How to Unwrap the Power of a Beautiful Question

The most important thing business leaders must do today is to be the ‘chief question-asker’ for their organization.

– Dev Patnaik

Patnaik is quick to add, “The first thing most leaders need to realize is, they’re really bad at asking questions.”

A questioning culture is critical because it can help ensure that creativity and fresh, adaptive thinking flows throughout the organization.

By asking questions, we can analyze, learn, and move forward in the face of uncertainty. However, the questions must be the right ones; the ones that cut to the heart of complexity or enable us to see an old problem in a fresh way.

Nothing has such power to cause a complete mental turnaround as that of a question. Questions spark curiosity, curiosity creates ideas, and ideas lead to making things better.

Questions are powerful means to employ (read unleash) creative potential – potential that would otherwise go untapped and undiscovered.

 THE QUICK SUMMARY – A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas by Warren Berger

In this groundbreaking book, journalist and innovation expert Warren Berger shows that one of the most powerful forces for igniting change in business and in our daily lives is a simple, under-appreciated tool–one that has been available to us since childhood. Questioningdeeply, imaginatively, “beautifully”–can help us identify and solve problems, come up with game-changing ideas, and pursue fresh opportunities. So why are we often reluctant to ask “Why?”

Berger’s surprising findings reveal that even though children start out asking hundreds of questions a day, questioning “falls off a cliff” as kids enter school. In an education and business culture devised to reward rote answers over challenging inquiry, questioning isn’t encouraged–and, in fact, is sometimes barely tolerated.

And yet, as Berger shows, the most creative, successful people tend to be expert questioners. They’ve mastered the art of inquiry, raising questions no one else is asking–and finding powerful answers. The author takes us inside red-hot businesses like Google, Netflix, IDEO, and Airbnb to show how questioning is baked into their organizational DNA. He also shares inspiring stories of artists, teachers, entrepreneurs, basement tinkerers, and social activists who changed their lives and the world around them–by starting with a “beautiful question.”


With the constant change we face today, we may be forced to spend less time on autopilot, more time in questioning mode—attempting to adapt, looking to re-create careers, redefining old ideas about living, working, and retiring, reexamining priorities, seeking new ways to be creative, or to solve various problems in our own lives or the lives of others.

When we want to shake things up and instigate change, it’s necessary to break free of familiar thought patterns and easy assumptions.

We need to learn to ask beautiful questions.

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.

The nonprofit sector, like much of industry, is inclined to keep doing what it has done—hence, well-meaning people are often trying to solve a problem by answering the wrong question.

People tend to approach and work through problems – processing from becoming aware of and understanding the problem, to thinking of possible solutions, to trying to enact those solutions. Each stage of the problem solving process has distinct challenges and issues—requiring a different mind-set, along with different types of questions. Expertise is helpful at certain points, not so helpful at others; wide-open, unfettered divergent thinking is critical at one stage, discipline and focus is called for at another. By thinking of questioning and problem solving in a more structured way, we can remind ourselves to shift approaches, change tools, and adjust our questions according to which stage we’re entering.

The Why stage has to do with seeing and understanding. The “seeing” part of that might seem easy – just open your eyes and look around, right? Not really. To ask powerful Why questions, we must:   

Step back.

Notice what others miss.

Challenge assumptions (including our own). 

Gain a deeper understanding of the situation or problem at hand, through contextual inquiry. 

Question the questions we’re asking. 

Take ownership of a particular question.

The What If stage is the blue-sky moment of questioning, when anything is possible. Those possibilities may not survive the more practical How Stage; but t’s critical to innovation that there be a time for wild, improbable ideas to surface and to inspire. If the word why has a penetrative power, enabling the questioner to get past assumptions and dig deep into problems, the words what if have a more expansive effect – allowing us to think without limits or constraints, firing the imagination.

The How stage of questions is where the rubber meets the road. It’s the point at which things come together and then, more often than not, fall apart, repeatedly. Reality intrudes and nothing goes quite as planned. to say it’s the hard part of questioning is not to suggest it’s easy to challenge assumptions by asking Why, or to envision new possibilities by asking What If. Those require difficult backward steps and leaps of imagination. But How tends to be more of a slow and difficult march, marked by failures that are alley to be beneficial – but don’t necessarily seem that way at the time.

Warren Berger, A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas


According to author Warren Berger, when it comes to questioning, companies are like people: They start out doing it, then gradually do it less and less. A hierarchy forms, a methodology is established, and rules are set; after that, what is there to question?

In A More Beautiful Question, Berger lists a series of questions from consultant Keith Yamashita that leaders should consider. To arrive at a powerful sense of purpose, Yamashita says, organizations today need “a fundamental orientation that is outward looking”—so they can understand what people out there in the world desire and need, and what’s standing in the way. At the same time, leaders also must look inward, to clarify their core values and larger ambitions.

At a future team meeting, ask the following questions, and record all answers.

  • How is our mission best expressed in everyday life?
  • Which of our values are most relevant in this season? Which of our values is most aspirational?
  • What ministry or program is having the most impact? Which is having the least? Why?
  • What area of spiritual growth is most underdeveloped among our body?
  • What are we most excited about in the next year?
  • What is most important in the next 90 days?
  • What do we want to celebrate five years from now?
  • How will the results of this exercise change the direction of your organization?


Are You Asking the Right Questions?

Our capacity for learning is a part of being a human being. From birth, we are on a fast track of learning – movement, speech, understanding, and so forth. Unfortunately, many people equate “learning” with “schooling,” and when you’re done with school, you’re done with learning.

We are uniquely endowed with the capacity for learning, creating, and growing intellectually – and it doesn’t have an expiration date tied to an event, like graduation.

The practice of lifelong learning has never been more important to leaders than it is today. The necessity of expanding your knowledge through lifelong learning is critical to your success.

Take reading, for example. Many of the most successful people in today’s organizations read an average of 2-3 hours per day. No longer limited to books, reading is a lifelong learning activity that can be done online anywhere at anytime.

Learning is the minimum requirement for success as a leader. Because information and knowledge on everything is increasing every day, your knowledge must also increase to keep up.

Learning how to learn is more important than ever. Dedicate yourself to trying and learning new ideas, tasks, and skills. You don’t need to be aware of everything all the time but learning new skills faster and better – that in itself is a tough skill to master.

THE QUICK SUMMARY – The Book of Beautiful Questions by Warren Berger

From the bestselling author of A More Beautiful Question, hundreds of big and small questions that harness the magic of inquiry to tackle challenges we all face–at work, in our relationships, and beyond.

By asking questions, we can analyze, learn, and move forward in the face of uncertainty. But “questionologist” Warren Berger says that the questions must be the right ones; the ones that cut to the heart of complexity or enable us to see an old problem in a fresh way.

In The Book of Beautiful Questions, Berger shares illuminating stories and compelling research on the power of inquiry. Drawn from the insights and expertise of psychologists, innovators, effective leaders, and some of the world’s foremost creative thinkers, he presents the essential questions readers need to make the best choices when it truly counts, with a particular focus in four key areas: decision making, creativity, leadership, and relationships.

The powerful questions in this book can help you:
– Identify opportunities in your career or industry
– Generate fresh ideas in business or in your own creative pursuits
– Check your biases so you can make better judgments and decisions
– Do a better job of communicating and connecting with the people around you

Thoughtful, provocative, and actionable, these beautiful questions can be applied immediately to bring about change in your work or your everyday life.


Nothing has such power to cause a complete mental turnaround as that of a question. Questions spark curiosity, curiosity creates ideas, and ideas lead to making things better.

Questions are powerful means to employ (read unleash) creative potential – potential that would otherwise go untapped and undiscovered.

When we are confronted with almost any demanding situation, in work or in life, simply taking the time and effort to ask questions can help guide us to better decisions and a more productive course of action. But the questions must be the right ones – the ones that cut to the heart of a complex challenge or enable us to see an old problem in a new light.

Questions can help steer you in the right direction at critical moments when you’re trying to 1) decide on something; 2) create something; 3) connect with other people; and 4) be a good and effective leader.

Decision-making demands critical thinking – which is rooted in questioning. It’s up to each of us to make more enlightened judgments and choices. Asking oneself a few well-considered questions before deciding on something can be surprisingly effective in helping to avoid the common traps of decision-making.

Creativity often depends on our ability, and willingness, to grapple with challenging questions that can fire the imagination. For people within an organization trying to innovate by coming up with fresh ideas for a new offering or an individual attempting to express a vision in a fresh and compelling way, the creative path is a journey of inquiry.

Our success in connecting with others can be improved dramatically by asking more questions – of ourselves and of the people with whom we’re trying to relate. While many of us tend to rely on generic “How are you?” questions, more thoughtful and purposeful questions can do a better job of breaking the ice with strangers or bonding with clients and colleagues.

Leadership is not usually associated with questions – leaders are supposed to have all the answers – but it is becoming increasingly clear that the best leaders are those with the confidence and humility to ask the ambitious, unexpected questions that no one else is asking. Today’s leaders must ask the questions that anticipate and address the needs of an organization and its people, questions that set the tone for curious exploration and innovation, and questions that frame a larger challenge others can rally around.

Warren Berger, The Book of Beautiful Questions


Developing the art of questioning does not require an advanced degree. As a matter of fact, one of the best ways to learn how to become a better questioner is to learn from the typical four-year-old girl.

If you have ever been a parent, you understand this. Studies show that children at this age may ask anywhere from 100 to 300 questions per day. While it may seem like child’s play, it’s actually a complex, high-order level of thinking. It requires enough awareness to know that one does not know – and the ingenuity to begin to do something about it.

Ask “why.”

To begin to develop the abilities of a better questioner, consider the broad questions developed by author Warren Berger in each of the four areas listed above.


  • Why do I believe what I believe? (And what if I’m wrong?)
  • Why should I accept what I’m told?
  • What if this isn’t a “yes or no” decision?
  • How would I later explain this decision to others?


  • Why create?
  • Where did my creativity go?
  • What is the world missing?
  • What if I allow myself to begin anywhere?

Connecting with others

  • Why connect?
  • What if I go beyond “How are you?”
  • How might I listen with my whole body?
  • What if I advise less and inquire more?


  • Why do I choose to lead?
  • What’s going on out there – and how can I help?
  • Am I looking for what’s broken – or what’s working?
  • Do I really want a culture of curiosity?

Excerpt taken from SUMS Remix 113-3, released February 2019


Part of a weekly series on 27gen, entitled Wednesday Weekly Reader

Regular daily reading of books is an important part of my life. It even extends to my vocation, where as Vision Room Curator for Auxano I am responsible for publishing SUMS Remix, a biweekly book “excerpt” for church leaders. Each Wednesday on 27gen I will be taking a look back at previous issues of SUMS Remix and publishing an excerpt.

>>Purchase SUMS Remix here<<

>> Purchase prior issues of SUMS Remix here<<