by   on January 30, 2021

Getting Why, or Getting to Why?

getting whyIs it about Getting Why, or Getting to Why.

I like to think of myself as a success hacker. Whether or not it’s wishful thinking, the core belief in calling myself that way is that one could hack the formula for success. I continue to try doing this in my interviews with successful people on The Design Your Thinking Podcast too. One of the most common answers I’ve come across is “because I keep asking ‘Why'”. Is asking ‘Why’ 5 times really good enough? Or, is there something we should be looking for? Let’s explore.

Quick Time Travel..

If you rode the time machine back to my school days, I was one of those kids that was bad with memorizing lessons without understanding them fully. I was actually, very bad at it. Once I remember in the 7th grade, my science teacher told my parents in a Parent-Teachers Meeting that your son needs to memorize laws in chemistry and physics. They also told my parents that he asks ‘Why’ too many times (I wasn’t getting why!!).

Fast forward to my adulthood, I was surprised to hear successful people say that they were successful because of asking ‘Why’. Isn’t that a paradox? Didn’t successful people go to school, the way I did? After years of observing people and breaking the rules at work, I think I found the answer – and I’d like to share and discuss that with you today.

Background to Getting Why

Before I shared the little formula I learnt to effectively get to ‘Why’, I need to talk about 3 other things that have an influence on this formula.

successful women1. What I Learnt About Success from these 5 Women?

In the past few months I’ve been speaking with product makers in exploring this Product Mindset on my podcast. I spoke to Indi Young, Laura Klein, Christina Wodtke, Donna Lichaw and Kate Rutter on various topics, but they also answered my one question “What is that one reason why you think you are successful?”.

Reserve your thoughts for a minute and go through the 5 things these wonderful women had to say about ‘Why’ they are successful.

  1. Empathizing with the team members and know exactly what it is to do something they are doing. – Laura Klein in episode43
  2. Relentless focus on who is the person you are serving and why. – Kate Rutter in episode51 and episode52
  3. Ability to step back and constantly ask the same question, which is “What’s the story”. – Donna Lichaw in episode63 and episode64
  4. Not taking things for granted – Christina Wodtke in episode72 and episode73
  5. Honesty and the ability to say “I don’t know” – Indi Young in episode66 and episode67

You might wonder what “empathy” has to do with asking”Why” and so with “story” or “taking things for granted” or “saying I don’t know”. While I’ll let you listen to these wonderful ladies, I’d like share the one advice I’ve received from countless people…

getting to why2. Ask Why 5 Times

This one is so famous that it has a Wikipedia page of its own. Everyone and his mom and dad might’ve received this advice. I’ve stopped giving this advice however because I realized it’s not about asking ‘Why’ 5 times, but what you are looking for. I was out with my son Vivaan to see someone in the hospital and he saw a bunch of wheel chairs. This is the conversation we got into:

Vivaan: What are these seats with wheels?

Me: These are called wheelchairs.

Vivaan: What is a wheelchair?

Me: Wheelchairs are chairs with wheels.

Vivaan: Why chairs have wheels?

Me: So that old people to move around.

Vivaan:Why do old people need wheelchair to move around?

Me: Some old people cannot walk. So they need a wheelchair.

Vivaan:Why they cannot walk?

Me: Because they don’t have strength in their legs.

Vivaan: Why?

Me: Because as they grow old, their legs would’ve got tired.

Vivaan: Why?

Me: Because their muscles become weaker.

Vivaan: What is ‘muscles’? (he heard that for the first time)

Me: Blah blah blah..

If you noted, the conversation started with a couple of ‘What’ and then 4 ‘Why’ and again looped back into a ‘Why’, and it wasn’t done yet. I’ve observed this with several conversations during user interviews and other activities. The point is, it’s not just about asking ‘Why’ 5 times. There was more.

And then came this thing in 2009…

3. ‘Starting With Why’

I read Simon Sinek’s book Starting With Why: How Great Leaders Inspire Everyone To Take Action back in 2010 (I think!) and was gung-ho about what the author talked about. The core message he conveys through the book is:

Every person knows What they do.

Your job title, function, the products you sell or services you offer.

Some people know How they do it.

The actions you take that set you apart from others.

Few people know Why they do it.

The purpose, cause or belief that inspires you.

He talks about the stories of inspiring brands like Apple in the way they Start With Why to build a strong and loyal customer and fan base. This is a smart way of connecting with our customers indeed. The question that continued to bother me was how does some discover this ‘Why’. To go a step further, what should I be looking for in order to discover this ‘Why’.

Getting Why…Getting to Why

From the 3 cases I presented in the background above, here are some observations I’d like to make.

  1. As you perhaps noticed in the 2nd case I discuss above – the conversation with my son, asking ‘Why’ 5 times does help if you have the right context set. If the context is unclear, it doesn’t matter how many ‘Why’ you ask – you will never find the answer you are looking for.
  2. From my guests’ success, you clearly see that it’s ultimately about asking ‘Why’, but do note the words in italics in each of what my guests had to share. It’s about knowing the what and who that helps them get the right context to ask ‘Why’.
  3. From the ‘Starting With Why’ it’s clear that our brain works quiet the opposite while getting to ‘Why’ as opposed to what it does when just getting Why.

The Getting Why Formula

getting to why formulaThe formula that I realized was key to Getting Why, like I described above, needed the context. Where does the context come from? As we saw above, it starts with the who and the what. Think of English grammar and the <Subject – Verb – Object>. I also like the perspective the Jobs To Be Done theory brings in at this point <When – situation – I want to – motivation – So that – expected outcome> with situation. Situation is key to context, and is addressed by where and when. Finally the job itself – how it is done. Given the context, the Getting Why…I mean, Getting to Why formula looks like this:

[[What / Who + When + Where] -> How] -> Why

I’ve used this formula for a quiet some time now. But recently Kate Rutter suggested this book called The Back Of The Napkin by Dan Roam. He talks about visual thinking in this book and introduces another key question to this mix – the how many / how much questions. I really liked this because it introduces quantity into the context, which is another key factor when it comes to understanding why. With this, the formula now looks like this:

[[What / Who + How much / How many + When + Where] -> How] -> Why

And do note that the ‘Starting With Why’ works quiet the opposite, like I mentioned above: Why -> How -> What. Interesting, isn’t it?

How to Apply the Getting to Why Formula?

If you had to apply this formula to my conversation with my son, you would naturally start with the what and who.

Vivaan: What’s a wheelchair?

Me: It’s a chair with wheels

Vivaan: Why chairs have wheels?

Me: Because old people can move around in them

Vivaan: Who are old people?

Me: Like all these people (how many) with gray hair with walking sticks.

Vivaan: Why do old people need wheelchairs?

Me: Because they cannot walk and still need to move from this room to another, when they need to go to the bathroom (where) or when they have to go to the front yard (where) to see their grandchildren play.

Vivaan:Why they cannot walk?


 the conversation continues.

Though the questions my son asks now are why questions, he is seeking/looking for the where and when. With this, he has been able to sense how wheelchair works and hence why wheelchairs are needed.

As my guests Indi Young and Christina Wodtke said in the beginning of this conversation, it’s important we start with “I don’t know” and “not taking things for granted”. Like Donna Lichaw says it’s all about knowing “what’s the story” – actors, scenery and action!


getting to why pictureThe next time you are looking to discover or understand something remember this simple formula for getting to why. It certainly leads to greater insights to both understand Jobs Stories and uncover the ‘Why’. It’s not about asking ‘Why’ 5 times, but what you are looking for, that really matters.

You get what you seek or look for. This getting to why formula helps you seek with a clear intention of understanding the full picture including the What, Who, Where, When and How much / many. Special thanks to Dan Roam for helping me understand the importance of How many / much.

This technique also works great if you are trying to remember things. Some people have spatial memory, some remember using time and some using sounds. I’ve sampled this with kids’ learning techniques and have found them unknowingly use similar techniques as well. These questions create a picture of the scene and it’s told that people remember pictures better than words.

Let me know what you think – click one of the tweets below and voice your thoughts or leave a comment. Also, don’t forget to signup for DYT Insider below to get the Tiny Book Of Triggers to trigger your Curiosity!

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  1. In talking about user research, I tell people there’s a difference between the question you ask and the question you want to get an answer to. But I really like the way you split why from getting to why; “why” is also a hot topic that people like to debate in user research circles (e.g, “NEVER ASK WHY”) – I don’t like “never” statements about user research and I’m always surprised when people say that “why” is too judgmental and makes people defensive. It’s kind of HOW you ask it, isn’t it?

    Anyway, this is a bit of a digression from your piece, but what it sparked for me

    1. True. The “judgemental” bit never crossed my mind. Very true. Just to add on, if the user is not warmed up enough you could get the deer-in-the-headlight stares to a “why”.

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