The One Question That Changes Every Conversation. Why?

I have always liked reading, but I did not find the time for it. About 10 years ago, I started to listen to books in the car. I have a lot of travel time and listening to books just works for me. I tend to switch between (science-)fiction and non-fiction.

When I encounter a problem or a new situation, read or hear something about a new model or framework, I’ll find a book and “read” it. Over the years I gathered quite a long list of books that helped me a lot in my daily work. In one on one talks with people, in explaining situations to customers, dealing with problems or just let me grow as an individual. When I talk to people I often hear myself saying. I read a book, where… But no clue in which book this was. That’s why I started this list of books. To have a library for myself, the lessons from each book as a quick summary, but also to be able to share it with others. I hope you enjoy it and find it useful. If you want to learn about more books, visit the Books section of this site.

At one of my earlier jobs, a manager pulled me aside. He had just completed a course in Neuro-Linguistic Programming, and he had a note to share with me: asking “why” was aggressive. It put people on the defensive. I should rephrase my questions, approach things differently.

I sat with that feedback for a while. And honestly, I never fully bought it. I was not trying to interrogate anyone. I just genuinely wanted to understand the big picture before diving into the details. Why are we doing this? What problem are we actually solving? Who cares about this outcome, and why?

Some time later I came across Simon Sinek’s Start with Why, and I finally had language for what I had been doing instinctively.

The Golden Circle

Sinek’s core idea is deceptively simple. Most organisations communicate from the outside in: here is what we do, here is how we do it, and if you are still listening, here is why. Leaders who inspire — and Sinek’s examples include Apple, Southwest Airlines and Martin Luther King — do the opposite. They lead with why, and let the what follow from that.

He calls this the Golden Circle: Why at the center, How in the next ring, What on the outside.

The classic example from the book compares two ways to talk about a computer company. The conventional version: “We make great computers. They are beautifully designed and simple to use. Want to buy one?” The Apple version: “Everything we do, we believe in challenging the status quo. We believe in thinking differently. The way we challenge the status quo is by making products that are beautifully designed and easy to use. We just happen to make computers. Want to buy one?”

The product is the same. The sequence is different. The effect on the listener is completely different.

Not just for grand visions

Here is where I diverge slightly from how the book is sometimes read. Many people take the Golden Circle as a framework for vision statements and brand strategy. Apple, Southwest, Martin Luther King: it feels like a tool for big things.

But I apply it to every single decision. Every project kickoff. Every presentation I give. Every consultancy assignment where a customer is asking me to build or change something.

Before I talk about solutions, I want to understand the why. Why are we doing this? Why do you need this now? What changes if we get this right? And equally: what does it mean for your organisation if this stalls or fails?

In the technical industry especially, I notice how quickly we skip past those questions. We work with very smart people who can reason about architecture, tooling, and trade-offs at a sophisticated level. The conversation accelerates fast. Before long, we are deep in the how and the what, and no one has paused to ask whether we all agree on the why.

That is often where things quietly go wrong. Not because of bad technical decisions, but because the problem being solved turned out not to be the problem anyone actually had.

Abstraction laddering in every conversation

What the Golden Circle gave me is a kind of discipline: lead with purpose, not with solution. When a team or a leadership table comes to me with a request, I treat the first fifteen minutes as sacred for that one question: why does this matter?

And most of the time, the why they bring in the door is not the same as the why we land on together. The first answer is usually functional, “we need a new platform,” “we want to modernise the stack,” “we are falling behind.” Push a little and a clearer purpose emerges: we are losing good engineers, we cannot respond to the market fast enough, the board is asking us to demonstrate value from technology investment.

Those are very different conversations. And they lead to very different choices.

Sinek’s TED talk on this is one of the most-watched ever for a reason. If you have not seen it, it is worth the eighteen minutes: https://youtu.be/u4ZoJKF_VuA. And if you want the full argument in book form, the summary is in the Books section.

Here’s my take

The manager who told me to stop asking why was not wrong that the word can land awkwardly. But the instinct behind it is exactly right. Every conversation has a level of abstraction at which it becomes genuinely productive. Getting there requires someone willing to keep asking until the actual purpose becomes visible.

That is not aggressive. That is just good leadership.