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Difficult Conversations: How to Discuss What Matters Most

Compiled by Chuck Olson

Title: Difficult Conversations: How to Discuss What Matters Most

Author: Douglas Stone, Bruce Patton, Shiela Heen

Copyright Date: 1999

Let’s cut to the chase.

Reality check #1: Life is full of difficult conversations.

Reality check #2: Wise is the person who owns a toolkit for doing them well.

Enter Difficult Conversations: How To Discuss What Matters Most by Douglas Stone, Bruce Patton, and Sheila Heen. This is a veritable handbook of clear thinking and practical advice. It is filled with constructs and pathways both to understand and to facilitate the challenging discussions that show up with remarkable regularity at the doorstep of every leader.

In these BookNotes, I have attempted to capture many of the takeaways from this well-written book.

Book Description:

We attempt or avoid difficult conversations every day—whether dealing with an underperforming employee, disagreeing with a spouse, or negotiating with a client. From the Harvard Negotiation Project, the organization that brought you Getting to Yes, Difficult Conversations provides a step-by-step approach to having those tough conversations with less stress and more success. You’ll learn how to: 
• Decipher the underlying structure of every difficult conversation 
• Start a conversation without defensiveness 
• Listen for the meaning of what is not said 
• Stay balanced in the face of attacks and accusations 
• Move from emotion to productive problem solving

Book Quotes:

We don’t outgrow difficult conversations or get promoted past them. The best workplaces and most effective organizations have them. The family down the street that everyone thinks is perfect has them. Loving couples and lifelong friends have them. In fact, we can make a reasonable argument that engaging (well) in difficult conversations is a sign of health in a relationship. Relationships that deal productively with the inevitable stresses of life are more durable; people who are willing and able to “stick through the hard parts” emerge with a stronger sense of trust in each other and the relationship, because now they have a track record of having worked through something hard and seen that the relationship survived.


The ability to manage difficult conversations effectively is foundational, then, to achieving almost any significant change. LOCATION: 161

Delivering a difficult message is like throwing a hand grenade. Coated with sugar, thrown hard or soft, a hand grenade is still going to do damage. Try as you may, there’s no way to throw a hand grenade with tact or to outrun the consequences. And keeping it to yourself is no better. Choosing not to deliver a difficult message is like hanging on to a hand grenade once you’ve pulled the pin. LOCATION: 337

It is true that some situations are unlikely to improve regardless of how skilled you become. The people involved may be so emotionally troubled, the stakes so high, or the conflict so intense that a book – or even professional intervention – is unlikely to help. However, for every case that is truly hopeless, there are a thousand that appear hopeless but are not. LOCATION: 367

What can we suggest that you haven’t already thought of? Probably quite a bit. Because the question isn’t whether you’ve been looking hard enough for the “answer” to difficult conversations, it’s whether you’ve been looking in the right places. At heart, the problem isn’t in your actions, it’s in your thinking. So long as you focus only on what to do differently in difficult conversations, you will fail to break new ground. LOCATION: 375

So it is best to keep your goals realistic. Eliminating fear and anxiety is an unrealistic goal. Reducing fear and anxiety and learning how to manage that which remains are more obtainable. Achieving perfect results with no risk will not happen. Getting better results in the face of tolerable odds might. And that, for most of us, is good enough. LOCATION: 387

In studying hundreds of conversations of every kind we have discovered that there is an underlying structure to what’s going on, and understanding this structure, in itself, is a powerful first step in improving how we deal with these conversations. It turns out that no matter what the subject, our thoughts and feelings fall into the same three categories, or “conversations.” And in each of these conversations we make predictable errors that distort our thoughts and feelings, and get us into trouble. LOCATION: 438

  1. The “What Happened?” Conversation. Most difficult conversations involve disagreement about what has happened or what should happen. LOCATION: 443
  2. The Feelings Conversation. Every difficult conversation also asks and answers questions about feelings. LOCATION: 447
  3. The Identity Conversation. This is the conversation we each have with ourselves about what this situation means to us. We conduct an internal debate over whether this means we are competent or incompetent, a good person or bad, worthy of love or unlovable. LOCATION: 451

The “What Happened?” Conversation is where we spend much of our time in difficult conversations as we struggle with our different stories about who’s right, who meant what, and who’s to blame. LOCATION: 471

The point is this: difficult conversations are almost never about getting the facts right. They are about conflicting perceptions, interpretations, and values. LOCATION: 482

Interpretations and judgments are important to explore. In contrast, the quest to determine who is right and who is wrong is a dead end. LOCATION: 487

In the “What Happened?” Conversation, moving away from the truth assumption frees us to shift our purpose from proving we are right to understanding the perceptions, interpretations, and values of both sides. It allows us to move away from delivering messages and toward asking questions, exploring how each person is making sense of the world. LOCATION: 489

The second argument in the “What Happened?” Conversation is over intentions – yours and mine…What I think about your intentions will affect how I think about you and, ultimately, how our conversation goes. LOCATION: 495

The error we make in the realm of intentions is simple but profound: we assume we know the intentions of others when we don’t. Worse still, when we are unsure about someone’s intentions, we too often decide they are bad. LOCATION: 496

The truth is, intentions are invisible. We assume them from other people’s behavior. In other words, we make them up, we invent them. But our invented stories about other people’s intentions are accurate much less often than we think. Why? Because people’s intentions, like so much else in difficult conversations, are complex. LOCATION: 498

But talking about fault is similar to talking about truth — it produces disagreement, denial, and little learning. It evokes fears of punishment and insists on an either/or answer. Nobody wants to be blamed, especially unfairly, so our energy goes into defending ourselves. LOCATION: 511

Difficult conversations are not just about what happened; they also involve emotion. The question is not whether strong feelings will arise, but how to handle them when they do. LOCATION: 526

The problem with this reasoning is that it fails to take account of one simple fact: difficult conversations do not just involve feelings, they are at their very core about feelings. Feelings are not some noisy byproduct of engaging in difficult talk, they are an integral part of the conflict. Engaging in a difficult conversation without talking about feelings is like staging an opera without the music. You’ll get the plot but miss the point. LOCATION: 538

Of the Three Conversations, the Identity Conversation may be the most subtle and the most challenging. But it offers us significant leverage in managing our anxiety and improving our skills in the other two conversations…In short: before, during, and after the difficult conversation, the Identity Conversation is about what I am saying to myself about me. LOCATION: 557

Instead of wanting to persuade and get your way, you want to understand what has happened from the other person’s point of view, explain your point of view, share and understand feelings, and work together to figure out a way to manage the problem going forward. In so doing, you make it more likely that the other person will be open to being persuaded, and that you will learn something that significantly changes the way you understand the problem. LOCATION: 591

But arguing is not only a result of our failure to see that we and the other person are in different stories – it is also part of the cause. Arguing inhibits our ability to learn how the other person sees the world. When we argue, we tend to trade conclusions – the “bottom line” of what we think. LOCATION: 674

Arguing creates another problem in difficult conversations: it inhibits change. Telling someone to change makes it less rather than more likely that they will. This is because people almost never change without first feeling understood. LOCATION: 681

There’s only one way to come to understand the other person’s story, and that’s by being curious. Instead of asking yourself, “How can they think that?!” ask yourself, “I wonder what information they have that I don’t?” Instead of asking, “How can they be so irrational?” ask, “How might they see the world such that their view makes sense?” Certainty locks us out of their story; curiosity lets us in. LOCATION: 808

The mere act of understanding someone else’s story doesn’t require you to give up your own. The And Stance allows you to recognize that how you each see things matters, that how you each feel matters. Regardless of what you end up doing, regardless of whether your story influences theirs or theirs yours, both stories matter…The And Stance gives you a place from which to assert the full strength of your views and feelings without having to diminish the views and feelings of someone else. Likewise, you don’t need to give up anything to hear how someone else feels or sees things differently. LOCATION: 860

The conclusions we draw about intentions based on the impact of others’ actions on us are rarely charitable. LOCATION: 955

Interestingly, when people take on the job of thinking hard about their own intentions, it sends a profoundly positive message to the other person about the importance of the relationship. After all, you’d only do that kind of hard work for somebody who matters to you. LOCATION: 1041

Separating impact from intentions requires us to be aware of the automatic leap from “I was hurt” to “You intended to hurt me.” LOCATION: 1062

When you share your assumptions about their intentions, simply be clear that you are sharing assumptions – guesses – and that you are sharing them for the purpose of testing whether they make sense to the other person. LOCATION: 1092

Focusing on blame is a bad idea because it inhibits our ability to learn what’s really causing the problem and to do anything meaningful to correct it. And because blame is often irrelevant and unfair. The urge to blame is based, quite literally, on a misunderstanding of what has given rise to the issues between you and the other person, and on the fear of being blamed. LOCATION: 1144

Blame is about judging, and looks backward…Contribution is about understanding, and looks forward. LOCATION: 1164

As a rule, when things go wrong in human relationships, everyone has contributed in some important way. LOCATION: 1214

One of the most common contributions to a problem, and one of the easiest to overlook, is the simple act of avoiding. You have allowed the problem to continue unchecked by not having addressed it earlier. LOCATION: 1329

The flip side of not bringing something up is having an interpersonal style that keeps people at bay. You contribute by being uninterested, unpredictable, short-tempered, judgmental, punitive, hypersensitive, argumentative, or unfriendly. Of course, whether you are really any of these things or intend this impact is not the point. If someone experiences you this way, they are less likely to raise things with you, and this becomes part of the system of avoidance between you. LOCATION: 1344

Taking responsibility for your contribution up front prevents the other person from using it as a shield to avoid a discussion of their own contribution. LOCATION: 1469

Feelings are too powerful to remain peacefully bottled. They will be heard one way or another, whether in leaks or bursts. And if handled indirectly or without honesty, they contaminate communication. LOCATION: 1505

The problem is that when feelings are at the heart of what’s going on, they are the business at hand and ignoring them is nearly impossible. In many difficult conversations, it is really only at the level of feelings that the problem can be addressed. LOCATION: 1535

Unspoken feelings can color the conversation in a number of ways. They alter your affect and tone of voice. They express themselves through your body language or facial expression. They may take the form of long pauses or an odd and unexplained detachment. You may become sarcastic, aggressive, impatient, unpredictable, or defensive. Studies show that while few people are good at detecting factual lies, most of us can determine when someone is distorting, manufacturing, or withholding an emotion. That’s because, if clogged, your emotional pipes will leak. LOCATION: 1554

It’s hard to hear someone else when we are feeling unheard, even if the reason we feel unheard is that we have chosen not to share. Our listening ability often increases remarkably once we have expressed our own strong feelings. LOCATION: 1577

Feelings are more complex and nuanced than we usually imagine. What’s more, feelings are very good at disguising themselves. Feelings we are uncomfortable with disguise themselves as emotions we are better able to handle; bundles of contradictory feelings masquerade as a single emotion; and most important, feelings transform themselves into judgments, accusations, and attributions. LOCATION: 1598

While there may be common themes, your emotional footprint will be different in different relationships. Your awareness of and ability to express emotions will vary depending on whether you are with your mother, your best friend, your boss, or the person sitting next to you on the plane. LOCATION: 1609

Too often we confuse being emotional with expressing emotions clearly. They are different. You can express emotion well without being emotional, and you can be extremely emotional without expressing much of anything at all. Sharing feelings well and clearly requires thoughtfulness. LOCATION: 1785

What does it mean to acknowledge someone’s feelings? It means letting the other person know that what they have said has made an impression on you, that their feelings matter to you, and that you are working to understand them. LOCATION: 1851

There are probably as many identities as there are people. But three identity issues seem particularly common, and often underlie what concerns us most during difficult conversations: Am I competent? Am I a good person? Am I worthy of love? LOCATION: 1897

A good rule to follow is: If you’re going to talk, talk. Really talk. And if you’re really going to talk, you can’t do it on the fly. You have to plan a time to talk. You have to be explicit about wanting ten minutes or an hour to discuss something that is important to you. You can’t have a real conversation in thirty seconds, and anything less than a real conversation isn’t going to help. If hit-and-run is all you can muster, it’s better not to raise the issue at all. LOCATION: 2293

In addition to your story and the other person’s story, every difficult conversation includes an invisible Third Story. The Third Story is the one a keen observer would tell, someone with no stake in your particular problem. LOCATION: 2436

At some level you know this, which is one of the big reasons asking for a raise causes anxiety. Try replacing “I think I deserve a raise” with “I’d like to explore whether a raise for me might make sense. From the information I have, I think I deserve one. [Here’s my reasoning.] I wonder how you see it?” This seemingly small change in how you begin should not only reduce stress but also get the conversation off on an even keel. In the end, you may learn that you don’t deserve a raise, or that you deserve an even bigger one than you initially thought you did. LOCATION: 2588

The easiest approach is first to talk about how to talk. Treat “the way things usually go when we try to have this conversation” as the problem, and describe it from the Third Story: “I know that in the past when I’ve raised the question of who’s getting promoted and what role race plays in that process, people have sometimes felt accused or exasperated. I don’t mean to accuse anyone, or to make people feel uncomfortable. At the same time, it feels important to me to discuss. I’m wondering whether we could talk about how we each react to that conversation, and whether there’s a better way we could address these issues?” LOCATION: 2597

Listening well is one of the most powerful skills you can bring to a difficult conversation. It helps you understand the other person. And, importantly, it helps them understand you. LOCATION: 2653

The problem is this: you are taught what to say and how to sit, but the heart of good listening is authenticity. People “read” not only your words and posture, but what’s going on inside of you. If your “stance” isn’t genuine, the words won’t matter. What will be communicated almost invariably is whether you are genuinely curious, whether you genuinely care about the other person. If your intentions are false, no amount of careful wording or good posture will help. If your intentions are good, even clumsy language won’t hinder you. LOCATION: 2725

Listening is only powerful and effective if it is authentic. Authenticity means that you are listening because you are curious and because you care, not just because you are supposed to. The issue, then, is this: Are you curious? Do you care? LOCATION: 2729

Perhaps surprisingly, our advice is not to turn off your internal voice, or even to turn it down. You can’t. Instead, we urge you to do the opposite – turn up your internal voice, at least for the time being, and get to know the kinds of things it says. In other words, listen to it. Only when you’re fully aware of your own thoughts can you begin to manage them and focus on the other person. LOCATION: 2738

Remind yourself that the task of understanding the other person’s world is always harder than it seems. Remind yourself that if you think you already understand how someone else feels or what they are trying to say, it is a delusion. Remember a time when you were sure you were right and then discovered one little fact that changed everything. There is always more to learn. Remind yourself of the depth, complexities, contradictions, and nuances that make up the stories of each of our lives. LOCATION: 2753

In addition to the stance of curiosity, there are three primary skills that good listeners employ: inquiry, paraphrasing, and acknowledgment. LOCATION: 2790

This illustrates an important rule about inquiry: If you don’t have a question, don’t ask a question. Never dress up an assertion as a question. Doing so creates confusion and resentment, because such questions are inevitably heard as sarcastic and sometimes mean-spirited. LOCATION: 2798

The second skill a good listener brings to the conversation is paraphrasing. Paraphrasing is when you express to the other person, in your own words, your understanding of what they are saying. There are two significant benefits to paraphrasing…First, paraphrasing gives you a chance to check your understanding…Second, paraphrasing lets the other person know they’ve been heard. LOCATION: 2889

It is a fundamental rule: feelings crave acknowledgment. Like free radicals, feelings wander around the conversation looking for some acknowledgment to hook onto. They won’t be happy until they get it, and nothing else will do. LOCATION: 2925

Ultimately, of course, people want their problems addressed. Questions like “What are we going to do about this?” “Why did you do what you did?” “How do you explain what happened?” are important. But order matters. Whether they say it or not, often people need some acknowledgment of feelings before they can move on to the “What Happened?” Conversation. LOCATION: 2948

While you may not agree with the substance of what the other person is saying, you can still acknowledge the importance of their feelings. LOCATION: 2961

The deepest form of understanding another person is empathy. Empathy involves a shift from my observing how you seem on the outside, to my imagining what it feels like to be you on the inside, wrapped in your skin with your set of experiences and background, and looking out at the world through your eyes. LOCATION: 2975

Listening to the other person’s story with a real desire to learn what they are thinking and feeling is a crucial next step. But understanding them is rarely the end of the matter; the other person also needs to hear your story. You need to express yourself. LOCATION: 2985

If you are sometimes lonely or despondent and never share this with those close to you, then you deny them the chance to come to know a part of you. You presume that they will not respect or like or admire you as much if they knew the way you really think and feel. But it’s hard to present only this sanitized version of yourself. Often, to hide parts of who we are, we end up hiding all of who we are. And so we present a front that appears lifeless and removed. LOCATION: 3035

Three guidelines for telling your story with clarity:

  1. Don’t present your conclusions as the truth
  2. Share where your conclusions come from
  3. Don’t exaggerate with “always” and “never”: give them room to change


Explaining your story clearly is a first step toward being understood. But don’t expect instant success. Real understanding may take some back and forth. If the other person seems puzzled or unpersuaded by your story, rather than putting it more forcefully or trying to tell it in a different way, ask how they see it. In particular, ask how they see it differently. LOCATION: 3218

No matter how good you get at reframing, the single most important rule about managing the interaction is this: You can’t move the conversation in a more positive direction until the other person feels heard and understood. And they won’t feel heard and understood until you’ve listened. When the other person becomes highly emotional, listen and acknowledge. LOCATION: 3316

A Difficult Conversations Checklist

Step 1: Prepare by Walking Through the Three Conversations

  1. Sort out What Happened.
  • Where does your story come from (information, past experiences, rules)? Theirs?
  • What impact has this situation had on you? What might their intentions have been?
  • What have you each contributed to the problem?
  1. Understand Emotions.
  • Explore your emotional footprint, and the bundle of emotions you experience. 3. Ground Your Identity.
  • What’s at stake for you about you? What do you need to accept to be better grounded?

Step 2: Check Your Purposes and Decide Whether to Raise the Issue

  • Purposes: What do you hope to accomplish by having this conversation? Shift your stance to support learning, sharing, and problem-solving.
  • Deciding: Is this the best way to address the issue and achieve your purposes? Is the issue really embedded in your Identity Conversation? Can you affect the problem by changing your contributions? If you don’t raise it, what can you do to help yourself let go?

Step 3: Start from the Third Story

  1. Describe the problem as the difference between your stories. Include both viewpoints as a legitimate part of the discussion.
  2. Share your purposes.
  3. Invite them to join you as a partner in sorting out the situation together.

Step 4: Explore Their Story and Yours

  • Listen to understand their perspective on what happened. Ask questions. Acknowledge the feelings behind the arguments and accusations. Paraphrase to see if you’ve got it. Try to unravel how the two of you got to this place.
  • Share your own viewpoint, your past experiences, intentions, feelings.
  • Reframe, reframe, reframe to keep on track. From truth to perceptions, blame to contribution, accusations to feelings, and so on.

Step 5: Problem-Solving

  • Invent options that meet each side’s most important concerns and interests.
  • Look to standards for what should happen. Keep in mind the standard of mutual caretaking; relationships that always go one way rarely last.
  • Talk about how to keep communication open as you go forward.



Chuck Olson

As founder and president of Lead With Your Life, Dr. Chuck Olson is passionate about inspiring, resourcing and equipping Kingdom leaders to lead from the inside out.  To lead, not with the external shell of positions, achievements or titles, but from an internal commitment to a deep, abiding and transparent relationship with Jesus. Serving as a pastor and leadership coach for over forty years, Chuck has a track record of building these truths deep into the lives of both ministry and marketplace leaders.

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