of follow-through, and
  • know that you’re imperfect and won’t demand perfection, a critical component of building any professional relationship

But this all starts with knowing how to tell a real-life story in a way that helps both you and your audience. This step-by-step guide will help you tell a story that achieves your goal.

The most effective way to use this guide is to imagine a scenario in which you need a story; for example, you might be training someone or selling to someone. You might need a manager or coworker to agree with you on something. Or, you might be pitching for investment. With that objective in mind, use these steps and best practices to choose your story and start fleshing it out.

Step 1: understand why people tell stories

Stories are at the heart of who we are as human beings. We’ve been telling stories for as long as we’ve had language.

We are hardwired to tell and listen to stories. They are how we connect. They are the foundation of our relationships, and we can use them in myriad ways.

Consider these key “whys” for using compelling storytelling and determine if the circumstances warrant a story:

Stories bring people together

Stories are central to human connection. We make decisions and form relationships based on emotions, not facts.

Personal stories build human connection and a sense of belonging. When we share stories, we bring people together.

Stories can build connections in many different ways. You’ll find yourself using each one as you become a more compelling storyteller:

  • Good stories get shared. Retelling a story involves building connections between the old and new tellers and the old and new audiences.
  • Stories don’t have to be new. You can remind audiences of a past event you were all present for, whether it was a failure, a success or a failure that turned into a success.
  • You share emotions together. Great stories are emotional, and the audience feels the characters’ emotions themselves. That forms a bonding experience, as there’s nothing like laughing together or overcoming a frustrating challenge together.

Stories solidify abstract concepts and simplify complex messages

Technical, abstract scenarios are commonplace at work. Things are rarely simple and concrete.

Stories can translate those complexities into concrete terms. You can use storytelling principles to:

  • connect with teams on an emotional level,
  • make data-heavy information accessible, and
  • make change more palatable.

For example, you might be a software engineer who sees the buildup of technical debt and bad code every day. However, product managers and CFOs don’t see it. You can tell people the facts, but nothing will change until they understand the problem and see a pathway to a solution.

A good story will translate the technical problems – outdated libraries, architectural drift and bogged-down project management – into terms that matter to the audience. In this case, it means more expenses, slow deadlines and failure.

Stories promote and shape ideas

People don’t like it when others tell them what to think. Stories help transform ideas and principles into inspirational, concrete scenarios.

Your teams might be about to transfer to a new customer relationship management (CRM) system, go through a merger and acquisition or have a new product initiative that will make your organization more competitive. Change is hard. It always meets some resistance.

Telling stories will pull your team into the conversation rather than telling them what to think. It allows you to connect with teams on an emotional level, encouraging them to care about the success of a big change.

Well-crafted stories demonstrating the benefits of change help. For example, you might share a story about how transitioning to new software was initially frustrating but ultimately made work easier. Or, you might share a memory about how reaching out to a new market made a struggling company a stronger industry leader.

Stories are emotional. They put ideas and hopes into real-world terms and form a connection with your audience.

Step 2: know when and where to tell stories

Now, it’s time to be more specific. How can storytelling help you at work? You know how you can use stories – to clarify, inspire, explain and share. You also understand when to use them: in times of big change or when there’s a potential misunderstanding, low morale or confusion.

Use this helpful workflow to see where your stories make sense and can do the most good:

  1. Are you giving a presentation? Incorporate stories whenever you’re sharing information that you want the audience to really remember and put to use. Craft a story for each key learning objective and takeaway. People remember 70% of facts told with a story, but only 10% told without.
  2. Is someone confused about what you’re saying? People in different departments or organizational tiers have different perspectives. Even people in the same role have different backgrounds, contexts and ways of thinking. If you sense that someone doesn’t understand what you’re saying, take a step back and tell a story to outline the problem and your solution. As you gain experience in the power of storytelling, you’ll remember when stories have been useful and incorporate them from the start.
  3. Are you in a leadership role? Done well, stories inspire and inform. Whether you’re a CEO, team lead or mentor, stories can motivate and leave a lasting impression. Professional stories that explain difficult decisions you have made or problems you have overcome help build your credibility as a leader. Sharing stories of mistakes you’ve made and moments of vulnerability also helps build personal relationships.
  4. Do you need to build rapport? This is often the case in professional contexts. Maybe you’re new to the organization, you’re part of a cross-departmental committee, or you’re meeting a prospective client for the first time. Stories give an insight into who you really are, your values and your motivations. Don’t forget to ask questions – dynamic storytelling, with back-and-forth between you and your audience, creates a positive interaction.

Step 3: include the elements of a good story

Now, it’s time to craft the story itself. It takes some finesse to turn an anecdote into an effective story. You’ll need to tell it, modify it to fit your audience and objective, and keep it short without accidentally cutting out an essential element.

The key is to consider the following five structural elements and keep them in mind. Mentally review your story as you tell it to make sure they are all there. If you’re outlining stories for a presentation, create quick bullet points so that you know ahead of time what all five parts are.

1. Identify the characters

Your story needs a clear cast of characters. Some stories only have one character: the protagonist. The protagonist is someone to root for. More complex stories may feature a protagonist, an opposing character (an antagonist) and even supporting characters.

If you can, tell your story in the first-person narrative style and make it clear that this is a real anecdote. This approach can make the story more relatable and significant, especially if it helps reveal vulnerability and a real struggle. You should aim to make the audience understand your perspective.

2. Structure

The structure is the series of events or the plot’s organization. There are many ways to tell a story, including a straight narrative, a big reveal and an explanation.

Some of your stories may be “rags to riches” tales of success, or a heroic story of how a mentor helped you solve a problem. Creating a structure that makes the most of the central idea will help you organize and pace the story elements so nothing feels rushed or over-extended.

3. Setting

Settings don’t have to be literal. You can tell a story about events that happened in a specific place, but the location’s details don’t necessarily matter.

Instead, focus on including details such as if the event happened with a startup, if it occurred during weekend overtime or if it happened the first day with a new CEO. The details of the setting should be relevant, help the audience understand the context of the event and help them imagine the scene so they develop meaningful connections.

4. Conflict

All great stories must have a certain sense of peril. What’s the key challenge the protagonist needs to overcome?

As a general rule of thumb, the story’s conflict should be the same as the situation you’re creating the story for. For example, sales training presentations might have a problem with sales resources or customer outreach.

5. Resolution

The resolution is the crux of the story. Everything else is really just building up to this moment. You explain how the characters resolved the conflict and then you make it clear how the story applies to the current moment.

Pro tip: it’s hard to know for yourself if your story has one or all of these characteristics, so ask for feedback.

Whether you’re doing a practice run in front of a friendly crowd or you’re asking for advice at the end of a session, see what someone in the audience thinks of your story. If the meaning is muddled, it seems manufactured or it’s outright boring, you need to know. This will enable you to make changes and try again. You can also get feedback on your tone, eye contact and body language.

Step 5: know how to end your story

Many people worry most about their story’s hook. There’s a good reason for that: a boring start to any story disengages the audience. However, it’s just as important to know how to end your story.

Consider these helpful tips:

  • Practice telling your stories within a limited time. It shouldn’t stretch much longer than one minute.
  • Know how to end the story if it isn’t working. Sometimes, stories fall flat, or the audience doesn’t want to follow you. Practice a few universal tactics for cutting a story short without losing confidence.
  • Craft a call to action. Don’t just let the story’s successful resolution speak for itself. Explicitly make a quick connection to the current moment and what you want your audience to do with the story.
  • End the story on a high note. Even if it’s about a challenge that didn’t end in success, find the positives in your story. Whether you’re prepping new sales reps for how to handle rejection or telling staff that you’re downsizing, the ending should be empathetic and authentic. It should give your audience a clear course of action.

Practice these 5 steps

Crafting compelling stories isn’t easy, but it’s worth it.

The more you practice storytelling, and the more you prepare ahead of time by thinking up strategically valuable stories or running through storytelling exercises, the better you can deliver during key presentations, interactions and pitches.

Streamline the creation and refinement process with storytelling tips, ideas for story structure and practical suggestions with the Pip Decks Storyteller Tactics Deck. You’ll have clear, pocket-sized guidance on what captivating story structures work best, how to pair stories together and how to use powerful stories to achieve your goals.

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