1-Page Summary

In business, in day-to-day interactions, and in personal matters, difficult conversations come up all the time — conversations where people’s thoughts, feelings, and perceptions about certain issues are in conflict. But if we can learn how to handle difficult conversations more productively, our relationships and our lives will improve.

Difficult conversations involve anything we find it difficult to talk about. In these conversations, we usually fear consequences, whether we bring up the issue or avoid it. If we avoid the subject, we risk our feelings festering or the situation worsening. If we bring up the issue, we risk upsetting the other person or not getting what we want.

Difficult conversations are so difficult first and foremost because of how we approach them. Most of us approach difficult conversations as though we are right and the other person is wrong, as though our feelings are the most important, and as though we have to either “win” the conversation, or risk “losing it.” To have better difficult conversations, we have to change how we think of difficult conversations, and how we approach them.

(Shortform note: There is a lot of information packed into this book, and consequentially this summary. While the 1-page summary hits all the major ideas of Difficult Conversations, the full summary goes into much greater detail and instruction on how to use these ideas.)

The Three Conversations Within a Difficult Conversation

The authors studied thousands of difficult conversations and discovered that they all shared the same basic structure comprised of three conversations going on within the difficult conversation:

  1. The What Happened Conversation
  2. The Feelings Conversation
  3. The Identity Conversation

In difficult conversations that don’t go well, we usually make crucial mistakes in each of these internal conversations.

The What Happened Conversation

In a bad difficult conversation, the What Happened Conversation is about who’s “right” and who’s “wrong.” In these conversations, we usually confuse intention with impact and believe, because we’re upset about something, that the other person intended to hurt us. We blame the other person for the issue, and view ourselves as victims. We essentially turn what could be a productive difficult conversation into an argument about who was in the right and who deserves to be punished.

The Contribution System

The antidote to this harmful version of the What Happened Conversation is to embrace something called the Contribution System. In any difficult conversation, no one person is to blame: difficult conversations arise when two people have both contributed to the situation to make it difficult. There are some exceptions to this rule, but in general, conflict arises when two people’s choices and beliefs clash with one another, meaning both people have contributed something to the conflict.

The Contribution System helps us focus on the ways we might have contributed to the issue so that we can take some ownership over the situation and make better choices in the future. It also helps us express the ways we think the other person has contributed in a productive fashion — the other person has less room to get defensive (which quickly turns a difficult conversation into a blaming conversation) if they feel we’ve taken some responsibility for our own actions as well.

The Feelings Conversation

In a bad difficult conversation, the Feelings Conversation gets suppressed and goes unmentioned, or becomes one-sided and ultimately turns into blame — most of us go into difficult conversations either:

Analyzing Your Emotional Footprint and Negotiating Your Feelings

The first antidote to this harmful version of the Feelings Conversation is getting to know our emotional footprint — what emotions we feel comfortable acknowledging and what emotions we don’t feel comfortable acknowledging, usually based on how our family handled emotions. Once we’re more aware of what emotions we easily identify versus what emotions we hide from even ourselves, we can start to be more aware of what triggers these emotions and how we can better manage them. All emotions are valid and acceptable — however, we can learn to act on our emotions in healthier ways.

Then, we need to negotiate our feelings with ourselves before going into a difficult conversation. Because we’re all comfortable with some emotions and uncomfortable with others, there are usually feelings lurking beneath the feelings we readily admit we have. We need to learn to delve deeper into our feelings and practice identifying and analyzing all the emotions that pop up for us in difficult situations. Once we do that, we can begin to negotiate, on our own, why these feelings are popping up, what past experiences and current triggers are bringing these feelings up, and whether the stories we’re telling ourselves about the current situation are fair or based in reality.

The Identity Conversation

In a bad difficult conversation, we view our identity as all-or-nothing: for example, if we hurt someone, we’re a bad person, or conversely, we’re a good person, and the other person’s complaints about us aren’t valid. In general, identity issues center on three unspoken questions:

  1. Am I competent?
  2. Am I a good person?
  3. Am I worthy of love?

In difficult conversations, we’re all worried that the answer to each question is no.

The And Stance

The antidote to this harmful version of the Identity Conversation is to develop a more grounded identity. Humans are complex: no human is all good or all bad. We all make mistakes, we all have complex intentions, and we’re all still worthy of love.

The And Stance allows us to complicate our identity and acknowledge our complexity by embracing the contradictions. You’re a good person and you hurt someone’s feelings. You’re competent and you made a mistake this time. You’re worthy of love and there are things you can work on to be a better person. You’re a good boss and you have to fire a long-time employee. You’re a good husband and you haven’t been paying attention to your wife’s feelings lately. Adopting the And Stance helps us break out of all-or-nothing identities, and ground our identity in reality instead of absolutes.

Guidelines for a Good Difficult Conversation

Once you’re aware of the meta-conversations and better ways to approach those conversations, you can start navigating the difficult conversation as a whole. Here are some basic tips and reframings that will help you have the best difficult conversation you can.

Replace Certainty with Curiosity

Instead of going into the conversation certain that you’re right, certain that the other person had bad intentions, or certain that the conversation is going to go well, focus instead on being curious about the situation. What is the other person’s side of the story? How do they interpret the events that occurred? How do they view your contributions? What, in their minds, would improve the situation? The more curious you can be about their perspective, the less accusatory you’ll be about what’s happened, and the more room they’ll have to participate with you and help you find a workable solution.

Separate Intention from Impact

Other people’s actions make us feel certain ways depending on our past experiences and personal emotional baggage. When we get hurt or upset, our first impulse is usually to assume the other person meant for us to feel this way. This is rarely the case. Just because someone hurt your feelings (impact) doesn’t mean that’s what they were trying to do (intention). We’re always quick to assume that other people have bad intentions, though we give ourselves a lot of leeway when we hurt someone because we know that wasn’t our intention.

Assuming someone meant to hurt you will color how you view them and will affect the course of the difficult conversation. Most of us assume bad intentions = bad people, and we’re far less likely to be curious about, understanding of, or accepting of the other person’s perspective if we view them as a bad person, rather than a good person who’s made mistakes.

Be a Good Listener

Listening is an incredibly important skill in a difficult conversation. One of the most common complaints the authors hear about difficult conversations is that the other person isn’t listening. This really means we need to get better at listening if we expect others to truly listen to us.

Humans long to be heard and understood. Have you noticed how often people will repeat themselves or double-down on an argument in a difficult conversation? This is a surefire sign that they don’t feel heard, and they don’t feel like the other person is trying to empathize with their perspective. Making sure your conversation partner feels heard, understood, and accepted first will make it easier for that person to hear your point of view.

If we’re having trouble listening to someone, it usually means we’re wrapped up in our own inner voice. Our inner voice, or inner dialogue, is running all the time — but during a difficult conversation, our inner voice is usually yelling about the three meta-conversations. Once you understand those three conversations and have worked through your own contributions, feelings, and identity, your inner voice will quiet down and you can be a better listener.

Three things you can do to be a good listener:

  1. Ask questions with the goal of learning instead of trying to prove a point.
  2. Paraphrase their responses to show that you’re listening and trying to understand them.
  3. Acknowledge their feelings, which might require you to listen for what’s going unsaid in the conversation.

Difficult conversations are really problem-solving opportunities, and problem-solving is a team sport. It will take both of you or everyone involved in a difficult conversation to get to the best solution, and getting to that solution will require you to work through the difficult conversation first. Once you’ve done your homework on the 3 meta-conversations and shifted how you approach the big-picture difficult conversation, you’ll be able to uphold your own end of it and help the other person participate better.

Introduction to Difficult Conversations

Difficult Conversations was written by members of the Harvard Negotiation Project, whose goal is to establish and circulate conflict resolution strategies. The first book published by the HNP, Getting to Yes, has been massively successful since its publishing in 1981. While Getting to Yes focuses on effective strategies for traditional negotiation, Difficult Conversations applies the “Harvard Method” more broadly to everyday disagreements. Negotiations happen in everyday life, and people don’t seem to want to have them. Or, more troublesome, things get worse when people do talk about the issues they’re facing. This is where Difficult Conversations comes in.

At their core, everyone is the same: we all have our own thoughts, feelings, and perceptions, and every day we interact with other people who have their own thoughts, feelings, and perceptions. Sometimes our thoughts conflict with someone else’s thoughts, or feelings with feelings, or perceptions with perceptions — that’s when difficult conversations arise.

Difficult conversations aren’t an anomaly you can solve once and be done with. Difficult conversations are a constant throughout life, at work, at home, and in the world. We never outgrow them, or get a promotion that saves us from them, or meet a person who’s so perfect for us we never have to have them.

Difficult conversations, if we engage in them successfully, are the mark of a healthy relationship in any realm, where people walk away with a better understanding of each other, a stronger sense of trust, and an experience they’ve struggled through together and survived. In fact, the success and survival of any relationship, business or personal, depends on the ability of those involved to master difficult conversations.

Where You Can Use This Summary

Change requires difficult conversations, and a major reason some organizations and— relationships— fail to adapt is that the people in them eventually have to have these difficult conversations, and they don’t have the skills to handle them.

In business, the principles you’ll learn in this summary are required just to maintain business as usual. Competition these days requires businesses to increase in size and scale — many successful businesses are global — while also adapting less hierarchical practices for the sake of flexibility.

Due to this increase in pressure, businesses have also spent the last two decades trying to cut costs, so much so that there isn’t much left to cut. According to the authors, performance and the ability to manage conflict efficiently are going to determine professional success for the next 50 years.

But this book is useful for literally everyone. Parents can benefit from this book, and so can kids. Spouses, partners, landlords, tenants, neighbors, team members, employees, colleagues, patients, doctors — everyone can use it. The principles in this book can make a marriage stronger, and can turn workplace disagreements in any realm into opportunities for innovation.

First, we’ll cover what difficult conversations are and what makes them difficult. Then we’ll discuss the parts of a difficult conversation, and the common mistakes we make in each part. Finally, we’ll go over how to begin and proceed with a difficult conversation for the best outcome.

A Note on Our Summary

Difficult Conversations is an excellent read and extremely useful. For our summary, we focused on extracting the principles you can put into use. The full book has extensive examples of the principles in practice — if you’re someone who learns best through situational examples, it would be well worth reading the whole book after you finish the summary.

We’ve regrouped ideas and chapter organization into a sequence that we believe is clearer than the original book’s.

Chapter 1: What Are Difficult Conversations?

A simple definition is this: a difficult conversation involves anything you find it difficult to talk about. Commonly, difficult conversations involve major categories like race, religion, sexuality, gender, or politics. But difficult conversations also include topics we feel insecure about, or issues that make us feel vulnerable, or matters that are important to us, or situations where the outcome is unknown, or instances that concern people we care about.

In short, the situations that require difficult conversations are many and varied:

Difficult conversations are usually conversations where we fear the consequences, whether we avoid having the conversation or we raise the issue. And there are risks no matter how you choose to proceed:

There’s No Magic Wand

When issues arise, we want there to be a magical fix that will make everything better without having to go through anything hard. But the reality is that there is no way to get through difficult conversations without difficulty.

Some people think that there’s a tactful way to have a difficult conversation so that everything ends up fine. Tact is good, but unfortunately, it’s not the answer. The problems at the heart of difficult conversations run deeper than tact, diplomacy, or positivity.

“Delivering a difficult message is like throwing a hand grenade.” There’s no nice way to throw a hand grenade, and it’s going to do damage, even if you keep it to yourself. The same is true of difficult conversations.

The first big-picture change to make is how we think of difficult conversations. We usually think of delivering or receiving bad news, as if it’s something that can be passed around and handed off. You’re either taking it, or you’re giving it. This is how difficult conversations turn into a war of opposite views: “I’ve got bad news, and you’re going to take it” is met with “I’m not going to take it — in fact, I’ve got bad news for you! You take it!”

It’s better to approach difficult conversations as learning conversations. Notice the shift in language: difficult, a negative word, to learning, a positive word that implies process and mistakes and progress.

Improvement requires change, and change is hard and awkward, and requires us to take an honest look at ourselves and break out of our comfort zone. But the rewards of improving will be worth the effort required. The principles in this book will help improve all your conversations, not just the difficult ones:

The question isn’t whether you’ve been searching “hard enough” for the solution to your issue, but whether you’ve been looking in the right places. The problem doesn’t lie in your actions or what you can do to make difficult conversations easier — the problem lies in your thinking.

For the Skeptics

It’s understandable if you’re skeptical. This book and this summary are not magic wands either. The problems inherent in difficult conversations are complex and unique, and there’s a cap on what you can learn from a book — but the information here can help.

It’s a reality that some situations will, unfortunately, be beyond repair, due to the people involved or the circumstances. But many situations will be positively impacted by the principles you learn here.

Difficult conversations will always be difficult, but it helps to keep your goals realistic. You can’t eliminate anxiety, but you can reduce the anxiety you feel about having these conversations. You can’t achieve perfect results, but you can achieve better results.

The Root of Difficulty: The Three Conversations

Difficult conversations are so hard because they’re actually three different ongoing conversations wrapped up in one:

And we make predictable errors in all three of these conversations:

All difficult conversations contain all three of these conversations, and we can’t change the challenges inherent in each one — but we can change the way we respond to those challenges, and we can learn how to manage and address all three conversations to have better difficult conversations.

We’ll cover each of the three conversations in separate chapters. Then, for the second half of the summary, we’ll transition into positive changes you can make for easier difficult conversations.

Chapter 2: What Happened Mistake #1 - Arguing About Who’s Right

In the What Happened conversation, people usually disagree — there wouldn’t be much reason to have a difficult conversation, and therefore the What Happened part of it, if everyone was in agreement. Each side typically thinks they’re right and that they hold the one single truth.

When we get into an argument with someone, we typically assume they’re the problem. We’re right, they won’t listen, they’re selfish, or naive, or controlling, or irrational — so we push our own opinion harder, or try to make them see the light.

But, of course, on the other side, they think we’re the problem too. And they think we’re stubborn, or selfish, or naive. In an argument, we rarely stop to pause and consider that it might be us who’s in the wrong — but this is because our story makes perfect sense to us. We know why we’re right; we have all the supporting evidence in our minds.

Why Doesn’t It Work?

Difficult conversations are usually about differences in perception, and in this case, the only truth is that there is no truth. Asking who’s right or who’s wrong goes nowhere.

Arguments are when two people’s respective stories make perfect sense to them, but the stories are in conflict. And when we focus on arguing our own “right” story, we lose the opportunity to explore the other person’s story and understand why they think they’re right.

Arguing any point but failing to understand the other person isn’t persuasive, it’s combative. Telling someone to change rarely results in them actually changing. People need to feel understood in their own story before they can start to change. For a disagreement to be productive, we have to understand each other’s stories enough to see how the opposing conclusion also makes sense. Understanding alone won’t solve the issue, but it’s the first step toward actually getting to a solution.

Different Stories and How They’re Formed

The stories we tell ourselves are built in systematic, if unconscious ways — they aren’t random or without cause.

How Our Stories Get Built

  1. First, we all take in information. But there’s so much information to take in that we can only take in a fraction of what’s being offered to us in a given moment — what we take in can be vastly different from what another person takes in, even if they’re sitting right next to us.
  2. Secondly, after we take in what information we can, then it’s up to our brains to interpret what that information means. This is yet another fork in the road where people can diverge.
    • Two factors that influence how we interpret information are 1) our past experiences and 2) the rules we learned about how things should or shouldn’t be done.
    • People’s actions and why they make sense only make sense in the context of their past. All our strong views are extremely influenced by our past experiences, and what we learned from our family or other early influences.
    • Usually, we’re unaware of just how much our past affects our present interpretation and judgment of information.
    • Our past experiences lead us to different conclusions that become “rules” to live by — the shoulds or shouldn’ts that get us into trouble in arguments. Difficult conversations occur when two people’s rules clash.
    • However, our conclusions and rules usually reflect self-interest: they support our view and interpret the information favorably based on our conclusions.
  3. Lastly, we draw conclusions about the information we’ve gathered and how we’ve interpreted it, and we make judgments.

People’s stories can diverge at any of those three steps, or all of them. In difficult conversations, we usually just assert our conclusions — the last step — without acknowledging the two preceding phases that lead us to those conclusions.

Only we have access to our past experiences and information that form our conclusions. We know ourselves better than anyone else knows us. So we should assume that other people know themselves better than we could ever hope to. We shouldn’t assume that we know what others’ stories are or how others’ stories were built.

Two Exceptions that Aren’t Exceptions

Two supposed “exceptions” to the principle that we should take others’ stories into account happen when 1) we are right and the other person is wrong, and 2) the other person’s story doesn’t matter because it won’t affect the outcome of the decision being made, such as when breaking up with or firing someone.

But I Am Right!

You might find yourself in a conversation where you do understand someone else’s story, but you still think that you’re objectively right. This usually means you’re right about a certain fact — but that the difficult conversation is about something else entirely. Being “right” won’t get you far in a conversation like this.

For example, a father wants his teenage daughter to stop smoking because it’s bad for her health. Objectively, he’s right about that fact — smoking is unequivocally bad for anyone’s health — but that isn’t what their difficult conversation is about. If the father believes he’s “right,” he’s missing the point.

The conversation is really about his daughter’s need for risk and excitement, which doing something “wrong” is fulfilling. Or it’s about not wanting to be controlled by her dad, and the doubling-down that happens when he tries to control her more. Or it’s about the confusion she feels doing something she knows is wrong but that her body tells her feels good, which her dad isn’t addressing.

In this situation, though the father may be right about the fact, he could probably get a lot further if he discussed the impact her smoking is having on him — that he worries about her constantly, that her great-grandmother died of cancer and he’s reminded of it every time he sees her cigarettes, or whatever the impact is — instead of the inarguable facts.

But It’s My Choice — Why Does Their Story Matter?

Most difficult conversations don’t actually involve someone with the power to dictate the outcome of the conversation, but a few cases do. Breaking up with someone or firing an employee fall into the latter.

And it’s true: technically, their story doesn’t matter if the decision has been made, and you don’t need to understand it. But trying to understand their story still has its merits, even if it won’t — or can’t — change the outcome. Understanding the other person’s story allows us to be clearer about the decision that has been made and compassionate towards them. It can turn a difficult situation like a breakup or a firing into a better experience for both parties.


Understanding won’t make differences disappear immediately. Nor does taking the time to understand someone else’s story mean that all stories are equally valid. But understanding will help you evaluate your views in light of new information and other interpretations, and understanding where both parties are coming from is the only way to begin to move forward.

Chapter 3: What Happened Mistake #2 - Assuming Intentions

We all know our own intentions, so we never question them. But we never know the other person’s intentions unless we ask — and we rarely do that in the midst of a difficult conversation. Instead, we assume we know what the other person intended to do. We assume that cutting remark was meant to hurt us, even though we know our own remark that seemed to hurt the other person’s feelings wasn’t meant to hurt them.

The best rule of thumb for going into difficult conversations is don’t assume the other person had bad intentions.

Intentions influence how we view other people: we judge someone more harshly if we think they intended to hurt us, or if we think their intentions are bad or ignoble.

Think of it this way: you’re in a rush to get back to the office after stopping off at a cafe to get a quick bite for lunch. You go to back out of your parking spot, but you find yourself blocked in by a fancy BMW, parked in the middle of the lot. What’s the first thought that jumps into your mind? Now, what if it was an ambulance with its lights on instead? This is a good metaphor for how we go into difficult conversations. The BMW represents the assumption that someone has bad intentions; the ambulance represents the assumption that something else important might be going on.

Difficult conversations are often a battle between intentions, and we make two key mistakes concerning intentions:

  1. We assume we know what the other person’s intentions are.
  2. We assume that expressing our good intentions means the problem is solved, and we don’t take the time to learn about what upset the other person.

Assuming Bad Intentions

We can never know someone else’s intentions — when we assume we know, we’re usually wrong. We usually assume someone else’s intentions based off the impact it had on us. It’s a retroactive reframing of how they intended something. Their comment hurt us, so they must have said it with the intention to hurt us. How we respond to something is not sufficient evidence to draw conclusions about someone else’s intentions.

We usually assume bad intentions so quickly that we don’t realize it’s an assumption — we think it’s a fact. Email and text-based communication can make it harder to assume the best about other people, because it’s harder to pick up on the tone of things and easier to fill in the gaps ourselves.

Furthermore, we usually assume the worst about other people, though we want them to assume the best about us. When we make a comment that hurts someone else’s feelings, we didn’t mean to be hurtful — we had other reasons for saying it. But when someone else hurts our feelings, their only intention could have been to hurt us. We give ourselves a lot of leeway that we don’t give other people. This is partially because we know everything that’s going on in our minds but less about how our actions or words are impacting other people.

Then, when we accuse someone of having bad intentions, they understandably get defensive. They make the same assumption about us that we’ve made about them — that we’ve accused them because we want them to hurt or feel bad. In difficult conversations, often both people think they’re the victim who was just defending themselves against the bad intentions of the other person. And these assumptions can become self-fulfilling prophecies.

Assuming Good Intentions Solves the Problem

Good intentions aren’t a free pass for hurting someone’s feelings. Difficult conversations can even devolve into an argument over intentions — “I said I didn’t mean to hurt your feelings when I laughed, okay? So why are you still upset?”

Usually, when someone says we meant to hurt them, what they’re really saying is we didn’t care enough not to hurt them.

Clarifying your intentions can be helpful, but it’s important to do it at the right time. If you start a conversation by clarifying intentions, it’s a surefire sign that you haven’t understood what really hurt the person or what they’re trying to say.

And intentions are usually more complex than plain good or plain bad. We want to believe that our intentions are totally good, but usually, if we’re honest with ourselves, intentions are a mixed bag — some good, some bad.

We aren’t always aware of our own motivation, so we need to explore and be willing to entertain the idea that our intentions might not be as good as we think they are. Defending our “good” intentions suggests we’re more interested in our own feelings than what’s going on in the relationship. “I didn’t mean to, so why are you upset?” The subtext here is “I don’t want to feel bad about hurting your feelings, so stop making me feel bad, no matter what you feel.”

Conversely, people who show they can think hard about their own intentions also show they care about the relationship.

Chapter 4: What Happened Mistake #3 - Blame

Similar to the first mistake in the What Happened conversation, most people go into difficult conversations wanting to blame the other person for what happened. “If only she hadn’t said or done X, this would never have happened.” In our version of events, who to blame always seems clear, and rarely is it us.

Focusing on blame isn’t constructive because it prevents us from learning what the real problem is and doing something to fix it. Blame isn’t relevant, and it isn’t fair. We often blame others because we don’t want to be blamed. We also blame others because we equate it with talking about our feelings — “You hurt my feelings, so you’re to blame.” The first part can be useful; the second part never is.

We can’t stop blaming until we understand what blame is, what motivates it, and how to move towards the idea of the contribution system instead.

What Is Blame?

Blame is about judgment and looking backwards. The issue of whether someone’s to “blame” is really about three connected questions:

  1. Did this person cause the problem?
  2. Should their actions be judged against some standard, and if so, what standard?
  3. Should they be punished?

“This is your fault” is really code for yes to all three of those questions. When we blame people, we explicitly put them in the role of the accused — so it shouldn’t surprise us when they get defensive.

Even if you can answer the question of who’s to blame, it doesn’t usually help solve the problem. With blame comes punishment, and punishment comes at a cost — understanding and punishment don’t usually go hand in hand. When people are afraid of being blamed and thus being punished, they’re usually less likely to be truthful or open about the matter, and less likely to apologize, since it seems like an admission of guilt.

Blame also obfuscates when there are bad systems at play, bigger than a single person who can be blamed. But usually no one person is fully to blame.

The Solution — the Contribution System

Contribution, on the other hand, is about understanding and looking forward. Contribution asks what we both did to get in this situation, and what we can do to get out of it together. The goal is to identify what contributions both parties made, and how each party’s reactions are part of an overall pattern in the relationship.

The contribution system is more likely to be productive and make the difficult conversation easier to have, because it promotes learning and change.

There are, of course, some extremes and exceptions — even though both parties contribute, there are still some cases where blame is necessary. For example, if a parent abuses a child, the child might have “contributed” something, perhaps too much noise or misbehaving or mouthing off, but their contribution in no way warrants the parent’s contribution, and blame can be placed on the parent over the child.

Three Myths about Contribution

1. I should only focus on my contribution. False. You shouldn’t overlook the other person’s contribution — usually, we find ourselves in difficult conversations because we’re already aware of the other person’s contribution. Admitting your own contribution doesn’t negate the other person’s, and it’s possible they contributed more to the problem than you did: but whether it’s split 50/50 or 5/95, both parties contribute.

2. Putting aside blame means I have to ignore my feelings. False. Sharing your feelings is an essential component of contribution. Speaking more directly about your feelings and taking ownership over them can help lower your desire to blame the other person.

If you find yourself wanting to blame the other person, try asking, “What feelings am I failing to express?” or “Have they acknowledged my feelings yet?” Most of us would prefer to receive understanding and acknowledgement in place of a right to blame.

3. “Contribution” means the victim is to blame. False. Victims are never to blame. However, they can still explore how their actions contributed to the situation. If we want to empower victims, we need to look at the ways they can change their contribution in the future. We can’t change other people’s contributions to situations — changing our own behavior gives us some control over the situation.

For example, if you’re walking along the street at night and you get mugged, you’re not “to blame” for getting mugged. If we want to blame or punish someone, we punish the mugger. However, if you want to learn from the situation instead of just blame someone, you have to review how your actions contributed to the situation. This gives you power moving forward. Maybe you won’t walk along that street at night alone anymore.

Four Subtle Ways of Contributing

Spotting your own contributions takes time and practice, but here are four less obvious ways that we contribute to difficult situations.

1. Avoiding. We can contribute to a difficult situation by failing to address it before it goes too far. Sometimes, we put things off because we hope they’ll blow over on their own. Sometimes, we stay silent because we fear the repercussions. Sometimes we complain to third parties instead of confronting the person with our feelings — this might help us feel better in the short-term, but it doesn’t solve the issue.

2. Being unapproachable. Your system of dealing with issues makes people less likely to bring things up with you. This could be any number of different things — you could seem uninterested, argumentative, unfriendly. And though you might think it’s not your problem to make yourself approachable if someone else has an issue, that mindset isn’t going to help you solve the problem.

3. Intersections. Intersections are points where the assumptions of two parties are at odds. Intersections are caused by differences that result in friction between two people based on background, communication style, preferences, or other assumptions. When we treat intersections like these as matters of right or wrong, we fail to move past them. You’re not right because you come from a different background than someone else; they’re not wrong because they come from a different background. When we contribute this way, we’re usually hoping the other person will fundamentally change without us having to say anything.

4. Problematic role assumptions. A great example of this contribution is family patterns where less healthy ways of connecting have become the norm. For instance, a young boy might fall into the role of “trouble maker” to get attention; his mother takes on the role of nag, urging her husband to do something about the boy’s behavior, and then yelling at her husband when he yells at their son, who starts to cry. Although no one particularly enjoys these patterns, they’re familiar and comfortable because they’re so ingrained in us, so we all fall into these problematic roles the second an issue arises. We force each other to play parts that aren’t necessarily productive. Everyone would have to change in order to change the system — in this instance, we need alternative examples of how to solve issues.

Spotting Contributions

Spotting how you contribute to situations takes time and patience, and shifting how you see your own contribution and others’ takes work and practice.

Analyzing Your Contribution

People generally fall into two styles of analyzing contribution: they’re either shifters or absorbers.

Shifters have a hard time seeing their own contributions — they shift the “blame” elsewhere, hence the name. They tend to see themselves as victims.

Absorbers focus too much on their own contributions — they absorb responsibility for both parties’ actions, hence their name. They fixate on the negative consequences of their own actions.

Knowing your style can help you be more aware of it and can also help you start to shift your style to a healthier one.

Two Tools to Help You Spot Your Contributions

1. Reverse the roles. Ask “What would they say I was contributing?” Think about their answers and try to see yourself through their eyes.

2. Try to be an objective third party. Pretend you’re a neutral consultant called in to help. How would you describe, in objective terms without judgment, what both people are contributing? You can also ask a friend to weigh in on the situation.

Helping the Other Person

Even once you’ve worked to better spot and analyze your own contributions, you might still have some difficulty getting the other person to do the same.

In difficult conversations, take responsibility for your own contributions sooner rather than later. This prevents the other person from using your actions against you, and might help them shift to a contribution approach instead of a blaming approach. It also may keep them from getting defensive.

Express it clearly if you feel like the focus is solely on you and your contributions. Help the other person understand their own contributions by being explicit about your reasoning. List what you see their contributions as. Be upfront about your observations. Discuss what actions and reactions are creating the system you both find yourselves in.

Clearly express what you’d like the other person to do differently. Tie it into your own contributions to help them feel less defensive — doing X next time will help me be better about Y. This cuts to the heart of the conversation system, what each person needs to change to improve the situation.

Remember, the goal is not to get an admission — the goal is to get a better understanding and discuss constructively what to do next.

Exercise: Practicing the Contribution System

Here are some questions you can ask yourself to help you take a more balanced approach to contribution. You can return to this exercise whenever a difficult issue arises.

Chapter 5: The Feelings Conversation

Difficult conversations aren’t just about what happened, but how we feel about what happened.

We tend to avoid our feelings, especially in difficult conversations, because we feel they get in the way of progress, or are embarrassing, or don’t matter. It’s also scary and risky to share feelings, and it leaves us feeling vulnerable.

But feelings are vital to any difficult conversation. Ignoring emotions removes an integral component of the content of the conversation. The authors describe it as “staging an opera without the music. You’ll get the plot but miss the point.”

The authors encourage you tohave your feelings, or they’ll have you.” This means emotions will come out one way or another, and you can either acknowledge and embrace your feelings and deal with them constructively, or you can deal with the aftermath of holding them back. If we manage our feelings, they can be useful; if we avoid them, they’ll color our communication, ruin our relationships, and make us feel worse about ourselves.

Why Feelings Have to Come Out

No negotiation, no matter how skillful, will resolve a difficult conversation if the feelings at the heart of the matter have been ignored. Difficult conversations that leave out feelings often leave both people feeling dissatisfied — and the emotions still find their way into the conversation.

Unresolved or unaddressed feelings can come through in our tone of voice, our posture, and our language. And you might think you can conceal it, but you’re wrong. Studies show that most people are bad at picking up on factual lies, but good at picking up on unspoken emotion. Unexpressed emotions can even cause you to totally break away from relationships based on how many unresolved feelings you have.

When we bottle up our emotions, it also makes us worse listeners. Usually, when people are having trouble listening, it’s actually because they’re having trouble expressing their own thoughts or feelings. Our hidden emotions routinely bring our focus back to ourselves. Instead, when we share our feelings fully, our head clears and we can focus on and be curious about the other person’s feelings.

Lastly, we suffer when we keep our feelings to ourselves. Our self-esteem usually drops, and we feel like pushovers for not being able to express ourselves. And, by not sharing our feelings, we keep an important part of who we are out of our relationships.

Managing Emotions

For some people, unexpressed emotions come out in unmanageable ways, like crying or exploding or lashing out at others. Some people think these episodes are proof that they “feel too much” — but the reality is that these episodes are the result of not sharing emotions enough.

The Feelings Conversation will only improve for the better if we work at getting better at sharing our feelings. The more skilled you become at that, the easier difficult conversations will become.

The basic guidelines for sharing your feelings are as follows:

Sorting Out Your Feelings

We assume we know what we feel, when in reality, most of us don’t. We recognize major emotions, but fail to identify the complexities or the reasons. Feelings are usually more subtle and complex than we realize. They sometimes disguise themselves as emotions we’re more comfortable with, or they can disguise themselves as judgments against or attributions to other people. (Shortform example: In reality, I might be angry about how poorly my job search is going, but I perceive it as really hating my roommate right now.)

Know Your Emotional Footprint

First, you need to know your own “emotional footprint,” what feelings we were taught are okay or not okay to feel or express. This is usually based on what our families taught us growing up. You can start to pinpoint your emotional footprint by asking yourself a simple set of questions:

(Shortform note: We’ve included these questions in an exercise at the end of this chapter to help you get to know your own emotional footprint.)

Every person has a unique emotional footprint, and it will shift depending on what relationship you’re in. For example, the way you behave emotionally with your coworker will be different than how you behave with a romantic partner. Observing your emotional footprint in different settings will help you flesh out the whole picture.

Accepting Feelings

Once you become more aware of your own emotional footprint, the next step is to start accepting that your feelings are normal and natural. There are no wrong feelings; feelings just are. It’s how we deal with our feelings that can be better or worse depending on the situation.

A good comparison is an arm or a leg. An arm and a leg are just body parts, just there — however, we can do things with our arms and legs that hurt other people. That doesn’t mean the arm is wrong, it means we need to change what we’re doing with it.

Feelings aren’t good or bad. Some may feel better or worse, but sometimes the worst feelings are the ones that help us improve the most. Your feelings won’t always make you happy, and they won’t always make sense, but they always are.

Furthermore, your feelings don’t determine whether you’re a good or bad person. Good people can have “bad” feelings. Everyone feels anger. Everyone fails. Actions speak louder than feelings, and those we can control.

When we hide emotions we’re uncomfortable with, we can end up blocking our other emotions, as well. Hiding our emotions inhibits our ability to show any emotions — happiness can get diminished alongside anger or fear or vulnerability. It can also lead us to take out our hidden feelings on others. Wanting to blame someone is a surefire sign that you’re hiding some feelings, or are unaware that they exist.

Sometimes, feelings can be so bad that we shut ourselves off from traumatic experiences and feelings that are too much to bear. This is normal. But these repressed feelings will still affect how you function, so it’s better to start exploring them and work through them when you can. Therapy and friends can help you do this.

The Validity of Your Feelings

Your feelings are just as important as someone else’s. Some of us have learned to prioritize other people’s feelings. When we put others’ needs and feelings before our own, we undervalue ourselves and teach others that it’s okay to ignore our feelings.

We think by hiding our feelings and dealing with someone else’s that we can “save the relationship,” whatever it is. But the reality is that holding our feelings back will erode the relationship slowly instead. Remember, feelings will come out, in some way, in some form. By not valuing our own feelings, we end up doing a disservice to the relationship we’re trying to improve.

Delve Deeper

Usually, there’s one emotion at the forefront of what we’re feeling — but there are often a lot of other smaller feelings beneath the main one. Look for those. Becoming more familiar with the range and nuances of feelings can help us identify all the feelings at the heart of the issue.

For example, every time a man calls his mother, she asks him how his job search is going, which he hates. The primary feeling might be that he’s annoyed his mom keeps asking — doesn’t she know he’d tell her if he got a job? — but there are probably a lot of other feelings at play here. He might be embarrassed that he hasn’t found a job yet, or feel guilty that his mom worries about him, or angry and sad that he hasn’t found a job yet. All these feelings are beneath the surface.

Negotiating Your Feelings

Feelings aren’t gospel truths — they’re perceptions, meant to be negotiated. The end goal is to negotiate your feelings with the other person involved in the difficult conversation — but in order to do that, one author offers up these two rules:

  1. Get all your feelings into the conversation, but...
  2. Negotiate them with yourself first.

Most of us assume our feelings should be shared “as is.” But feelings are based in our perception of things — and our perception of things can change. Feelings are formed in response to thoughts. To start to change your feelings, you have to alter your thinking.

Imagine that you’re scuba diving, and a shark glides into view. Your first thought is, “Sharks are dangerous,” so your first feeling is to be afraid, maybe even panicked. Then, you realize it’s a reef shark, which doesn’t feed on humans, so your panic subsides. Maybe you even become curious about the shark’s behavior now that you know what it is. This is a change in perception, not a change in the “issue,” the shark. Changing your perception of an issue can change your emotions regarding that issue.

Three Steps to Negotiate Your Feelings

1. Examine your story. Our perception is essentially the story we’re telling ourselves about what’s going on. To alter our thinking, we have to become aware of the story going on inside our heads. Articulate the story you’re telling yourself about the situation. Then ask yourself what story the other person might be telling themselves.

2. Examine the intentions. Remember, going into difficult conversations, we’re almost always assuming we know how the other person intended something to come off. This is part of the story we tell ourselves, and also needs to be examined. Is it possible the other person acted unintentionally? What about your own intentions?

3. Remember the contribution system. How have both parties contributed to the situation? What patterns in the relationship or in either party’s behavior are reinforcing this contribution?

Half of the work in these questions you can do on your own — that’s essentially your homework leading up to a difficult conversation. But you won’t be able to get all the answers until you finally talk to the other person. The other half of the work requires their answers.

Sharing Your Feelings

It’ll be hard to express your feelings in a difficult conversation, because you must negotiate your feelings with the other person’s. The goal is to describe your feelings carefully and specifically. Being emotional isn’t the same as sharing your emotions — you can be externally emotional without expressing anything clearly at all.

Avoid venting. This greatly reduces your ability to be productive in the conversation, and greatly increases the change of sparking the other person’s defensiveness.

Avoid Judgments

Judgments aren’t feelings, but they often emerge from our feelings. Sharing judgments can feel like sharing feelings — but when we express judgments, the other person doesn’t know what we’re feeling and will likely get defensive.

“You’re so irresponsible” is a judgment, whereas “I feel hurt when you forget X” is a feeling. It’s helpful to use the phrase “I feel” to make the statements focus on you and your feelings.

However, “I feel hurt when you act irresponsibly” is a combination — there’s still judgment in this expression of feeling, and the other person will probably get defensive. It’s best to think of sharing feelings in correlation with specific actions, not in correlation with generalizations about the other person.

How to Express Feelings

Here are three guidelines for expressing feelings in a difficult conversation:

1. Introduce feelings back into the conversation. Remember that feelings are important. They don’t need to be rational to be expressed — but they do need to be expressed to be dealt with. Get them out first, then decide what to do with them.

2. Express the full spectrum of what you’re feeling. Because we’re often feeling positives alongside negatives, this can change the nature of the conversation, bring some complexity to the matter, and allow the other person to understand you as well as their own impact better.

3. Share first, then evaluate. Evaluating your feelings too soon or allowing the other person to evaluate your feelings too soon will short-circuit the conversation by qualifying or judging the emotional content before its been expressed. Both parties should get to share their pure feelings (remember: feelings, not judgments) first — then you can problem-solve together later.

Reciprocating Expression of Feelings

Both people can have strong feelings at the same time — and they most likely will. Your partner’s feelings don’t cancel yours out, and vice versa. Make sure you both get equal time to share your feelings. Don’t monopolize the conversation, and don’t let the other person do it either.

Acknowledging feelings is important too. Don’t skip this step. Both people need to feel like their feelings are actually being heard and understood before you move on to problem-solving (this is especially important in large-scale conflicts, such as town meetings, where people often jump to problem-solving without acknowledging the feelings expressed). If something is important to you and the other person isn’t getting it, you really only let yourself down if you don’t make sure they understand.

——

Sometimes feelings are the heart of the matter; sometimes they’re not. But in any difficult conversation regardless, it’s a crucial skill to be able to communicate your own feelings effectively, and understand and acknowledge the other person’s feelings.

Exercise: Discovering Your Emotional Footprint

Use this exercise to help you home in on your own personal emotional footprint by starting to understand your family’s footprint and how it affects your present emotional footprint.

Chapter 6: The Identity Conversation

The Identity Conversation is an internal conversation about who we think we are and how we see ourselves. It’s what you’re saying to yourself about yourself. This is probably the most nuanced and difficult of the What Happened components.

Difficult conversations threaten our identity — who we think we are. The Identity Conversation is about what’s at stake for us in a difficult conversation. The anxiety we feel when we think about approaching a difficult conversation is at least partially because these conversations can shake our idea of ourselves.

There are three core identity questions that give us anxiety during difficult conversations:

  1. Am I competent? We all like to think we are — so if you’re the person getting fired, your boss is suggesting that you are not, in fact, competent.
  2. Am I a good person? Most of us see ourselves as the heroes in our own stories — but if you’re breaking up with your partner unexpectedly, they might say a lot of things that make you feel like you’re a bad person.
  3. Am I worthy of love? We all hope to be loved and accepted — so if you share with your mother that you feel hurt when she never asks about your life and she responds negatively, that reaction makes you feel like you might not deserve love.

In difficult conversations, when other people react in ways that challenge our identities, it can throw us off balance and make us feel panicked, shut down, depressed, or fearful — and those emotions continue to play out in our own heads as the difficult conversation continues.

There’s no way to circumvent identity issues — all of life is about grappling with who we are. We are going to lose our balance in difficult conversations over identity issues. After difficult conversations, we might even need to mourn aspects of our identity the way we would mourn a loved one who died.

But there are things we can do to recognize what our identity issues are, cope better once our identity has been challenged, and think objectively about ourselves. All of this will help us manage the Identity Conversation more easily.

Spotting Identity Issues

We’re usually not aware when identity issues come up in difficult conversations. We know we feel hurt or embarrassed or anxious, but we don’t know why — then sometimes, we blame these feelings on the other person, as though they’re “making” us feel that way.

Start observing what things knock you off balance in conversations, difficult or otherwise. Ask yourself why. What facet of your identity is at risk? What would it mean if the thing you fear was true?

All-or-Nothing Identities

The major difficulty most people face is that they view their identity as all-or-nothing. I’m either all good, or all bad, right or wrong, nice or mean, helpful or selfish — no in-between. If I’m a good person, that means I’ve never done anything bad in my life.

No human is all-or-nothing, period. All-or-nothing makes our identities particularly unstable, since everyone has done good and bad things in their life, or been competent in some cases and incompetent in others. When we view our identities as all-or-nothing, we’re only left with two courses of action when something contradicts how we see ourselves:

  1. We deny it outright. We have an all-or-nothing positive view of ourselves, and any negative criticism gets immediately dismissed. We focus only on why negative feedback is false or incorrect. Denial requires energy because it provokes the question we fear might be true - “I’m actually a bad person all the time.”
  2. We take it as true and exaggerate it. We let someone else’s feedback define us and determine how we see ourselves. We have an all-or-nothing negative view of ourselves, and tiny mistakes snowball into negative absolutes about ourselves. You might be on time 99% of the time — but if you show up late once, you tell yourself, “I can never do anything right.” Of course, this negative absolute is objectively untrue.

Neither of these options is a healthy way of responding to information that challenges our identity.

The goal is for us to feel grounded in our identity: aware of the complexities, and open to new information. To become more grounded, we need to do two things:

  1. Learn about which identity issues are important to us so we can be aware when they come up in conversation.
  2. Learn healthy ways to integrate new information about our identities — which requires us to let go of all-or-nothing thinking.

Developing a Grounded Identity

The best thing you can do for yourself and your Identity Conversation is to adopt the And Stance about your identity. Humans are complex. No human is perfect, and no human is worthless — yet those are often the only options we feel we have. The And Stance lets us acknowledge the mixtures that we are, and allows for us to maintain an identity throughout our actions, whatever they are. You can be a good person and you can have to fire someone. You can be a good person and hurt someone’s feelings. We’re constellations of positive and negative qualities: the more complex we allow ourselves to be, the sturdier we’ll feel in the face of identity issues.

There are three things everyone can start to accept about themselves:

  1. We will make mistakes. There are no perfect people. We fear making mistakes because we’ll look weak or incompetent — yet the most competent people are the ones who can admit their mistakes and correct them.
  2. Our intentions are complex. As we previously discussed, we almost always have personal motivations and intentions that are more than just good or bad.
  3. We have contributed to the issue. Issues aren’t created by one person alone, but by the friction between two (or more) people.

Regaining Balance in a Difficult Conversation

Conquering identity issues is about learning to regain our balance once we’ve been knocked off our feet in a difficult conversation. Here are four things you can do to help you keep and regain your balance.

1. Let Go of Controlling Their Reaction

One of our major anxieties over difficult conversations is that the other person will react badly to what we have to say. We’re already vulnerable, and we feel like a negative reaction from someone will be too much to handle. Or we don’t want to hurt other people and withhold what we want to say. Sometimes, self-protection is involved: if you have to fire someone, you don’t want them to feel bad, but that’s mainly because you don’t want to feel bad.

Wanting to avoid hurting someone else and wanting to protect our own feelings can lead us to sometimes deprive the other person of their reaction. When we break bad news to someone and they get upset, our first reaction is to say something like, “You’ll be fine, it’ll be fine, it’ll blow over.” The other person might hear, “You’re not allowed to be upset over this” instead.

Let the other person know everything you need them to know and give them the space to feel how they’re going to feel. This way, you have control over what you can have control over — what you say — and they have control over how they react.

2. Prepare Yourself for Their Response

Before the conversation, imagine them responding in the worst possible way. Then ask yourself what that would say about you, how you’d feel, and how you might respond. Preparation will lower your chances of being surprised or caught off-guard, and it will also help you make peace with the worst possible outcome.

3. Use the Future as a Barometer

Will you care about this in three months? What about 10 years? This thought can give you comfort that you’ll eventually feel better. Most things we spend time worrying about are not things we’ll think of on our deathbeds.

This can also help guide you in tough moments. Imagine looking back on this difficult time. What do you hope to have learned from this experience? What advice would yourself from the future give you about how to handle it?

4. Bring Up Identity Issues Explicitly

Not every identity issue needs to be brought up with others, but some do. Bringing the identity issue to the surface can help both parties deal more efficiently with the difficult conversation at hand.

For example, a question like this can both share how you’re feeling and get to the heart of what the other person is thinking: “It sounds like this conversation is about whether I’m a good spouse or not. Is that how you’re feeling?” Your spouse now understands you’re hearing this conversation as a potential judgment on a big identity issue.

If You’re Overwhelmed

Remember also that you can always take a break during a difficult conversation. If you feel like the identity issues are too overwhelming, ask to take a break to think about what the other person has said. Even a short break might help.

If you’re overwhelmed, you won’t be able to participate in the conversation as effectively. Excuse yourself and take some quiet time to reflect. Check yourself for denial or exaggerations. What’s the worst thing that could happen, and what can you do to turn the situation around?

Remember that the other person’s identity has also been implicated. They’re going through the same thing you are. You can help them by reminding them that identity isn’t all-or-nothing. Remind them of positive things between you or about the situation.

Lastly, ask for help. There are some identity issues that we can’t deal with on our own. Most of us view asking for help as a show of weakness — but think about how you feel when a friend asks for help. Most likely, you appreciate when someone you care about asks for help, and appreciate the chance to do something for them. Why should you be any different? Asking doesn’t mean you won’t be disappointed or let down — we don’t always get the help we ask for. But asking does give people you care about the chance to come through for you.

Chapter 7: Whether to Start a Difficult Conversation

Now that we’ve covered the three meta-conversations in-depth, these next chapters are about how to move through a difficult conversation. The first question is important - should you have a difficult conversation, or just get over it?

We can’t have every single difficult conversation in life — there are too many. So sometimes, it’s best to let things go. But how can you tell what issues to let go and what issues to raise?

Consider the purpose of the conversation, rule out conversations that won’t help, and consider whether it’s better to merely let go.

What’s the Purpose of the Conversation?

The main purpose of any difficult conversation should be mutual understanding. This doesn’t mean mutual agreement. Difficult conversations are about working to understand each other’s stories better, so you can make better collective decisions about what to do next.

If your purposes are focused on learning and solving together, the situation would benefit from a difficult conversation. But in some cases, a difficult conversation isn’t the best path forward.

Four Situations Where Conversations Won’t Help

1. If the conflict is inside of you, raising the issue won’t necessarily help. Sometimes conversations are more difficult than they have to be because so much is going on inside of us instead of between us and another person. This is why having a conversation with yourself is important. If it feels like the conflict is mostly in your own head, have longer conversations with yourself first.

2. Talking might not be the best way to address the issue — changing your actions might be better. Once you sort out how you feel, you may realize a better solution is to change how you behave, instead of raising the issue with someone else.

For example, a city doctor still had family in the suburbs, and his mother constantly asked him when he was going to come home and run the family business. Though the doctor primarily felt irritated with his mother when she asked, he went through the conversations and realized that she missed him and was sad that he couldn’t see his family as much. Instead of having a difficult conversation, he began calling his mother more and traveling more often to the suburbs so she felt more involved in his life.

3. Ask if your purpose for having the difficult conversation makes sense. We often launch into difficult conversations without knowing why or what we hope to gain by having them. What if you asked the head of NASA what the purpose was of a certain space mission, and she replied, “I really don’t know. I thought we’d just get the ship up there and then decide as we went along.” This isn’t how we want NASA exploring space, and it isn’t how we want to head into difficult conversations, either.

Sometimes our goals are too distant or unrealistic to achieve, for example, changing the other person completely. That’s a purpose that doesn’t make sense and won’t end well. Recalibrate your purpose and expectations before deciding to have a difficult conversation.

4. You don’t have enough time to prepare for the difficult conversation. Often we want to get something off our chests immediately, but we’ve put in neither the time nor the preparation to have the difficult conversation. Don’t hit and run — these worsen the situation and don’t address the complexity adequately.

Letting Go

Once in a while, no matter what we do, nothing will solve the problem. Or, after we go through our own side of the three conversations, we decide it’s best not to have the difficult conversation. The healthiest option we have then is to let the issue go.

Letting go usually takes time. It usually isn’t easy to let go of something that’s bothering us, and we’ll have to put in practice and effort to be able to let go of it. There’s no “appropriate” amount of time to be upset by something, so don’t let anyone tell you there is. Feeling pressure to get over something is one more way to keep yourself fixated on it.

Letting go requires us to:

Here are some things you can do to help yourself begin to move past the situation. Keep these things in mind as you try to let go of the issue:

  1. You don’t have any responsibility to make things better — your only responsibility is to do your best. You might want to make a relationship better, but you can’t do it on your own. It takes both people to improve any relationship. You can only try your best to improve it in the ways you can.
  2. The other person has their own limitations. They’re as imperfect as you are. People slip up and make the same mistakes, especially if it’s a long-held pattern for them. They might not be capable of changing the way you need them to right now.
  3. A single conflict does not define who you are. It’s more difficult to let something go if you incorporate the conflict into your identity. This is what makes racial conflict or other identity-based conflicts so difficult to resolve. Reconciliation can feel like it robs people of their communal identity, or it can feel like a betrayal of some identity. Remember that your purpose in any conflict should be to fight for what’s just and equitable — you don’t need just any conflict to survive.
  4. Letting go doesn’t mean you don’t care. It could just be the wrong situation to have a difficult conversation, or you don’t feel you have the skills yet to manage a constructive conversation.

It’s okay to give up in difficult conversations. Sometimes, you’ll have to. Remember that you can’t change someone else, or control their behavior. You can’t force someone to face an issue or admit their responsibility. The only thing you can control is yourself. Giving up still requires a difficult conversation to be had — with yourself. You’ll have to work through why it’s a healthier choice to give up, and you’ll have to work towards forgiving yourself for giving up.

Exercise: Separating Intention from Impact

Use this exercise to practice separating someone else’s intentions from the impact their behavior had on you, either by reflecting on a past issue or working through a current one.

Chapter 8: Beginning a Difficult Conversation

The beginning of a difficult conversation is usually the most stressful moment, where we either learn that bad news is coming our way, or that the person we’re talking to is going to get upset.

We also usually start the conversation in unhelpful ways. Difficult conversations are difficult: most of us treat the beginning of them like we treat swimming — we close our eyes and just jump in.

As a reflection on what we’ve covered so far, here are the attitudes to take into a difficult conversation:

Two Bad Openings

These are the two most common ways we start a difficult conversation, and the two least helpful ways to do so:

1. We start in directly with our own perspective. If the other person agreed with how we saw things, we wouldn’t be having the difficult conversation. Most of the time, the other person doesn’t know there’s an issue, or has their own perspective on it — so going in with our own perspective right away can make it seem like we aren’t interested in solving the problem together.

2. We express judgments about their character, and trigger their identity conversation immediately. This is why it’s so important to do away with judgments. The issue is not a judgment on the other person’s character, it’s an instance of friction between two people. Especially at the beginning of a difficult conversation, dispensing judgments shows you’re not really interested in a conversation or your own contribution.

Sometimes the opening lines are deceptively judgmental, even when you’re trying to discuss your intentions.

Both of these beginnings are common because they’re based in how we see things — but they also immediately put the other person on the defensive. If the tables were turned, and the other person started a difficult conversation by insulting your character, would you be willing to sit and listen to them explain further?

The Correct First Two Steps

If your purpose is to understand the other person’s story, express yourself, and solve the problem together, you need to start the conversation off to set the tone for those things to happen. Start with these two steps.

First, Start from the Third Story

The Third Story is the objective story a mediator or other third party would tell about the current situation. Mediators try to tell the third story in a way that makes both parties feel understood. The goal of the Third Story is to tell a story that both parties can agree to. It requires them to understand each party’s feelings and use the And Stance to connect the actions and impact that caused the issue.

Mediators know that no one view is right or wrong, they’re just different. The Third Story sets out to illuminate the difference between the views. For example, a mediator working with two roommates on an issue about who does the dishes might summarize it this way: “Jason and Jill have different preferences around when the dishes are done and what constitutes appropriate cleanliness. Each is unhappy with the other’s approach.”

To start from the Third Story, you don’t have to know the other person’s story, you can just focus on the difference. “I was taught that dishes should be done immediately after you use them, and that it’s a sign of disrespect to leave dirty dishes in the sink — but it seems like you have a different perspective.”

Starting from the Third Story doesn’t mean giving up your point of view, it means starting from a neutral place so you can invite the other person to share and participate in the conversation. Starting from the Third Story shows we care about the other person and are trying to improve the relationship for both people.

Even if you don’t get to start the difficult conversation, you can still bring in the Third Story at the earliest opportunity. Use what the other person said as their side of the Third Story, and bring it back around to the difference between your perspectives and your desire to explore the issue.

Then, Invite Them to Participate

Once you’ve told the Third Story in a way that both parties can agree to, you essentially have to invite the other person to join you in a conversation about mutual understanding and problem-solving.

Express your purpose up front. You want to understand their side better, share your side, and then discuss how to move forward. For them to agree to participate, they need to know what they’re agreeing to. This also helps focus them on the right purpose.

But remember: invitations can be refused. You can’t force someone to participate, no matter how badly you want to. You can only invite, and then it’s up to them to agree or refuse.

Explicitly put them in the role of your partner in the tasks at hand. They’re not solely the problem, and you need them to work this issue out. Let them know that they have equal footing in the conversation (if that’s true), and that finding a satisfactory solution depends on their involvement.

Here are some phrases to use that invite the other person to participate:

The partnership has to be offered genuinely, or it won’t be received well because it won’t seem like you really mean it. If you’re having trouble viewing them as a partner and not just the problem, be open about that: “The story I’m telling myself is that you’re being inconsiderate. I know that’s unfair to you. Help me put this in perspective and better understand where you’re coming from.”

Finally, remember to be persistent. This doesn’t mean you can force them to participate, but you might have to work to get them to understand what you’re asking for. Most people aren’t used to being treated as an equal in a difficult conversation, so it could take some time to shift their mindset about how you’re trying to have the conversation.

General Advice for Starting a Difficult Conversation

Here’s a good structure for approaching the beginning of any difficult conversation:

  1. Start with the Third Story.
  2. Try to understand their story.
  3. Share your story.

This structure will go the farthest in bringing the other person along with you and easing them into the difficult conversation.

You can also help guide them through the Three Conversations — What Happened, Feelings, and Identity — by asking questions or explaining the conversations to them. Each of you should talk about past experiences that have influenced how you see the current situation. Ask about the other person’s intentions and share the impact their actions had on you. Share what’s going on in your Identity Conversation, and ask what might be going on for them.

Of course, a real conversation is interactive, and it won’t necessarily go exactly according to schedule. But once you understand the components, you can work with them on the fly. To understand the other person’s perspective, you’ll need to improve your skills of asking, listening, and acknowledging. To share your perspective, you’ll have to hone your sense of deserving to share your story, and improve your ability to share it concisely. To keep a difficult conversation on track, you’ll have to develop your ability to negotiate it back into the correct focus, if and when it starts to veer off course.

Three Conversations That Might Be More Difficult to Start

Some conversations might feel like they’re harder work than others. Here are three common conversations that feel more difficult, and some ways you can make them a little easier:

The Bad News Conversation

Sometimes, you’ve got to be the bearer of bad news — firing someone, breaking up with someone, and so on — but you should still aim to have a conversation. It doesn’t mean you’re going to change your mind, but it does mean you respect the other person enough to want them to understand your side and share their side, and to resolve as many of the negative feelings as possible.

It’s best to deliver the bad news first — don’t draw out conversations where you’ve already decided.

If there’s good and bad news, specify that you have both. There may be a logical order to deliver the news in, or you can let the other person decide what they’d like to hear first.

Asking for Something

Sometimes difficult conversations are focused on our desire for something, such as a raise. It can feel one-sided in a different way: “I want a raise, so I’ve got to talk my boss into giving me one.” But these, too, should be conversations instead of demands.

It’s best to still invite the other person to participate and explore the issue with you. It isn’t unassertive to approach the conversation this way — it’s more realistic. If you’re asking your boss for a raise, you can’t strongarm them into giving you one, you need them to agree that you deserve one.

“I wonder if it would make sense…” is a great phrase to use in these conversations. “I’d like to explore…” is another one.

Previously Difficult Conversations

Sometimes we’ve already had a difficult conversation where someone reacted badly, so it makes us hesitant to enter into the conversation again and get the same bad reaction.

The first step is to talk about how to talk about it this time. The real issue now is the way this conversation goes based on past experiences.

Start with a Third Story about that: “I know that when I’ve tried to talk to you about how busy your schedule is in the past, you’ve felt annoyed or agitated. That’s not my goal. I’m just worried about you. I wonder if we can talk about how to address this issue for both of us, and if there’s a better way the conversation could be had.”

Chapter 9: The Importance of Listening

Humans want to be heard. We want to feel like someone else cares about us enough to listen. Listening is a vital skill for difficult conversations. Not only does it help us understand the other person better, but it helps them understand us better as well.

Listening can transform a difficult conversation into a learning conversation. It requires us to be curious about the other person, to reframe our purpose from persuading the other person to learning about them. We need to ask questions to better understand the other person and acknowledge the other person’s feelings.

One of the most common complaints the authors hear about difficult conversations is that the other person isn’t listening. This really means we need to be better at listening first. When we feel others aren’t listening to us, we tell ourselves they’re stubborn, don’t care what we have to say, or don’t understand it. So we often double-down, repeat ourselves, and talk over the other person.

The reality is that people stop listening when they don’t feel heard. If we feel like someone isn’t listening to us, they probably feel the same way about us. The way to get someone to listen to you is to put genuine, concerted effort into making sure they feel heard first.

Making Someone Feel Heard

The goal in a difficult conversation is to shift our mentality from assuming we already understand someone to wanting to understand them better.

The key is to be genuinely curious. No matter how good you might be at doing the things listed on a good listening checklist, people can usually tell whether it’s authentic or not.

Managing Your Inner Voice

One major thing that prevents us from being authentically curious is our inner voice — what we’re thinking but not saying. When we focus on our inner voice, we’re at best only half-listening to the other person.

Typically, your inner voice is thinking about the three conversations we covered - What Happened, Feelings, and Identity. Listening to your inner voice will start to give you answers and questions to explore in those three areas.

There are two things that can help you start managing your inner voice:

1. Negotiate your brain back to curiosity. You can start to change your inner voice by reinforcing the right thing. Remind yourself that it’s a delusional assumption to think you already understand someone else. Remind yourself of a time you thought you were right, but discovered you’d been wrong. Remind yourself that other people are just as complex as you: if you wouldn’t want someone else assuming they understood you without listening, don’t do it to someone else.

2. If your inner voice is too strong, talk instead of listen. Sometimes our feelings are too overwhelming to listen. When this happens, first let the other person know that you want to listen to them, but you’re having a hard time focusing. You can try giving a sound bite of what’s preoccupying your mind, to let the other person know where you’re at right now: “I want to hear about your perspective, but I’m feeling defensive right now.” Hopefully saying this might quiet down your defensiveness for a moment, and you can let the other person finish what they have to say and then come back to your feelings.

Or you might decide that you can’t listen or talk right now because you’re too overwhelmed. Express that this conversation is important to you, and you want to come back to it when you feel better prepared to have it.

Tips for Good Listening

Good listening requires three skills that can be learned by anyone. These three skills are interconnected skills centered on whether you’re really listening or whether you’re trying to prove a point.

Skill #1: Ask Questions with the Goal of Learning

If you’re not sure about your goal, ask yourself why you want to ask the question. If your answer is anything other than “to learn about the other person,” it’s probably not a good question to ask.

Don’t ask questions that are really statements. Often, we want to express a statement in a difficult conversation, and we mistakenly think it’s more polite to ask it as a question instead. This usually comes off snide or passive-aggressive. Instead of hearing your feelings or opinions, the other person will most likely focus on the attack and get defensive.

Don’t ask questions to prove the other person wrong. Questions you ask with the intention of proving someone wrong aren’t focused on learning, they’re focused on persuading or humiliating someone else. They usually serve as traps for the other person — and trapping them into an answer isn’t aligned with the goal of learning. Again, the outcome will be defensiveness.

Ask open-ended questions. You’ll get more information with these than with yes or no questions, or multiple-choice questions. Again, the goal should be to learn about the other person — you can only do that by getting them to talk. Use phrases like “tell me more about…” or “help me better understand…” to get the other person talking.

Ask for more specific information, especially on anything you’re confused about. Questions like, “What leads you to say that?” or “Can you give me an example?” or “How would that work?” can be helpful.

Ask them about the Three Conversations: What Happened, Feelings, and Identity conversations.

Give them the option to not answer. Questions should be invitations, not demands. The other person should be able to refuse to answer your questions without any punishment. It builds trust if someone declines to answer a question and you show that it’s okay. People often feel freer to answer questions if they feel they have the option not to.

Skill #2: Paraphrase Their Responses

Paraphrasing someone’s response means expressing, in your own words, your understanding of what they’re saying.

Paraphrasing helps you double-check whether your understanding is correct, and gives the other person an opportunity to clarify if you’re misunderstanding something. This also confirms for the other person that you’ve heard them, and are trying to understand them.

We usually repeat ourselves because we’re not sure if someone’s understood us — once we know they have, we can focus on listening to them in return. If you notice the other person repeating themselves, it probably means they don’t feel understood yet.

Skill #3: Acknowledge Their Feelings

Feelings desperately want to be acknowledged, and acknowledging someone else’s feelings requires empathy. Empathy is “a journey with a direction but no destination.” Empathy requires us to move beyond observing someone from the outside, and imagine what it would be like to be them on the inside.

It won’t be perfect — we’re all too complex to ever be totally understood by someone who isn’t us. But psychologists discovered that it’s more important to feel like someone is trying to empathize with us than believing they’ve done it successfully.

Acknowledgement is about showing the other person that you’re working to understand their feelings. Usually, this step requires us to paraphrase the things the other person isn’t saying.

Another way to think of this is: feelings usually come with a number of unasked questions. Even an expression of anger that seems focused on an event probably has a silent question at its heart. 3 examples of unasked questions are:

  1. Is it okay that I’m feeling this?
  2. Do you care about my feelings?
  3. Do you care about me?

Acknowledging people’s feelings gives a resounding yes to each of those questions. This helps them feel safer and ready to move forward in the conversation.

Verbal responses aren’t always necessary — a nod or a look might be enough. But it’s incredibly important to acknowledge feelings before you try to solve the problem. Order matters. Most of us skip straight to offering solutions because we think the issue is that there’s a problem that needs to be fixed. Usually, people want their feelings heard first and foremost.

Remember: acknowledgement is not agreement. You might not agree with what the other person is feeling, but you should be able to acknowledge that their feelings are still important. You’ll never get through a difficult conversation if you don’t believe the other person’s feelings are important — it will most likely turn into an argument.

Chapter 10: Uphold Your End of a Difficult Conversation

Understanding the other person in a difficult conversation is vital — but it’s vital for them to understand you, too, and you’re responsible for how thoroughly you express yourself.

If you have difficulty expressing yourself, you may be insecure about how much you deserve to speak. Remember: what you have to say is worth saying. You have the right to share your thoughts, feelings, and past experiences. Even if you’re talking to a superior, your views are equally important — no more, no less.

(If you tend to feel that you’re not entitled to speak, delve into your Identity Conversation. Who from your past made you believe that? What would it take for you to feel entitled?)

Begin at the Heart of the Matter

Start with what’s most important to you. Many of us try to drop clues about how we feel instead of stating it outright, or we try to ease our way into the conversation.

Subtext Isn’t the Solution

Subtext is indirect communication — through jokes, offhand comments, or other behavior. For instance, if you’re upset at your spouse for sharing in cleaning duties, indirect expression includes statements like, “The house really could use a clean-up,” or, “Do you really need to watch football every weekend?” What you really mean is, “I feel like we’re not equal partners in the household, and you don’t respect me.”

Don’t embed your meaning in subtext. You might think this will soften the impact on the other person and make it less risky for you to share. But this comes across as passive-aggressive and makes it more difficult for us to be understood. In the example above, the first two statements are far different from the real meaning, and lead to very different reactions.

Perhaps you wish you didn’t have to speak up or share or bring the subject up at all, that the other person could just read your mind and solve the issue for you. But this is a fantasy. The realistic goal is to know each other better, acknowledging that it will never be perfect.

Here are some phrases for starting productively:

Avoid Leading Questions

Leading questions convey an opinion but demonstrate that you’re unwilling to share it directly. Performance reviews sometimes start this way: “How do you think you’ve been doing?” This will only activate the other person’s anxiety and immediately trigger their defensiveness, and they’ll probably imagine that what you have to say is far worse than what you actually think.

The best plan of action is to share your thoughts directly at the beginning, while also acknowledging that you want to know how the other person feels about the situation as well.

Use the “And Stance” to Present Your Own Complexity

Humans are complex. Too often, we try to simplify ourselves so that we can be easily understood by other people. However, this usually means our message is incomplete, and either we don’t share everything that’s on our mind out of fear of hurting the other person, or we only share the negative thoughts instead of including the positive ones that make the issue important to us.

(Shortform example: A parent might say to their child, “I don’t feel like you’ve been working hard enough in your college classes.” This is technically sharing their thoughts, but it leaves out a crucial part of the message: “I think you’re so bright and have so much potential, and I don’t feel like you’ve been working hard enough in your classes.” This represents a full, complex thought, and gives the child all of the information at the root of the issue.)

Sharing thoughts this way helps you represent your perspective clearly and accurately.

Three Guidelines for Sharing with Clarity

1. Your conclusions are not the “truth.”

As we know by now, presenting our feelings as facts usually makes the other person feel attacked, defensive, or resentful.

Expressing your opinions as facts can be more subtle than you think. “Spanking children is just plain wrong” is an opinion masquerading as a fact. If you say this in conversation with your friend about the way she treats her kids, you’ve given her no choice but to get defensive. “I don’t believe it’s right to spank children” presents it as a personal opinion instead.

Be especially wary of using these words: “inappropriate,” “should,” or “professional.” These all carry judgment that is entirely based on someone’s personal opinion. If you have to use them, make sure you preface your statement with, “My view is that…” But the book suggests avoiding these words entirely.

2. Share what leads you to your conclusion.

You are the expert on yourself: You have information that no one else has access to, and past experiences that shape your perspective. These are important to share, because they contextualize your opinion.

For example, if you were spanked as a child and feel frightened every time your friend does it, it’ll go a longer way to change her opinion about the issue if you share that information: “I don’t believe it’s right to spank children. I got spanked as a child and I always felt so afraid. I still get frightened when you do it, even though it isn’t happening to me.”

3. Don’t use “always” and “never.”

In the throes of a difficult conversation, we often exaggerate: your husband makes a negative comment about your outfit, and you jump right to, “You always criticize my clothing. You never say anything nice.” These words are good at communicating frustration, but have major pitfalls.

They’re rarely accurate, and turn the conversation into one about frequency instead of the heart of the matter. They also usually make the other person get defensive immediately. “That’s not true! I don’t always criticize, and I do say nice things! Just last week I told I like your new dress.”

They also make it harder for the other person to consider changing their behavior. These words suggest that change is impossible, and can make the other person feel defeated before they’re even given a chance to change.

It’s better to go into a difficult conversation assuming that the other person doesn’t know how their actions are impacting you, and assuming that they’re a good person who will want to change their behavior once they become aware of how it’s impacting you. Share what you have to say in an inviting and encouraging way that gives the other person new ways of behavior to consider.

Assume They Want to Understand You, then Help Them Do It

In a difficult conversation, both people need help understanding the other person.

We already know that paraphrasing what someone else is saying helps demonstrate that we understand them and acknowledge what they have to say. But you can use it the other way. You can ask them to paraphrase your feelings to check that they’re understanding you and that you’re being clear.

Also, remember that people take in information differently. Some people want to understand the big picture first; others want the details first. Some people learn fast, some take more time. The more you understand the other person, the more you can help them understand you better.

To that end, you can also ask the other person how they see it and why they see it that way. If it seems like the other person is confused or resistant to your story, put the ball in their court to see what you can understand from their answer.

Chapter 11: Controlling a Difficult Conversation for a Better Outcome

In an ideal world, everyone you enter into a difficult conversation with would have read this book and can deftly and productively handle the conversation. But that is rarely going to be the case.

More often, you’ll enter into a difficult conversation with someone who does all the wrong things. Your goal is understanding, theirs is being right. You acknowledge contribution, they blame.

You can still have a productive difficult conversation with someone who hasn’t read this book — you do it by leading the conversation. There are three “power moves” that can help you lead the conversation in spite of the other person’s lack of cooperation: reframing, listening, and naming the dynamic.

Reframing

Reframing is listening to the other person’s contributions and translating them into more helpful ones. It usually uses the Three Conversations as the translation categories.

Reframing helps keep a conversation on track when the other person is heading down a destructive path, and helps you translate negative statements into useful ones. And it almost always works: anything the other person says, you can usually reframe it as a helpful contribution to a learning conversation.

You can reframe:

Some examples of how to reframe:

Though a single sentence can’t turn a whole conversation around, hopefully, these examples give you an idea of how to reframe constructively.

You can also use the And Stance to help reframe issues between you and another person. This can help you incorporate the other person’s perspective and still share your own.

Listening

As discussed before, listening allows you to understand the other person’s perspective, which will always be constructive for you.

Most of us assume that listening is a passive role, but it can be very active. When you listen, you get information that is crucial to directing the conversation. If they get emotional, listen and acknowledge their feelings. If they refuse to accept your version of the story, paraphrase what you’re getting from their story and ask them questions about their perspective. If they accuse you of something, try to understand where they’re coming from before you defend yourself.

If you get overwhelmed in a conversation, or if you aren’t sure how to proceed, ask them questions, and listen.

Naming the Dynamic

Naming the dynamic is essentially bringing into the conversation what’s happening in the conversation. It allows you to articulate the trouble spots of the conversation, and is especially useful when the other person won’t follow your example and hogs the conversation.

Naming the dynamic can help clear the air between you by cutting to the core of what’s going on in the conversation in the present. However, it can also take the conversation off course, and can sometimes escalate tension — so it’s probably best to use it as a last resort.

Here are examples of naming the dynamic constructively:

Chapter 12: The Last Phase — Problem-Solving

You’ve finally unpacked what happened and how it makes you both feel, and have started to understand each other’s stories much better. But ultimately, you still have to work together to solve the issue, and you may disagree on how best to go about it. This is the problem-solving stage.

Problem-solving is essentially collecting the information you just received and coming up with some test options that might help solve both sides’ issues. Problem-solving in difficult conversations requires both parties to consider compromises and accommodation of the needs of the other person.

Test Your (Differing) Hypotheses

Differences in perspective usually stem from assumptions or hypotheses that conflict with each other. We usually keep these assumptions to ourselves, or we might not even know they’re assumptions.

If you can identify what the conflicting assumptions are, then you can come up with a fair test to see whose assumption is more valid, or how much more valid it is.

Example: Your neighbor’s dog has been keeping you up with his barking. You talk to your neighbors and discover they just had a baby and have been keeping the dog outside at night because they’re afraid he’ll hurt the baby. It’s not a fair test to propose they get rid of the dog — it only really addresses your issue. It could be a fair test, however, to propose keeping the dog inside for a few nights and shutting the door to the baby’s room, which addresses both parties’ issues.

Problem-Solving Tips and Tricks

1. Communicate what still doesn’t make sense about their perspective. Remember, as you’re participating in a difficult conversation, you’re trying to follow the other person’s reasoning. If you’re having trouble following the reasoning, then there’s information missing that would help their side make sense.

2. Let the other party know what would persuade you, and ask what would persuade them. If you go into a difficult conversation unwilling to be persuaded, you’re not really going into it interested in their side and in solving the problem. Acknowledging that you could be persuaded gives you room to be straightforward about your views and what you need to resolve about the issue.

3. Ask what they would do in your position. This might help you discover other assumptions they have about the situation, or understand their reasoning. “How would you feel if you were in my shoes, and what would you do? Why?”

4. Ask for help coming up with creative solutions. “Can we find a creative way to deal with both our issues? Are you willing to try to find a solution with me?”

5. Look for external standards of fairness. Sometimes, the best place to look for a solution is outside of the difficult conversation you’re having. For example, with the barking dog, maybe there are local ordinances about noise that set a standard that will help solve the dispute, or maybe this issue has come up in the neighborhood before and other people have found alternative solutions.

Agreement Is a Team Sport

Some people feel anxiety over problem-solving, over the task of finding a solution that meets both parties’ needs. They usually feel this anxiety because the goal of a difficult conversation, in their mind, is to make the other person happy — to meet their needs.

But it takes two people to reach an agreement. Unless both people are satisfied, even if it means having to compromise, there is no agreement. You shouldn’t compromise or agree to their terms just for the sake of getting the conversation over — this will breed resentment and ill-will.

“I’m not persuaded that…” is a good phrase for letting the other person know that they’re being demanding without providing good reason. For example, an editor might respond to a pushy writer: “I can see that you’re determined to have this article reviewed, but I’m not persuaded that I should do it now, while I’m on my vacation.” This is clear about the problem, and puts the onus on them to convince you.

Sometimes, agreement won’t resolve the conflict. No matter how deft the conversation is, there are irreconcilable differences sometimes. You can’t come up with an option that satisfies you both. In these instances, it’s up to you to decide if you can settle for a less than ideal solution for you, or if you can live with the consequences of sticking firm to what you need.

If you decide to stick firm to what you need, explain what needs of yours aren’t being met by the solutions proposed in the conversation and why you’re walking away from solving the issue. Then, know that you’ll have to accept whatever consequences there are.

Appendix: Ten Common Questions About Difficult Conversations

The authors included a list of 10 common questions they receive about Difficult Conversations, and how they’d respond to these questions.

Q1: Is Everything Relative?

Q: Are you saying everything is relative? Aren’t things sometimes true, and aren’t people sometimes wrong about their opinions?

A: Facts are facts. Everything else is everything else.

Facts aren’t relative — but it can be hard to distinguish between what’s fact and what’s subjective. You can measure facts and verify them. But opinions, judgments, values, assumptions, interests, predictions — these are all subjective and are not facts. It’s crucial during a difficult conversation to be able to distinguish between facts and everything else.

For example, if you get a $30 bill at dinner and leave a 15% tip of $6, it’s a fact that you’ve done the math wrong: a 15% tip would be $4.50. However, if you’re at dinner with someone who leaves a 15% tip and you tell them that 20% tips are the appropriate amount, that’s an opinion, not a fact. Even if you’re opinion is based on a survey that says 20% is the usual amount that people tip — the survey is a fact, but your judgment is still subjective

People also disagree about what is true. No matter how true we think someone is, someone else in the world will feel completely different. Maybe instead of wondering whether there are absolute truths, we should wonder whether humans are even capable of perceiving absolute truths. Our existence is subjective in and of itself: maybe the only absolute truth we can be sure of is that there are no truths we can be absolutely sure of.

The more passionately we feel about things, the less likely we are to view people who disagree with us as three-dimensional human beings. But ask yourself how you would feel if the reverse was true: If someone else thinks your views are evil, do you think they’re acknowledging the complexity of who you are as a person? Do you think the information they receive about you and your views is fair, balanced, and empathetic, or do you think it’s shallow, sensationalized, and simplified? This might make you realize you’re being narrow-minded.

Q2: What About Bad Intentions?

Q: What if the other person is trying to lie, bully me, or ruin the conversation to get what they want?

A: Sometimes people do have bad intentions. However, remember that you can’t control how someone else behaves. You can only control how you respond to their bad intentions.

Don’t reward their bad behavior by giving over. Bowing out of the conversation to avoid the difficulty will only reinforce that their behavior pays off, and they’ll keep doing the same thing whenever they want something.

Don’t respond by falling to their level. You’ll ruin your own reputation by doing the same thing they’ve done. A lie in response to a lie just makes you both liars.

Do try to understand why they’re behaving that way. Though some people do have bad intentions, most people have reasons and justifications for why they behave certain ways. Only once you understand where they’re coming from can you begin to persuade them that there are other ways to deal with the issue.

When all else fails, name the dynamic and spell out the consequences. Make it clear that you understand what they’re doing and clarify what that is, and then talk them through how it’s impacting you and what you’re going to do if they continue to behave this way.

Q3: Difficult People

Q: Aren’t some people actually more difficult to deal with? What about mental illness?

A: Some people are absolutely more difficult to deal with than others, whether there’s mental illness in the picture or not. The communication skills you’ve learned in this summary will still help you deal with even the most difficult people.

Mental Illness

Remember that, similar to the last question, mental illness often has its own logic that is beyond the victim’s control. They’re not deliberately trying to frustrate others.

For example, someone suffering from OCD feels like they have to complete certain routines or there will be negative consequences. Even if the consequences are imagined, completing the rituals is their attempt to protect themselves. This is a logical thought pattern.

Remember that you cannot control how other people act, and you can’t guarantee an outcome when dealing with other people.

What to Try for Difficult People

Clarify that you’re trying to help them, not fix them. People want to be understood, acknowledged, and cared for — if they feel like you’re trying to fix them, that implies that they’re broken or bad, and they’ll probably get defensive despite your intentions.

Go for a “Big Reframe.” If you’ve listened, you should have a decent idea of what’s underlying the difficult behavior, and you can try to bring a big picture idea into the conversation that speaks to that issue.

Remember that people have their blind spots. If you have an employee who’s gotten negative feedback about her combative demeanor at work, it’s possible that your employee doesn’t know what constitutes combative behavior, and isn’t aware of when she’s behaving that way. This is why it’s crucial to make sure people have all the information, especially the information missing from their story.

Focus on the alternate view and its implications. Especially when people get wrapped up in whether something’s true or not, ask them to think through what it would mean if the opposite view was true?

Remember that aggression usually stems from fear. It’s easy to be upset with someone when we think they’re mad for no reason; it’s harder to be upset with someone if you assume they’re acting out of fear.

Speak to joint contribution. People aren’t difficult in a vacuum — acknowledge what you might have contributed to the situation in the hopes that this might cool them down and help them open up to an understanding of their own contribution.

Finally, remember that patience and persistence go a long way in difficult conversations. If you know someone’s difficult, set aside more time to talk with them. The more you can keep a level head, the more productive the conversation can be. The more mental prep work you’ve done on your own end before heading into the conversation, the more persistent you can be with someone who needs bigger pushes to get to breakthroughs.

Q4: What About Bosses?

Q: What about people who have all the power in a situation, like bosses?

A: It’s true that in some situations one party will have much more say over the outcome of a difficult conversation. In these situations, focus on the power of influence over action.

You can’t fire your boss, but she can fire you. Acknowledging up front that your boss has the power to make the decision might actually make her more open to hearing your ideas — she knows this isn’t a conversation about whether you get to do something or not.

Make sure you’re coming from a place of requesting — and clarify how it benefits your boss. “I’ve been thinking that X change might have a positive impact on Y output. What would you think about a change like that?” A statement like this is a request that your superior consider something, and might make them more receptive to your suggestion.

Listen to your boss. This is an especially good tip for bosses who seem to shut everything down right away. Ask questions, try to learn what’s influencing their decision, and listen to what they have to say.

Reluctant or Abusive Bosses

If your boss is unenthusiastic about talking to you, try these steps:

If your boss gets verbally, emotionally (or physically) abusive:

Q5: I’m the Boss, Do What I Say

Q: What if I’m the boss or parent — can’t I tell my employees or children what to do?

A: You absolutely can. It’s a common misconception (and a frustrating one to the authors of the book) that Difficult Conversations says you shouldn’t make decisions or execute them, all you should do is listen, that everyone has to agree before you can move forward. This is not true.

The authors place such importance on listening because failure to listen is a far more common mistake than failure to decide and assert. Simply telling people what to do only works in some scenarios. But sometimes, ordering people around won’t be successful — that’s when this information comes in handy.

One thing authority figures can do to reduce the need for difficult conversations is to clarify when something is a command and when it’s something else. Be clear about when you are making a decision and telling someone what that decision is.

Then also be clear when you are doing something else. Because you’re the authority figure, you set the expectations for interactions. Be clear when you’re:

We said in previous chapters that listening and asking questions is the best place to start from — but questions only help us when we want to learn, while statements help us when we need to convey information.

Q6: Is This Approach Too American?

Q: This is an American approach to conversation. Can it work in other cultures?

A: While cultures may vary in terms of how they handle difficult conversations, the authors of the book found that the structure of difficult conversations remains the same around the globe. Difficult conversations in any culture are always about what happened, the feelings involved, and each person’s identity.

But every culture has its norms of how to approach difficult conversations. The principles in this summary can be applied and filtered through your own cultural norms to help you be clearer and more direct in difficult conversations.

Additionally, because of the growing multinational context of our world and business cultures, the principles learned here can help people from different cultures be more sensitive to their impact on each other and more communicative about their intentions and feelings, leading to more effective and productive conversations across cultures.

Q7: Phone and Email Conversations

Q: What should I do in conversations that aren’t face-to-face? Or even in phone calls?

A: Email and text messages deprive us of many key elements for effective communication: facial expression, vocal intonation, body language. They also don’t allow for interruption or interaction, or clarification in the moment. They’re distinctly one-sided.

Though we tend to think of these forms of communication as less emotional, the opposite is true: these forms are actually more challenging precisely because they’re still emotional and lack the aforementioned information. Does that exclamation mark suggest excitement or sarcasm? Are these words in all caps because the person’s communicating anger or emphasis?

Tips for Reading Emails or Texts

Keep in mind that you don’t know exactly how they intended things to come off — better to assume they had good intentions than bad.

If you find yourself getting emotional reading an email or text, stop reading. This is the luxury of impersonal communication — we can put it away at any time.

Call them or schedule a meeting to respond. Remember that the difficulty with emails or texts goes both ways. If you send an email or text back, they can misinterpret what you have to say. Trying to resolve issues over text or email turns into a vicious cycle, and rarely gets anywhere productive.

Tips for Writing or Responding to Emails or Texts

Be extremely explicit about your intentions, reasoning, and emotional states if appropriate. The more you can contextualize what you’re writing, the less chance there is for the receiver to misinterpret your words.

Let someone know if it’s going to take you awhile to respond. Better to send a short “I’ll respond to this email in a few days when I’m not traveling anymore” note or something similar to ease the other person’s mind. Silence can cause people to assume you’ve had a bad reaction or that you don’t care.

Check in about intentions if possible. If you receive an email or text that leaves you unsure about how someone meant something, ask them to clarify what they intended before responding.

If all else fails, ask for missing information, more thoughts, or rationale. You can try to have a difficult conversation over text or email, but you’ll need to try the same steps — find out where they’re coming from, and learn as much as possible before you form your response.

Q8: Emotions in the Workplace

Q: Should people really bring their emotions into the workplace? Shouldn’t business be about merit and productivity?

A: Humans have emotions; there’s no way around them. People have emotional reactions, even at work — maybe even especially at work since we pour a fair amount of our lives into it. Ignoring feelings or casting them out of the workplace is not only inadvisable, it’s nearly impossible.

But there are more appropriate and less appropriate ways to handle them and address them at the workplace.

Here are a few pointers on sharing your emotions:

As a recipient of emotions, the main fear about allowing emotions into the workplace is that the only way to deal with someone’s feelings is to give them what they want. But addressing emotions in the workplace can 1) prevent them from overwhelming people at work and 2) favoring acknowledgement over “fixing” the feeling.

Q9: It Takes Too Much Time

Q: Who’s actually got the time to do this in real life?

A: No one. We’d all rather be doing anything else than struggling to learn about our annoying neighbors and why their dogs won’t stop barking. Difficult conversations are difficult — they’re emotionally exhausting, uncertain, and unappealing.

But life comes down to spending your time better. In situations where difficult conversations are needed, you’re most likely already spending time and energy on the issue. If we added up all the time we spend on issues complaining, replaying scenes in our head, and lying awake at night, the reality is that having a difficult conversation would probably save us time in the long run.

The more you practice the principles from this book, the faster and more adept you’ll get at having difficult conversations and the less time you’ll spend on them.

Q10: I Can’t Get Past the Identity Conversation

Q: I go back and forth between thinking I’m perfect or thinking I’m horrible, and I can’t seem to break out of that binary identity conversation. What should I do?

A: The Identity Conversation is the intersection of our natural wiring, past experiences, and how we interpret information. For the time being, we can’t change our wiring and we can’t change what’s happened in the past — but we can change how we interpret information, and what stories we tell ourselves about ourselves and our experiences.

Our identities are usually formed by our relationships to other people, but then they become second nature to us. And people don’t respond particularly well to change: if you’re the peacekeeper in your family and then suddenly start creating conflict by expressing your personal desires, chances are high that you’ll get negative feedback from your family, and feel pressured to return to your old identity. Personal issues we face are usually products of this warped identity experience.

Tips for Working on Identity

Explore where the identity came from, and reevaluate it. Sometime in your life, something or someone taught you to be the way you are. Who was it? What was the situation? What were the benefits of learning that way to be?

When we say you can change the story you tell yourself, there’s a limit on how much you can healthily do this. Processing your experiences and changing your story about them isn’t about creating new, fake stories to take their place. It’s about contextualizing the events that created this identity, acknowledging that we’re more complex than any one identity, and in some cases mourning for the way things played out.

Remember that humans are complex and flawed. We’ve all been lazy, and we’ve all been motivated. We’ve all shown strength and weakness. In fact, over the course of a day we exhibit thousands of opposite and contradictory behaviors.

We can help broaden our identity by creating positive experiences in the direction of our weaknesses.

Ask people to hold you accountable and reinforce behaviors you want to develop.

Lastly, treat yourself with empathy. Life is hard. We make mistakes. The more we can accept ourselves for the whole picture of who we are, good and bad, and forgive ourselves, the more balanced we’ll feel about ourselves and the more opportunities we’ll have for growth.

Exercise: Navigating the Three Conversations

Remember, it’s helpful to do some work on your own before heading into a difficult conversation. Use this exercise to help you work through a past or present issue — and come back to it anytime you find yourself approaching a difficult conversation.