A More Beautiful Question

By: Warren Berger



Would the world be better off if we asked more and better questions? This is something that Warren Berger sets out to answer is his great book, A More Beautiful Question.

A recent study has shown that the average four-year-old British girl asks an average of 390 questions a day. Which begs the obvious question - why do we ask them less and less as life goes on?

And perhaps more importantly for us in the business world, how can we do a better job of asking them. After all, a recent research study has shown that the most creative and successful business leaders are expert questioners.

Berger defines a beautiful question as the following:

A beautiful question is an ambitious yet actionable question that can begin to shift the way we perceive or think about something - and that might serve as a catalyst to bring about change.

Let’s explore the ways we can all ask more beautiful questions in our businesses, and in our lives.

The power of questions, and why we can’t stop asking them

As Berger points out, good questioners are very comfortable with their own ignorance. In fact, it’s one of the things that drives almost all scientists towards new discoveries. As Stuart Fierstein - the author of the book Ignorance - puts it:

“One good question can give rise to several layers of answers, can inspire decades-long searches for solutions, can generate whole new fields of inquiry, and can prompt changes in entrenched thinking. Answers, on the other hand, often end the process.”

However, being willing to question is one thing, questioning effectively is another. Great questions can spawn multi-billion dollar companies that leave their mark on the world. Consider the evolution of Netflix, which was started when Reed Hastings forgot to return some videos to Blockbuster, and was charged what he considered to be exorbitant late fees.

Hastings asked himself “why should I have to pay these fees?”, and “how am I going to explain this to my wife?” That question led to the next question, “What if a video-rental business were run like a health club?” He then set himself the task of figuring out exactly how he could build a video rental company that had a monthly membership and no late fees.

Fast forward to today, and Blockbuster is of course out of business, and Netflix has moved on to another ground-breaking set of questions, including “what if we not only rented the films and shows, but made them too?”

The power in asking great questions comes to life in a 3-step process - asking why, what if, and how. It sounds simple, but the devil is in the details.

Let’s get started.


The first stage is “why”, and it has to do with seeing and understanding the world in a different way. For instance, Edward Land was prompted by his daughter to ask the question: “Why not design a picture that can be developed right away?”

This question would lead to the development of the Polaroid instant camera, which was a groundbreaking innovation at the time.

We live in a world that values moving fast and advancing, and looks down on anybody or anything that wants to pump the brakes and question why things are being done a certain way. So, one of the reasons that we are not very good at asking questions is that we are almost always discouraged from doing it.

So, the first thing we need to do in order to ask great questions is to get comfortable with not having the answers in a world that punishes that very thing. As Paul Bennet, the creative director at renowned design firm IDEO says, “I position myself relentlessly as an idiot at IDEO…being comfortable with not knowing - that’s the first part of being able to question.”

One of the benefits of doing this is that it allows you to ask naive questions. And that allows you to bring clarity to otherwise complex issues by forcing the person you are asking questions to simplify their thinking down to its very essence.

Once you are able to let go and ask seemingly naive questions, you’ll start to generate a lot of questions about the world around you. One technique for becoming an ever better questioner is to “open and close” your questions. The example Berger gives in the book is “why is my father-in-law difficult to get along with?” This is an open-ended question without a clear answer.

However, when you close that question, you end up with “Is my father-in-law difficult to get along with?”, which forces you to confront the assumption of the original question. This process works both ways - you should close your open questions, and open your closed questions. You’ll start to see the world from completely new perspectives if you do.

What If

Now that we’ve sufficiently questioned some base assumptions about our world, it’s time to move on to start imagining how things might be different by asking “what if”.

One of the best ways to do this is through the combination of ideas. As David Kord Murray, a former NASA rocket scientist who later became the head of innovation at Intuit points out in his book Borrowing Brilliance:

“The nature of innovation [is that] we build new ideas out of existing ideas.”

For instance, Walt Disney asked himself “what if this amusement park could be like a movie, brought to life?” The good news for us is that according to the latest neurological research, the human brain is built just right for this type of task, constantly searching through the random data in your brain and asking “what if I put this together with that?”

The only problem is that we don’t consciously control this process because most of it happens in the unconscious mind. That’s why the first step - the “why” question - is so important. According to Chen-Bo Zhong, a professor at the Rotman School, if the conscious mind creates a big question, the unconscious mind will go to work on solving it.

Another point here is that the brain uses the knowledge it has in order to search for these connections. So, the more knowledge you have, and the more diverse it is, the more possibilities you’ll have to create unexpected connections. If you want to be creative and innovative, it pays to learn as much as you can in as many areas as you can, even if the payoff isn’t immediately obvious.

Although a lot of this happens unconsciously, there are tactics and strategies you can utilise to give the process a kickstart. One strategy that finds its roots in the work of the creativity guru Edward de Bono is to “think wrong”. You ask questions that at first seem to be the worst ideas you can come up with. For instance, “What if a restaurant provided customers with a menu only when they leave?”

Or, consider the question “what if a company started selling socks that didn’t match?” This is the exact question asked by a bunch of dinner companions that lead to the creation of the company LittleMissMatched that sells pairs of mismatched socks to young girls who want to make a colourful fashion statement.


Now that we’ve created our why question, brainstormed a bunch of “what if” questions, it’s time to move on to the how.

In this stage, the world’s most creative minds know that they are not very good at deciding which ideas are winners and which are duds, so they employ something called rapid prototyping. Rather than debating an idea to death, they find a way to test it quickly and cheaply, and then look at the results. As Joi Ito, the head of the MIT Media Lab puts it:

“These days it’s easier and less expensive to just try out your ideas than to figure out if you should try them out.”

In fact, there’s no reason why anybody with a good idea should be slowed down by the execution phase. These days there are experts around the world you can find and tap into simply by sending an email.

Jack Andraka found this out when he was fifteen years old and had an idea for developing a new, highly effective and inexpensive way for screening for certain types of cancer. Using the incredible store of knowledge he’d accumulated in his free time by reading medical journals, he formulated his “what if” question:

“What if I exposed a single-wall carbon nanotube with an antibody to a protein overexposed in pancreatic cancer?”

He needed an incredible amount of help - including a lab and experts to help him prove out his idea. So, he emailed almost everybody he could find in his area that knew something about pancreatic cancer and asked for help. Eventually he found a scientist who was willing to open up his lab to him, who helped him finalise his screening test that is now being used around the world.

Questioning in Business

Now let’s explore some of the most powerful questions you can ask yourself in a business context. “What if our company didn’t exist?” This question can help you think about all of the things that are not currently working in your business, and have you consider old programs, practices and products that should be scrapped or reconsidered.

“What if money were no object? How might we approach the project differently?” By temporarily removing restrictions, your people will be free to think about the best possible solution for a problem. You might find your team comes up with groundbreaking ideas that can be scaled back to make them affordable.

“What are we against?” We spend a lot of time thinking about what stand for in business, but not a lot of time thinking about what we might make a stand against.

“What is something that I believe that nearly no one agrees with me on?” This is a question that Peter Thiel, the famous venture capitalist thinks we should all be asking ourselves. The best new ideas are often the ones that most people believe can’t be done.

“Should our mission statement actually be a question?” If you have a mission question, it sends the message to the company that we haven’t arrived at our destination yet, and asks them to figure out ways to help you get there. The mission of the company then becomes to come up with new ways of accomplishing the mission. This is a much more powerful place to be starting from.

“How might we create a culture of inquiry?” As Berger points out, when a culture is inquisitive and constantly questioning things, it gives people the permission to explore new ideas and share across silos. This should start at the top by the leader asking a lot of disruptive and provocative questions.


We don’t ask nearly enough questions in our businesses, and in our lives. If we could all cultivate the habit of asking why, what if, and how on a regular basis, we would be more creative, innovative, and ultimately more successful. So here’s one final question to end off this Book Brief: why not start right now?