Ask Why, And Keep Asking

· Sunday, June 28, 2026 · Mike Riversdale

I think I've written about "why" and asking it multiple times before ... hold on, let me go have a look ... yup, here, here, here, and here.

Asking 5 "whys" is the finest approach at getting to the true heart of anything. With each "why" you will drop through the levels of fog, honing in with each stage to the true issue lying underneath the surface / visible comments.

In my experience you will find you're discussing emotions anywhere after the 2nd or 3rd "why?", and the more you ask the more raw and core to the person will be the replies, be aware of where you want to go and what you are willing to handle as not everything needs to become a discussion on personal childhood trauma.

I find 2, maybe 3, is all you really need at work to uncover the real reasons for someone's thinking on a subject.

Five whys (or 5 whys) is an iterative interrogative technique used to explore the cause-and-effect relationships underlying a particular problem. The primary goal of the technique is to determine the root cause of a defect or problem by repeating the question "why?" five times, each time directing the current "why" to the answer of the previous "why".
The method asserts that the answer to the final "why" asked in this manner should reveal the root cause of the problem. The number of whys may be higher or lower depending on the complexity of the analysis and problem.

[source: Wikipedia: Five Whys]

As a humorous/serious example this from Schrödinger's Prat (@Rhodium103@mastodon.social / May 07, 2026)

UK Gov: "We'll ban under-16s from social media!"
People: "Why?"
UK Gov: "Because it's dangerous for them."
People: "Why?"
UK Gov: "Because of bullying, and algorithms that promote hate."
People: "Have you considered holding the bullies and those who tweak the algorithms responsible?"
UK Gov: "..."
People: "..."
UK Gov: "..."
People: "..."
UK Gov: "Well, clearly you're anti-growth and anti-business and anti-Britain and anti-semitic."

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