How to tell that one story that will close the deal

An introduction to the Inside Out model and its impact (Part 1)

Alli McKee
Aug 23, 2017 · 4 min read

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?

Inside Out Story, with parallel structure to Start with Why

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?

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Alli McKee

Written by

CEO and Founder, Stick.ai - Illustrating Ideas in real time with NLP + ML. Painting and Improv on the side. TEDx Stanford.

Show and Sell

Storytelling is the new Selling. Show and Sell brings together the best of strategy, storytelling, and design to show companies how to sell more, faster with stories that stick. Brought to you by stick.ai.

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