Written by I have facilitated numerous workshops, strategy days, narrative sessions, and conference experiences. Regardless of the setting or participants, a consistent pattern emerges. Typically, the most senior, outspoken, or confident individuals are the first to contribute, filling the room with their perspectives. However, as the session transitions to deeper reflection, it is often a quieter participant who introduces a profound idea, causing everyone to pause and absorb the insight.
This individual brings forth an idea that refuses to conform or behave like the others. It disrupts the established flow, compelling everyone to reconsider their thinking. Such an idea transforms the session from a polite discussion to a lively, energetic exchange, where creativity flourishes, and boundaries are pushed beyond mere good ideas.
Much like unleashing a Kraken, an unpredictable, many-limbed sea creature, this disruptive idea shakes up the room, challenging assumptions and sparking fresh dialogue.
As the mood shifts, participants move from sharing ideas to recounting personal stories. These moments reveal new connections between past experiences and the present discussion, deepening understanding and engagement.
Stories Misbehave, and That’s So Good
The process of discovering stories is not about extracting opinions or gathering data points. Instead, it is about creating an environment where hidden stories can emerge. It encourages those who might normally keep quiet to share their experiences openly.
The risk is that, without the right conditions, these valuable stories remain unspoken. Not because of a lack of content, but because the environment must welcome the unfinished, personal, quirky, and bold ideas. The conversation thrives when these elements are embraced.
Organisations frequently discuss psychological safety. There is an important distinction between feeling safe enough to agree or respectfully disagree and feeling safe enough to voice something unexpected, incomplete, or not fully articulated.
The best stories and insights often appear before they are fully formed, typically from the person who nearly withheld their unconventional narrative.
Many organisations invest in listening to their people through pulse checks, engagement surveys, drop-down menus, and rating systems. These tools are useful for measuring quantifiable data or capturing sentiment at a specific moment, but they fall short of revealing deeper meaning, relationships, or beliefs. Such measurement systems tend to play it safe.
And that isn’t good.
Because the most impactful ideas and stories rarely fit within conventional tools like drop-down menus or rating systems. The most valuable insights about culture, teams, or conference experiences often arrive in the form of stories that were almost left untold.
The Challenge
The question then becomes: How can we create spaces where stories and ideas can run free—playful and mischievous, pushing us beyond what we think we know into the realm of genuine insight?
I have spent the past year dedicated to answering this question.
The journey began with a message from Arne at the Future Skills Academy: “Would you run a Storytelling Challenge with us?” This challenge was conducted online, guiding participants to write and share a story in just ten minutes each day.
The Birth of the Storytelling Challenge
Upon receiving the invitation, I immediately agreed and set about developing thirty fill-in-the-blank prompts. These prompts were carefully crafted to explore various facets of storytelling, including messaging, character, lessons, structure, and more. The challenge launched last year and received overwhelmingly positive feedback, prompting clients to request adaptations for their conference participants.
To scale the project further, I collaborated with Lex Li, the founder of Deckle, an engagement platform. Together, we created a gamified version of the challenge for conference delegates. This partnership marked a pivotal moment and began our own narrative of innovation and collaboration.
From Experimentation to Experience
The Storytelling Challenge did not originate as a commercial product. Its roots lie in experimentation and the desire to foster a playful, honest, and insightful environment for sharing stories.
Running the challenge across different time zones, industries, and contexts yielded remarkable results. Strangers shared intimate, meaningful stories that would not have been possible to share in a typical meeting or feedback form. The fill-in-the-blank prompts provided just enough structure to encourage participation.
This approach enabled effective story listening for all participants, as we hungrily consumed the stories that flowed before us on the screen.
We now have the Storytelling Challenge as it is today.
The challenge consists of a series of fill-in-the-blank prompts. Each prompt offers a story framework, inviting participants to supply the content. Instead of facing a blank page or a feedback box, participants find a ready-made structure to guide them: “Something happened, it made me think, what I took from it was.” This scaffolding propels them forward before doubt can prevent sharing.
The process is simple. Most people complete a prompt in under three minutes. The stories are not superficial; the structure removes friction. When participants don’t have to worry about where to begin or how to frame their thoughts, their stories flow easily. Most people have something to say; they just need the right entry point.
Responses are collected on the Deckle platform, making them accessible and shareable across teams, organisations, or entire conference experiences. The platform captures insights from those in the field and in the boardroom, from delegates who might skip post-event surveys, from team members who are quiet in groups, and from stories that would never appear in a pulse check.
The challenge goes deeper than surveys because it seeks meaning, not scores. It surfaces insights that only appear when people are engaged and comfortable enough to share. And for conference organisers, it creates a feed of content for screens and social media.
That is where the best work arises. Not from predictable responses, but from stories that felt just a little too unusual until the right conditions made sharing possible.
The Storytelling Challenge creates those conditions.
We are running the original version again, May 1 to 30, 2026 – join the Storytelling Challenge here.
Or curious about how it can work for your event or employee engagement, find out more here.
Narrative Strategy and Storytelling for Organisations 