Why, Oh Why, Oh Why?

On our love hate relationship with the question “why”

Ali A Hussain
4 min readAug 17, 2021

A couple of days ago my elder threw his milk bottle after he finished it into his brother’s crib. And I immediately found myself yelling, “R, why did you throw the bottle in M’s crib?” And there I saw it staring at my face. My tone said reprimand. The keyword was “why”. Why, oh why did I use the word “why” as a reprimand? This is the word that I want him to love. I want to be the kind of dad that he would ask a lot of “why” questions. I want to the kind of dad that will get him into the habit of critical thinking by asking him a lot of “why” questions in return. And here I was using “why” to reprimand him.

A child looking with a focused sad face
Is this curiosity or sadness? Focus or disappointment? I don’t know but the question in their head in either case is “Why?” // Photo by Juan Encalada on Unsplash

I use to be involved in an Austin group called Authentic Relating. It involves games designed to help you know yourself better and to relate with others with more integrity, at a deeper less superficial level. One of these games is called Curiosity. In this game a person asks questions about the other that they are genuinely curious about. After having recently heard about Toyota’s Five Whys method I suggested play-testing a variation on Curiosity at a facilitator meet. The twist was that your curiosity must be a “Why” question. It did not go well.

Marble head of Socrates
A lot easier to love Socrates if he never subjected you to the Socratic method // Image courtesy Wikipedia article on Socrates

As I asked my game partner on why she wants to get a boyfriend, I started to recognize just how incisive the question “Why” is. It is the question that allows us to get to the heart of a matter. It is also the question that shakes the very foundation of all our thoughts, with one word challenging all of our fundamental truths that we hold to be true. It is the question that can immediately make anyone defensive.

It is the kind of question that if you ask too much you’ll expose even the most learned experts have their knowledge based on unproven assumptions. That is after all the kind of rigorous interrogation Socrates subjected the experts of Athens to. It is also the kind of questioning that drove the experts of Athens to kill him.

Most of us that have studied Agile know the power and effectiveness of the Lean philosophy coming out of Toyota. And have heard of the technique called “Five Whys” for finding the root cause of. In this technique you circle around a problem in search of the root cause, continuing to ask “why” until a meaningful systemic root cause is discovered and solving that rather than the symptoms. It is called “Five Whys” because there is a rule of thumb of roughly five times you ask the why question before you’ll hit the root cause. But if anyone has tried this in the absence of a trained facilitator they will likely find themselves at best in a room full of silence, at worst a blame game that wrecks team cohesion.

The key to a successful session is making sure you have the right facilitator in place. This facilitator is a strong leader having the ability to keep the team focused, maintain psychological safety, and reach an actionable root cause. This most simple of techniques of just asking why, can really only be practiced in the hands of an extremely capable leader. Such is the power of the question “Why”, it can either lead you on the way to change the world, or it can completely destroy you.

As a leader I know I have skillfully asked questions to bring out the best in someone. I have much to my chagrin also used it to destroy someone. The difference between the two questions is simple. In the former, you have a genuine curiosity to hear their answer. In the latter your “Why” is a rhetorical question making the statement, “There is no reasonable answer to why someone would do this.” I am going to confess to an even bigger sin. I’ve also tried to pass off when I tried to do the latter as an innocent misunderstanding when I was trying to do the former. But it never works. After all we start learning to look for that subtext in the question “Why” at a very young age.

What should I have done with R instead? Well I should have said, “R, why did you throw the bottle in M’s crib?” Yes the exact same thing. Just with a kinder tone. And followed it up with a genuine attempt at communication with a barely verbal toddler. Trying to understand his “why” and sharing mine. In the mean time though this father owes his son an apology tomorrow morning.

Scrabble pieces spelling “I AM SORRY”
R is such a great boy. Apologizing for his mistakes. His father needs to learn more from him // Photo by Brett Jordan on Unsplash

Update 2021–08–21: A few people asked me if I apologized to R. So I thought I’d add an update. Yes, I did the morning after I wrote this post. But before I did that, he had already offered me the milk bottle so I was extra apologetic and extra appreciative.

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Ali A Hussain

Building the accelerator for tech services/consulting companies