Digital transformation storytelling: 5 powerful tips

Want to tell better digital transformation stories - to a variety of people? Try these approaches to memorable storytelling in documents and presentations
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Rocket coming out of computer to represent moving faster in digital transformation

As part of digital transformation, are you working to get your team aligned on business priorities? Maybe you are trying to sell the executive committee on a new investment? Perhaps you are trying to explain to your operations teams the business impact of the latest systems outage?

You have to grab your audience's attention and bring them on a journey to understanding, empathy, and urgency.

In these and many other examples, you must gain an audience’s attention, explain a key concept, and hopefully bring them to decisive action. In the gap of time you have, whether it’s a 280 character tweet or a forty-minute keynote, you have to grab your audience’s attention and bring them on a journey to understanding, empathy, and urgency.

As you’ve likely heard already, successful message delivery requires passionate and memorable storytelling. But what does that mean in practice? You’re (at least in your day job) a technology, digital, or data leader – not a poet, songwriter, or philosopher.

5 digital transformation storytelling tips to try

I started my career in writing and speaking more than fifteen years ago and now have 700+ articles published and speak at 40 events yearly. But I confess, I am not a natural storyteller: I learned the art through practicing, observing other speakers, and reading great stories. Let’s examine five tips that will make you a better storyteller, whether you’re presenting to your board, peers, teams, at conferences, or virtually.

1. Understand your goals and define audience takeaways

Before getting into the details of what you’re presenting and which stories to include, spend time reflecting on your presentation goals.

Are you trying to secure an investment, drive a mindset change, share insights, or address a team’s behaviors? Then, identify the key takeaways for your audience and what transformation you are trying to trigger or accelerate.

Bring people into a mindset where they actively listen.

The stories you tell should serve these two objectives and bring people into a mindset where they actively listen, so you’re not just telling people what you want them to do.

[ Get answers to key digital transformation questions and lessons from top CIOs: Download our digital transformation cheat sheet. ]

2. Tell a data-driven story with a hero and pain points

The next points are guidelines on how to formulate your story.

  • Identify the hero. Who is the hero of the story, and what is their primary pain point? Think back to the most memorable storylines from Star Wars to Marvel comics, and the story always includes a hero or heroine struggling to do good in the face of obstacles.

  • Use data to set a business context. Unlike science fiction, telling a story to drive digital transformation requires business context, and the best way to do this is to include data, analytics, and insights in the storyline. Use data to illustrate the magnitude of the problem, time dimensions to create a sense of urgency, or metrics that help explain the potential business impacts.

  • The key is showing how sticking with the status quo can lead to the hero’s downfall.
    Reveal the antagonist as status quo. All stories require an antagonist, and in digital transformation, the antagonist often describes an old behavior or way of doing things. The key is showing how sticking with the status quo can lead to the hero’s downfall.
  • Invite audience participation. For the story to sink in, your audience must see themselves as the heroine or a teammate ready to save the day. If you can interact with your audience, you ideally want them to finish the storyline by sharing their thoughts and ideas.

  • Be prepared to improvise. What if the audience’s ideas don’t align with your punchline? How will you handle a quiet room where the audience doesn’t participate? What happens if you must manage a heckler or a very active audience?

Your work is only halfway done after creating the storyline. Observing the audience, listening for feedback, and improvising around the core of your story leads to the next step.

3. Practice and refine your story

Ever see someone fumble a good story by taking too long to get to the punchline? Most of us are not natural storytellers, and the best way to go from crafting a story to being ready to present it is to practice.

You have a few options for practicing, depending on the type of story you’re telling and the audience. Some examples and options:

  • If you’re pitching an investment, then select key stakeholders and schedule one-on-one time with them to pre-sell the idea. Don’t go through the whole story, otherwise, your presentation will be redundant and boring. Instead, pick out the points most pertinent to the stakeholder, run it by them, and adjust your story based on their feedback.

  • If your digital transformation story targets your peers, consider using your direct reports as a testing group. Your lieutenants should role-play and be asked to provide you honest feedback.

  • If you’re presenting to your team or at a conference, try using a video recording to tell and review the story. Watching yourself on video can help finetune wording, pauses in the delivery, and when to interject passion into your story.

[ Read also: 9 must-read books to make you a stronger communicator. ]

4. Deliver the story with passion and end with only a few takeaways

You’ve drafted a story and practiced it, so what are some key considerations on delivering it memorably?

Make sure you conclude with just a select group of memorable takeaways.

Look to drive engagement and increase audience attentiveness by using body motion, eye contact, voice inflections, facial expressions, and hand motions. But probably the most important aspect of storytelling is to release your passions at the right moments. You can’t always script when to do this, as you have to gauge the audience and express your passions at impactful times during your story.

Finally, make sure you conclude with a select group of memorable takeaways. Choosing just a few can be hard when you’re leading long presentations, but overloading everyone at the end of a story with everything they should remember is a mistake. The audience will more likely walk away and retain nothing, so pick no more than three closing sound bites.

5. Continuously refine your storytelling craft

It takes commitment to develop your storytelling techniques, and there are several books that I recommend on the art of storytelling, books that exemplify great stories, and digital transformation books that include storytelling. Another great option is to watch some top TED Talks or review these examples of storytelling with data visualizations.

Also, recognize that you’re likely to make mistakes on this journey. Before delivering a story or presentation, let someone you trust know that you will ask them for feedback afterward. And when you observe a great speaker, make sure to make a mental note of some things they did well that you’d like to replicate.

One last thing I recommend is to keep a short list of your real-world stories and add to it frequently. You never know when you’ll need a good story to include in your digital transformation presentation, and having a list to pick from simplifies and provides options.

[ Get exercises and approaches that make disparate teams stronger. Read the digital transformation ebook: Transformation Takes Practice. ]

Isaac Sacolick is the president and founder of StarCIO, a technology learning company that guides leaders on digital transformation. A lifelong technologist, Isaac has served in startup CTO and transformational CIO roles.