Dig Deeper: The Why Game

Ever ask a kid why they want something? Their first answer is never the real reason.

“Why do you want that toy?”

“Because it’s COOL!”

“Why is it cool?”

“Because it transforms!”

“Why do you like things that transform?”

“Because I can make up stories with it!”

NOW we’re getting somewhere.

I explain my version of this technique in-depth in Chapter 9 of I Need That because it’s central to understanding what truly drives purchase decisions.

Emily Heyward calls it “The Why Test” in her book Obsessed.

Others call it “The 5 Whys,” though I’ve found you often have to go farther than five to get right to the bottom.

Here’s WHY it matters: People rarely understand their own true motivations. The first answer is always barely scratching the surface.

You want to identify the underlying root cause to understand the buyer’s Coveted Condition: the long-term desired future state that motivates them most irresistibly.

Think of someone preparing to spend big money on a luxury SUV. They might say it’s for safety. Or cargo space. Or handling in winter.

But keep asking why:

“Why do you need the extra safety features?”

“To protect my family.”

“Why is that particularly important right now?”

“Because I just became a parent.”

“Why does that make you think about a luxury brand?”

“Because I want to feel like a successful parent.”

THERE it is.

The real motivation isn’t safety specs or cargo capacity, which are available brand to brand. It comes down to identity. The need to feel like you’re crushing it at this whole parenting thing.

This is where dog brain and tank brain collaborate. One pushes for immediate satisfaction, the other seeks deeper validation.

When you truly understand these deeper motivations, you can speak to what your customer actually needs — not just what they say they want.

Action for today: Pick your product’s most common customer request. Ask “why” at least seven times. Write down each answer. The gold lies in those deeper layers.

Need help uncovering your customers’ true motivations? Let’s explore what’s really driving their decisions… just hit reply.

Laurier

Product Payoff: When Peloton launched, the founders could have focused on convenience or workout metrics. Instead, they dug deeper and discovered members weren’t merely seeking convenient group exercise. They wanted to feel like real athletes, on their terms. That insight transformed home cycling from a compromise into an aspiration.