Difficult Conversations: Summary Review & Takeaways

This is a summary review of Difficult Conversations containing key details about the book.

What is Difficult Conversations About?

Difficult Conversations provides a step-by-step approach to having those tough conversations with less stress and more success. Readers will 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, and move from emotion to productive problem-solving.

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Who is the Author of Difficult Conversations?

Douglas Stone is the principal at Triad (an international corporate education and organizational consulting firm based in Cambridge, MA), and a Lecturer on Law at Harvard Law School.

Sheila Heen is an author and the CEO of Triad Consulting in Harvard Square, where she specializes in working with executive teams on issues where there is strong disagreement and emotions run high. She has worked with corporate clients on six continents, with the US White House, the Singapore Supreme Court, and with theologians with disagreements on the nature of truth and God.

What are the main summary points of Difficult Conversations?

Here are some key summary points from the book:

  • Transformation requires difficult conversations. They are opportunities for growth and elevation.
  • There’s no point in avoiding difficult conversations. They are part of life and pillars for any successful and healthy relationship—business or personal.
  • Difficult conversations are difficult because of how we approach them. We first need to change how we think about them.
  • We’re jumping into conclusions and judgments too fast. Our ‘shoulds’ or ‘shouldn’ts’ are what get us into trouble in arguments. An argument occurs when two people’s shoulds clash.
  • In any difficult conversation, no one person is to fully blame: Both parties contributed to the issue in one way or another.
  • Generally speaking there are three types of difficult conversations:
    - The “What Happened Conversation”,
    - The Feelings Conversation”,
    - and “The Identity Conversation”
  • The “What Happened Conversation” is about who’s “right” and who’s “wrong.” We often view ourselves as victims and thus find ourselves blaming the other for their wrongdoings.
  • The antidote to the “What Happened Conversation” is to take ownership and focus on the ways we might have contributed to the situation. That way, the other person has less room to get defensive.
  • The “Feelings Conversation” is about both parties' emotions and their validity. Most people go into difficult conversations suppressing their feelings, or alternatively, convinced that their feelings are the only ones that matter.
  • The antidote to the “feelings conversation” is becoming more aware of our emotional footprint — what emotions we feel comfortable and uncomfortable acknowledging, what emotions we bring from the past, and whether the stories we’re telling ourselves are empowering or true.
  • In this context, It’s important to remember that all emotions are valid. It’s about how we use them in more constructive and healthy ways.
  • The “Identity Conversation” is about the internal conversation that each party has with himself. In general, identity issues center on three underlying questions: “Am I competent?” “Am I a good person?”, and “Am I worthy of love?” — we’re usually worried that the answer to each question is no.
  • The antidote to the “Identity Conversation” is to let go of harsh judgments and absolutes and build a more grounded identity, where we know our value and where we know we’re worthy of love, no matter what the situation is. Yes, we may have made a mistake, but we are competent, good, and loveable.

What are key takeaways from Difficult Conversations?

Takeaway#1. Stop Turning a Blind Eye

Some conversations are more difficult to have than others. This is especially true when you raise a challenging subject such as religion, race, sexuality, politics, or the recent behavior of your partner, family member, or friend.

Difficult conversations can leave us feeling vulnerable when we’re unsure of how the other person will react (or indeed, when we’re sure they will react badly!). This is why your brain will go round in circles pondering, “Should I or shouldn’t I raise this subject?”, after all, sometimes it’s better to turn a blind eye and put up with what’s bugging you right? Wrong!

Communication is the key to getting what you want. So, you almost always want to have that difficult conversation. Sometimes, the other person may not be aware of the situation or how their behavior is affecting you. Those situations can l be resolved quite easily. Other times conversations are more challenging but absolutely critical. Rather than keeping quiet, learn to keep the peace by facing difficult conversations head on and watch your life improve.

Takeaway#2. The Blame Game Has To Stop

Every difficult conversation consists of 3 concurrent elements; blame, feelings, and identity.

Blame comes up when you have the ‘What Happened?’ conversation in which you argue over who is right and who is wrong whilst assuming the other person’s intentions. Each individual thinks they’re right and their opposition wrong. Claims and accusations made with the focus on ill intent spiral so that blame and guilt can be applied to a past event or an indirect result of whatever is being argued over.

Next, the emotions come flying in with the ‘Feelings Conversation’. This brings up feelings of anger, fear, hurt, disappointment, disrespect, and/or frustration.

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Finally, there’s the question of character, which you likely want to keep intact. This is where the ‘Identity Conversation’ comes into play. You may elect to avoid a difficult conversation just to maintain your self-image as a good person , rather than as someone who is nasty or aggressive. There is, however, a way to have this conversation without, feeling like your character is being attacked.

Takeaway#3. Turning a Difficult Conversation into a Learning Conversation

When you’re curious rather than in attack, blame, or victim mode, you can turn the conversation into a learning experience without needing to doubt yourself or silence your emotions.

The ‘What Happened’ conversation becomes a learning experience that halts feelings of offense when you pause to consider where your opponent is coming from. Instead of thinking of the other person as incredibly irrational, marvel at how they can look at the same situation and come up with a completely different conclusion. Pause to consider what their perspective looks like and if they know something you don’t. Don’t jump to conclusions and presume that the other person has bad intentions. When you feel insulted, look at the other person's actions rather than their words. For example, if your friend said you look tired, could they just be showing concern and wanting to know that you’re ok?

Blame is a tactic that does more harm than good, because it is based on judgment that, then, incites resentment in the other person. So instead of playing the blame game, work out everyone’s contribution to the situation by sitting down and discussing the situation calmly and rationally. Ask “How did we get into this situation” and “How can we change this situation moving forward?”

Takeaway#4. Explore, Negotiate, and Share Your Feelings

Emotions are tricky to deal with and even harder to name and share. Embarrassment is especially tricky when we feel embarrassed as this usually causes us to suppress our feelings. By exploring our ‘emotional footprint’ and learning what’s happening deep down the “Feelings Conversation” can be turned into a “Learning Conversation”.

Many of us have learned as children that it’s ok to express some emotions but not others. Consider how you learned to categorize some feelings as ‘inappropriate’. Did your parents tell you off when you cried? When you were angry? When you were needy? Learn to identify your feelings by being curious and by naming them as they arise.

For example, if you feel you’re always fighting with your partner or are resentful that they are always nagging you, ask yourself “Do I make assumptions about his/her intentions?” “Does he/she do it because they want to punish me or because they have my best interests at heart?” Do I blame my partner and ignore my own impact?” Address your assumptions and the situation will shift so that your emotions can too.

You want to share your feelings with the other person, both good and bad in a thoughtful, calm, and controlled manner. Don’t throw your pent-up emotions at them as this only makes the situation worse. Don’t just say “I’m angry at you”, say “I’m grateful for your concern, but I’m also angry/annoyed at you because I...”

Takeaway#5. Nothing Is Set In Stone

Minus the occasional blind spot, you know who you are as a person but probably judge yourself in absolute terms - kind or mean, calm or angry, capable or incapable, loved or unloved. Absolute terms are damaging and can confuse you about your identity. Always remember the various shades of gray. Nothing is black or white. Your identity is made up of many components.

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Think about the traits or characteristics that are important to you--those that you’re proud of and don’t want to lose. For example, say that you consider yourself to be a very loyal person, but one day, you receive a very attractive job offer from a competitor. You hesitate in accepting the offer because you don’t want to seem disloyal to your current employer. In this situation, you will want to explore the complex ties to your identity, in this case, loyalty, by challenging your thoughts, remembering that nothing is black or white. Consider the fact that you’ve been loyal to your current employer for 10 years despite being underpaid with no chance of a pay raise. Do you have to remain loyal to your current employer forever? What about remaining loyal to your family by taking the better job offer and therefore taking better care of them? Don’t waste time in your life by getting defensive every time someone challenges your self-perception. Rarely is a situation all-or-nothing.

The ‘Identity Conversation’ can also be boosted when you stop thinking that you can control the other person’s reaction. This will ensure the conversation remains on track and that you can stay focused. Trying to phrase your words carefully so that your partner doesn’t get angry is pointless, as you can never predict the other person’s reaction. Come to terms with that fact and you won’t feel as unsettled when you come face to face with an unexpected reaction.

Takeaway#6. Create a Neutral Story in the Third Person

Difficult conversations are hard to start and are often broached from inside your own story. Unfortunately, your perspective is rarely a good place to start the conversation as it will likely threaten the other person’s self-image making them defensive and/or aggressive as they work to protect their perception of themselves.

The solution to having a difficult conversation without causing hurt and upset is by telling the story in the third person, as if it’s being told by an impartial observer.This way, the differences of both parties involved are observed. For example, if you are angry about your flatmate leaving the place dirty, your own story would probably be “I do all the cleaning around here”. Your flatmate meanwhile would have a story about you being OCD with the cleaning. Neither of these stories are good places to start a difficult conversation. By creating a third story “Our definitions of cleanliness differ” you can have a more productive and meaningful conversation as no one will pass judgment on a neutral statement hence no one will get defensive so you can look for a solution that satisfies both of you.

Book details

  • Print length: 250 Pages
  • Audiobook: 5 hrs and 40mins
  • Genre: Nonfiction, Business, Self Help

What are the chapters in Difficult Conversations?

1. Sort Out the Three Conversations
2. Stop Arguing About Who's Right: Explore Each Other's Stories
3. Don't Assume They Meant It: Disentangle Intent from Impact
4. Abandon Blame: Map the Contribution System
5. Have Your Feelings (Or They Will Have You)
6. Ground Your Identity: Ask Yourself What's at Stake
7. What's Your Purpose? When to Raise It and When to Let Go
8. Getting Started: Begin from the Third Story
9. Learning: Listen from the Inside Out
11. Problem-Solving: Take the Lead
10. Expression: Speak for Yourself with Clarity and Power
12. Putting It All Together

What are good quotes from Difficult Conversations?

"The single most important thing [you can do] is to shift [your] internal stance from "I understand" to "Help me understand." Everything else follows from that... Remind yourself that if you think you already understand how someone 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." (Meaning)

― Douglas Stone, Difficult Conversations Quotes

What do critics say?

Here's what one of the prominent reviewers had to say about the book: “Does this book deliver on its promise of an effective way through sticky situations, whether ‘with your babysitter or your biggest client’? It does.” — The New York Times

* The summary points above have been concluded from the book and other public sources. The editor of this summary review made every effort to maintain information accuracy, including any published quotes, chapters, or takeaways

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Chief Editor

Tal Gur is an author, founder, and impact-driven entrepreneur at heart. After trading his daily grind for a life of his own daring design, he spent a decade pursuing 100 major life goals around the globe. His journey and most recent book, The Art of Fully Living, has led him to found Elevate Society.

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