The Right Way to Prepare for a High-Stakes Conversation

Before commercial pilots push back from the gate, they complete a comprehensive preflight check to verify that every system functions correctly during the journey ahead. Before surgeons make the first incision, they conduct a safety check, confirming patient identity, procedure details, and equipment readiness. Before software engineers ship new code, they check for bugs and vulnerabilities. Yet when business leaders approach their most consequential conversations—those make-or-break negotiations, difficult performance discussions, or strategic decision-making sessions—they too often dive in without the right mental preparation. This oversight can be costly, as cognitive rigidity severely limits our ability to discover new and relevant information and collaborate well with others. The solution lies in conducting a “Curiosity Check”: a brief but systematic assessment of your openness to vital new information. This form of mental readiness can significantly improve your effectiveness in high-stakes conversations. The Hidden Cost of Certainty Consider the last time you entered an important conversation convinced you already knew the outcome, the other party’s position, or the optimal solution. Perhaps you were preparing to deliver difficult feedback to an underperforming employee, negotiating a complex deal, or presenting a strategic recommendation to your board. If you’re like most leaders, you likely spent considerable time preparing your arguments, anticipating objections, and rehearsing your key points. While this kind of preparation has its place, relying on it exclusively comes at the cost of examining your own assumptions and cultivating genuine curiosity about what you might be missing. This preparation gap creates what behavioral scientists call “confirmation bias”—a mindset where you not only seek information that confirms your existing beliefs but actively filter out disconfirming evidence. If you can cultivate genuine curiosity—especially under conditions of stress or threat—the benefits are enormous. Curiosity increases your ability to process new information and respond creatively to complex problems. It activates the brain’s learning and reward centers, increasing your capacity for insight and creative problem-solving. Curious individuals demonstrate greater resilience when facing unexpected information, such as pushback from your direct reports, colleagues, or boss. The Curiosity Check Despite study after study showing the cognitive, emotional, and relational benefits of curiosity, few executives have a reliable method for assessing and optimizing this mindset before critical interactions. To bridge that gap, I developed the Curiosity Check, which involves three steps and should take no more than five minutes before any significant conversation: Step 1: Locate your current mindset on the Arc of Curiosity. The Arc of Curiosity (which was inspired by a model from the nonprofit organization Braver Angels) can help you become aware of your initial mindset walking into a conversation. Think of it as your leadership equivalent to the pilot’s most important gauge on a cockpit dashboard. The left half represents three Zones of Certainty: Self-Righteous Disdain, Confident Dismissal, and Skeptical Tolerance. The right half represents three Zones of Curiosity: Cautious Openness, Genuine Interest, and Fascinated Wonder. See more HBR charts in Data & Visuals Ask yourself: “If I encounter disagreement in this conversation, which zone will I mentally jump to?” Be brutally honest. Are you approaching this interaction with disdain for the other party’s potential pushback? Are you dismissive of perspectives that differ from your own? Or are you genuinely open to learning something new? Most leaders, when they’re honest with themselves, recognize they typically enter high-stakes conversations in one of the Zones of Certainty. While this positioning provides psychological comfort and apparent confidence, it undermines conversation effectiveness. The act of locating your mindset on the Arc of Curiosity invites what psychologists call “metacognition”: becoming aware of your own patterns of thinking. Having this self-awareness sets the stage for mindset shifts. Step 2: Set your curiosity intention. Now that you know your starting point, use the Arc of Curiosity to identify which mindset you want to adopt. It’s often unrealistic to reach the zone of Fascinated Wonder. Instead, commit to moving one or two zones to the right of where you begin—for example, if you’re starting from Confident Dismissal, aim for Cautious Openness. If you’re at Skeptical Tolerance, try getting to Genuine Interest. Regardless of your starting point, pick a mindset shift that’s ambitious but feasible, and set your intention to anchor there. Step 3: Ask yourself curious questions to make the shift. While your intention matters, you also need tools to help you realize it. “Curiosity Sparks” are small but targeted questions that can help shift your mindset rightward on the Arc of Curiosity. Here are five Curiosity Sparks to consider: What might the other person be struggling with that I’m unaware of? What good (but unspoken) concerns, reasons, or information might underlie their disagreement with me? How might my words or actions be impacting them in ways I don’t intend? What incorrect assumptions might I be making about the situation, issue, or other person? Even if my assumptions are correct, what else might be going on that I’m unaware of? What unspoken insights or ideas might the other person have that could address our challenge? Sometimes it’s tough to consider these Curiosity Sparks on your own, especially if you’re stuck on the left side of the Arc of Curiosity. It helps to ask a trusted friend, colleague, mentor, or even an AI bot to help you think them through. Curiosity Checks in Action Sarah*, a VP of finance I worked with, was preparing to deliver a harsh performance review to Michael. He had historically been her highest-performing director, but he had been underperforming for the past six months despite multiple warnings that his performance was becoming a problem. Sarah had spent weeks documenting his errors and preparing her “shape up or ship out” conversation. She anticipated every excuse Michael might offer and steeled herself to rebut them with facts and examples. Before the conversation, Sarah did a quick curiosity check and assessed herself as being in Confident Dismissal—certain that Michael was coasting on past success and ignoring her pushes. Setting an intention to reach at least Cautious Openness, she used the Curiosity Spark: “What might Michael be struggling with that I’m unaware of?” This small shift led her to start the conversation not with accusations but with genuine questions about what challenges Michael was up against. Within minutes, Michael revealed that he’d been secretly managing his partner’s cancer treatment while trying to maintain his professional image and avoid burdening anyone else. Sarah’s questions transformed what could have been an unnecessary termination into joint problem-solving about temporary adjustments and support systems, ultimately saving a valuable employee and strengthening their working relationship. Elsewhere, the executive team at a midsize tech company I worked with was deadlocked over whether to delay their next software release launch by six months: Engineering insisted they needed more time while marketing argued that the competitive window was closing. Just as things were about to hit a boiling point, engineering lead David called a 10-minute break and asked his team to privately perform a curiosity check. When they reconvened, David began by admitting they’d been dismissive of marketing’s urgency and asked them to elaborate on the market pressures they were seeing. This simple intervention revealed new data about competitors’ offerings—information that convinced even David and his team that their original approach would be too slow. By the end of the meeting, both teams collaborated on a creative solution: a phased launch that introduced some new features much sooner than planned but also reserved more time for engineering to pressure-test the most complex features. . . . In a world where information is abundant but insight remains scarce, curiosity may be the ultimate competitive advantage. If you wouldn’t fly on a plane that hadn’t had a preflight check, why head into a high-stakes conversation without first checking your most vital mindset: curiosity? The question isn’t whether you’ll face disagreement and pushback in your next high-stakes conversation—it’s whether you’ll be mentally prepared to transform that into insight and constructive action. Curiosity is a choice, and that choice begins before you speak your first word. By honestly assessing where you sit on the Arc of Curiosity, setting realistic intentions to move toward greater openness, and deploying targeted Curiosity Sparks, you can transform your most challenging interactions from battles to be won into opportunities for mutual discovery and collaborative problem-solving. * Names and certain details have been changed throughout for privacy. Editor’s note, October 17, 2025: This article was updated to use the term “Arc of Curiosity.”

The Right Way to Prepare for a High-Stakes Conversation

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