Ask

Ask Plot Summary

Introduction

Imagine sitting in a boardroom, heart racing as you present your carefully crafted proposal to senior executives. The silence that follows feels eternal. You can sense there's something wrong, but no one speaks up. Later, you discover through office gossip that your proposal had a critical flaw that everyone noticed but no one mentioned. If only someone had voiced their concerns, you could have fixed the issue before it derailed the project. This scenario plays out countless times daily in offices, homes, and communities worldwide. We often fail to access the wisdom that surrounds us because we don't know how to ask the right questions in ways that make others feel safe to share their thoughts. Through years of research and real-world experience, we now understand that the most valuable information—insights that could transform our decisions, relationships, and careers—often remains unspoken. The good news is that we can all develop the skill of asking in ways that unlock this hidden wisdom. By cultivating curiosity, creating psychological safety, asking quality questions, and truly listening to learn, we can tap into the collective intelligence around us. This isn't just about getting better information; it's about building deeper connections and creating environments where truth can flourish.

Chapter 1: The Invisible Problem: Why Critical Information Stays Hidden

Jim Cutler was a successful leader at a consulting firm, heading a growing Human Capital business division. After several years of building this division and bringing in millions of dollars in revenue, Jim felt confident about his leadership and the business's trajectory. Curious to learn how he could improve further, he asked a colleague named Amelia to conduct an anonymous 360-degree review with his peers and employees. When Amelia returned with the feedback, Jim was stunned. While his colleagues praised many aspects of his leadership style and the innovative ideas his team produced, they also shared a harsh truth: they believed Jim lacked the commercial drive that someone in his position needed. This criticism was particularly painful because it came from colleagues Jim considered close friends—people whose spouses were friends with his, people whose weddings he had attended, people he socialized with regularly. Jim couldn't understand why these friends and colleagues had never shared these concerns with him directly. Why had they waited until an anonymous review to express their thoughts? They knew he valued direct feedback. The organization's culture even emphasized open communication and learning. Yet somehow, this critical information had remained hidden from him until now. This scenario illustrates what research confirms happens constantly in organizations and relationships everywhere. People routinely withhold vital information, even when sharing would benefit everyone involved. Studies show that over 85 percent of managers admit to remaining silent about important concerns with their bosses on at least one occasion. Nearly half of employees say they don't feel comfortable speaking up about issues that concern them. The costs of this silent epidemic are enormous. Teams make poorer decisions, relationships suffer from unaddressed tensions, and innovation stalls because diverse perspectives remain unexpressed. When critical information stays hidden, everyone loses—from individuals to entire organizations. What makes this problem particularly insidious is its invisibility. We don't know what we don't know, and we can't address problems we aren't aware exist. The good news is that by understanding why people withhold information, we can create conditions that make it more likely they'll share their valuable insights with us.

Chapter 2: Choose Curiosity: Breaking Free from Certainty Loops

On a tropical island where tourism was the economic lifeblood, a crisis was brewing. The island's hotels faced increasing competition from other destinations offering lower prices, and tourist arrivals had been declining for years. Hotel managers wanted more flexible labor contracts to enhance guest experiences, while the labor union saw these changes as attempts to demand more work without additional pay. The standoff threatened to trigger a strike that could devastate the island's economy. The situation was complicated by the island's colonial history: corporate managers were mostly white with foreign educations, while union workers were predominantly Black descendants of enslaved people. This painful history, combined with modern inequalities, added layers of distrust to an already tense relationship. Both sides were completely certain of their positions. The hotel managers viewed the union leaders as stubborn obstacles to necessary change. The union saw the managers as exploitative and dismissive of workers' concerns. Each group believed their story was the only valid interpretation of reality, and this certainty prevented them from seeing any common ground. During a last-ditch meeting to prevent a strike, the facilitator introduced a framework called "the ladder of understanding" to help both sides recognize how their certainty was blocking learning. This tool showed how people select tiny slices of information from any situation, process that information through their existing beliefs and experiences, and reach conclusions that confirm what they already thought. When we race up this "ladder" to conclusions without questioning our process, we get trapped in what the facilitator called "certainty loops"—where we see only what confirms our existing views. By walking both sides through this framework, the facilitator helped them see that their certainty was preventing them from hearing each other. The union leaders began asking questions about the economic pressures facing the hotels. The managers grew curious about workers' experiences and concerns. As curiosity replaced certainty, new possibilities for collaboration emerged. The human mind naturally seeks certainty—it's how we make sense of a complex world. But this desire for certainty becomes problematic when it blocks our ability to learn from others. Choosing curiosity means intentionally looking for new information and different perspectives, especially when we feel most convinced we already know the truth. It requires us to ask: What might I be missing? What does this situation look like from another viewpoint? How might my own experiences and biases be shaping what I notice and conclude?

Chapter 3: Make It Safe: Creating Space for Honest Sharing

Emily Weiss didn't set out to disrupt the beauty industry when she launched Glossier, but that's exactly what happened. Within a decade, her direct-to-consumer beauty brand achieved a billion-dollar-plus valuation. The secret to this remarkable success wasn't just innovative products—it was Glossier's revolutionary approach to customer relationships. From the very beginning, Weiss recognized that beauty brands weren't truly communicating with customers; they were talking down to them rather than engaging in genuine conversations. Before creating a single product, Weiss interviewed hundreds of women worldwide, discovering a significant disconnect between beauty brands and their customers. Unlike traditional companies that kept customer service departments isolated or outsourced, Glossier integrated customer feedback into every aspect of the business. They created comfortable digital spaces, including Slack channels, where loyal customers could provide detailed feedback on products. While most companies struggle to get basic survey responses, Glossier built an enthusiastic community eager to share honest insights that became invaluable to the brand's development. What made Glossier's approach work so well? The company created psychological safety—an environment where people felt it was comfortable, easy, and appealing to share their honest thoughts and experiences. This wasn't accidental but deliberate. Glossier demonstrated three essential elements of safety: they created genuine connection with customers, they opened up about their intentions and processes, and they showed they could handle whatever feedback came their way without becoming defensive. Creating safety is essential whenever we want others to share openly with us. Research by Harvard professor Amy Edmondson shows that psychological safety—the belief that one won't be punished or humiliated for speaking up—is the single most important factor in whether people report critical information in workplaces. In her studies of hospital intensive care units, Edmondson found that team members were far more likely to report medical errors when they felt safe doing so, which ultimately saved patients' lives. Making it safe requires understanding that sharing often feels threatening to people. Our brains register the pain of social threats no differently than physical blows. When we ask someone to share their thoughts or give feedback, particularly on sensitive topics, we're asking them to be vulnerable. It's our responsibility to show them we're trustworthy before expecting them to open up. This applies to all relationships, but becomes especially critical when power differences exist—between managers and employees, doctors and patients, or across other social divides. Creating safety isn't just a nice gesture; it's often the difference between accessing vital information or remaining dangerously in the dark.

Chapter 4: Quality Questions: Tools to Unlock Others' Knowledge

Isaac, the CEO of a health-care startup, faced a painful problem: the subcommittee of his board that had promised to help him raise his next round of funding wasn't following through. For months, they had neither made larger investments themselves nor rallied their networks. Isaac had tried everything—nudging, urging, cajoling—but nothing worked. With current funding running dry, he finally realized he needed to find out why they weren't helping. Isaac arranged to meet Anna, a board member he considered the straightest shooter of the group, at a neutral restaurant setting. Though nervous about what he might hear, Isaac opened the conversation by making it safe for Anna to speak candidly: "I appreciate you making time to talk, and I'm hoping we can have a really candid conversation about the challenges we've been facing in the fund-raising committee. I hope you'll feel free to tell me all your views, unfiltered, and don't worry about sparing my feelings." Then Isaac asked his first quality question: "What do you think is going on?" Anna's response revealed the board's concerns about the company's strategy, specifically that their product might not stand out in an increasingly crowded market. This was a crucial insight Isaac had completely missed. Rather than becoming defensive, Isaac dug deeper with follow-up questions: "Can you say more about what you mean by the strategy needing adjustment?" and "What are some examples of the competitors you're thinking of?" These questions helped him uncover that the board members weren't confident in the evidence supporting the product's competitive edge—which explained their reluctance to approach investors. By asking quality questions and remaining genuinely curious throughout the conversation, Isaac discovered information that had been invisible to him for months. In just one hour, he gained critical insights about his board's concerns and clear direction for his next steps—either making a more persuasive case that they were ready for funding or returning to product development. Quality questions help us learn something important from the person we ask. They signal true curiosity, are clear and direct, invite honesty, tap into the other person's full story, and create mutual benefit. Unlike "crummy questions"—those that are clumsy, sneaky, or attacking—quality questions open up learning rather than shutting it down. Most of us have a limited question repertoire, often defaulting to closed-ended questions that yield minimal information, rhetorical questions that aren't really questions at all, or leading questions designed to manipulate rather than learn. We've been culturally conditioned to avoid asking questions, especially in professional settings where we feel pressure to project confidence and certainty at all times.

Chapter 5: Listen to Learn: Hearing What's Really Being Said

Atul Gawande, a renowned surgeon and author, once found himself in a challenging situation. He was treating a belligerent prisoner who had slashed his own wrist with a tube of toothpaste. The man hurled racist, threatening remarks at a nurse and cursed nonstop while Gawande tried to stitch his wounds. The verbal abuse was so intense that Gawande momentarily questioned whether all people truly deserve care—a bedrock principle of medicine. Then Gawande remembered something he'd learned about communication: when people speak, they express more than just their thoughts. They are also expressing emotions they want heard. Instead of tuning out the prisoner's words, Gawande decided to listen more closely, focusing on the emotions beneath the verbal attacks. This led him to say something unexpected to his patient: "You seem really angry and like you feel disrespected." The effect was immediate. The man stopped cursing, his tone changed, and he began sharing his experience of spending two years in solitary confinement. "All it took to see his humanity—to be able to treat him—was to supply that tiny bit of openness and curiosity," Gawande later reflected. Both men relaxed, and he was able to complete the medical care. This story illustrates a fundamental truth: how we listen matters profoundly. The quality of our listening shapes what gets shared and how the other person feels about themselves and their contribution. Despite its importance, most of us were never taught how to listen effectively. Research shows that while 96 percent of people think of themselves as good listeners, we retain less than half of what people tell us, and the average person listens with only 25 percent effectiveness. True listening involves tuning into three channels simultaneously: content (the facts and claims being made), emotion (the feelings behind the words), and action (what the person is trying to do through their communication). Most of us focus solely on content, missing crucial information conveyed through the other channels. Effective listening also requires eliminating distractions—both external ones like phones and emails, and internal ones like judgment and fear. We must learn to "zip our lips" and become comfortable with silence, allowing space for others to gather their thoughts and share more deeply. We need to watch our facial expressions and reactions, ensuring they invite continued sharing rather than shutting it down. Perhaps most importantly, we need to check our understanding by paraphrasing what we've heard and asking if we've gotten it right. This simple practice demonstrates our attentiveness and gives the other person a chance to clarify their meaning. It also opens the door to further sharing through thoughtful follow-up questions like "Can you tell me more about that?" or "What else is on your mind?"

Chapter 6: Reflect and Act: Turning Insights into Meaningful Change

After years of strong growth at Transcend, an educational organization, co-CEOs Aylon and Jeff faced an unexpected challenge. Their largest project team, which was taking on new clients with intense needs, was experiencing significant strain. Despite several attempted solutions, the team's morale continued to decline, and they risked losing talented people they'd hired just a year earlier. Recognizing the need for direct intervention, Aylon invited the project team of nearly twenty people to Chicago for two days of planning and rebuilding. The meeting began with what was intended to be a simple icebreaker: "In the previous year, what could I have done better, and what could the people around me have done better?" Instead of quick responses, team members took turns sharing emotional stories about their struggles, unmet needs, and moments when work felt overwhelming. What was scheduled as a three-hour opening session extended to occupy three-quarters of the two-day meeting. The leadership team listened as teammates shared painful workplace challenges—situations created, at least in part, by leadership decisions. While difficult to hear, this honest feedback provided crucial insights that ultimately helped turn the project around and retain over 90 percent of the team. But the story doesn't end with listening. After the Chicago meeting, Aylon and Jeff engaged in deep reflection about what they'd heard. They examined how their story about the organization—that its strong, mission-driven culture could withstand rapid growth without formal management structures—had led to decisions that overburdened their team. This reflection led to concrete actions: investing in onboarding, training, communication structures, and performance management systems. A month later, at the organization's annual retreat, they took the brave step of publicly sharing their reflective process with the entire organization. They explained how the feedback had affected their understanding of the situation, what steps they were taking as a result, and how the experience had revealed blind spots in their leadership approaches. Though uncomfortable, this public reflection was transformative—not only for the leaders but for everyone present. Team members responded with a standing ovation, saying they'd never seen leaders make themselves so vulnerable yet inspiring such confidence. When someone shares valuable insights with us, we owe them two essential responses: reflection and reconnection. Reflection involves sifting through what we've heard to separate useful information from noise, then turning that information to examine it from multiple angles. We need to consider how it affects our understanding of the situation, what actions we should take as a result, and what it might reveal about our deeper assumptions and ways of being. Reconnection means circling back to the person who shared with us, expressing gratitude for their input, and letting them know what impact their sharing had on us—including what we plan to do with the information. Even when we decide not to act on their input, sharing our reflective process helps maintain trust and encourages continued openness.

Chapter 7: Building a Culture of Asking: From Individual to Organization

Irene Rosenfeld, then CEO of Mondelēz International (the parent company of Oreo), received an urgent call one day. A board member had discovered packages of Oreo cookies containing nothing but crumbled messes. If this quality control issue had reached a board member, it was likely affecting customers worldwide. How had this happened, and why was she just finding out now? Rosenfeld discovered that a newly installed packaging machine was malfunctioning, but employees on the production line hadn't escalated their concerns. Perhaps they feared being bearers of bad news or slowing down progress when demand was booming. Whatever the reason, critical information hadn't reached those who needed to know until it was too late. While there were no health concerns, the problem took months to fix and cost the company significantly. This experience led Rosenfeld to ask a profound question: What would need to change for the organization to consistently tap into its own collective intelligence? The answer was developing a culture of asking throughout the company—not just among individual leaders but embedded in the organization's DNA. Organizations that excel at asking take several crucial steps. First, they tap into the genius of end users—their customers or clients—by creating multiple channels for feedback and developing ongoing relationships with consistent users. Second, they find wisdom in their front lines by engaging staff in strategy and decision-making, acknowledging the value of their unique perspective, and creating safe spaces for honest sharing. These organizations also build asking into their people practices—hiring for curiosity, training employees in asking skills, establishing feedback rituals, and evaluating people on how well they learn from others. They lead learning cycles by setting concrete learning agendas, building these objectives into leaders' responsibilities, and creating formal structures where teams systematically gather and make meaning of insights from inside and outside the organization. Perhaps most importantly, leaders in these organizations become "learners in chief"—modeling vulnerability, openly sharing their own challenges and dilemmas, seeking feedback publicly, and acknowledging those who provide input. This isn't always comfortable; leaders often feel pressure to appear all-knowing. But when they demonstrate that asking and learning are valued, it transforms the entire culture. The payoff is immense. Organizations that cultivate asking tap into their collective genius—the combined knowledge, creativity, and wisdom of all their stakeholders. This leads to better decisions, more innovative solutions, stronger relationships, and greater adaptability in an increasingly uncertain world.

Summary

Throughout our journey exploring the power of asking, we've discovered that the most valuable information—insights that could transform our decisions, relationships, and work—often remains unspoken unless we actively seek it out. The barriers to sharing are powerful: fear of consequences, inability to find the right words, lack of time or energy, and doubt that anyone truly cares what we think. Yet when we develop the skill of asking, we can overcome these barriers and unlock the wisdom that surrounds us. The path begins with choosing curiosity—intentionally looking for new information and different perspectives, especially when we feel most certain we already know the truth. It continues with making it safe for others to share by creating connection, opening up about our intentions, and demonstrating that we can handle whatever they tell us. We then pose quality questions designed to help us learn something important, and we listen deeply through all three channels: content, emotion, and action. Finally, we reflect on what we've heard and reconnect with those who've shared, letting them know the impact of their contribution. By practicing these steps consistently, we not only make better decisions and develop stronger relationships but also create cultures where truth can flourish and collective genius can emerge. In a world facing unprecedented challenges, learning to ask may be the most important skill we can develop—one that helps us break free from certainty, connect across differences, and tap into the wisdom that surrounds us every day.

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Jeff Wetzler

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