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  • Writer's pictureMatthew Lerner

The problem with asking "why?"

Updated: Nov 14, 2023

“Why” is very much en-vogue these days, and I think that’s a problem. You’ve got "The Five Why’s," "Why we Sleep,” and "Why we Buy." And somehow Simon Sinek’s book “Start with Why” is both #2 and #8 on the UK nonfiction best seller list. I’m ready to take the other side of that argument…


Of course we need to understand why. But asking “why” is a terrible way to find out why.

You may be wondering why. 😏

When you ask customers (or investors) “why,” they generally lie, offering plausible-sounding but incorrect answers. And once they provide that incorrect answer, it blinds them to their true motivations.


Why we lie: Purchase, investment and consumption decisions are surprisingly complex. Often we don’t fully understand our true motivations, and uncovering them takes skill. But we believe we understand ourselves. So, when someone asks us “why” (e.g. “why did you buy X?”) we say the first thing that comes to mind, usually a justification for our decision rather than the actual cause. And then we anchor to that mistaken belief, thanks to…


The “commitment consistency bias" — Once we state a belief, even an incorrect one, we accept it as truth. This commitment to our faulty explanations makes finding the actual truth tricky. But it gets worse…


After we commit to a belief, we’re more likely to notice evidence that supports it, and less likely to notice evidence that contradicts it. That’s called the “confirmation bias.”


In short, once we answer the question "why" we have a hard time entertaining differing points of view – such as the actual reason we made the decision.

What should we ask instead?

In customer interviews try these three questions in order:

  1. "What will that enable you to do?" — It’s like asking why, but focuses them on the actual context of the decision.

  2. "Why is that important to you?" or “What’s at stake there?" — Often the true reasons are emotional, this question helps uncover emotions.

  3. “Who else cares about that outcome?" — Often we make decisions based on what we suspect others might think of us.

I hope this helps!

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