🟢 5 whys vs 0 whys

The right amount and style of questioning

(2.5 min read)

Much of life is unlearning something you’ve learned earlier.

Quite difficult sometimes.

Arguably more important than learning something new.

Your old beliefs, assumptions, and habits can hold you back.

Below, I’ll share why nowadays I try to ask “why” less than I used to.

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Relentlessly diagnosing

My first job out of Princeton was to work for Ray Dalio, a billionaire obsessed with operating in a principled manner.

I love that idea.

One of his principles that he drilled into us was:

A root cause discovery process might proceed like this:

~~~~~~

The problem was due to bad programming.

⤷ Why was there bad programming?

Because Harry programmed it badly.

⤷ Why did Harry program it badly?

Because he wasn't well trained and because he was in a rush.

⤷ Why wasn't he well trained?  ⤷ Why was he in a rush?

...

Ray explains:

You must go deeper in order to understand what about the people and/or the design led to the failure.

This is difficult for both the diagnoser and the [responsible parties], and it often results in people bringing up all kinds of irrelevant details.

Be on your guard because people will often look to cover themselves by diving into the weeds.

(Taiichi Ohno of Toyota Motor popularized a similar framework, “Five whys”.)

It makes a lot of sense.

When you identify a true root cause of a problem, you can then permanently resolve that root cause, which will fix that problem and often other current or future symptoms of that same root cause.

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Probably because of my INTJ personality and because I hadn’t known any different since I was so young and this was my first job, I adopted the principles hardcore.

Older people at the company sometimes felt I was too brusque.

And people outside of work definitely did.

Katie still teases me about my 2006 OkCupid profile, which said something about “values truth more than harmony”. (Thank goodness she didn’t click ❌.)

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However…

Speed

I first started to see the benefit of not digging into root causes all the time when I ventured out as a solopreneur.

I kept hearing from successful business owners “You’re too smart for your own good” and other euphemisms.

They credited their own success with their habit of quickly embracing “what works”, as learned from mentors or via their experiments.

In a small business, how nimble and lightweight and minimalist you are really matters.

Spending extra resources trying to understand too much can bog you down and block you from picking up momentum and gaining traction.

“Do this, and don’t do this,” is the kind of advice that I’ve had a tough time following blindly.

My tendency has been to always question everything and truly understand from first principles before I adopt a practice.

If I were to go back to the beginning of my solopreneurship days, I’d spend more energy finding mentors that I could thoroughly trust, and then I’d trust them more implicitly and move faster.

Alignment

A second reason to ask “why” less is because it knocks people off balance.

If you and the other person are not A) already in a relationship where they expect to be challenged directly, and B) in that mood right now and ready for it…

…then they will likely feel uncomfortable and judged (silently criticized) when you ask “why” about something.

Katie (my partner, who is a psychologist) says it can feel insulting.

She recommends using roundabout approaches instead.

Instead of asking “Why did you do that?”, try more indirect approaches like:

• “I’m curious about what led you to that decision.”

• “I may be missing some context. Could you walk me through your thought process?”

• “Interesting. I’d love to understand more about your perspective on this.”

The goal is to invite an explanation without sounding accusatory or judgmental.

Direct “why” questions can put people on the defensive, even if that’s not your intent.

You’re probably reading this like 🙄🤦‍♂️ because it’s obvious to you.

But I’ve needed this reminder. 😉

I’m often insatiably curious.

It’s important to explicitly label my curiosity and enthusiasm so that my good intentions are clear because otherwise I can sound aggressive rather than supportive.

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What are your thoughts on the various question words?

• Who

• What

• Where

• When

• Why

• How

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🕙 What we learned in recent posts:

🟢 The Misunderstood but Powerful Tool: Comparative Advantage (with free calculator)

🟢 What am I even doing?

🟢 The 1 thing you must sacrifice to get what you want

🟢 The cheat code I learned from Steve Jobs and Ray Dalio

🟢 [See all posts]

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