How to Have Impossible Conversations

Rating: 5 out of 5.

I’ve had the pleasure of having many contentious conversations over the past couple of years. This book dissects many of the problems and cognitive distortions present in these types of arguments and poses solutions to all of them.

All of the best techniques I’ve accidentally stumbled upon over the years (Rappaport’s Rules, understanding falsifiability, etc) are here, plus more. I particularly enjoyed its focus on epistemology: understanding why someone holds a belief gives more leeway to challenge its foundations. I also appreciated the use of scales: “On a scale of 1-10, how sure are you?”—These types of questions open room for doubt which can be explored without needing to force it. There is a lot of good phraseology and techniques for even the most advanced quarreler to learn from.

The one thing I had a little issue with is their fairly frequent use of “…if this still isn’t working, walk away.” I get why—some people are so obstinate as to be unreachable. It feels like a copout though, and for those of us who truly enjoy debate, I would rather keep fighting as long as we can maintain some level of civility. But yes, they’re right, most people should bow out.

Highly recommend this book. If people would just adopt the most basic techniques, such as assuming your interlocutor has good intentions, the world would be a much better place.

Personal Takeaways:

  • Do not parallel talk. Parallel talk is taking something someone says and using that to reference yourself or your experiences.
  • Model language for your partner. For example, if someone refuses to answer a yes or no question, have them ask you that question. “Should women be stoned for adultery?” “No.” By making a concrete statement you model for them the statement you’d like to see in return. Boghossian got a Muslim community leader to admit his answer was “Yes.” this way when he was previously giving endless qualifying remarks.
  • When in doubt, start with how or what. How and what questions don’t lend themselves to yes-and-no responses as do questions beginning with can, is, are, does, and do. For example, ask, “How does this seem to you?” as opposed to “Does this look good?”
  • Focus on epistemology People have developed practiced responses to having their conclusions challenged. Often referred to as “talking points,” these are rehearsed statements/messages given in response to frequently heard arguments. Focusing on epistemology helps people explain how they arrived at their conclusions, providing a fresh route around rehearsed messages.
  • Use scales. Ask people their level of conviction on a topic on a scale of 1-10. If they are less than a 9 or 10, we might be able to increase their doubt more. Also ask people their level of knowledge on a topic from 1-10. If the level of confidence outweighs the level of knowledge, inquire.
  • Use scales on yourself. If they’re above a 6 on a 1 to 10 scale, ask, “I’m 3 on that 1 to 10 scale that X is true. I’m not sure how I’d get to where you are, at a 9. I want to see what I’m missing. Would you help walk me through it?” Used in this way, scales are an opportunity to have someone guide you step-by-step through their epistemology. This is effective because they’re explaining the epistemological gap without you having to think on your feet and generate questions.
  • Keep a log of your conversations. Note what lowers confidence levels and what does not. Refine. Discard. Repeat.
  • Utilize Rapoport’s Rules. Restate their opinion in a manner they’d agree with wholeheartedly, state areas of agreement, mention what you have learned from them on the topic, and only then can you say as much as a word of criticism.
  • Seek Disconfirmation. The single most effective technique to instill doubt and help people change their minds is to ask, “Under what conditions could [insert belief] be wrong?” If someone states their belief is not disconfirmable, they’re claiming to be absolutely positive about an aspect of reality where the belief operates. Colloquially, an unwillingness or inability to change one’s mind is called “incorrigibility,” philosophically it’s termed “epistemic closure” or “doxastic closure,” and in other domains like religion and pop morality it’s known as “conviction.” This idea behind disconfirmation sometimes appears in the philosophical/epistemological literature either under the term defeasible, or in the philosophy of science literature as falsifiable.
  • Synthesize your own beliefs with theirs. Synthesizing means modifying your beliefs by using your partner’s beliefs and disconfirmation statements. The goal is to clarify and strengthen your position and get closer to having true beliefs, not to produce agreement. Synthesis involves collaboratively arriving at a better understanding of the topic and developing a more refined, nuanced view.
  • Altercast for civility. If you say to someone who’s texting, “Wow, you’re a really fast texter,” you’ve altercasted them as a fast texter. They’ll then embrace that role and want to text more quickly… Altercast your partner into the role of better conversationalist. Say, “You’re good at having civil conversations.” Or, simply, “You’re good at keeping your cool.”
  • Use mirroring, but do not overuse it. When mirroring, you repeat the last few words of what someone said. For example, if someone exclaims, “I am just so sick and tired of these people pushing everyone around and trying to get their way,” you say, “Get their way?” McMains and Mullins provide the following example: “A trapped armed robber in a bank might say, ‘I have to get out of here with the money. It’s for my kid. It’s not for me.’ A good mirroring response would be ‘For your kid?’ To which the robber might say, ‘Yeah, He’s got a fever and an infection and we don’t have money for the pills he’s supposed to take. He needs the money for the pills.’”
  • Focus on values. At the core of nearly all impossible conversations lies at least one person’s inability to provide (realistic) disconfirmation criteria for beliefs or denial that any such criteria exist…“Why do you feel that belief is more justified than competing beliefs?” and “Does the intense feeling that a belief is true make it more likely to be true?” “What values would have to change for your view to no longer be true?”
  • Shift to superordinate identities. When a conversation centers on race, gender, or any other divisive marker in identity politics, people can become defensive and tempers can flare. If you find the conversation getting heated or stuck, shift the focus to superordinate identity markers instead. Rather than dividing, these unify people. Superordinate identity markers go “up” and include commonalities among people, not down to identity features of certain groups (black skin, particular sex organs, etc.). Crudely, “You’re white (or Muslim) and I’m black (or Christian), but so what, because we’re both Americans and both human beings.” Notice how this statement moves the conversation toward common ground at the identity level.
  • Beware the backfire effect. The seemingly paradoxical outcome when our existing convictions are actually strengthened by evidence that contradicts them.
  • Beware of identity effects. The general idea of social identity theory is that one’s moral standing is tied to the moral standing of the groups with which one identifies. For example, if a conservative identifies as a conservative, every reason she has to view conservatives as good gives her a reason to believe that she must be good too, by association with the “good” group.
  • Recognize psychological bias. People are extremely prone to believe incorrect conclusions based upon “the evidence” because of our susceptibility to two biases: confirmation bias and desirability bias.


  • Say, “Would every reasonable person draw the same conclusion?” If the person says yes, follow up with, “I’m a sincere, reasonable person and I’m having trouble drawing the same conclusion. How do I get there?”
  • “I’m having trouble understanding. How did you go about setting your bar for doubt so high? I’m wondering why some simpler problem, like why after all this time a dead Bigfoot has never been found, isn’t good enough to cast doubt?”
  • If you wish to pursue a conversation with someone who holds a belief that is not disconfirmable, then ask the following questions, with brief follow-ups, in this sequence: Epistemological questions “Then the belief is not held on the basis of evidence, right?” “Are you as closed to revising other beliefs or just this one? What makes this particular belief unique?” “What are some examples of other beliefs you’re not willing to change?”

Useful Expressions:

  • The mark of an educated mind, it has been said, is to understand a statement without having to accept it.
  • Though many arguments seem to be about matters of substance, they’re often just disagreements about the meanings of words.

Common sense in uncommon practice:

  • 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).
  • 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.
  • Anger tells us that something needs to change. If we are to bring about that change most effectively, we need to know the source of our anger.” In these cases, you need to alter course and not press the issue. And yes, it must be you who changes even if your partner is angry—or dreadfully wrong—because you cannot control other people; you can only control yourself.

Published by Jasper

Aspiring polymath. I do my best to understand all sides of an issue. I read primary sources and opposing viewpoints to get to the truth. I enjoy debate and can change my mind given sufficient reason.

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