Why Ask Why?

A brainstorming approach that helps you find clarity by asking five questions.

Diana Lillicrap 7.22.2026

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When my kids were young, they used to ask “why?” about everything. I would tell them something and they would ask, “but, why?” I would try to explain, and they would have another “why?” question.

It was exhausting, but I realized it was their method to break things down until they could understand a concept in terms that made sense to them. Questioning and persistence gave them clarity.

This approach of asking questions until you’ve answered them in the most simplified manner, can be an effective way for adults to find clarity too. In fact, you can use it in your brainstorming process to solve problems and come up with new ideas. Here’s how.

State your problem

Start by writing out your problem. Be as clear as you can with the language you use. For example, maybe your problem is that “sales for our premium product line are too low.” Keep it simple and direct.

Ask why five times

Now ask yourself why the problem exists and write out the answer. Follow that answer with another question of why, and so forth until you’ve asked why five times. By the time you are through, you should be at the core of your problem.

Our example would look something like this.

Problem: Sales for our premium product line are too low.

Q1: Why are sales for the premium product line low?

A1: No one understands the value of spending more for the premium product.

Q2: Why doesn’t anyone know the value?

A2: We haven’t done a good job of communicating the value and benefits of the premium option compared to other options.

Q3: Why not?

A3: We haven’t clearly defined the value or created language to position it against other options.

Q4: Why not?

A4: We haven’t taken time to gather proof points or develop compelling language.

Q5: Why not?

A5: Good question. I guess we should do that.

When you get to a possible solution, go back and start the process again. Consider where you could ask different “why” questions or offer up different answers and reasons along the way. After a few times through, you will get to the heart of your issue and have several ideas on how to solve your problem. 

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