What The Wizard of Oz Teaches Us About Sales
In the spirit of Halloween, let’s talk about one of my favorite movies: The Wizard of Oz.
(Fun fact: the movie had its world premiere at a small-town theater on Cape Cod—about 1,000 yards from where I live today!)
As a kid, I loved everything about it—except the Wicked Witch and her flying monkeys. What I didn’t realize was how much The Wizard of Oz can teach us about sales.
We learn in the end that at any moment, Dorothy could have clicked her heels and gone home. In the end she chose familiarity, safety and comfort over adventure, predictability over change.
When our prospects decide to “do nothing,” they’re doing exactly that—they’re clicking their heels three times and going back to Kansas.
Dorothy had every reason to stay in the Emerald City. She was celebrated, had loyal friends in Toto, the Scarecrow, Tinman, and Lion, and could have built a new, exciting life. Yet she chose to return to her quiet life on the farm.
Why?
Because the pain of change felt greater than the cost of staying the same.
That’s exactly the calculation our buyers make every day.
Our job in sales isn’t just to find pain—it’s to understand whether that pain has become untenable or is about to become untenable. Is there a great cost to the people and the business?
Before we can help them follow the Yellow Brick Road toward a better solution, we have to make sure they’re truly ready to take that first step.
When my teams or I qualify a prospect, we use what the “4 W” questions, designed for a natural conversation on the first call:
- What happened that made you decide to speak with us?
→ The catalyst for action—the moment pain turns into movement. - Why will you make a change now?
→ The real business problem and the desired outcome. - When do you need to be in production?
→ A timeline check without asking, “When are you buying?” - Who owns this project?
→ The executive sponsor who owns the outcome.
Notice what’s missing: budget.
Did Dorothy ask the Wizard what the balloon ride would cost? No. She “found” her budget by taking on the challenge of eliminating the Wicked Witch. Your prospect will too—if the pain is great enough and the value clear enough.
Once you’ve qualified, move into Discovery—a stage that deserves its own time and preparation.
Use a structured approach like Gap Selling and prepare a Problem Identification Chart (PIC) ahead of the meeting. Research their company using AI tools, LinkedIn, and their website to form sharp, relevant questions.
Ask yourself:
👉 Do they need a heart (empathy)?
👉 A brain (insight)?
👉 Or courage (confidence to change)?
And most importantly—can your solution provide it?
Only after you’ve done this should you show a demo or “create the vision” of their life after change.
Your proposal isn’t just a price quote—it’s a value statement with outcomes and expected ROI, showing why change is worth the pain.
And beware the Flying Monkeys—the skeptics and internal blockers who might swoop in to derail your champion or economic buyer.
This is where sales leadership meets storytelling. Keep the journey clear, build trust, and make the destination worth reaching.
Here’s where the analogy ends.
Depending on your perspective, you’re either helping your prospect find Kansas—a safe, stable home—or Oz—a bright new world of possibility.
Either way, your role is the same: Guide them, step by step, down the Yellow Brick Road together.
Good selling—and Happy Halloween! 🧙♀️🚴♂️
