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Summary of Difficult Conversations
Summary of Difficult Conversations


Difficult Conversations considers just how vital communication is across all parts of our life. Excellent communication is essential for formal negotiations but is also crucial for everyday interactions. Specifically, though, as humans, we struggle with certain types of conversation. Because of this, we avoid these difficult conversations even if they are essential for our or others’ success. Douglas Stone, Bruce Patton, and Sheila Heen use this book to shed light on why specific conversations are difficult and why we deal with them poorly. Finally, the book suggests how we can utilize specific techniques to have more productive discussions.

About the authors

This book is written by three authors who work and teach together at Harvard Law School. Specifically, Douglas Stone, Bruce Patton, and Sheila Sheen work on the Harvard Negotiation Project. This project primarily focuses on dealing with issues of negotiation and conflict resolution. Working on this project has undoubtedly guided the content of this book, as conflict resolution in some of the most difficult circumstances is their academic pursuit. 

The fundamentals

“Difficult conversations are almost never about getting the facts right. They are about conflicting perceptions, interpretations, and values”

– Douglas Stone

This book is based on the premise that we face difficult conversations every day. These difficult conversations include, for example, having to apologize to loved ones or telling your boss that you are looking for other jobs. Every day we have a decision to make: Do we avoid these difficult conversations, or do we tackle them head-on?

There is a wide range of conversations that can be considered difficult and will depend on the individual. Difficult conversations are not just limited to the highly common types of conversations about sexuality, race, gender, politics, and religion. They can be any conversation that makes us feel vulnerable, awkward, or uncomfortable. These are the conversations that we are most likely to put off and leave for another time, and even include things like returning an item you recently bought but without a receipt. 

Based on their time working on the Harvard Negotiation Project, authors Douglas Stone, Bruce Patton, and Sheila Heen have identified approaches that can be taken to make traditionally difficult conversations less stressful and more productive. Through their guidance, the authors believe that readers can learn to deal with these difficult conversations while treating the recipient of the conversation with decency and integrity. 

Sort Out the Three Types of Conversation

In the first chapter of this book, the authors outline how each difficult conversation has three hidden conversations underpinning it. This concept is something that the authors noticed after studying hundreds of conversations. Importantly, they also identified that if people can understand the structure of their difficult conversations, they can make them more productive. 

Type 1 – The What Happened Conversation

These conversations relate to disagreements over what happened, or what should have happened. This type of conversation can take many forms. For example, the conversation could consider one or multiple of the following: who said what, who did what, who’s right, who meant what, and who’s to blame. 

Type 2 – The Feelings Conversation

Additionally, every difficult conversation involves those involved wondering whether their feelings, in the moment, are valid. Should you be angry/upset? Is it fair if the other participant in the conversation does not acknowledge how you are feeling? Additionally, you might be wondering whether you have hurt the other participant’s feelings in the conversation. Emotions must be addressed in the conversation. 

Type 3 – The Identity Conversation

The identity conversation is the conversation we have with ourselves, rather than the conversation we have with others. The identity conversation is a conversation you have with yourself about what this situation means to you. With difficult conversations, we often second guess ourselves, considering whether we are coming across as competent, kind, and lovable. These conversations involve questioning our identity. We worry that these conversations will impact our self-image and our self-esteem.

Every single conversation involves confronting all three of these types of conversation. Each of them underpins difficult conversations and, therefore, we must learn how to manage each type simultaneously. 

The Learning Conversation

Whether we like to admit it or not, starting a difficult conversation can often be motivated by selfish reasons. We want to prove a point, give somebody a telling off, or ask something of the other person. However, understanding the mistakes frequently made within the three structures of difficult conversations should help you view difficult conversations differently. You will start to appreciate the complexity of the perceptions and intentions you and your fellow conversation participant hold. By doing this, you will no longer be using difficult conversations to deliver a message based on yourself. Instead, you will be sharing information and asking questions. All in all, your conversation will be moving towards a conversation that is based on learning. This type of conversation will help you solve the issues surrounding the what happened conversation. 

Instead of approaching difficult conversations believing that you are right, engaging in a learning conversation involves an acceptance that each participant will bring different information and perceptions to the table. Each of us has important information that we are, as of yet, unaware of. The goal of these difficult conversations should be to explore these differences in a productive way. 

Improving the What Happened Conversation

“Interpretations and judgments are important to explore. In contrast, the quest to determine who is right and who is wrong is a dead-end”

– Douglas Stone

The first tip provided by this book, so that you can start adopting learning conversations, is to put yourself in the other person’s shoes. It is often easy to finish a difficult conversation being confused about how irrational the other person is without even considering the situation from their perspective. You must learn to accept that the other participant is a different person with different perspectives; therefore, it is normal for them to have completely different conclusions. Differences in views are often due to you having differences in the information you have been exposed to. Therefore, you should avoid being offended by someone disagreeing with you and investigate whether the other person knows something that you don’t yet know. 

Secondly, the authors of this book encourage their readers to avoid assuming the other person has ill intentions. They provide an example of when a friend comments on how tired you are. Instead of seeing this as an insult, consider how your friend is probably just looking out for your health and wellbeing. They care for you. In sum, don’t always assume the worst of the participants in your conversations. 

Finally, you need to stop blaming others. If the other participant misunderstands you in a heated conversation, it isn’t necessarily solely their fault. Identify each person’s contributions in the conversation and take responsibility for working through the situation together, so that you can come to a mutual understanding.

Try and ask yourself the following questions:

  • Where did the miscommunication begin?
  • How did you both contribute to the mess?
  • What can you both do to move forward?

Improving the feelings conversation

“Receiving feedback sits at the intersection of these two needs—our drive to learn and our longing for acceptance”

– Douglas Stone

Controlling our feelings and emotions during a difficult conversation is harder than it sounds. Our emotions are often uncontrollable. We also suppress our true feelings when we feel embarrassed or hurt. Although the learning conversation can also help us address our feelings by acknowledging the importance of the other person’s emotions, expressed emotions, and unexpressed emotions, more tips can be utilized. 

Firstly, you must address your own emotions during difficult conversations. You must consider why you react the way you do within certain situations. For example, think about how you handled emotions as a child and whether this translates across to how you now handle difficult conversations. Plus, when you were younger and while growing up, how did those around you react to the way you handled difficult conversations emotionally? 

Having identified your natural emotional footprint during difficult conversations, it is essential to negotiate these emotions. Your perceptions and views underpin your emotions. Therefore, try and reconsider your perceptions within these difficult conversations. Rather than reacting automatically to difficult conversations, try and consider other perspectives. Even considering that there is an alternative perspective that is viable can calm down your automatic emotional responses to a difficult conversation. 

Finally, the authors recommend sharing your emotions. Your difficult conversations will remain unproductive if you are unwilling to share both the good and bad emotions associated with those conversations. Instead of just stating, “I am angry”, ask the other person why they find this conversation important and provide a deeper reason for the emotions you are currently feeling. Additionally, avoid accusatory exaggerations when explaining how the conversation is making you feel and why it is doing that. You do not want to be accusing the other person through claims of “you always” or “you never”. This is unfairly labeling the person. Instead, try and help the other person understand your viewpoint and your emotional reaction. Then, ask them how their viewpoint and emotional reaction differs, as well as why. 

Improving the Identity Conversation

“Working to keep negative information out during a difficult conversation is like trying to swim without getting wet”

– Douglas Stone

When considering identity, it is easy for us to list a few terms that describe how we identify ourselves, e.g., loyal, loving, or dependable. The issue with identity conversations is when we only utilize absolutes. Often we see ourselves as either being loyal or a cheater, loving or hateful, dependable, or unreliable. Identifies are never absolutes. The issue with identifying in absolutes, though, lies in difficult conversations. These conversations can quickly make us question our identity, and, as we identify through absolutes, we see difficult conversations as an attack on our self-image. For instance, perhaps you see yourself as a loyal person. Imagine receiving an offer to work at a competing firm, an offer that pays more and is in a role you would prefer. Accepting this offer could lead to you becoming confused about your identity if you work in absolutes. Accepting the position would make you a disloyal person, right? Instead, you should challenge that thought and consider how you have been loyal in the past, you have been grossly underpaid in your job, and you are prioritizing more loyalty to your family by providing for them through a better-paid job. This example showcases how identity is not all or nothing. 

These examples offer support for the book’s notion that we should stop wasting our time and energy on challenging others who question our self-identity. Instead, accept that you will make mistakes. Accept that your intentions are complex and that you have most probably contributed to this problem’s difficulty. Doing these things will help you accept that the other participants in difficult conversations can also make mistakes. 

As well as stopping yourself from working in absolutes, the book also encourages its readers to remind themselves that they cannot control another person’s actions. Plus, you can only control the way you react to the person’s actions. You can imagine how the other person might respond and how these responses might question your identity. Also, try and think of the conversation on balance. Taken in the context of a longer scale of time, such as in 3 months or 10 years’ time, this conversation will probably be unimportant. Therefore, instead, use these conversations as a time to learn rather than something to place all your importance. 

Finally, the book recommends sometimes taking a break from a difficult conversation. It is easy to become emotionally overwhelmed during difficult conversations, as these conversations are often linked with both of your identities. If you feel overwhelmed, you should ask the other participant for some time to think about what they have said. 

Tell the Third Story

“Explicit disagreement is better than implicit misunderstanding.”

– Douglas Stone

When beginning a difficult conversation, it is hugely important that you remember to never start with your side of the story. Starting with our story risks threatening the self-image of the other person. Instead of telling the story from your point of view, or their point of view, start the story by explaining the situation from an impartial observer’s perspective. Speak objectively about the situation. After you have done this, you can then extend an invitation to the person you want to have a conversation with, so that the conversation starts with a mutual understanding of solving a problem. This mutual understanding allows the conversation to start without judgment and for it to be framed like you are working together to find a solution. 

The conversation should then start with you explaining how you want to understand their perspective better. Try and emphasize how you want to come to an agreement together, that you want their help to make the outcome a productive one. 

Finally, make sure that you are persistent. It is likely that defensiveness will still creep into the conversation. Be open to these responses and let them share their defensive emotions, and then you can share yours. Make sure you listen to the other person’s responses, demonstrating that you understand what they are saying.

Final points and the 5 steps to successful difficult conversations

As humans, we often shy away from difficult conversations. However, they are some of the most important conversations, and we just need to approach them in the right way to make them productive. Try and transform each conversation into a learning conversation. Accept that others will have a different perspective. Remember that each person has strengths that will help make the conversation a productive one. Recognize the emotions that you often experience during difficult conversations, consider why this might be, and learn to share them. The other person’s emotions are just as valid as yours. Finally, remember that your identity does not work in absolutes, and it can also change. Rather than becoming immediately defensive when something in a difficult conversation challenges your identity, try and consider if what they are saying is true and, if it is, own up to it. 

Before every difficult conversation, make sure that you have in mind the following points:

  1. Prepare yourself for the conversation by considering the three conversations for both sides. So, think about what happened from both points of view, be clear on your emotions, and ground your identity
  2. Decide whether it is even worth raising the conversation. For it to be worthy, it must be underpinned by good purposes. These are learning, sharing, and problem-solving. Avoid difficult conversations that are merely based upon blaming and judging others
  3. If you decide that the conversation is worth engaging with, make sure you start with the third story. Start the conversation as an impartial observer and move towards inviting them to join you in solving the problem
  4. Explore their three stories, and then yours. If the conversation goes off-course, then make sure you reframe it back on track
  5. Problem-solve throughout the conversation. For the conversation to be productive, you should identify things that could solve both sides and ways in which future conversations could be engaged in productively

Related Books

Crucial Conversations

Nonviolent Conversation

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