Difficult Conversations - Deepstash
Difficult Conversations

Difficult Conversations

Douglas Stone, Bruce Patton, Sheila Heen


Handling Difficult People

Learn more about communication with this collection

How to communicate effectively with difficult people

How to handle conflict

How to stay calm under pressure

Handling Difficult People

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8 mins to read

The Fundamentals

The book is based on the premise that we face difficult conversations daily. For example, apologizing to loved ones or telling your boss that you are looking for other jobs. Daily we have a decision to make: Do we avoid these difficult conversations, or do we tackle them head-on?


3.18K reads

Various conversations can be considered difficult, and these will depend on the individual. Difficult conversations are not solely limited to common 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 likely to put off and leave for another time. For example, returning an item you recently bought can be a difficult conversation


2.29K reads

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. 


2.06K reads

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: who said what, who did what, who’s right, who meant what, and who’s to blame. 


2.12K reads

Type 2 – The Feelings Conversation

Additionally, every difficult conversation involves those involved wondering whether their feelings are valid. Should you be angry/upset? Is it reasonable 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. 


1.83K reads

Type 3 – The Identity Conversation

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

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


1.58K reads

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 difficult conversations should help you view them 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.


1.36K reads

Instead, you will be sharing information and asking questions. All in all, your conversation will be moving towards a conversation based on learning. This type of conversation will help you solve the issues surrounding the what happened conversation. 

You shouldn't approach conversations believing you are correct. engage in a learning conversation that involves accepting that each participant will bring different information & perceptions to the table. Each of us has essential information that we are unaware of. REMEMBER: the goal is to explore these differences productively. 


1.17K reads

Improving the What Happened Conversation

First, Put yourself in the other person’s shoes. It's often easy to finish a difficult conversation confused about how irrational that person is without considering their perspective. You must learn to accept that the other participant is a different person with a different perspective. Therefore, it is normal for them to have inconsistent conclusions. View differences are often due to differences in the information you have been exposed to. Therefore, you should avoid being offended by someone who disagrees with you & investigate whether the other person knows something you don’t yet know. 


1.05K reads

Secondly, this book’s authors 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 perceiving this as an insult, consider how your friend is looking out for your health and well-being. They care for you. In sum, don’t always assume the worst of the participants in your conversations. 


944 reads

Finally, you need to stop blaming others. If the other participant misunderstands you in a heated conversation, it isn’t necessarily their fault. Identify each person’s contributions in the conversation and take responsibility for working through the situation together. Adopting this approach will allow you to come to an understanding.


952 reads

Try to 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?


1K reads

Improving the Feelings Conversation

Identify Your Emotional Footprint

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. The learning conversation can help us address our feelings by acknowledging the importance of expressed and unexpressed emotions. However, this conversation requires specific skills. 


890 reads

Firstly, you must address your own emotions during difficult conversations. 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 aligns with how you now handle difficult conversations. Plus, consider how those around you reacted to how you handled difficult conversations when you were younger. 


842 reads

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


754 reads

Share Your Emotions

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. Do not just state, “I am angry.” Instead, ask the other person why they find this conversation essential and provide a deeper reason for your emotions. Additionally, avoid accusatory exaggerations when explaining how the conversation makes you feel and why you feel this way.


717 reads

You do not want to be accusing the other person through claims of “you always” or “you never.” These statements are unfairly labeling the person. Instead, try to 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. 


704 reads

Improving the Identity Conversation

Avoid Absolutes With Identity

When considering identity, it is easy for us to list a few terms that describe how we identify ourselves. The issue with identity conversations is when we only utilize absolutes. Often we perceive ourselves as either being loyal or a cheater, loving or hateful. Identities are never absolutes. Difficult conversations can quickly make us question our identity. Hence, as we identify through absolutes, we visualize difficult conversations as an attack on our self-image.


681 reads

Perhaps you consider yourself a loyal person. Imagine receiving an offer to work at a high-salaried competing firm in a more enjoyable role. Accepting this offer could lead you to become confused about your identity if you work in absolutes. Accepting the position would make you disloyal, right? Instead, you should challenge that thought. Consider how you've been loyal in the past & still been grossly underpaid in your job. Plus, you would be prioritizing more loyalty to your family by providing for them through a better-paid job. The e.g - showcases how identity is not all or nothing. 


620 reads

Mistakes are Inevitable

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 probably contributed to this problem’s difficulty. Doing this will help you accept that the other participants can also make mistakes. 


620 reads

The authors encourage the readers to remind themselves that they cannot control another person’s actions. Instead, 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 to review the conversation on balance. This conversation will probably be unimportant in the long-term. Therefore, instead, use these conversations to learn rather than somewhere to place all your importance. 


595 reads

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. 


595 reads

Tell the Third Story

When beginning a difficult conversation, you must 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, start the story by explaining the situation from an impartial observer’s perspective. Speak objectively about the situation. 


640 reads

After you have done this, you can extend an invitation to the person you want to have a conversation with. In this way, you start the conversation with an understanding of solving a problem. This understanding allows the conversation to start without judgment. Plus, the conversation will be framed like you are working together to find a solution. 


610 reads

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

Finally, make sure that you are persistent. Likely, 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. Ensure you listen to the other person’s responses, demonstrating that you understand what they are saying.


567 reads

Final Points and the Five Steps to Successful Difficult Conversations

Final Points

As humans, we often shy away from difficult conversations. However, they are some of the most important conversations. We need to approach these conversations in the right way to make them productive. Try to transform each conversation into a learning conversation. Accept that others will have a different perspective. Remember, each person has strengths that will help make the conversation a productive one.


582 reads

Recognize the emotions 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. 


562 reads

The Five Steps to Successful Difficult Conversations

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 for blaming and judging others.


589 reads

3. If you decide 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 be sure you reframe it back on track.

5. Problem-solve throughout the conversation. Identify ideas that could solve both sides and ways in which future conversations could be engaged in productively.


615 reads



Book summaries mostly ...


This book is based on the premise that we face difficult conversations daily. Have a read

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