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The latest episode of Presales Podcast featured an insightful conversation with Jon Billett, Founder of StoryQuadrant, who shared his unique perspective on storytelling in presales. Hosted by Jack Cochran, General Manager of Presales Collective, the episode challenged conventional thinking about storytelling, transforming it from a soft skill into a structured, scalable system.
Listen to the full episode now!
From Soft Skill to Industrial Skill
One of the most compelling insights from the conversation was Jon's reframing of storytelling itself. "Storytelling is an industrial skill," he emphasized. "Like any scalable process in a tech company, it's built on structure, not sentiment."
Jon explained that just as engineering follows architecture patterns and product teams use frameworks and roadmaps, storytelling should work the same way. It's about having a structured system for creating clarity, consistency, and memory at scale across an organization.
"Everybody would nod and agree, yes, we should tell more stories," Jon noted about traditional enablement. "But there was never anything beyond that." Most organizations encourage storytelling without providing the structure to do it well.
The Four Types of Stories That Matter
When Jon asks presales professionals what types of stories they want to tell, 80-85% say "success stories." The problem? Most success stories aren't actually stories. They are simply case studies listing facts that happened to a company.
Jon introduced a framework of four critical story types, which he calls the Story Quadrant:
1. Your Story: How you present yourself matters. Research shows we judge trustworthiness within a tenth of a second, and there's a critical four-minute threshold where you need to dig beyond pleasantries to find shared interests or commonality. "These timeframes are very limited," Jon noted. "Your goal is to get people on board and connect with them within about a four-minute period."
2. Their Story (Discovery): Jon explained that prospects didn't just wake up one morning and decide to buy technology. "You're stepping into the exposition of a story," he said. "You've got to look both ways" understanding what they've tried before (what failed, what succeeded but couldn't scale) and envisioning the future transformation once they've successfully implemented your solution.
3. Positioning Stories: Surprisingly, only one person has ever told Jon they wanted to tell positioning stories, yet these are crucial early in the sales cycle. "How is this not right?" Jon wondered. "Positioning stories…you need them before success stories in the majority of cases." These stories use hooks, information gaps, trends, pain points, differentiators, and contrast to convince prospects why they should be buying your technology.
4. Success Stories: While everyone wants these, Jon emphasized they need to be true transformational narratives, not data dumps. They should take the company on a journey, showing where they were before, the arc they followed, and where they ended up, written as proper stories with emotional resonance.
The Most Important Story: What They Tell After You Leave
Perhaps the most profound insight came from Jon's experience as a magician and member of the Magic Circle. He discovered that "the best tricks are the ones that can be explained easily after the fact."
At a recent charity event, Jon performed technically complex tricks that gave him personal satisfaction, but the one everyone remembered? Sticking a sword through a balloon without popping it, which was technically one of the easiest things he did. The story people tell AFTER you are done with them is what is going to survive and live on in peoples’ minds.
"If you're spending 60 minutes presenting to somebody, you run the risk of creating something that they just can't retell," Jon explained. The question every SE should ask:
"How do you ensure that when you're not in the room, the story that you want to be told is being told?"
The answer lies in keeping presentations tight with a solid through line, using strategic phrasing and emotion. You also need to focus on the very ending, what is being said and talked about right before people leave the meeting. "That is the most important moment," Jon emphasized. "That's what they're leaving with, how they feel, and what they remember."
The Power of Contrast
When Jack asked Jon for one technique that presales professionals could implement immediately, Jon didn't hesitate: create a moment of contrast.
"Show the customer, the prospect, the world perspective before and after your solution," Jon advised. "Contrast becomes really clear in the mind. If there's no contrast, there's no curiosity. If there's no curiosity, there's no memory."
He explained the cognitive chain: "Novelty engages attention. Attention creates focus. Focus then creates memory. It all starts from novelty." By showing a novel illustration of what the world is like today versus what it could be like in the future, you create a vivid, lasting memory.
Overcoming the Biggest Barrier
Jon identified the first barrier teams must overcome: "Most people believe in their inability to tell stories." Even in a safe space, most will say they're not good storytellers, but they know someone who is.
The irony? "We are so convincingly good at telling stories," Jon pointed out, referring to the negative narratives we tell ourselves about our own abilities. We tell a great story to ourselves about how we’re no good at telling stories.
The solution is helping people realize they already do this every day. "We all make sense of the world around us in this format," Jon said. In his workshops, the first step is getting people to create stories and realize they can do it, building confidence so they don't hide behind demos or corporate pitch decks.
The Stakes Are Getting Higher
Jon noted a concerning trend: "AI is making everybody sound the same." With so many tech companies now using similar phrasing and terminology, buyers are struggling to differentiate between vendors. "The buyers are listening to all these tech companies saying the same thing. Not many people are denying that, which I find quite funny. So you know it's happening, and nobody's doing anything about it."
In this increasingly homogeneous landscape, structured storytelling becomes essential for differentiation and surviving the years ahead.
Looking Ahead
The conversation with Jon Billett challenged many assumptions about storytelling in presales. It's not about having the right personality or natural talent. It's about understanding structure, practicing frameworks, and building systems that scale across an organization.
As Jon noted, "You've got to have a structure, a foundation that you work from. Otherwise, what happens is everybody is building their own flows and their own what feels right."
For presales professionals looking to elevate their game, the path forward is clear: stop treating storytelling as a soft skill and start approaching it as the industrial skill it is.
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