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Questions Are the Answer

A New Approach to Your Most Vexing Problems at Work and in Life

3.9 (495 ratings)
24 minutes read | Text | 9 key ideas
What if the secret to unlocking your next big idea lies not in the answers you seek, but in the questions you dare to ask? In "Questions Are the Answer," Hal Gregersen unveils the transformative magic of rethinking the way we pose queries. Journey through a tapestry of insights woven from over 200 interviews with brilliant minds, from social innovators like Debbie Sterling to economic mavericks like Richard Thaler. Each story illuminates how bold, unconventional questions can shatter barriers and spark genius, offering a toolkit for anyone yearning to ignite their own creative breakthroughs. Uncover the art of inquiry as a dynamic force for change, capable of transforming the mundane into the extraordinary.

Categories

Business, Nonfiction, Self Help, Psychology, Design, Leadership, Audiobook, Management, Entrepreneurship, Personal Development

Content Type

Book

Binding

Kindle Edition

Year

2018

Publisher

Harper Business

Language

English

ASIN

B076H27PRJ

File Download

PDF | EPUB

Questions Are the Answer Plot Summary

Introduction

We live in a world filled with unprecedented challenges and opportunities, yet our approach to problem-solving often remains stagnant. The quest for better answers has dominated our educational systems, workplace cultures, and societal structures, but this singular focus has created a significant blind spot. The key to breakthrough solutions rarely lies in finding better answers to existing questions, but rather in formulating entirely new questions that challenge underlying assumptions and redirect our mental energy down more productive pathways. This paradigm shift from answer-seeking to question-crafting represents a fundamental reorientation in how we approach innovation and growth. By examining the conditions that foster catalytic questioning—from embracing wrongness to seeking discomfort to cultivating quiet reflection—we discover that questioning capacity is not an innate talent but a learnable skill that can be deliberately developed through specific practices. The journey toward becoming a more effective questioner requires both personal courage to challenge status quo thinking and the creation of environments where creative inquiry can flourish. Through real-world examples spanning business innovations, scientific breakthroughs, and personal transformations, we witness how reframed questions have repeatedly unlocked solutions to seemingly intractable problems, offering a practical blueprint for applying this approach in our own work and lives.

Chapter 1: The Power of Questions: Reframing Problems for Breakthrough Solutions

Behind every significant breakthrough lies a reframed question. Consider George Eastman, the founder of Kodak, who transformed photography by asking: "Could photography be made less cumbersome and easier for the average person to enjoy?" This simple reframing led to the development of the first Kodak camera in 1888, replacing wet emulsion plates with dry film technology and introducing a revolutionary business model where customers sent the camera back to the company for developing rather than doing it themselves. The power of questions extends beyond mere information-gathering; they can fundamentally reshape how we perceive problems. Questions that challenge assumptions—what Elon Musk calls "first-principles thinking"—break through the mental models that constrain conventional thinking. When Michael Dell questioned why computers cost five times more than the sum of their parts, he created a business model that disrupted the entire industry. Similarly, when biomedical engineer Jeff Karp asked what nature could teach us about creating adhesives for wet internal organs during surgery, he found inspiration in slugs, snails, and sandcastle worms. Catalytic questions share two crucial qualities: they dissolve barriers to thinking by challenging false assumptions, and they channel energy down new, more productive pathways. They have a paradoxical quality of being surprising in the moment they are asked but seeming obvious in retrospect. They open up space for people to do their best thinking without putting them on the spot or demanding predetermined answers. While many people assume creative ideas are unpredictable lightning bolts of insight, the truth is that breakthrough solutions consistently emerge from deliberate questioning practices. By gaining greater awareness of questioning as a skill and capacity that can be strengthened through deliberate practice, we can begin to systematically uncover the "unknown unknowns"—the things we don't know we don't know—which often harbor both our greatest opportunities and our most dangerous threats. The distinction between different types of questions matters enormously. Not all questions lead to innovative thinking; some merely test recall or seek convergence on established facts. The most valuable questions are divergent, inviting multiple possible answers and creative thinking. When appropriately framed and asked in the right spirit, questions become the catalysts that transform ordinary problem-solving into extraordinary innovation.

Chapter 2: Barriers to Questioning: Why We Don't Ask Enough

Our natural curiosity and questioning capacity begin to diminish early in life through systematic suppression across multiple environments. Educational settings are among the first places where questioning is actively discouraged. Researchers have documented this phenomenon for decades: Edwin Susskind found that in elementary classrooms, teachers asked an average of eighty-four questions per hour, while students collectively asked just two. George Fahey observed that high school students typically asked just one question per month. As education scholar James T. Dillon summarized, "Students do not ask questions in classrooms... students are heard to ask remarkably few if any at all." This suppression continues in workplaces, where questioning can be perceived as challenging authority or disrupting efficiency. Power dynamics play a crucial role in this suppression. Those in positions of authority often see questions as challenges to their status, while subordinates learn that career advancement depends more on providing good answers than asking provocative questions. The phenomenon extends even to healthcare settings, where studies by Anita Tucker and Amy Edmondson revealed that frontline workers who quietly solved recurring problems without questioning underlying systemic issues were considered "ideal employees," despite this behavior undermining organizational learning. Psychological factors further inhibit questioning. Carol Dweck's research on mindsets shows that people with a "fixed mindset" view questioning as threatening because it potentially exposes inadequacy, while those with a "growth mindset" see questions as opportunities for learning. The fear of appearing ignorant or incompetent creates a powerful disincentive to question, especially in public settings. This explains why even when people recognize problems, they often remain silent rather than risk the social consequences of speaking up. Cultural differences also influence questioning behaviors. Geert Hofstede's research on cultural dimensions identifies several factors that impact questioning propensity: power distance (how much inequality is accepted), uncertainty avoidance (comfort with ambiguity), and individualism versus collectivism. In cultures with high power distance, subordinates expect to be told what to do rather than to question authority. In uncertainty-avoidant cultures, deviant opinions face disapproval, and there's a belief that "there can only be one Truth." The consequences of these barriers are profound. Organizations like Kodak, which once revolutionized photography through questioning, later failed to question their own business model in the face of digital disruption. The taxicab industry similarly failed to anticipate how ride-sharing would transform transportation. Without deliberate intervention to create spaces where questioning is valued and rewarded, these barriers will continue to stifle innovation across all domains of human endeavor.

Chapter 3: Creating Conditions for Productive Inquiry

Productive questioning doesn't happen naturally in most environments—it requires deliberately crafted conditions that suspend normal rules and encourage different behaviors. This insight became clear during a classroom brainstorming session when switching from answer-generation to question-generation instantly energized a previously lethargic group. This simple reset—asking participants to brainstorm questions rather than answers—created a space where creative thinking flourished. Creating such conditions begins with understanding that behaviors emerge from context, not in isolation. Tony Hsieh, founder of Zappos, exemplifies this approach by creating physical and organizational environments designed to maximize "creative collisions." His trailer park community in Las Vegas and Zappos' Holacracy management system both aim to reset conventional conditions and foster new patterns of interaction. Similarly, Clay Christensen emphasizes how behaviors cannot be legislated in isolation but emerge from underlying conditions that either encourage or discourage them. The Question Burst technique offers a structured approach to creating question-friendly conditions. This three-step process begins by selecting a challenge you care deeply about and inviting diverse participants to help consider it from fresh angles. Participants have just four minutes to generate at least fifteen to twenty questions, with two critical rules: only questions are allowed (no answers), and no preambles or explanations are permitted. The exercise concludes by identifying the most intriguing questions that suggest new pathways forward. Data collected from over 1,500 leaders reveals the emotional impact of this exercise: participants consistently report feeling more positive, energized, and capable of tackling their challenges after just four minutes of focused questioning. This shift from negative emotions like frustration, confusion, and helplessness to positive ones like curiosity, excitement, and hope creates the motivational energy needed for creative problem-solving. Beyond structured exercises, productive questioning requires broader cultural and environmental support. Ed Catmull established Pixar's "Brain Trust" sessions where directors receive candid feedback on works in progress, creating a special setting where questioning is not only permitted but expected. Pixar later instituted "Notes Day," shutting down operations to ask company-wide: "How could we work better? How can we operate better? How can we be more efficient?" Creating these conditions requires psychological safety—what Amy Edmondson describes as "a shared belief that the team is safe for interpersonal risk-taking." Google's Project Aristotle research identified psychological safety as the strongest predictor of team success, more important than individual talent or resources. Importantly, these safe spaces for questioning aren't meant to shelter people from challenging ideas but rather to create environments where people can dare to engage with disconfirming information and voice potentially controversial questions without fear of rejection or humiliation.

Chapter 4: Catalytic Questions: Breaking Down Assumptions and Channeling Energy

The most powerful questions challenge fundamental assumptions, breaking through mental models that constrain our thinking. These catalytic questions operate on multiple levels, first by dismantling what cognitive psychologists call "category mistakes"—flawed assumptions about how things work—and then by redirecting energy toward more productive pathways. Michelene Chi's research on conceptual change reveals why this process is so difficult: our mental models usually serve us well, making us resistant to questioning them. We rarely practice questioning at this deep level because "in our everyday environment, our initial categorizations are mostly correct." Creating the condition of "wrongness" deliberately helps catalytic questions emerge. Jeff Wilke of Amazon explains this as updating mental models through both "crucible experiences" and deliberate questioning practices. He notes, "If you never ask questions and you never experience anything new, your model becomes stale. But if you seek out things that you don't know, and you have the courage to be wrong, to be ignorant—then you build a more complete model." Lior Div, founder of cybersecurity company Cybereason, demonstrates this approach in his work detecting advanced cyber threats. His breakthrough came from questioning the assumption that security systems should focus on keeping bad actors out. "The thing is," he explains, "they're already in." This reframing led to revolutionary solutions focused on monitoring attackers' behavior rather than just strengthening perimeter defenses. Chuck Klosterman observes that modern society has developed a "culture of certitude" where people increasingly hold views with absolute conviction, making it harder to engage in the kind of questioning that could lead to better solutions. Roger Martin similarly notes that when people are certain they possess "the truth," they won't attempt to find better solutions and become trapped in either/or thinking. The antidote is cultivating what Martin calls "integrative thinking"—the capacity to hold opposing ideas in mind simultaneously without panicking or settling for either alternative. Pixar and Disney Animation demonstrate how deliberately creating conditions for wrongness can foster innovation. Their "Brain Trust" and "story trust" processes subject works in progress to intense questioning and criticism. Directors describe these sessions as simultaneously dreaded and invaluable. Jared Bush of Disney explains, "As a filmmaker, you're putting yourself out there. It's not just a product. These stories are incredibly emotional...so when you say, 'Here's a deep piece of my psychology,' and then people say, 'Here's why that sucks,' it's hard not to feel that like a personal attack." Yet he adds, "At the end of it, though, you know you are going to learn something." Organizations like Charles Schwab institutionalize the seeking of wrongness through practices like "brutally honest reports" and regular check-ins with diverse stakeholders. CEO Walt Bettinger explains his philosophy: "The difference between successful executives and unsuccessful ones is not the quality of their decision-making. Each one probably makes 60 percent good decisions. The difference is the successful executive is faster to recognize which were the 40 percent that were wrong and adjust."

Chapter 5: Questioning Skills: Building a Culture of Constructive Inquiry

Questioning skills flourish under three specific conditions that can be deliberately cultivated: feeling more wrong, feeling more uncomfortable, and being more quiet. When people place themselves in situations where they experience these conditions, their questioning capacity naturally expands. By creating these conditions for themselves and others, leaders can transform organizational cultures and unlock innovative potential. The condition of discomfort comes from deliberately stepping outside familiar environments and routines. Lindsay Levin's "leaders' quest" takes executives to unfamiliar settings—like a West Virginia coal mine—where they confront perspectives radically different from their own. These encounters create productive conflict that challenges assumptions. Research confirms that living in multiple countries significantly enhances innovative capacity; Mason Carpenter and Gerard Sanders found that companies led by CEOs with international experience delivered roughly 7 percent higher market performance on average. Discomfort yields three specific benefits for questioning: the element of surprise from encountering new things and perspectives; the power of distraction that allows subconscious processing; and the benefit of conflict that forces confrontation with different worldviews. Rod Drury of Xero recounts how spending time with small business owners revealed that "it was never about accounting software" but about helping them manage cash flow—an insight that led to a breakthrough business model. The condition of quietness requires deliberately shifting from transmission to reception mode. This means developing better listening skills, becoming more approachable, actively seeking "passive data" (as Clay Christensen calls the unstructured contextual information around us), and creating space for reflection. Tony Piazza, an expert mediator who has resolved thousands of disputes, emphasizes that effective questioning requires "diligently, zealously letting go of your preconceptions in order to be present with people." Reading deeply, practicing meditation, and creating moments of solitude all support this condition of quietness. Ed Catmull describes how meditation helps him access insights that remain below conscious awareness: "There was something happening in my head and I felt it. Like this deep visceral thing, this churning... And I couldn't help it by going to the whiteboard, I couldn't do anything like that on a piece of paper. I'm just sitting there in this highly anxious state, and all of a sudden, boom, up it pops." Building a culture of constructive inquiry requires leaders to model these behaviors consistently. As Simon Mulcahy of Salesforce explains, he must constantly remind himself: "Don't tell. Ask questions. Don't tell. Ask questions." This mantra represents the discipline required to overcome the natural tendency to broadcast solutions rather than facilitate discovery. Leaders can amplify this effect by supporting those who raise challenging questions, designing meetings to prioritize inquiry over advocacy, and rewarding questioning behavior throughout the organization.

Chapter 6: From Questions to Action: Translating Insight into Impact

The journey from catalytic question to transformative solution requires deliberate effort to channel the energy generated by fresh insights. Rose Marcario's story illustrates this process: After a moment of personal crisis while stuck in New York traffic, she asked herself, "Is this what I've become? Is this what success is?" Unlike many who experience such moments but fail to act, Marcario channeled this energy into major life changes, eventually becoming CEO of Patagonia where she leads with a questioning approach. Successful organizations systematically channel questioning energy through various approaches. Patagonia continually escalates its questions, moving from founder Yvon Chouinard's initial question "How can I make a living without losing my soul?" to increasingly ambitious challenges: "What kind of organization does a leader who cares about that tension build?" "How could we manage to operate with net-zero impact?" and ultimately "How do we make it uncomfortable for other businesses not to follow us?" Each question builds on previous insights while expanding the scope of impact. Hyatt Hotels demonstrates a different approach by cascading questions through a structured innovation process. Beginning with "What are we missing in the customer experience?" they discovered that 37 percent of their guests were women—a proportion they hadn't been tracking. This insight led to more specific questions about women travelers' needs, which revealed that many felt trapped in their rooms when traveling alone. Through a carefully designed process of listening, defining needs, brainstorming, prototyping, and testing, Hyatt developed their "Escape Bar" concept, creating welcoming social spaces for solo travelers. Managing the emotional arc of a questioning initiative is crucial for sustaining momentum. Questions initially create positive energy by offering glimpses of new solution pathways. Research by Teresa Amabile and Steven Kramer shows that the feeling of making progress is vital to continued engagement. Leaders must therefore structure the journey from question to answer with attention to this emotional dimension, ensuring that initial enthusiasm isn't lost when implementation proves challenging. Tony Robbins, renowned for his coaching work, focuses on helping clients identify their "primary question"—the question they unconsciously ask themselves most often. By making this explicit and potentially replacing it with a more empowering question, he helps clients redirect their mental and emotional energy. This relates to what Marc Benioff calls "innovation capital"—the credibility built by successfully implementing innovative ideas that gives certain people's questions more catalytic power than others. Storytelling skills play a vital role in channeling questioning energy by engaging others in the journey. Neurobiologist Paul Zak's research shows that character-driven stories with emotional content help listeners understand points better and recall them longer. At Pixar, storytelling techniques are deliberately used to leave space for audiences to form their own interpretations. As Mo Willems explains about his children's books, he wants to "give the reader 49 percent—not even 50—so they have to figure out: What is this book really about?" This approach mirrors how catalytic questions work: they invite others into an imaginative space where they can discover new insights for themselves.

Chapter 7: Raising the Next Generation of Questioners

The future of innovation depends on cultivating questioning skills in younger generations. Nobel Prize-winning physicist Isidor Rabi credited his mother's unique approach with setting him on the path to scientific discovery. While other mothers asked "Did you learn anything today?" his mother asked, "Izzy, did you ask a good question today?" This simple shift in emphasis taught him to value inquiry above knowledge acquisition. Educational reform advocates Dan Rothstein and Luz Santana argue that teaching students to formulate their own questions should be a universal educational goal. Their approach addresses a fundamental problem documented by decades of research: conventional education systems systematically suppress questioning. Studies consistently show that teachers dominate classroom questioning while students rarely voice their curiosity. The consequences extend beyond academics—when young people don't learn to question effectively, they grow into adults who lack this essential skill for innovation and problem-solving. Several practical approaches can help develop questioning capacity in educational settings. The Workshop School in Philadelphia maintains a "box of questions" from which one is randomly drawn each day for discussion, with students themselves contributing new questions. Teachers can highlight the questions that led to important discoveries rather than just teaching established facts. Increasing "wait time" after asking questions—from the typical one second to at least three seconds—dramatically improves students' language and logical reasoning capabilities. Most importantly, schools must celebrate students who ask challenging questions rather than rewarding only those who provide correct answers. Project-centered learning provides an ideal environment for developing questioning skills. Models like Montessori education, International Baccalaureate schools, and innovative programs like Room 13 International (where students run their own art studios as businesses) demonstrate how learning driven by student questions produces superior outcomes. When Simon Hauger started an after-school program where students converted cars to hybrid systems, he noticed "the kids at school were learning more in my afterschool space than in my class" because "real problems were driving the academic learning." The digital environment presents both opportunities and challenges for developing questioning skills. On one hand, the internet rewards curiosity by providing immediate answers to questions, potentially encouraging more inquiry. On the other hand, social media often reinforces certitude rather than questioning, with users expressing strong opinions rather than exploring alternative perspectives. Families can counterbalance these influences through practices like Tiffany Shlain's "technology Shabbat"—a weekly day without devices—or Bea Perez's "table talk" family meetings where children can raise questions and receive help thinking through problems. College campuses and workplaces must also cultivate questioning skills. Law professor Owen Fiss describes how his mentor Harry Kalven's approach to teaching created "an escalation of insights" through carefully crafted questions. Similarly, businesses can foster questioning through practices like creating "question boxes," holding regular off-site sessions focused on fundamental challenges, and modeling questioning behavior at all levels of leadership.

Summary

The transformative power of questions lies not in their ability to seek information, but in their capacity to reframe problems in ways that reveal entirely new solution pathways. By challenging assumptions and channeling energy in new directions, catalytic questions break through mental barriers that keep individuals and organizations trapped in outdated thinking patterns. The conditions that foster such questioning—embracing wrongness, seeking discomfort, and cultivating quietness—can be deliberately created in any context, from classrooms to boardrooms to family dinner tables. The journey to becoming a more effective questioner involves both personal and collective dimensions. Individually, it requires developing what might be called a "keystone question"—a guiding inquiry that shapes how we approach challenges and opportunities. Collectively, it demands creating environments where questioning is valued above premature answers, where diverse perspectives are actively sought, and where the pursuit of better questions becomes an ongoing practice rather than an occasional exercise. As we face increasingly complex global challenges, our capacity for innovative solutions depends not on having all the answers, but on nurturing generations of people who ask better questions. By shifting our focus from answering to questioning, we unlock creative potential that remains dormant when we rush to solutions without first examining the questions that frame our understanding.

Best Quote

“The best way to encourage more of the behavior you want is to create the conditions in which that behavior will arise naturally. This is absolutely true of the questioning required for process improvement in a workplace.” ― Hal Gregersen, Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life

Review Summary

Strengths: The book addresses essential subject matter and offers valuable insights into the process of asking questions, which can lead to unique conclusions.\nWeaknesses: The writing is described as dull, akin to a cost accounting class. The book, along with others on creativity, is criticized for focusing too much on novelty without considering the moral implications of questioning. The effort required to implement the book's strategy is seen as a barrier for most people.\nOverall Sentiment: Mixed\nKey Takeaway: While the book provides important insights into the art of questioning, its emphasis on novelty and unconventionality is critiqued for lacking moral reflection, and the writing style is not engaging.

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Hal B. Gregersen

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Questions Are the Answer

By Hal B. Gregersen

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