Books Business Innovation Strategy

Recent Read: “A More Beautiful Question” by Warren Berger


In the world of business, as in many others, answers (and answerers) get all the glory. We like answers: they give direction, settle arguments, erase doubts, and do many other useful things. Questions, especially in business, are not so popular. Strong questions can confuse direction, start arguments, give birth to doubts, and generally annoy (managers especially). Given the above, you tend to find more business books with answers than questions on any given executive bookshelf. The other day, however, someone (and I don’t know who it was), left a book on my desk with an interesting title: A More Beautiful Question, written by the journalist Warren Berger. In it, Berger takes on some issues worth considering: Why don’t we like questions? How do you ask good questions? Why are so many questions in business bad? How can a great question define our life’s purpose?

Why don’t we like questions?

For Berger, the answer to the preceding question is clear: education. In his view, we all start out as great questioners but early in our educational journey the aim of our teachers becomes not to make us great questioners but great answerers. This phenomenon goes back to the early days of industrialization, which was also the time when mass education took hold in Western societies. Berger notes that this confluence produced an educational system modeled after factories and that this model hasn’t changed very much since then, even though our economic model certainly has undergone tremendous transformation. As he notes:

Logically, as we move from industrial society to more of an entrepreneurial one, it makes sense that we would want to trade in the factory/obedience model of schooling for more of a questioning model. But as the world changed and the workplace changed with it, the old educational model hasn’t evolved much — and for the most part hasn’t adapted to the modern economy’s need for more creative, independent-thinking “workers.”

For Berger, then, this shift in our educational journey from questioning (which we do so well around the age of five) to answering, which takes over when we get to middle school, slowly kills, in most people at least, their fundamental human curiosity and need to ask questions. His book, then, is an attempt to get us to bring back, at least in part, that natural ability to ask great questions about our business, world and lives.

How do you ask good questions?

If we have indeed lost some of our questioning power by the time we are deep into most of our careers, then how can we start to re-learn that ability? Berger proposes a three-step process for getting to, and working through, a great question.

Step 1: Ask Why?

Why questions are fundamental in Berger’s mind, and he gives many examples of great innovations and even companies that arose from this kind of question. Why do we have to wait days to see photos we just took? Why can’t someone with an artificial foot run? Why can’t paralyzed people walk? Why can’t I rent one room in my house out for one night only? All of these questions led to great innovations, says Berger, and we should make this kind of questioning a key part of our innovation thinking. Key to this ability, he says, is being able to “pull back”from our current state/role/problem to ask a great why question. Indeed, the inability to pull back is precisely why so many experts are not always best at asking great questions about their own field. A lifetime of education in a subject has made them great answerers about medicine or business but not great questioners.

Step 2: Ask What If?

Once we have a good Why question, writes Berger, we should move on to finding the right What if questions. The best What if questions are combinations, and recombinations, of ideas and elements that allow us to see a problem in a new way. As he notes, citing the NASA scientist David Kord Murray:

If, as Murray notes, the most creative ideas result from “long distance” connections (bringing together ideas that seem unrelated and far apart), then that means the most promising connective inquiries do not merely ask, What if we combine A and B?, but rather, What if we combine A and Z? (or better yet, A and 26?) To forge those illogical connections, Murray advises, “You must quiet the logical mind.”

Step 3: Ask How?

Once we have landed on a great Why? question and sorted through all our What if?scenarios, the last step in Berger’s process is to ask How and thereby find a path to our desired new state or innovation. A good example from his book is the work of Van Philips, who lost his left foot in a water-skiing accident at the age of twenty-one. Philips was given a chunky wooden foot and told to get used to living with its weight and pain, but he refused to do so. Instead, he started asking why artificial feet could not actually be made better than natural feet. He then asked: What if we made them not from wood but from the strongest and lightest materials we have at hand? That question led him to ask: What if our goal was not to give an amputee the ability to walk but the ability to run as well as someone with both natural feet? Once he landed on this statement as his goal, he then spent many years working on how to do so, experimenting with shapes and forms until he invented the running blade that David Pistorious made famous at the Olympics.

A key to this final stage is to focus on one, or at most a few, How problem(s) rather than many, according to Berger. In his view, it’s optimal that we embrace one challenge fully and to understand that there will be setbacks in getting to a successful outcome. As he notes: “when it comes time to act on an idea, you have to narrow possibilities and converge on the one deemed worthy of being taken to the next level.” Moreover, for him working in isolation is wrong. It’s critical that our How exploration be subject to the scrutiny and critique of others. The public nature of our search is important for two main reasons. First, it allows other to contribute to our solution. Second, it makes us accountable to others for our effort.

Why are so many questions in business bad? 

As I noted earlier, executives are not very fond of questions or questioners. We’ve all been in meetings where things seem to be moving toward a conclusion and someone asks a question that stops or even regresses the conversation. Indeed, early in my career I had a colleague who said very little in meetings, but when he did it was usually an insightful comment that pointed out some error the rest of us had made. He wasn’t a great answerer, but he was a phenomenal questioner. Unfortunately, notes Berger, people like my colleague are not always welcome in business, which is ironic since so many great companies start out attempting to answer a great question. As he notes, “that motivating principle gets buried over time” as success, like education perhaps, shifts the emphasis in a company from asking great questions to answering them.

Berger spends a lot of time in his book giving examples of good questions for business leaders to ask, but my favorite is this one: What if our company did not exist? By asking this question, and then imagining what an innovator would do with a successful Why/What If/How process, we might see a whole new world of possibilities and competitive threats our daily management routine obscures. It’s almost the business equivalent of the classic film, It’s A Wonderfull Life, in which the main character is allowed to see the outcome of a world into which he had never been born. Like that character, perhaps it’s good to pause regularly and ask what others might do differently, if we did not come to work in our offices every day and do what we do.

The Beautiful Question

The last part of Berger’s book takes a step back from business and places the art of questioning in the context of “the good life.” For him, a great question can define a person’s entire existence. For this to happen, questioning the question itself is also part of the process. Berger acknowledges how difficult that is for most people, especially as one achieves higher and higher levels of success:

For people geared to achieving the success of just getting things done, the idea of slowing down or, worse still, stepping back, can seem counterintuitive — and seemingly at odds with cultural messages urging us to “go for it” or “lean in” as we pursue challenges and embrace opportunity. But while the notions of “stepping back” and “leaning in” might seem contradictory, someone who pauses, at times, to question and consider, can also fully engage, act boldly, and seize opportunities. Stepping back to question can actually help with leaning in by providing a clearer sense of direction and purpose.

Doing what Berger suggests is hard, of course, but he is right. Throughout all of my career I have seen too many people striving towards a goal that they neither fully understand nor really want to achieve. They run a race defined by insecurities, parents, spouses or society. Sadly, so many of them spend their whole lives in this chase, realizing only at the finish line that it was a race not worth running, at least not for them. Paradoxically, writes Berger, the best life question is not one we chose but the opposite:

As to which [life] question to chose, to some degree the question chooses you. It’s the one that resonates with you for some reason only you understand. What will make it a beautiful question for you, and with staying with, is the passion you feel for it. Look for a question that is “ambitious yet actionable” — or, as the physicist Edward Witten puts it, a question that’s hard enough to be interesting, but realistic enough that you have some hope of answering it.

As I read Berger’s book, I reflected on so many of the big questions that I have tried to consider in my career ( and writing about business): Why do we live with mistakes even when we are fully capable of finding the right answers? Why do people stay in jobs they hate when change is possible? What makes any team, large or small, great? Even now, I spend most of my time thinking about the one question that connects my first job as a journalist to my current role managing a content team: How do stories change us and how we see the world?

As good as Berger’s book is, it’s not without flaws. Even though he’s a journalist, Berger’s not a particularly engaging writer (in this effort at least). He does not spend enough time discussing all the many challenges to asking great questions that arise in every day business (and life). He does not draw in any lessons or examples from some of the great questioners in history. In an obvious omission, he fails to put his model in context alongside other question-based learning paradigms like the Socratic model. Lastly, like most business books, he sins in giving the same advice over and over in different forms. However, despite these shortcomings, I heartily recommend A More Beautiful Question to everyone, leaders and followers alike.

“An unexamined life is not worth living,” said Socrates in Plato’s Apology. Indeed, we sometimes forget that behind every great answer there is a great question. All credit to Berger for reminding us of this easily overlooked but essential truth and to whoever left this great little book lying on my desk.


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