How to tell that one story that will close the deal
An introduction to the Inside Out model and its impact (Part 1)
My first enterprise sales pitch, I dove straight into the demo.
I knew my buyer was busy and wanted to see our product. Hanging up, I thought I’d nailed it.
But after the demo (customized with his company’s logo, colors, even fonts), he went cold for weeks, as I realized I’d made the classic rookie mistake.
I somehow clawed my way to a second chance (with too many followups to count), and spent the entire next meeting not talking, but listening.
And asking the most important question over and over again — Why?
I realized my job was not to sell a product, but an idea. An idea so compelling that they would want to make it their own.
Next time, I pitched a story — starring not my product, but my customer. Once I’d discovered his “why,” I could shape my story to it. And in doing so, I ended up turning a prospect into a champion.
Since then, he not only supported the product within his team, but spread it to other teams — expanding our pilot by orders of magnitude.
Why? Because I had crafted a story from the inside out.
The Pre-Story Struggle
As I was trying to figure out how to sell a B2B product in the beginning, I came across dozens of templates, blogs, and advice. I saw it all boiling down to three main approaches. But no one method worked for all of my different prospects.

There had to be a better way.
I decided to take a new approach, blending my experience in storyboarding as a Bain consultant, design thinking as an IDEO.org designer, and creating content as an artist and educator. The goal was to get beyond the flurry of “10 Slide Templates” and get to the core issue: How do you actually build a story that will sell?

From Slide Decks to Inside Out Stories
Through months of experimenting by building stories to pitch customers, a three-step model started to emerge that I’ll call the Inside Out Story.

First, discover the values that matter to your customer. What matters most to them? Is it cost savings? Organizational efficiency? Their own reputation with their team?
Then shape a structure based on the context. How do they make decisions? Are they more analytical? Or driven by emotion and brand?
And finally, create, choose, and customize content. Which language or industry terms do you need to include? What are the best visuals to show your solution? How do you support — rather than stifle — the conversation?

The Impact
This shift in approach has changed the trajectory of Stick’s sales. I’ve noticed that the tone of conversations has shifted, from selling a product to forging a partnership. It’s also led to more flexible meetings that feel like conversations, rather than presentations. And in more complex enterprise selling situations, it’s helped the message spread across teams and departments.

Over the next few posts I’ll break down each of the elements — values, structure, and content — and share results from some of the experiments I’ve run while selling my own product, Stick, to different types of buyers across different types of companies:

Stay tuned, and please reach out with feedback, comments or thoughts — How does story fit into your sales process?

