Alli McKee
Nov 22, 2017 · 4 min read

Before starting a tech company, I was an art teacher.

I had taken a “sabbatical” of sorts from my management consulting job to get a new perspective on the world, and was starting to teach in Johannesburg.

On Day 1 of my new Creativity Class, I walked into a classroom of aspiring creatives — singers, dancers, actors — many of whom claimed they “couldn’t draw.”

Passing out pens, a stack of sketchbooks, and printouts of the drawing to copy, I delivered the only instruction of this exercise: Copy this image, without moving the paper.

Pablo Picasso’s Portrait of Igor Stravinsky, 1920. Adapted from Drawing on the Right Side of the Brain

The exercise was designed to help the students overcome their “I can’t draw” block by breaking the whole into parts: fingers into lines, eyes into angles, wrinkles into spaces. Focusing not on what the whole should be, but what the parts are.

Twenty focused minutes later, I asked them to turn their sketchbooks upside down. Or rather, right-side up:

“You guys realize that you ‘can’t draw’ — but you just copied a Picasso?”

So what does this have to do with sales?

While I wish enterprise sales at an early-stage company was really as clearcut as a five-step Qualification-Discovery-Validation-Negotiation-Decision process, the reality is that it’s messier than that. “Left-brain” metrics and processes are critical. But they won’t close the deal on their own.

With seemingly impossible challenges — whether it’s re-creating a Picasso or closing a big deal as a startup — it helps to bring your right brain to the table.

Here’s how.

1. Look, don’t label

Drawing something right-side up means there’s mental conflict: between what you are seeing (lines, angles, open spaces) and what you’re thinking it should look like (eyes should look like this, lips usually look like that).

For an early stage company, this is what enterprise sales feels like. You so badly want to fit into the clear-cut repeatable sales process, with clear labels that you hear other bigger companies talking about.

But the reality is that you aren’t jumping from one colored Chevron to another. You’re listening, observing, navigating, turn by turn.

2. Break it down

Re-create a Picasso. Close a six-figure deal

These are daunting tasks that seem impossible — whether you’re an amateur artist or an early stage startup.

So what do you do? You break it down. By turning it upside down and drawing one inch at a time, you can actually see what’s in front of you.

Not only is this less daunting, but you’ll notice details you missed when you were trying to focus on the whole picture.

3. Pin it up

If you’ve ever taken an art class, you know that the most important part is the Critique.

Whether it’s a drawing or a deal, you’ve got to “pin it up” and talk about it with your team. Don’t just critique the outcome, but the process you took to get there.

And then, you’ve got to really pick it apart. What went well? What did you do similarly to your peers? Differently? What worked?

Then, the most important question of all:


About the Author: Alli McKee helps companies develop their strategic messaging and brings it to life with visual design. After years creating strategic stories as a consultant at Bain & Company and designing visually at IDEO.org and in art, she’s working with B2B sales and marketing organizations to help them win more business. Through strategy, story, and design, her work enables companies to make their ideas sell — and stick.

Connect on LinkedIn to read more daily updates on startups, sales, and design.

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.

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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