Why? Why? Why? Why? Why? What If? How?
- May 12
- 6 min read

If you had a magic wand, what would you wish for?
I cofounded a business called Yumpingo after we asked a restaurateur that question.
They dreamed of seeing a comic book thought bubble above every customer, to know what they were really thinking.
Why?
Restaurants are experiences, but they had no good way to understand, measure and improve those experiences.
Why?
Restaurant feedback was not collecting enough objective and actionable feedback.
Why?
The majority of guests never left feedback.
Why?
Because leaving feedback was either really boring (paper surveys), awkward (“How was your meal?”), or only something you did if you were ecstatic or furious (review sites).
Why?
There was no seamless way to capture the thoughts of the silent majority of guests.
How do you fix that?
What if …
… we could capture the sentiment of every guest before they even left the building?
… feedback wasn't a chore, but a seamless and enjoyable part of the (otherwise very dull) bill-paying process?
… we could turn subjective feelings (like the saltiness of a steak, or the attentiveness of the waiters) into objective metrics that could be tracked?
Could we build this?
How …
… do we make it fast? (We designed a 1-minute review)
… could it integrate perfectly with a busy restaurant's workflow? (We offered in-the-moment surveys through devices, emails and text messages)
… do we make it valuable and actually drive change? (We provided recommended actions to the restaurant teams prioritised by the expected impact on guest sentiment)
And that is how you start a new business.
We asked a sequence of questions: Why? Why? Why? Why? Why? What If? How?
And through the answers we created an effective feedback service that allowed restaurants to manage their experience with the same precision they used to manage their food costs.
Then we repeated this question sequence over and over again, for the next decade, to build a successful product, organisation and business.
Questions or Answers?
When questioned about answers Albert Einstein said, “If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask… for once I know the proper question, I could solve the problem in less than five minutes.”
Questioning is an essential skill for a scientific genius, but it's also key for the rest of us too.
You need it for decision making (through critical thinking), connecting with others (building empathy and likability), leadership (establishing a vision and a challenge culture) and creativity (questioning the status quo and exploring new possibilities.
Two centuries ago it was possible to have all the answers.
The last person who had a comprehensive grasp of all the scientific knowledge available in his time was Thomas Young (1773–1829).
He made fundamental discoveries in physics (wave theory of light), physiology (how the eye focuses), and Egyptology (deciphering the Rosetta Stone).
But since that time the volume of knowledge has exploded.
Today more information is created in a single day than existed at the time Thomas Young was doing his thing.
Known answers are everywhere and easy to access through the Internet, and now via AI.
The result is that the value of answers is falling.
And the value of questions is increasing.

A single questioner can now almost instantly tap into vast resources of answers to be able to resolve larger and more complicated problems than ever before.
In the age of AI the skill in demand is the ability to ask great questions (aka prompt well).
Our ability to think critically, empathetically, challenge and be creative, are the abilities that are (at least for now) uniquely human.
“Computers are useless, they only give you answers.” - Picasso
Why … Why? Why? Why? Why? Why? What If? How?
This is what I call the innovation sequence.
It’s two existing questioning concepts that work well when you smash them together - Sakichi Toyoda’s ‘5 Whys’ and self-proclaimed questionologist Warren Berger's ‘Why, What If, and How’:
Why 5 Whys?
Every problem (or future opportunity) has a root cause.
And the way to uncover it is to dig down with questions.
In the 1930’s Sakichi Toyoda, the inventor, industrialist and founder of Toyota, created the 5 Whys method for his business.
When something goes wrong in a complex system, the temptation is to fix the immediate symptom and move on.
But because the core problem remains unsolved it will continue to affect the system in the future.
The simple use of 5 Whys ensured his teams actively sought out and fixed the core issues.
Japanese car manufacturing became hugely efficient and successful in the 1970s and 80s in part because of this mindset of scientific improvement.
And with their very visible success Toyoda’s management idea spread around the globe.
It’s a simple and effective method that works if you have a problem on your production line, but it’s also great if you want to:
fix your washing machine,
reduce silos between functional teams,
make sure your interviews pinpoint the best candidate for a job,
or uncover a business problem to solve.
It’s simple, but it’s needed because people and businesses are naturally terrible at doing this.
A 2017 survey in Harvard Business Review of 106 C-suite executives across 91 companies from 17 countries, highlighted that a full 85% agreed that their organisations were bad at problem diagnosis, and 87% agreed that this flaw carried significant costs.
With that as the situation, utilising the 5 Whys is an amazingly easy superpower to grow.
Why Stop at 5?
You have to draw the line somewhere, so why not five?
If you ask “Why?” endlessly, you will eventually get trapped in a cycle of small and less consequential issues.
And humans do have a limit of patience.
It’s why we kept our feedback surveys short.
We asked the 5 Whys ourselves, then built a whole business on asking hundreds of thousands of restaurant guests 5 Whys too.
Why … What If? & How?
Why? is problem finding.
It’s great for managers focusing on how to fix or optimise an existing process.
But when you need to be innovative and create a new process or product you need to ask this sequence of questions that was defined by Warren Berger.
What If? is idea finding.
This is where entrepreneurs and leaders start thinking differently to pure managers who would stop at ‘Why?’
By asking ‘What If?’ you’re starting to think divergently, opening yourself out to all possibilities.
You’re now actively seeking inspiration, while challenging your biases, assumptions and the status quo.
And you’re much more likely to find novel ideas for improvements or solutions that will transform the problem you discovered.
How? is strategic action.
This is how you converge on the best ideas, then find a way to make them real.
It’s thinking practically how to develop and implement a new idea or process and bring the idea to life.
It’s the quality of the ‘What If?’ and ‘How?’ questions that transform an identified problem into a successful innovation or startup.
“The important and difficult job is never to find the right answers, it is to find the right question. For there are few things as useless - if not dangerous - as the right answer to the wrong question.” - Peter Drucker
What's a Questionologist?
Warren Berger uses the term questionologist to describe an expert questioner.
The most successful business people and innovators are questionologists.
The authors of the book The Innovator's DNA, spent eight years studying 500 innovators and 5,000 executives to uncover what made innovative leaders different.
They identified five core discovery skills, and one of them - questioning - was the catalyst for all the others.
The innovators in their study asked more questions.
In a typical hour-long meeting, innovative leaders spent an average of 15–20 more minutes questioning than their less innovative peers.
And the more innovative they were, the more questions they asked, with the top 5% of innovators ranked in the 95th percentile for the frequency of questioning.
Innovators also operated with a high question-to-answer ratio.
In those meetings they’d typically ask two questions for every one answer they provided in meetings.
Delivery-driven executives in comparison did the opposite and provided answers or instructions far more than they asked questions.
And the innovators asked the best quality questions.
This is a chart of the innovators questioning skills looking at how they used “What if?’ questions, or challenged the status quo.

Questionologists use the innovation sequence.
“Look for people who have lots of great questions. Great questions are a much better indicator of future success than great answers.” - Ray Dalio
The great news is that anyone can become a questionologist.
Studies of identical twins have shown that genetics account for one-third of our ability to think creatively.
All the rest of our capacity to be innovative comes through learning, experimenting and practice.
And this continuous learning effort is also how the innovators got to where they did.
As a journalist Warren Berger developed his questioning skills from years of interviewing sources, then he spent years questioning … questioning.
Are you striving to be a questionologist too?
Wedell-Wedellsborg, T., “Are You Solving the Right Problems?”, Harvard Business Review (2017)
Dyer, J. H., Gregersen, H., Christensen, C. M., “The Innovator’s DNA”, Harvard Business Review (2009)
Gregersen, H., “Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life”, Harper Business (2018)
Berger, W., “A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas”, Bloomsbury (2016)
Berger, W., “The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead”, Bloomsbury (2019)



