How to spot great opportunities: ask “Why?”

Ameet Ranadive
PM Insights
Published in
10 min readJan 28, 2018

I recently read a fantastic book called A More Beautiful Question by Warren Berger. The book’s central thesis is that asking questions can help us develop breakthrough creative insights. We can follow a structured process of asking Why? What If? How? questions to develop our innovative ideas.

The Why stage is about seeing and understanding; the What If stage is about imagining; and the How stage is about doing.

Why is where it all begins, where we first identify and define the problem that we want to solve. The power of asking an insightful Why question is that it can help set the direction for all of our subsequent efforts. The types of Why questions that often unlock the greatest innovation are the following:

“Why does a particular situation exist?”

“Why does it present a problem or create a need or opportunity, and for whom?”

“Why has no one addressed this need or solved this problem before?”

Edwin Land and the Polaroid Instant Camera

Edwin Land demonstrates Polaroid color instant photography.
Fritz Goro/The LIFE Picture Collection/Getty Images.

Berger shares the story of Edwin Land, and how asking a Why question led to the creation of the Polaroid instant camera. In 1943, Land was on vacation with his family in New Mexico. He was snapping some photos of his three-year-old daughter. In those days, you used to have to take your film to a darkroom or processing lab for processing. His daughter asked him a simple question:

“Why do we have to wait for the picture?”

As Berger writes:

Land found that he had no good answer for her. He took this as a challenge, a ‘puzzle she had set for me,’ as he described it.

“Stimulated by the dangerously invigorating plateau air,” Land recalled in a speech years later, “I thought, ‘Why not? Why not design a picture that can be developed right away?’”

From that simple Why question, Land launched his quest to develop the first instant camera. Polaroid created an entirely new market for instant cameras, bringing photography to millions of customers.

How to create Why? questions

Innovators ask Why questions when they look at an existing, less-than-ideal reality and ask the question:

Why does it have to be this way?

As I mentioned above, Why is about seeing and understanding. To really see, you must “attempt to adjust the way you look at the world so that your perspective more closely aligns with that of a curious child.”

In order to do this, Berger argues that we must do the following:

1. Step back

2. Notice things that others miss

3. Challenge assumptions (including our own)

Step back

We’re often moving so fast, knee-deep in the details of our work, that we can miss the fundamental Why questions that we should be asking. Stepping back requires us to stop doing and stop knowing in order to start asking, Why?

In order to stop doing, we need to regularly make time to pause, reflect, and ask questions. In order to stop knowing, we need to be willing to temporarily let go of our expertise. As Berger writes:

“Whether in life or work, people become experts within their own domains — generally confident that they already know what they need to know to do well in their jobs and lives. Having this sense of knowing can make us less curious and less open to new ideas and possibilities… If you feel this way, you’re less likely to ask questions.”

Beginner’s mind

One technique for enabling us to step back from knowing is called beginner’s mind. Shunryu Suzuki, a Zen monk and teacher, first popularized the concept of beginner’s mind:

“The mind of the beginner is empty, free of the habits of the expert… In the beginner’s mind there are many possibilities, but in the expert’s there are few.”

According to Suzuki, such a mind is “open to all possibilities” and “can see things as they really are.”

Detached

Kleiner Perkins venture capitalist Randy Komisar advocates being detached as a way to develop the beginner’s mind, and to open yourself to new possibilities. As Berger writes about his conversations with Komisar:

“The key to adopting this manner of observing and questioning is to make an effort to become, in his word, ‘detached’ — from everyday thoughts, distractions, preconceived notions, habitual behaviors, and even from oneself. ‘Basically, you begin to observe yourself as if you were a third party.’ If you can achieve that sense of detachment, your thinking becomes more ‘flexible and fluid,’ Komisar maintains, and ‘you find yourself in a better position to question everything.’”

Empty bucket

TED founder Richard Saul Wurman uses the analogy of an empty bucket in order to step back and develop the beginner’s mind. As Berger writes:

“It helps him [Richard Saul Wurman], when approaching any new situation or subject, to think of his mind as ‘an empty bucket.’ The job is to slowly and methodically fill that bucket, Wurman says, and you begin by asking the most basic of questions.”

Notice things that others miss

Stepping back from doing and knowing is not enough to ask innovative Why questions. In addition, we have to be able to notice things that other people miss.

Paul Graham in his essay “How to get startup ideas” discussing the importance of noticing. Peter Thiel has also written about the importance of discovering a “secret” in order to make vertical progress, from zero to one. According to Thiel, a secret is an idea that was once unknown and unsuspected — something that you have noticed that others have missed.

Vuja de

One technique for noticing what others miss is to approach things from a vuja de perspective. As Berger writes:

“Upon stepping back and reexamining something you’ve been looking at the same way for years, you might suddenly feel as if you’re seeing it for the first time… If you’ve experienced this, it feels a bit like deja vu in reverse. With deja vu, you go somewhere you’ve never before been yet and it seems oddly familiar; conversely, when you look at something familiar and suddenly see it fresh, this is a case of vuja de.”

Vuja de is a term favored by Stanford University professor and author Bob Sutton.

“Sutton has argued that if we train ourselves to look at the world around us through a vuja de lens, it can open up a range of new possibilities — fresh questions to ask, ideas to pursue, challenges to tackle, all previously unnoticed because they were camouflaged in overly familiar surroundings. Adopting this view, business leaders and managers are more apt to notice inconsistencies and outdated methods — as well as dormant opportunities.”

The general manager of design firm IDEO, Tom Kelley, “has written that vuja de provides the ability to ‘see what’s always been there but has gone unnoticed.’”

Keep looking

Why do many people fail to notice important insights? IDEO’s Kelley “thinks it’s because we don’t generally take the time required for close observation. When people fail to notice what’s right in front of them, it’s often ‘because they stopped looking too soon.’”

As Berger writes:

“Great questioners ‘keep looking’ — at a situation or a problem, at the ways people around them behave, at their own behaviors. They study the small details; and they look for not only what’s there but what’s missing. They step back, view things sideways, squint if necessary.”

The ability to keep looking requires you to have curiosity, the ability to focus, and the persistence to continue searching. It means that you don’t settle for the obvious answers. Your persistent curiosity drives you to repeatedly ask Why, dig deeper, and view the problem from multiple angles.

First principles

The last technique for noticing what others miss is thinking from first principles. Elon Musk of Tesla describes the essence of First Principles Thinking as follows:

“First principles is kind of a physics way of looking at the world. You boil things down to the most fundamental truths and say, ‘What are we sure is true?’ … and then reason up from there… I think it is important to reason from first principles rather than by analogy. The normal way we conduct our lives is we reason by analogy. We are doing this because it’s like something else that was done or it is like what other people are doing… it’s like slight iterations on a theme.”

Most people are quick to reason by analogy. They look at how others have approached the problem, and build upon that approach. They accept the status quo way of looking at the problem. As a result, they engage in largely conventional and incremental thinking. And they fail to discover any fundamental insight — they fail to notice what others miss, because they’re limiting their approach to what others have already seen.

When we approach a problem using first principles thinking, we reframe the problem, discover fundamental truths and insights, and reason up from there. We are in some ways applying the beginner’s mind to solving the problem, by discarding the previous thinking and engaging in the problem as if we were the first one ever to try and solve it. The first principles approach is much more likely to notice things that others miss.

Challenge assumptions

Stepping back and noticing things that others miss greatly help us formulate insightful Why questions. The last step that Berger advocates is to challenge assumptions (including our own).

Question defaults

Wharton Professor Adam Grant in his book Originals discussed the approach of questioning defaults to attain the vuja de perspective.

“The hallmark of originality is rejecting the default and exploring whether a better option exists… The starting point is curiosity: pondering why the default exists in the first place. We’re driven to question defaults when we experience vuja de.”

When you automatically accept the default in a situation, you are limiting your thinking to what already exists. To open more possibilities and generate more Why questions, push yourself to question those defaults. By adopting the beginner’s mind and taking a vuja de approach, you will be in the right mindset to question the defaults in a situation.

The Five Whys

To better understand and question assumptions, we can use a process known as the Five Whys. Berger discusses how Toyota uses this process:

“For decades, the company [Toyota] used the practice of asking why five times in succession as a means of getting to the root of a particular manufacturing problem.”

We can use the Five Whys to discover the non-obvious explanation for a problem. Although originally designed for root causing an issue, we can also use Five Whys to better understand a situation and discover motivations for customer behavior. Berger shares the example of how IDEO used Five Whys to explore the motivation behind exercise:

Why do you exercise? Because it’s healthy.

Why is it healthy? Because it raises my heart rate.

Why is that important? So that I burn more calories.

Why do you want to do that? To lose weight.

Why are you trying to lose weight? I feel social pressure to look fit.

If you stopped at the first Why, you may not have discovered the insight that people are motivated to exercise because of social pressure to look fit and instead have settled for the default assumption that people are doing it in order to be healthy. When you’re designing a product to help people exercise, you can keep this deeper motivation in mind to unlock greater innovation.

Opening and closing questions

Another great way to challenge assumptions is to use a technique to open and close questions. Berger writes about this approach, developed by the Right Question Institute:

“You can improve a question by opening and closing it. For instance, suppose one is grappling with the question ‘Why is my father-in-law difficult to get along with?’…

“This question is open-ended because it has no definitive answer. But note what happens when we transform this question into a closed, yes-or-no question: ‘Is my father-in-law difficult to get along with?’

“Worded this way, the question almost forces one to confront the assumption within the original question — and to consider that it might not be valid (because the father-in-law, in this scenario, might have other relatives and friends with whom he gets along swimmingly). So this might cause me to go back and revise that original question to make it more accurate: ‘Why is my father-in-law so difficult for me to get along with?’”

In this post, I discussed the importance of asking Why questions in order to unlock creativity and innovation. In particular, we want to ask questions like,

Why does this situation exist?

Why does it have to be this way?

Why has nobody solved this problem before?

Asking Why is about seeing and understanding. In order to do this, Berger argues that we must do the following:

  1. Step back
  2. Notice things that others miss
  3. Challenge assumptions (including our own)

Berger provides practical advice for how to do each of these activities.

In order to step back, we have to both stop doing and stop knowing. To stop doing, we have to create time to pause, reflect, and ask ourselves and other questions. To stop knowing, we have to adopt a beginner’s mind, try to become detached from what we know, and think of our mind as an empty bucket that we would like to fill with understanding. As we become experts in something, we become less curious and less open to new possibilities — so it’s important to step back and stop knowing.

To notice things that others miss, we should adopt the vuja de approach of looking at a familiar situation as if we’re seeing it for the first time. This will help us see what’s always been there but has gone unnoticed. We should also push ourselves to keep looking at a problem for a long period of time, and from multiple perspectives, in order to get past the obvious answers. We should also think from First Principles: boil things down to fundamental truths and reason up from there. This helps us avoid reasoning by analogy, where we won’t notice things that other miss but instead limit ourselves to what others have seen and done.

And finally, to challenge assumptions, we should question defaults, use the Five Whys, and try opening and closing questions. By using the Five Whys, we will move past the conventional assumptions for why a situation or problem or behavior exists, and develop deeper insights. And by playing with our questions — for example, converting an open to a closed question — we will force ourselves to confront the underlying assumptions within our questions.

I’ve read many different blog posts and books about creativity, innovation, and “thinking differently.” Warren Berger’s A More Beautiful Question was the first book I’ve encountered that offers very practical advice for how to ask the important Why questions that spark innovation. I’m looking forward to applying many of the lessons I’ve learned here in my work as a product manager. I hope that you will take advantage of this knowledge too!

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Ameet Ranadive
PM Insights

Chief Product Officer at GetYourGuide. Formerly product leader at Instagram and Twitter. Father, husband, and travel enthusiast.