How to “Rule” Tough Conversations

Art by Januz Miralles

Art by Januz Miralles


By Cory Allen



We assume we know what everyone else is thinking because we know what we think they are thinking. But we have no idea what others are thinking. And in actuality, we don't even know what we’re thinking. According to Dr. Joe Dispenza our brain processes 400 billion bits of information a second. We are only aware of 2,000 of those. This information blind spot is often the reason we find ourselves in frustrating conversations.

The Curse of Knowledge is real. When a person tries to explain something to someone else, they tend to leave out pieces of information that seem basic to them. Not good. This is a form of information bias. Communicating this way leaves out huge chunks of conceptual connective tissue. This makes the listener feel lost and confused. The confusion of the listener usually frustrates the person talking because what they are saying is “so obvious” to them. This leads to communication breakdown.

Another component of bad communication is a person’s failure to listen beyond what they want to hear. I don’t know a fancy term for this, so I’m going to make one up. Let's call it The Curse of Ignorance. This is a form of confirmation bias where one only interprets reality in a way that proves them to be correct. We do this all day, every day. If you don’t think you do it, well then, you’re doing it right now.

Put these curses together and you get a low chance of clarity and a high chance for defensiveness. Think of how many times you’ve been in a frustrating conversation with someone where they will not listen and are not making sense. That’s it right there: two people passing The Curse of Knowledge and The Curse of Ignorance back and forth until they wear themselves out.

To speak is to force your hallucination upon another person. We shape each other’s reality through what we say. Our language also shapes nature. The human ability to communicate with articulate nuance is so powerful that it enabled our species to break out of the food chain. This is no small task. We rule the animal kingdom. One of your daily annoyances could be trying to avoid surprise cougar attacks on your way to work. We were fortunate to be able to communicate on a high level, get organized, and one up the furry fanged beasts of the Earth.

The more complex something is, the more opportunities there are for problems. While our ability to communicate is one of our most powerful tools, it is far from flawless. It can be hard to understand people with the clarity that we need due to the wiring of our minds. We assume that what we know, is all there is to know because it’s all we can know at that moment. So, we always think we know what’s up. When two conversing people think this, they can get into trouble.

Rapoport crushing it.

Rapoport crushing it.


Anatol Rapoport was a sharp guy. He was a mathematical psychologist that contributed to game theory and was an early developer of social network analysis. Among his many gifts to humanity were his rules for effective constructive criticism. From what I can tell, it seemed that he spent most of his life talking about complex, brain-stretching theories, and wanted to find a clean way to sharpen ideas without getting caught up in some smarty pants’ ego.

Philosopher Daniel Dennett is a big proponent of these rules and with good reason. He has spent decades pulling apart some of the most triggering topics of our time, such as religion, consciousness, and free will.

One day I realized that it made sense to use Rapoport’s Rules for general misunderstandings instead of saving them for intense analysis. It works like a charm. In the rest of this article, I'm going to show you how to apply Rapy’s rules to tough conversations in daily life. It's a good way to bring clarity to your relationships and cut away excess frustration, resentment, and confusion.

Dennett did a fine job reducing Rapoport’s rules to simple points. I’m going to use his summations of the rules (which I have further pruned) and explain how to apply them to strained conversations.


Rule 1: You should attempt to re-express the other person’s position clearly, vividly, and fairly.

This is the juiciest and most important of the rules. Frustrating conversations are usually fueled by blind spots created by The Curse of Knowledge and The Curse of Ignorance.

When you find yourself in one of these situations have the other person, as apparent to them as it might be, repeat what they feel like you are missing. Then, repeat their argument or frustration back to them. If they agree that you understand their position, then you can move on with the conversation. If they do not agree that you have stated their position clearly, then have them repeat it. After they do, try to explain it to them again. Repeat this until they agree you have successfully explained their position.

Hearing something about yourself can be hard, especially if emotions are running high. The first syllable of criticism usually makes a person’s ego get defensive and clenched up. This makes it hard to actually hear what someone, who most likely cares about you, is trying to tell you.

The people you spend a lot of time with--like a partner, coworker, or close friend--know things about you that you don’t know. Think about it: you’ve spent thousands of hours together. They have been watching your behavior from the outside like a strange laboratory experiment. You, likewise, have been doing the same to them. It’s a two-way street.

As much as we want to believe that we know everything about ourselves, we do not, and never will. People that experience us from the outside are free from the burden of our self-awareness and internal dialogue. While we are caught up in the story in our heads, they are watching how we actually exist in the world.

When a person expresses constructive criticism, it’s usually coming from a good place. You are in a relationship together and they are trying to strengthen that bond by relating (go figure). It’s like the psychological version of someone telling you that you have a piece of spinach stuck in your teeth. They aren’t doing it to be rude. In fact, they chose to willingly enter an uncomfortable conversation on your behalf.

Hearing that you have something stuck in your teeth can be embarrassing for a moment. But you’re much better off if you address it after it has been brought to your attention.

Set superficiality aside. When the criticism deals with personal behavior, it is in direct connection to one's ego. People’s egos are so fragile that even slightly questioning it can cause one to spiral into a defensive mode. They turn into the fierce barking dog, not out of anger, but out of fear. They want you to back off. If they can scare you away, then they are free to continue through life with the “spinach” in their teeth and their precious ego unchallenged.

No one wants to go through life with a bunch of food stuck in their teeth. So why would a person want to go through life with a negative behavioral equal? They don’t. But aspects of the mind are invisible, which makes them easy to ignore and explain away. This is why it’s important to be patient, set your delicate ego aside, and actually hear what someone is telling you.

Repeating a person’s argument back to them until they agree you are describing it properly ensures that you are hearing what they are telling you. It’s easy to think you get it and rush to gratify your own confirmation bias. When you have an outside observer verify your understanding, it is a true test of your mind for blind spots.


Rule 2: You should list any points of agreement.

When having a critical conversation, it is important to point out where you both agree. People tend to defend their side of an argument in any way that will help prove their point. They do this without knowing it like they are on defensive autopilot.

Truth is often stretched and absurd connections are made when someone is stressed or tired while putting forward their side of a critical conversation. People normally don’t do this in an attempt to straight up lie. It is a symptom of desperation. In trying to explain their point of view, one becomes so exhausted that they grasp for words to deepen their argument and accidentally scoop up extra junk. 

During this phase of an argument, the "opponent" will listen for words and points to use as proof that you’re wrong. Or at the very least, intellectually untrustworthy. As unfortunate as it might be, this type of thing tends to make tough conversations spiral out of control. This is why Rule 1 is so important. It clarifies the point and saves energy.

An agreement is a bridge that connects two people. It’s important to understand and preserve it. Once the connecting bridge breaks, it’s hard to get that rope across the canyon again to build a new one.

Just imagine trying to build that bridge if the other side of the canyon hated you.

Just imagine trying to build that bridge if the other side of the canyon hated you.


Rule 3: You should mention anything you have learned from the other person.

Noting what you have learned from another person shows that you are listening, open and that you accept their feedback in good faith. It is an opportunity to build trust with the person you're speaking to. This is done by telling them that you understand what they are saying, appreciate it, and will take it to heart.

Accepting and repeating what you have learned from another person establishes equal respect. It makes it clear that the relationship is fair, balanced, and that both points of view are important.


Rule 4: Only then are you permitted to offer a rebuttal or criticism.

Ok. The person you’re talking to has voiced their point of view. You have repeated it back to them, pointed out where you agree, and noted what you have learned. Now you can explain your side of the argument. At this point, you will most likely express context or where you feel they have genuine misunderstanding.

Explaining your point of view can frame your behavior in a constructive way. Doing this can help make sense of your actions to the person that has come to you with criticism. Giving the motivation for your behavior will generally draw helpful connections for them. This has the potential to bring a clarity to the situation and can resolve hurt feelings, anger, resentments, or personal suffering.

Keep these rules in mind, but don’t be a robot.

As weird as it might seem, using these rules in tough conversations really will bring clarity to the thinking of both people involved. The human mind is a typhoon of thought and egos are electric. It’s helpful to have a method of staying on track so that important conversations can progress in healthy ways.  

Of course, one doesn’t need to be a detached robot and pull out a laminated 4 x 6 index card with these rules on them every time a tough conversation arises. Being present and connected during a hard conversation is critical. All I’m saying is that these rules are handy things to keep in mind and can give productive shape to otherwise shapeless conversations.

We aren’t taught how to have authentic critical chats in school or by our family members. Everyone has to figure it out on their own and most people never do. Having real conversations is hard. People are scared of doing it because doing it wrong might lead to hazardous results.

I hope these rules calm the fear of real talk and strengthen the relationships in your life. Or at the very least, I hope they keep you from having your sneakers set on fire in the bathtub and your car keys flushed down the toilet.




Cory Allen