Difficult Conversations - Deepstash
Difficult Conversations


7.47K reads

Difficult Conversations

by Douglas Stone, Bruce Patton, Sheila Heen

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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?


1.04K reads

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. 


544 reads

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. 


573 reads

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. 


498 reads

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. 


385 reads

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.


322 reads

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. 


236 reads

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. 


200 reads

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.


149 reads

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.


132 reads

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. 


118 reads

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. 


133 reads

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.


127 reads

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.


129 reads


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• Book summaries, mostly •


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