A week without “why” and how it changed my thinking

Pasquale
4 min readJun 2, 2021

Truth be told, and if I’m being a bit candid, I really dislike the word “why”. Now, if you find yourself asking inside your head, “but why?” then this article might be for you.

Some of the explanations in this article might be overly simplified, but I still encourage the underlying concepts to be explored.

Background

A few years ago I read two books that really helped shape my thinking and eventually I devised an experiment for myself to help unpack whether or not it was effective. At the time I was still pretty early in my tech career and needed a different way of thinking to help not only target my questions but help myself understand low-level concepts as someone who did not have a traditional tech background. The books in question, and no I’m not sponsored or receive money from plugging them, are:

Now, if you’re saying something to yourself like, “I’m not in sales or negotiation, why should I care?” then just hang tight for a little bit. The reason these books had such an influence on me was that they both focused on changing the way you shape your question asking and, in turn, your understanding of a situation because of how your own question asking demands your engagement to a situation. Specifically, Voss mentions in his book to intentionally avoid “why” questions to prevent limited and unfocused answers.

Have you ever had a conversation with a young child who asks “why” all the time? If so, then you understand the logic loop we’re looking to avoid and this is where the challenge comes in.

The Challenge

The challenge I asked myself was pretty straightforward and simple.

For one entire week, do not ask a single “why” question.

Sounds easy on paper, but if you rely on “why” a lot then this could be a bit more of a daunting task. The end goal here is not to frustrate you or completely remove “why” from your vocabulary, but it’s to challenge your own way of thinking and help ask better questions in order to receive better answers.

Instead of “why”, implement other, better, question words into your conversation that start with “what” or “how”.

So how does this work in practice?

A Scenario

Let’s apply this to an all too familiar, and intentionally vague, scenario in the tech world, a software outage.

A code change is introduced that breaks your SaaS product for every single customer. During a post-mortem, you are working with a coworker who introduced the change to determine what happened and establish a root cause.

You: Why did the app go down?

Coworker: I updated a dependency to a newer major release.

You: Why didn’t you know it wasn’t going to break?

Coworker: I didn’t. Everything seemed fine when I deployed the change.

Okay, you know a “why” but “how” do you dig into this more? Start implementing some “how” or “what” questions.

You: How did you validate the update wouldn’t break existing functionality?

Coworker: I ran our test suite against the update, but there were no regression issues found.

You: How was the issue reported to us?

Coworker: A customer reported it to us.

There are a few key differences about the second conversation that are worth pointing out:

  • The first “how” question asks for a specific reason for the app’s failure — it’s more targeted than “why” something happened.
  • The second “how” aims to understand how you discovered the issue as opposed to asking “why didn’t we catch it?” Obviously, you know now that you didn’t catch the issue but asking the “how” helps you understand more completely.

Using more targeted words in conversation, you’re able to receive more targeted answers. Based on this short conversation alone you can learn a lot about this situation where you otherwise wouldn’t have had such specificity.

Wrapping up

Removing “why” from my vocabulary helped me not only ask more of others but more of myself. In time, I was able to start crafting more questions that not only answer the questions I needed answers to but also pushed me to understand more about the situations I was in before even asking questions. It’s an exercise in both questions asking and personal accountability to be engaged.

So, wrapping up, next time you’re tempted to ask “why”, use a different question word and challenge yourself.

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Pasquale

A hack of a hacker, OSCP holder, let's break stuff