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1-Page PDF Summary of Difficult Conversations

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.

But difficult conversations, if we engage in them successfully, are the mark of a healthy relationship. In fact, the success and survival of any relationship, business or personal, depends on the ability of those involved to master difficult conversations. Difficult Conversations will help you ask for that raise, bring up issues with your spouse, understand your kids better, and get to the bottom of your feud with your neighbor.

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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.

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PDF Summary Introduction to Difficult Conversations

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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...

PDF Summary Chapter 1: What Are Difficult Conversations?

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“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...

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

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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...

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PDF Summary Chapter 3: What Happened Mistake #2 - Assuming Intentions

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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.

  • For example, if your colleague questions your reasoning in a meeting, you assume it’s because they’re trying to embarrass you in front of the boss — but if you question your colleague’s reasoning in a meeting, you know it’s because you’re trying to be helpful.

Then, when we accuse someone of having bad intentions, they understandably get defensive....

PDF Summary Chapter 4: What Happened Mistake #3 - Blame

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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.

  • (Shortform example: We see this in corporations all the time — someone, usually a bigwig like a CEO, takes the fall for something that the corporation at large participates in. People want someone to blame, they blame the person in charge, they get rid of that person, then the system is allowed to continue in the same fashion.)

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.

  • Even though from our perspective the blame looks one-sided, in reality everyone has contributed in some way. For example, in baseball, think about a pitcher and a batter facing off. Whether the face-off results in a home run or a strikeout is the result of the interaction between the two individuals. You can focus...

PDF Summary Chapter 5: The Feelings Conversation

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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:

  • Sort out what your own feelings are.
  • Negotiate them with yourself first.
  • Share your feelings — not your judgments — with the other person.

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...

PDF Summary Chapter 6: The Identity Conversation

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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,...

PDF Summary Chapter 7: Whether to Start a Difficult Conversation

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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...

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PDF Summary Chapter 8: Beginning a Difficult Conversation

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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.

  • What is said: “I was upset by what you said to our boss about our work.” What is implied: “You are either a betraying scumbag, or you were dumb enough not to realize the ramifications.”
  • What is said: “If you move away, it’s going to tear the family apart.” What is implied: “You’re selfish and don’t care about the family.”

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...

PDF Summary Chapter 9: The Importance of Listening

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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...

PDF Summary Chapter 10: Uphold Your End of a Difficult Conversation

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Here are some phrases for starting productively:

  • “For me, what this is really about is…”
  • “What I’m feeling is…”
  • “What’s important to me is…”

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...

PDF Summary Chapter 11: Controlling a Difficult Conversation for a Better Outcome

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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.

  • For example, a mother reacted badly to her adopted daughter wanting to find her birth mother: “You won’t find what you’re looking for and you’ll just get hurt.” The daughter can use the And Stance to reframe this comment: “You might be right, I might put a ton of time and energy into it and not find anything, or find something that upsets me, and I still feel like I have to try. Here’s why…”

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...

PDF Summary Chapter 12: The Last Phase — Problem-Solving

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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.

  • For example, an employee who’s been asked to work an extra weekend might say, “I understand that you want someone to be able to deal with the supplier issue, but it seems to me that Bill, the assistant manager on the schedule this weekend, can handle it. But maybe you have reservations about Bill that could persuade me he’s not up to the challenge?”
  • In the same conversation, that employee might say, “I’ve offered plenty of good reasons why I don’t feel it makes sense for me to work the weekend, yet you don’t seem persuaded. Do you have reasons you haven’t expressed yet? Is there anything I could say to persuade you?”

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...

PDF Summary Appendix: Ten Common Questions About Difficult Conversations

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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...