How to Have Impossible Conversations

A Very Practical Guide


By Peter Boghossian

By James Lindsay

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From politics and religion to workplace negotiations, ace the high-stakes conversations in your life with this indispensable guide from a persuasion expert.

In our current political climate, it seems impossible to have a reasonable conversation with anyone who has a different opinion. Whether you're online, in a classroom, an office, a town hall—or just hoping to get through a family dinner with a stubborn relative—dialogue shuts down when perspectives clash. Heated debates often lead to insults and shaming, blocking any possibility of productive discourse. Everyone seems to be on a hair trigger.

In How to Have Impossible Conversations, Peter Boghossian and James Lindsay guide you through the straightforward, practical, conversational techniques necessary for every successful conversationwhether the issue is climate change, religious faith, gender identity, race, poverty, immigration, or gun control. Boghossian and Lindsay teach the subtle art of instilling doubts and opening minds. They cover everything from learning the fundamentals for good conversations to achieving expert-level techniques to deal with hardliners and extremists. This book is the manual everyone needs to foster a climate of civility, connection, and empathy.

"This is a self-help book on how to argue effectively, conciliate, and gently persuade. The authors admit to getting it wrong in their own past conversations. One by one, I recognize the same mistakes in me. The world would be a better place if everyone read this book."  —Richard Dawkins, author of Science in the Soul and Outgrowing God


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When Conversations Seem Impossible

THIS BOOK IS ABOUT HOW TO COMMUNICATE EFFECTIVELY WITH people who hold radically different beliefs. We live in a divided, polarized era, and we’re not talking with each other. The repercussions of this are vast and deep, including the fear of speaking openly and honestly, an inability to solve shared problems, and lost friendships.


Nearly two decades ago, one of this book’s authors, Peter, was discussing affirmative action with a colleague (SDL), a white female who described herself as a liberal. As conversations about controversial topics tend to do, it quickly became heated. Then, as is par for the course in these situations, before long it went downhill, fast. Let’s take a look back:

SDL: You keep denying that it [affirmative action] is fair.

Boghossian: Yeah, that’s because it’s not. Who’s it fair to?

SDL: I told you already. Traditionally marginalized groups, like African Americans. They’re coming from a deficit. They didn’t have the same opportunities that you and I had.

Boghossian: But why does that require manufacturing outcomes?

SDL: You sound like a broken record. Because they’re Americans, and they deserve better. You don’t understand because you’ve never had those struggles. You’ve gone to good schools and never dealt with even a fraction of what they deal with on a daily basis.

Boghossian: Let’s say you’re right. I don’t think you are, but let’s say you are. What evidence do you have that affirmative action is a way to remedy past injustices?

SDL: I don’t have any evidence. It’s the right thing to do because—

Boghossian: So you have no evidence. You have complete confidence in a belief for which you have no evidence.

SDL: You’re not listening.

Boghossian: I am listening. I’m trying to figure out how you could believe so strongly in something with no evidence. Do you think African Americans are better off with Clarence Thomas? Do you think it was a good thing that he’s a Supreme Court justice, or would African Americans be better off with a liberal white male?

SDL: You’re [expletive] annoying. Seriously. I can’t believe you’re a teacher.

Boghossian: I’m sorry you feel that way. Maybe if you could better defend your beliefs you wouldn’t be so annoyed with someone who’s asking you softball questions.

SDL: What do you teach your students?

Boghossian: You’re not my student. And don’t get so upset.

SDL: You’re an asshole. We’re done.

She was right. Peter wasn’t listening; he was annoying; and he was being an asshole. In this brief exchange, he interrupted, used “but” in response to her statements (probably the least wrong thing he did), shifted topics, and didn’t answer her questions. He was so focused on winning—and even intellectually embarrassing her—that he ruined the conversation and closed the door to productive future exchanges. SDL walked out on the conversation, but she should have walked away sooner.

Conversations between people who hold radically different beliefs about religion, politics, or values have always been challenging. In that sense, the conversation between Peter and SDL wasn’t likely to go smoothly, but it didn’t have to go that badly. There are good and bad ways to have conversations with people who hold radically different beliefs, and better approaches aren’t just imaginable, they’re achievable. Because our current cultural environment is deeply polarized, it’s even harder than usual to converse productively across these divisions.

Even since Peter’s conversation with SDL nearly twenty years ago, our conversational spaces have fractured, and people have far more difficulty conversing with people who hold strongly different views. The bickering and bad faith seem endless: liberals versus conservatives,1 religious people versus atheists, Democrats versus Republicans (in the United States), this sect versus that, some identity group versus some—or every—other one, and the angry, reactionary, or radical fringes against the bewildered and exhausted center.

Across these divides and many others, people struggle to talk with each other. Sides have been chosen, with battle lines drawn. In this space, few people know how to talk to “the other side,” and many consider those who believe differently to be an existential threat—that is, someone whose presence threatens everyone else’s very existence. And it seems like there’s neither a solution nor an escape. We don’t even know how to cope with disagreements over family dinners, yet we find ourselves having heated arguments with acquaintances and on social media. Many people deal with this by hiding from contentious conversations. That’s fine, and in certain circumstances it may even be the right thing to do. However, it’s only an occasional solution. It’s also vital to learn how to have these difficult—even seemingly impossible—conversations.


When we say “impossible conversations,” we mean conversations that feel futile because they take place across a seemingly unbridgeable gulf of disagreement in ideas, beliefs, morals, politics, or worldviews. We don’t mean exchanges that occur in situations in which some people are absolutely unwilling to speak with you. Extreme examples where people are violent or threatening, or adamant in their refusal to talk or even to listen, are not what we mean by “impossible conversations.” When someone refuses to speak with you, there’s no conversation to be had. No book can teach you how to force someone to converse if they won’t speak with you. These circumstances, however, are exceptionally rare. Most people will engage you most of the time on most topics.

Although productive discussions with people who hold radically different beliefs can be extremely difficult, they are only literally impossible in fringe cases. Usually, the more invested someone is in their beliefs, the more they want to speak about them. The difficulty in these cases isn’t having someone speak to you; it’s that a give-and-take seems hopeless because the person across from you fails to speak with you and instead speaks at you. In such cases, you’re viewed as a receptacle to pour ideas into, or as an opponent to be debated and vanquished.

How to Have Impossible Conversations teaches you how to have conversations with anyone who’s willing to speak with you, even though those people and those conversations seem impossible. Maybe someone’s angry, or maybe your political differences seem so profound that a civil discussion feels impossible. But if someone’s willing to talk with you, even if they’re an extremist, die-hard believer, or intense partisan, this book will teach you how to effectively communicate with them.

Of course, it’s easier to not engage in conversations with those who hold different views, but avoidance is not always possible. Someone might approach you; you might find yourself “trapped” with friends or family when religion or politics comes up; or you might find the topic too important to leave alone. When you find yourself in these situations, it’s far better to know how to navigate than not. This book will empower you to handle such conversations, even when they become heated. It will give you options.


Ultimately, How to Have Impossible Conversations is about talking to people who hold different beliefs. What people believe matters, and what you believe matters. If you believe it’s cold, you’ll want to put on a jacket because you believe that it will make you warmer. So, too, with moral and political beliefs. If you believe foreign invaders are stealing our jobs and raping and murdering our citizens, you’re more likely to vote for a strongman who’ll promise to seal the borders and keep you safe (and if you believe your political opponents want open borders, you’re even more likely to vote accordingly). If you believe fascists are everywhere and verging on a government takeover, you’re more likely to sympathize with the pleas of those who advocate for violence by “punching Nazis.” Beliefs matter because people act upon their beliefs—whether those beliefs are true or not (and it’s far easier to be wrong than right).

Beliefs can also change, and there are good and bad ways to change them. Conversation is a good way. Force is a bad way, for all the obvious reasons—plus, it’s downright ineffective. Despite what some people’s frustration tells them, people never change their beliefs by being punched in the head by someone who hates them. In almost all cases, the best way to engage beliefs is through open conversation. This is because conversation is something done with someone (the con- in conversation stems from Latin roots meaning “with”) and can be a gentle and effective intervention on their beliefs. Conversation is inherently collaborative, and it creates an opportunity for people to reconsider what they believe and thus potentially change how they act and vote. In fact, conversation offers you the opportunity to reconsider what you believe and reassess how you should act and vote.


Our response to this pervasive social dysfunction is to treat having impossible conversations as a skill to be mastered and a habit to be engaged. Don’t be afraid to voice your opinion. Don’t fear disagreement. Don’t hesitate to ask questions. People are waking up and realizing that there is political capital to be gained, friendships to be had, insight to be gleaned, and intellectual integrity to be harnessed by meaningfully engaging others and even crossing moral aisles. You can be part of this renaissance. To join, you only need to know how to productively engage people in ways that are less likely to make them defensive and more likely to help them hold their beliefs less tenaciously. You can achieve this by using proven, evidence-based techniques like those found in this book.

Over the course of this book, we’ll explain how to create productive dialogue out of what might otherwise have been dueling sermons. Demands for you to “listen and believe” can nearly always be replaced with you listening, understanding, and then instilling doubt. We know because we’ve had countless conversations with zealots, criminals, religious fanatics, and extremists of all stripes. Peter did his doctoral research in the Oregon State Prison System conversing with offenders about some of life’s most difficult questions, and then built upon those techniques in thousands of hours of conversations with religious hardliners. James developed the ideas for his books and articles by engaging in extended conversations with people who hold radically different views about politics, morality, and religion. This book is the culmination of our extensive research and a lifetime of experience in conversing with people who profess to be unshakable in their beliefs.

In our highly polarized society—as we cope with the increasing demands of a revolutionary social media economy—impossible conversations are inevitable. The goal, then, should not be to hope you can avoid them, or to skulk in the shadows when confronted with different beliefs, but to seize the opportunity. Learn what you need to do to hear and be heard. Stand up. Speak up. But speak wisely. How to Have Impossible Conversations offers solutions to the problems of timidity, incivility, fear, and distrust that blight our conversational landscapes.


How to Have Impossible Conversations contains thirty-six techniques drawn from the best, most effective research on applied epistemology, hostage and professional negotiations, cult exiting, subdisciplines of psychology, and more. It has a simple format, organized by difficulty of application: fundamentals (Chapter 2), basics (Chapter 3), intermediate (Chapter 4), advanced (Chapter 5), expert (Chapter 6), and master (Chapter 7). Some techniques teach you to intervene in the cognitions of others, instill doubt, and help people to become more open to rethinking their beliefs. Other techniques are oriented toward truth-seeking. Some are just plain good advice. Their underlying commonality, regardless of your conversational goal, is that they all empower you to speak with people who have radically different political, moral, and social worldviews.

We’ve streamlined and simplified conversational questions and templates for you. There is no fluff. We’ve included exactly what you need to immediately have effective conversations across deep divides. And if you’re interested in exploring the literature, extensive endnotes cite the relevant research. These, however, aren’t necessary for success. You can be just as effective without reading the endnotes, but if you want to delve into more detailed explanations of why our techniques work, that’s where to begin.

Many sections also include vignettes of actual conversations. From these, you’ll see how to incorporate new skills and techniques into discussions, without it feeling unnatural or contrived, or like you’re doing a hard sell. Some sections also contain brief stories from real-life mistakes we’ve made. From these, we hope to demonstrate how valuable it would have been if we had these techniques.

Our advice is to take your time with each chapter before moving on to the next. More advanced chapters build upon earlier chapters. Consequently, we urge that you read this book sequentially and not skip ahead. To make the best use of How to Have Impossible Conversations, have real face-to-face conversations in which you practice the techniques you’re learning, chapter by chapter, before moving on to the next. This is especially true with Chapters 2 and 3, which you’ll undoubtedly think you’ve already mastered; these chapters contain indispensable tools upon which the success of more advanced techniques, strategies, and approaches depend.

Finally, we believe we’re entering an era of renewed interest in effective, across-the-aisle dialogue. People are sick of not being able to speak about controversial subjects and of having to constantly walk on eggshells when voicing their opinions. This book is for those who have had enough. Enough name-calling. Enough censuring. Enough animosity. It provides a comprehensive tool set that enables you to take charge of your conversations. You’ll learn how to intervene in someone’s thinking and help them change their own mind and how to mutually search for the truth. Even with hardliners and ideologues. Conversations that remain civil, empower you, and change even the staunchest of minds are possible—even across deep divides. Here are the tools to have them.


The Seven Fundamentals of Good Conversations

How to Converse with Anyone, from Strangers to Prison Inmates


Why are you engaged in this conversation?


Be partners, not adversaries


Develop and maintain a good connection


Listen more, talk less


Don’t deliver your truth


People have better intentions than you think


Don’t push your conversation partner beyond their comfort zone

You think that the heads of state only have serious conversations, but they actually often begin really with the weather or, “I really like your tie.”

—Madeleine Albright

Everything is based upon fundamentals—everything. If you are able to execute a complex maneuver in ballet, for example, it is because you understand basic elements of the art. All expertise is built upon fundamentals.

Engaging in civil and effective conversations is a skill. It takes knowledge and practice, and you’ll need to begin with fundamental principles. Later, when they become ingrained, you won’t have to think about their use. They’ll come naturally. But without them you can expect frequent upsets, derailed conversations, and strained relationships.

Most basic elements of civil discussion, especially over matters of substantive disagreement, come down to a single theme: making the other person in the conversation a partner, not an adversary. To accomplish this, you need to understand what you want from the conversation, make charitable assumptions about others’ intentions, listen, and seek back-and-forth interaction (as opposed to delivering a message). Learning to listen is the first step in the give-and-take of effective conversations. You’ll need to overcome the urge to say everything that’s on your mind. Finally, you’ll need to know when to end your conversation gracefully.

In all, this chapter teaches seven fundamentals for good conversations: identifying your goals; forming partnerships; developing rapport; listening to the other person in the conversation; shooting your own messenger (that is, not delivering your own truth); keeping in mind the other person’s intentions, which are probably better than you assume; and knowing when to walk away.

Even if you master no more than these fundamentals, almost all of your conversations will improve dramatically—with everyone. Without them, any other skills you attempt to master will lack the necessary foundation and won’t be nearly as effective. In what follows, therefore, we address the seven fundamentals in the most logical order.


What’s Your Purpose?

People enter into conversation for vastly different reasons. Often, people just wish to talk and connect, but at other times more functional goals are at work. These include any of the following:

Reaching mutual understanding (parties seek to understand each other’s position, but not necessarily to reach agreement).

Learning from each other (figuring out how other people arrived at their conclusions).

Finding truth (collaboratively figuring out what’s true or correcting mistaken beliefs).

Intervening (attempting to change someone’s beliefs or their methods of forming beliefs).

Impressing (parties seek to impress a conversational partner or someone who might be watching).

Yielding to coercion (feeling forced to speak with someone).

In each case, if you first identify your conversational goal(s), then your path will become easier. Ask yourself, “Why am I having this discussion? What are my goals? What do I want to get out of this?” Your answer might be any of the instances above, or you might just want to keep your conversation light, friendly, and agreeable.

You can have more than one goal, have no particular goal, or change your goals mid-conversation. These are all fine, but you must be clear to yourself about your goals when beginning a discussion.1 Start by asking yourself whether you’re more interested in finding the truth or helping someone reconsider what they believe. Maybe it’s both, or maybe you’re leaning more heavily toward one than the other. Once you know your goals, use the conversational techniques that best help you achieve them.


During the 1970s, Peter’s mentor, Portland State University psychology professor Dr. Frank Wesley, investigated why some US prisoners of war (POWs) defected to North Korea during the Korean War. His research showed that virtually all of the defectors came from a single US training camp. As part of their training, they had been taught that the North Koreans were cruel, heartless barbarians who despised the United States and single-mindedly sought its destruction. But when those POWs were shown kindness by their captors, their initial indoctrination unraveled. They became far more likely to defect than those POWs who either hadn’t been told anything about the North Koreans or had been given more neutral accounts of them.

Conversation Partners

The way to change minds, influence people, build relationships, and maintain friendships is through kindness, compassion, empathy, treating individuals with dignity and respect, and exercising these considerations in psychologically safe environments.2 It comes naturally to all of us to respond favorably to someone who listens, shows kindness, treats us well, and appears respectful. A sure way to entrench people in their existing beliefs, cause disunity, and sow distrust is through adversarial relationships and threatening environments. It is easy to dislike someone who is mean-spirited, treats you poorly, doesn’t listen, or disrespects you. You can doubtless recall examples from your own life.

Fortunately, it’s fairly easy to create trusting, safe communicative environments and avoid conflict.3 Here’s how: View yourself as a conversation partner. That is, treat others as if you’re working together to have a fruitful conversation—because you are. Seeing your conversations as partnerships is the single biggest step you can take to ensuring conversations stay civil and to building relationships instead of damaging them. Adopting this stance is also surprisingly easy.

From Winning to Understanding

Question: How do you switch from viewing people as opponents, moral degenerates, or even enemies to valued partners and collaborators?

Answer: Shift your goal from winning to understanding.


Make understanding your conversation partner’s reasoning your (initial) goal.4 Abandon adversarial thinking (conflict, strife, arguing, debating, ridicule, and the idea of winning), and adopt collaborative thinking (cooperation, partnership, listening, and learning).5 Shift from, “This person is my opponent who needs to understand what I’m saying,” to “This person is my partner in a conversation and I can learn from him—including learning exactly why he believes what he believes.”

You may be saying to yourself, I can talk to a lot of people like a partner, but I couldn’t do that with a racist! Yes, you can.6 If the black musician Daryl Davis can have civil conversations with Klansmen and help them abandon the KKK (and he can: he has a closet full of their relinquished hoods to prove it), then you can talk to a racist, or to anyone holding any belief system, and discover why they believe what they believe.7

One key to realizing you can have seemingly impossible conversations is recognizing that discussions are natural learning environments for both people. Treating an individual as a partner in civil dialogue does not mean accepting their conclusions or buying into their reasoning.8 (The mark of an educated mind, it has been said, is to understand a statement without having to accept it.9) It means thinking along with someone so that you understand not just what they believe but also why they believe it—in that process, maybe they’ll come to understand your reasoning, or see that their reasoning is in error, or maybe you’ll discover that you’re harboring a false belief.10 Conversational partnership isn’t about agreement or disagreement, it’s about civility, charity, and mutual understanding.11

At worst, you’ll have to endure hearing something truly vile, in which case you will come away from the conversation with a better understanding of why people hold repugnant beliefs. More likely, you’ll foster comfortable conversational environments, build relationships, better position yourself to understand and address similar arguments, and maybe even revise your own thinking.12

There’s a catch, of course. You can’t control someone else’s behavior. You can only control your own. So, you have to be the one who initially attempts to understand your conversation partner’s reasoning—even if they’re unwilling to reciprocate. You’ll also have to take an active role in establishing and maintaining the partnership dynamic and be ready to walk away if that becomes impossible. We’ll say more on this in the chapters that follow.

Forming Partnerships

Here’s how it works in practice, in a few easy points:

1. Make your goals of collaboration and understanding explicit.13

Say, “I really want to understand what led you to those conclusions. I hope we can figure this out together.”

2. Give your partner room to decline the conversational invitation, not answer your questions, or end the conversation at any time.

Do not pressure someone to converse if they’re uncomfortable participating.14

3. Ask yourself, not your partner, “How could someone believe that?”; and ask it in earnest, with curiosity instead of incredulity.

As you try to figure out the answer, the likelihood increases that your conversation will stay on track and not turn nasty.


Anthony Magnabosco (AM) is a Street Epistemologist.15


  • "This is a self-help book on how to argue effectively, conciliate, gently persuade. The authors admit to getting it wrong in their own past conversations. One by one, I recognize the same mistakes in me. The world would be a better place if everyone read this book."—Richard Dawkins, author of Science in the Soul and Outgrowing God
  • "In a Free Republic there would be no 'impossible conversations', which begs the question: are we truly free anymore? After reading, listening and conversing with Peter and James, I am convinced that they are the Galileo's, I. Kant and even William Tynsdale of our time."—Glenn Beck
  • "I thought I knew all I needed to know about conversations and arguments. I was wrong. I just knew a lot about debates and rows. In their insightful and highly readable new book, Peter Boghossian and James Lindsay offer all kinds of ingenious pathways to constructive dialogue. At a time when public discourse has degenerated into mud-slinging and when campuses favour every kind of diversity except viewpoint diversity, this is an invaluable contribution. I guarantee that reading it will make you more -- much more -- persuasive."—Niall Ferguson, Milbank Family Senior Fellow, The Hoover Institution, Stanford
  • "In these polarized times, people live inside social media echo chambers of their own extremism, growing ever more self-righteous. This smart, scientifically grounded book, teeming with social and emotional wisdom, teaches how to break that isolation and effectively converse with someone with very different opinions. It will make you more adept at challenging, even changing, someone's beliefs, biases and sacred values. And it might even pave the way for making some of those changes yourself."—Robert Sapolsky, John A. and Cynthia Fry Gunn Professor of Neurology and of Neurosurgery, Stanford University
  • "Drs. Boghossian and Lindsay offer critical advice regarding how to talk about contentious issues in today's political climate. How to Have Impossible Conversations is a necessary guide to navigating disagreements -- and building bridges -- using approaches backed by evidence and science."—Debra W. Soh, Ph.D., science columnist and political commentator
  • "This fascinating book provides not only useful instruction on how to talk with someone who thinks differently, it also offers a powerful method of questioning and reducing confidence in unsubstantiated beliefs to help people think about what is true."—Helen Pluckrose, Editor, Areo Magazine
  • "In the course of my work over the past quarter century I have been having impossible conversations with Holocaust deniers, creationists, anti-vaccination advocates, 9/11 Truthers, chemtrail conspiracy theorists, believers in astrology and ESP, proponents of alternative medicine, religious fundamentalists of many faiths, and dozens more people with whom I disagree vehemently. I've gotten pretty good at it but I had no idea what I was doing until I read How to Have Impossible Conversations, a sterling compendium of the most effective techniques of communication. I wish I'd had this important book at the start of my career as I would have saved myself many a fruitless dialogue. This book is the start of healing our contentious and divided age."—Michael Shermer, Publisher Skeptic magazine, Presidential Fellow Chapman University, author of Why People Believe Weird Things, The Moral Arc, and Heavens on Earth, and for 18 years a monthly columnist for Scientific American
  • "We live in a time when discussing controversial issues, even with good friends, is becoming almost impossible. Peter and James have written an indispensable roadmap to prevent us from heading off the cliff."—Dave Rubin, The Rubin Report
  • "We have arrived at an impasse. It is everywhere, and feels permanent. As algorithms steer our attention, we are each locked within a warren of echo chambers. Each day, this digital water we swim in causes a deepening entrenchment of our beliefs, and a growing willingness to caricature our opponents. When forced into contact with the other, we are repelled, indignant. How could anyone be so stupid? And we are shocked to discover the one thing that unites us with them is that they feel exactly the same way in return! It is not hard to spot the danger in this dynamic. It undermines the most basic logic of democracy, and threatens to derange the west, if not the world. But Boghossian and Lindsay have drawn up a plan to bridge the divide. They have bottled an antidote: A how to guide for talking to the enemy. Each drawing on decades of experience having impossible conversations, the authors have written what may be the ultimate instruction manual for crossing enemy lines and living to tell the tale. And not a moment too soon."—Bret Weinstein, PhD
  • "There are two ways to participate in civil conversations in our hyper-politicized age -- build a time machine, or read this book."—Marc Andreessen, General Partner, Andreessen Horowitz
  • "Everywhere that people gather and have a discussion -- every bar, cookout, and water cooler -- should have a copy of this book nearby. It might lower the temperature of our disagreements, and help us learn a few things from each other instead of just defending our own biases at the top of our lungs."—Tom Nichols, author of The Death of Expertise

On Sale
Sep 17, 2019
Page Count
272 pages

Peter Boghossian

About the Author

Peter Boghossian is a full time faculty member in the philosophy department at Portland State University and an affiliated faculty member at Oregon Health Science University in the Division of General Internal Medicine. He is a national speaker for the Center of Inquiry and an international speaker for the Richard Dawkins Foundation for Reason and Science. He is the author of A Manual for Creating Atheists. He lives in Portland, Oregon.

James Lindsay holds degrees in physics and mathematics, with a doctorate in the latter. He has authored two previous books: Everybody is Wrong about God and Dot, Dot, Dot: Infinity Plus God Equals Folly. He lives in Knoxville, Tennessee.

Learn more about this author