Storytelling is life. And work.

Better Conversations, Better Conversions: The Art & Science of (Financial) Storytelling

The gold standard for human interactions is the power of curiosity, understanding, questions, metaphorical thinking, and the back-and-forth of dialogues. You might get something out of this article, but you may not but you may be curious to find out. Good, let’s go.

Why does storytelling matter?

Financial professionals often deal with complex concepts and data-heavy analyses. However, the most successful understand that numbers alone don’t drive decisions—stories do. By weaving data into relatable narratives, advisors can help clients visualize their financial journey and make more informed choices.

Prepping and the ‘Story Spine’

You can run your story in a scenario, a narrative for the client or prospect. Depending on how you prepare your story, the preps enable you to develop a ‘story spine‘ in yourself.

Once upon a time, there was ___. Every day, ___. One day, ___. Because of that, ___. Because of that, ___. Until finally, _ _.

When you think with a piece of paper or your notes app and write this out, then fill it out, you will find that this simple prep can help you frame a whole story. Please take a minute and try it. I read about this years ago, and Pixar made it a little more famous since their plots follow this simple rubric.

How to Apply to an Insurance (Risk Attitude) Conversation.

Once upon a time, a client struggled with understanding the risks they faced and wanted to be covered in a changing risk environment (really, they wanted peace of mind).

Every day, they were asked about various risks and what coverage they needed from their team and clients.

One Day, there was an incident. It was an insurable event, but they lacked coverage for the amount of liability. It was a wake-up call.

Because of that, the board and leadership needed a complete conversation around risk that provided the right types of coverages and revisited the risk attitude the company required.

Because of that, a detailed discussion was had around the risks faced, tolerances, and all the details involved. This was not a pitch but a collaborative, realistic assessment and the peace of mind that comes with the covered feeling.

Until finally, a set of products and premiums were quoted up, and in the end, a shared sense of ‘We are covered’ and we finally have an understanding of confidence around our risk(s)

When these preps become a habit, add a touch of AI, maybe a handful of Agents (agentic AI), which can become a powerful tool for humans and agents.

Anxiety = Uncertainty x Powerlessness

This emotional equation, which is lifted from Chip Conley’s book Emotional Equations, applies to these kinds of conversations. When you contemplate where uncertainty is and how frustrating it can be to be uncertain in running a business, protecting and providing the peace of mind that comes from certainty around what risk is all about. The storytelling and dialogue mitigate the powerlessness to act, understand, and obtain peace of mind.

An Approach

I believe in the power of storytelling to drive change and create meaningful experiences. This philosophy extends to financial conversations as well. By approaching financial discussions with empathy, creativity, and a focus on the human element, we can transform complex financial concepts into engaging narratives that resonate with clients[personalization].

Here is a link to a chapter in a forthcoming book I am working on:
https://keepmoving.company/curveball-questions
Techniques and other heuristics that you can apply have power. Get or develop your own, or steal mine. The best storytelling doesn’t need to be ‘good’. It needs to be memorable and move people.

Remember, every financial decision is part of a larger story. As storytelling humans, we help clients understand and shape their financial narratives. By mastering the art of economic storytelling, we can turn conversations into conversions, creating value for our clients and businesses.

Some additional reading about how to orient yourself to be storytelling-focused. I am thinking about how to shift your mindset to make more of every story you tell.

Ultimately, it’s not just about the numbers – the stories we tell and the connections we make. So, keep the conversation flowing, and watch as better dialogues lead to better outcomes.


Another post for even more reading…

3 is a magic number, even more so in storytelling.