How to ask Why

Toyota permanently impacted the engineering world when it introduced the 5 Whys method of interrogation. Strikingly simple, its goal is to get behind superficial causes and find the root cause of a problem. It seeks to drill straight into a problem by repeatedly asking “why” in response to each answer. Today, 5 Whys has been adopted as a critical tool by major business management systems like Kaizen, lean manufacturing, and Six Sigma.

In my career as a software engineer, I sometimes made things that failed or broke and then received this kind of questioning. It was often harrowing. Each time my boss or the product owner opened their mouth, I knew they were about to question what I had just said. I had to justify myself at each step, and the justifications would also have to be justified.

Consider what it feels like to read these questions. What voice says them in your mind?

“Why did you not meet your deadline?”

“Why did you choose that approach?”

“Why didn’t you do it a different way?”

Do you hear a caring, interested voice? Or do you hear a challenging voice, maybe even contentious?

Technically, there’s nothing wrong with these questions. When I read them, though, it’s easy for my mind to assume I’m under attack. My brain starts to produce fight-or-flight hormones right away. Sometimes I turn defensive within seconds.

A “why”-driven investigation doesn’t have to be triggering for the subject. In fact, any time we want to know “why”, we can say it several different ways to help the other person feel safe to answer. That’s important, because when a person feels defensive or deeply uncomfortable, it’s hard for them to answer honestly.

When conducting an analysis or investigation, I want it to move forward productively, so I try to shape the process so others can participate easily.

Here are three ways to soften the question “why” without losing its purpose. Try them out one-by-one, then mix them together to see what impact you can create in your next review meeting or retrospective event.

Use an indirect tone

The first thing I do is, unfortunately, nearly impossible to demonstrate here: I soften my tone when I ask direct questions. As a rule of thumb, the more direct the question, the softer I make my tone.

Here’s a question you can probably ask without any change in tone:

“What was your team’s velocity during this sprint?”

Here’s a question I would to soften my tone to ask:

“Why was it only 30 story points, when the prior sprints were 50 and 55?”

My tone of voice indicates the directness of my intention. A direct intention is one that drills into the subject’s inner world, like I’m mining for something I want to extract from them. An indirect intention invites the subject to share their inner world for some other purpose, like they’re giving me a gift.

Ask direct questions in a way that implies an indirect intention for asking.

For example, if you intend to show that you’re simply curious about the answer, ask it the same way you would ask, “Why do centipedes have 100 legs but millipedes have 1000?”

And if you intend to show that you care more about their feelings than the answer, ask it the same way you would ask, “How are you doing after the car wreck?”

As practice, try changing your tone to show these indirect intentions:

  • You’re checking an item off a list as a matter of procedure
  • You’re conspiring with the subject to share a secret
  • You’re working with the subject to create an improv joke

Put the subject on your team

What’s the difference between these two questions?

“Why did the rocket explode at T-minus-5 seconds?”

“Why do you think the rocket exploded at T-minus-5 seconds?”

The first question is part of an investigation. It asks for a stone-cold-fact. The subject is put on the spot to speak the truth, and if that’s a hard truth, it’ll be hard to speak.

The second question asks for speculation. The subject can tell the truth if they know it, or they can make their best guess. It’s subtle, but this difference in wording implies to the other person that it’s okay to make a mistake with their answer. That lowers the pressure when answering.

Shifting the context of a hard question from investigation to speculation has another powerful effect: it invites the subject onto my team. We’re both looking for possible answers together, and that’s a much safer position to be in.

There are similar words and phrases I add to “why” for the same effect:

“Why do you suppose/imagine…?”

“If you had to guess, why…?”

“In your opinion, why…?”

Try them out. Do they sound natural? If not, come up with some that fit your way of speaking.

Downgrade the question’s power

Coaches and leaders often talk about powerful questions and rank “why” as the most powerful among them.

The linguistic architecture of powerful questions diagram [adapted]. The Art and architecture of powerful questions. Vogt, Brown, & Isaacs (2003, p. 3).

“Why” is powerful because it’s the most open-ended thing that can be asked. It makes no assumptions about what the answer is going to look like…and that’s part of what makes it such a hard question to answer: the subject doesn’t have any idea of which answers are “good” and which are “bad”.

I find it helps people when I put guardrails on the question “why”. I like to change it into one that has some structure: “what”.

Asking “what” means I assume that something specific — something other than the subject themself — is the answer to the question. It’s a subtle effect, but it can help keep the subject from feeling anxious. Here’s an example:

“Why did the rocket explode?”

(In the subject’s head: He might be thinking I did it!)

“What caused the rocket to explode?”

(In the subject’s head: He thinks something else did it.)

Switching from “why” to “what” can be a useful way to start a line of questioning. If the answer to the question above is that tribbles found their way into the cooling system, a continuation of questions could look like this:

“How did the tribbles get onto the rocket?”

One was found in an astronaut’s backpack.

“How did it get into the backpack?”

The astronaut probably put it in there.

“Why did they put a tribble in their backpack?”

Tribbles are irresistibly cute.

Do you see how more powerful questions can be used as the answers get closer to the root cause? By switching to a less powerful question and building back up, you can help the subject manage any anxiety or stress at the outset.

Practice, practice, practice

Uncovering answers is a complex skill. There are excellent methods for reviewing, investigating, and analyzing information to find deep truths. Similarly, working and communicating with people is a complex skill. When seeking a truth held in someone else’s head, these skills have to be used together.

Analytical skill is improved through practice. So is conversational skill. Take these methods and play with them. See what works in various situations. Try combining methods into a single question or sequencing them in a line of questioning.

Pay attention to the result each time, and you’ll learn quickly. Before long, you’ll find yourself uncovering valuable information more quickly, and everyone involved in the process of investigation will feel better, too.

Part 2: How to set up the question

Update: This article explores how to ask a powerful question. I added more thoughts here, discussing how to set up the question before asking it.

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