How to Have Impossible Conversations
A Very Practical Guide
byPeter Boghossian, James Lindsay
Book Edition Details
Summary
"How to Have Impossible Conversations (2019) is a guide to having frank conversations that don’t end in tears. Philosopher Peter Boghossian and scientist James Lindsay argue that however prickly the topic, we all profit when we air our disagreements – provided we’re out to learn something, not just shout our opponents down. These blinks will explore techniques that facilitate respectful dialogue, from rules of building rapport to the art of convincing your sparring partner to reexamine her assump"
Introduction
In today's polarized world, meaningful dialogue across political, religious, and moral divides seems increasingly elusive. Whether it's heated discussions at family dinners, workplace tensions over social issues, or online debates that spiral into hostility, we often find ourselves either avoiding difficult conversations altogether or engaging in ways that deepen divisions rather than bridge them. Yet the ability to have productive conversations with those who hold radically different beliefs isn't just valuable—it's essential for our personal relationships, professional success, and the health of our democratic society. This book offers a comprehensive roadmap for transforming seemingly impossible conversations into opportunities for genuine understanding, mutual respect, and even meaningful change. Drawing from decades of research in psychology, negotiation, and conflict resolution, these proven techniques will empower you to engage confidently across any divide while maintaining your authenticity and values.
Build Foundations for Civil Dialogue
At the heart of every successful difficult conversation lies a fundamental shift in perspective: viewing your conversation partner not as an opponent to defeat, but as a collaborator in a shared quest for understanding. This foundational principle transforms the entire dynamic from adversarial to cooperative, creating the psychological safety necessary for genuine dialogue to flourish. Peter Boghossian discovered this principle's power during his work in the Oregon State Prison System, where he taught critical thinking to inmates. Initially, his conversations about justice and morality often devolved into heated arguments. However, when he began approaching these discussions with genuine curiosity about how inmates had arrived at their beliefs, something remarkable happened. Instead of defensive pushback, he encountered openness and thoughtful reflection. One particularly memorable conversation about the nature of justice began with an inmate declaring that justice meant "standing up for what you believe in." Rather than immediately challenging this definition, Boghossian explored it through careful questioning, asking about scenarios where this principle might lead to harmful outcomes. The transformation was striking. As Boghossian modeled genuine listening and intellectual humility by admitting his own uncertainties, the inmates began questioning their own assumptions. The conversation evolved from a debate into a collaborative exploration of complex moral questions. This shift occurred because Boghossian had established the essential elements of productive dialogue: rapport, genuine curiosity, and shared commitment to understanding rather than winning. Building these foundations requires mastering several key skills. First, establish rapport immediately by finding common ground and showing authentic interest in your partner's perspective. Second, listen more than you speak, using minimal encouragers like "I see" and "tell me more" to keep the conversation flowing. Third, avoid delivering messages or trying to convince through facts alone—instead, focus on understanding how your partner arrived at their conclusions. Finally, assume positive intentions and remember that most people are doing their best with the information they have, even when their conclusions differ dramatically from yours. The goal isn't to eliminate disagreement but to create an environment where disagreement can be productive rather than destructive. When you approach conversations as learning opportunities rather than battles to be won, you open the door to genuine transformation—both for yourself and for those with whom you engage.
Navigate Contentious Topics with Confidence
Entering conversations about deeply divisive topics requires specific techniques that prevent discussions from spiraling into hostility while maintaining the possibility for meaningful exchange. The key lies in understanding that most contentious conversations are actually three conversations happening simultaneously: one about facts, one about feelings, and one about identity and what it means to be a good person. Anthony Magnabosco, a street epistemologist who conducts filmed conversations with strangers about their deepest beliefs, demonstrates these techniques masterfully. In one memorable exchange, he approached Kari, a woman who had just returned from hiking, and asked if she'd be willing to discuss her beliefs about God. Rather than immediately diving into theological arguments, Magnabosco spent several minutes building rapport, asking about her hiking experience and establishing a comfortable connection. Only after creating this foundation of trust did he begin exploring her beliefs about faith and divine intervention. When Kari explained that she believed God had helped her through difficult times, Magnabosco didn't challenge her conclusion directly. Instead, he asked thoughtful questions about how she could distinguish between divine intervention and her own inner strength. As their conversation progressed, Kari began expressing uncertainty about some of her previously firm beliefs. The transformation occurred not because Magnabosco had presented compelling counterarguments, but because he had created a safe space for Kari to examine her own reasoning process. To navigate contentious topics successfully, begin by asking calibrated questions that start with "how" or "what" rather than yes-or-no questions. These open-ended inquiries invite explanation and reflection rather than defensive responses. Focus on understanding your partner's epistemology—how they came to know what they think they know—rather than challenging their conclusions directly. When disagreements arise about fundamental terms, define key words upfront to avoid talking past each other. Most importantly, be willing to acknowledge extremists on your own side, demonstrating that you're not a tribal partisan but someone committed to reasonable dialogue. Remember that changing minds happens slowly and often occurs after the conversation has ended, during private reflection. Your goal isn't to achieve immediate conversion but to plant seeds of doubt that allow for future growth and reconsideration.
Transform Opponents into Partners
The most powerful conversations occur when you successfully shift the dynamic from adversarial to collaborative, helping both participants feel like they're working together toward greater understanding. This transformation requires advanced skills in emotional intelligence, strategic communication, and genuine empathy. The technique of building "Golden Bridges" illustrates this principle beautifully. During a public discussion in Australia, a participant confidently argued for a particular position throughout most of the conversation. Near the end, when presented with a perspective she hadn't considered before, she paused thoughtfully and said, "I really never thought about that before. I think that's right. Yeah. That's right." Rather than responding with triumph or saying "I told you so," her conversation partner simply acknowledged her openness and thanked her for the engaging discussion. This Golden Bridge allowed the woman to change her mind gracefully without feeling humiliated or defeated. The conversation continued positively because the woman felt supported in her intellectual journey rather than attacked for her previous position. She had been given what negotiation experts call an "exit ramp"—a way to modify her views while maintaining her dignity and sense of being a thoughtful person. This approach recognizes that people rarely change their minds when they feel cornered or embarrassed; instead, they dig in deeper to protect their self-image. Building Golden Bridges requires several specific techniques. Use collaborative language that emphasizes partnership—say "we" and "us" rather than "you" and "your." When someone shares a belief, avoid immediately responding with "but" and instead use "yes, and" to acknowledge their perspective while adding your own insights. If emotions run high, address feelings directly by saying things like "I can see this is really important to you" or "I understand why this would be frustrating." Most importantly, be genuinely willing to change your own mind when presented with compelling information. Model the intellectual humility you hope to see in others by admitting uncertainty and acknowledging when you've learned something new. This vulnerability creates psychological safety that allows both participants to explore difficult topics without fear of judgment or attack. When you successfully transform opponents into partners, conversations become collaborative explorations rather than zero-sum battles, opening possibilities for mutual growth and understanding that seemed impossible at the outset.
Master Advanced Persuasion Techniques
The most challenging conversations require sophisticated approaches that go beyond basic listening and questioning skills. These advanced techniques address the deeper psychological and emotional dynamics that drive human belief formation, particularly around moral and identity-related issues. One of the most powerful advanced techniques involves what experts call "altercasting"—essentially inviting your conversation partner to step into a role that encourages more thoughtful consideration. Peter Boghossian employed this technique when speaking with his daughter's teacher, who was planning to present only one perspective on gentrification to her students. Rather than criticizing her approach directly, Boghossian said, "Thank you for telling us that. You strike me as a fair person, one who's interested in critical thinking and teaching different perspectives on issues. Will you be teaching other perspectives on gentrification as well?" The teacher immediately responded, "Yes. Absolutely. There's a book that offers another side of the issue that kids can read." This exchange succeeded because Boghossian cast the teacher in the role of someone committed to fairness and intellectual rigor, then allowed her to live up to that identity rather than forcing her to defend a potentially narrow approach. The technique worked because it aligned with her self-image as an educator committed to developing students' critical thinking skills. Advanced persuasion also involves understanding and addressing the moral foundations that underlie different worldviews. Research shows that conservatives and liberals often talk past each other because they prioritize different moral values—conservatives emphasize loyalty, authority, and sanctity while liberals focus primarily on care and fairness. Effective communicators learn to speak in their conversation partner's moral language, framing arguments in terms that resonate with their fundamental values. Another crucial advanced skill involves seeking disconfirmation rather than confirmation. Instead of asking "What evidence supports your belief?" ask "Under what conditions could that belief be wrong?" This shifts the conversation from defending positions to examining the foundations of certainty. When people discover they cannot imagine any evidence that would change their minds, they often begin questioning whether their confidence is truly warranted. These techniques require practice and genuine commitment to understanding rather than manipulation. They work because they address the deeper human needs for respect, autonomy, and meaning that drive our most important beliefs and decisions.
Summary
The art of impossible conversations ultimately rests on a profound recognition: every person you encounter is doing their best with the information and perspective they have available, and beneath even the most challenging beliefs lies a human being worthy of respect and understanding. As the book emphasizes, "People don't knowingly desire bad things"—they act based on what they believe will create positive outcomes, even when their methods or conclusions differ dramatically from our own. This insight opens the door to genuine dialogue across any divide. The path forward requires both courage and humility: the courage to engage rather than avoid difficult conversations, and the humility to approach them as learning opportunities rather than battles to be won. Start today by identifying one relationship where improved communication could make a meaningful difference, then apply just one technique from these pages. Remember that transformation happens gradually, through countless small moments of genuine human connection. Your willingness to bridge divides through respectful dialogue doesn't just improve your own relationships—it contributes to healing our fractured world, one conversation at a time.
By Peter Boghossian
