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Difficult Conversations

Difficult conversations are conversations where things are at stake, where we know we will disagree with the other, where strong feelings are involved. For instance, asking for a raise or ending a relationship. These are conversations that prevent us from sleeping because we keep replaying them in our minds. This book tries to address how to handle these conversations better and the mistakes we often make. The main assumption of the book is that there are three parallel conversations - one about the facts, one about the feelings, and one about the identity, and that all need to be addressed during the oral conversation.

TLDR

This book is about “Difficult Conversations,” i.e., conversations that are not easy to conduct because something is at stake or may lead to arguments.

The hypothesis of the book is that behind the verbal exchange there are three parallel conversations:

One about the facts—the things that happened
One about the feelings
One about our identity—how we are perceived

In such conversations there is an asymmetry between the two participants: what they know, how they interpret messages, values, feelings, and interests. If everyone had access to the same information, the conversation wouldn’t be difficult.

The book aims to help you handle this kind of conversation. However, it is not a “manual”; there is no one‑size‑fits‑all recipe.

Below are the points that caught my attention.

Introduction

These situations are examples of difficult conversations:

Asking for a raise
Ending a relationship
Giving a critical performance review
Saying no to someone in need
Confronting disrespectful or hurtful behavior
Disagreeing with the majority in a group
Apologizing

No matter how lucky or competent we think we are, we will have to face these conversations at some point. Having them is a healthy sign; otherwise, it would be a dictatorship.

As companies become less hierarchical, more people share decision‑making authority, which increases the chances of conflict.

With the internet and new technologies, the price of many businesses has been driven down. There are no longer differentiating factors between two companies providing a similar product. Winning a contract now depends on influential skills.

The author warns that after reading the book, difficult conversations will still be difficult and challenging. However, it does help you become better at handling them, reducing fear of conflict and anxiety.

A Difficult Conversation Is Anything You Find Hard to Talk About

Some conversations are difficult because:

We feel vulnerable
Something is at stake
The outcome is uncertain
We care deeply about what is being discussed
Our self‑esteem is impacted

The outcome of these conversations is uncertain. We fear them, find them unpleasant, and try to avoid them. We often face the dilemma that keeps us up at night: “Should I raise the issue, or should I wait or keep it to myself?” Like Schrödinger’s cat, you never know until you try.

The Problem

Sort Out the Three Conversations

There is what is said with words and what is not said. We often talk about facts, but we rarely talk about our feelings and the way we think. Feelings are often kept private, and reasoning can seem obvious to us.

The three types of conversation are:

Fact – “What happened?” Who made the mistakes? Does the work need to be redone? Who was first?
Feelings – Angry? Hurt? Humiliated? Are my feelings justified?
Identity – What does this mean for us? Are we a “good” or “bad” person? Lovable? This is the image we have of ourselves and the one we project. Compared to feelings, identity is a long‑term characteristic.

What We Can and Can’t Change

Difficult conversations will always happen in our lives. We can improve how we deal with them by stopping the assumption that the other person knows everything:

No one sees the situation through your eyes. Share the facts, your reasoning, and ask the other what they know and how they think.
Discuss feelings when appropriate.
Stop acting as if your identity does not matter.

What Happened?

We must distinguish between truth, perception, interpretation, and values.
“The train left at 8 a.m.” is a fact.
“Jesus vs. Buddha” is a question of values.

“We can all be right at the same time while disagreeing at the same time.”

Difficult conversations are never just about facts; they are always about perception, interpretation, and values. We need to talk about all of these to understand the other person.

While we don’t discuss these things enough, we wrongly assume we know the other person’s intention.

We often take shortcuts by trying to find a culprit. Most of the time the fault or contribution is shared by several people. Focusing on who to blame distracts us from understanding why it went wrong.

Feeling

In these conversations we need to manage strong feelings such as anger, hurt, or shame. If no strong feeling is involved, it usually means you don’t care, and the conversation isn’t truly difficult.

Identity

Compared with feelings, which are more instantaneous, identity is a long‑term view of ourselves:

Who am I in the world?
What impact does this have on my future?
Do I have self‑doubts?

Before, during, and after the conversation, we are constantly talking to ourselves.

Shift to a Learning Stance

Moving to a Learning Conversation

One way to handle difficult conversations better is to fill the information gap by exchanging information about what you know that the other doesn’t. The authors call this the learning conversation, where we learn about the other person’s facts, values, and reasoning. This allows everyone to express themselves, so no one regrets not having said something.

Why We Argue, and Why It Doesn’t Help

There is often a paradox: we think they are the problem while they think we are the problem. We may label them as:

selfish
naive
controlling
irrational
…

We tend to minimize our own contribution and treat ourselves as first‑class citizens. We may hide information that is not to our advantage. From our perspective everything looks fine (i.e., we are not responsible), but this collides with the other person’s story, who has different clues.

A difficult conversation may stop because the other person has no time, is fed up, or threatens physical harm. Even if they back down, it doesn’t mean they accept defeat.

We disagree because:

Observation – we don’t see the same thing
Interpretation – we view the glass as half full or half empty, influenced by past experiences and implicit rules
Conclusion – we often reflect self‑interest

From Certainty to Curiosity

To understand why we reach different conclusions, we need to confront all three points. Be curious about the other person’s observations, why they think that way, and you’ll begin to see why you arrived at different states.

When asking questions, feed the other person with your observations. Otherwise, at the end of the conversation you’ll know why you disagree, but they won’t, and they’ll likely stay in their position.

Exception

When you are right but the other person denies it (e.g., someone is drinking excessively but refuses to accept it), another approach is to look at the consequences.

Regarding bad news, such as firing someone: technically you don’t have to learn the other’s story, you will fire them anyway. However, discussing the situation, what you know, and what they know helps to do it smoothly, so they understand why they must go.

Don’t Assume They Mean It: Disentangle Intent From Impact

It is not uncommon for Person A to try to please Person B, but for Person B to perceive it as an offense. We cannot reliably guess why the person acted (the intent) because various biases interfere:

We assume the worst case
In the same situation we threaten ourselves differently
We confuse intentions with results
A bad intention may be hidden behind a good one, or a good intention may be executed clumsily
We link bad intentions with bad character
This creates defensiveness, and the argument shifts from the problem to personal criticism
Labeling someone’s character can become a self‑fulfilling prophecy

Intentions are part of human complexity. Some actions are not based on rationality. Expressing our intent clearly is difficult without delving deep into our feelings.

Instead of guessing the other person’s intent, ask three questions:

Action – What did the person do?
Impact – What did it cause for you?
Assumption – What do you hypothesize the person intended? (Remember, this is only a hypothesis.)

We often focus on the action first, miss the impact (which may be masked by feelings), and treat assumptions as truth. This reminds us that we cannot read another’s mind.

Abandon Blame: Map the Contribution System

Mapping contribution means identifying who is involved in the problem and putting yourself under scrutiny. It is not about assigning blame; it is about uncovering each person’s role.

By discovering who is responsible for what, we dive into why it happened and see the true source of the problem. This step must be done without judgment; otherwise, you trigger identity issues and may turn the other person into a non‑cooperative partner.

Finding Hard‑to‑Spot Contributions

Avoidance – e.g., someone didn’t talk to their boss because of fear, leading to the current problem
Being Unapproachable – a form of avoidance: two people don’t communicate because one is perceived as weird, hierarchically distant, or too busy
Intersection – people don’t share certain characteristics or preferences, creating a 1‑to‑1 avoidance that prevents collaboration
Role Assumption – Person A assumes Person B will do something for whatever reason, but the assumption is wrong

Tools to Identify Contribution

Invert the role: try to see the situation from the other person’s shoes.
Ask someone external to the argument.

Reflect internally:

What am I contributing?
What are they contributing?
Who else is involved?

Then discuss your observations, make your reasoning explicit, and explain what you would have done differently.

The Feelings Conversation

Have Your Feelings, or They Will Have You

Issues with Feelings

Feelings are not always expressed directly because we often mask them. However, if ignored, they can leak and explode during the conversation. Unexpressed feelings make it hard to listen.

How to Solve the Issue

Learn to identify your feelings (harder than noticing you’re hungry).
Recognize your emotional footprint: the feelings you deem acceptable to express and those you suppress.
Accept that feelings are natural and normal; recognizing the hidden part is fine.
Understand that even good people can have bad feelings or moods.
Appreciate that their feelings are as important as yours.

Love, anger, hurt, shame, fear, self‑doubt, joy, sadness, jealousy, gratitude, loneliness

Translating Feelings

Feelings are often expressed indirectly:

Judgments – “If you were good, you would do X” (X affects my feeling positively)
Attribution – “Why are you trying to [my feeling]?”
Characterization – “You are such a ___”
Problem‑solving – “You must do this and that”

People who initially blame someone usually have strong feelings.

Negotiating with Feelings

A compromise blends options: trying to soothe two emotions at once. It’s like having one red sock and one blue sock—one matches a blue tuxedo, the other matches a red dress your wife bought you.

Negotiation is not merely compromise; it’s about getting the best possible outcome for both parties.

Identify where feelings arise in the problem.
Map the full spectrum of emotions.
Share without evaluating.

Both sides can have strong feelings simultaneously. Naming them (“I felt ___”) helps avoid the trap of judgment or attribution.

Both people need to acknowledge that the other’s feelings have been heard. This signals that the reason for the argument matters to you. However, acknowledgment should not be premature. If facts and observations are not yet on the table, acknowledging feelings can be unhelpful. It serves as a checkpoint.

Sometimes feelings are the spark for arguments. Consider parent‑child interactions: arguments may arise simply because the child seeks recognition or attention that is not being given.

The Identity Conversation

Ground Your Identity: Ask Yourself What’s at Stake

When you leave a job—whether for better pay, a new location, or any other reason—you may still have good relationships with colleagues and mentors. Saying “I’m leaving” is a difficult conversation because your identity is at stake.

We are facing another person, but also ourselves. You might ask yourself:

Am I competent?
Am I a good person?
Am I worthy of love?

These questions often require validation from someone else— a mentor for skills, a friend for moral character, a family member for love.

When reflecting, avoid the all‑or‑nothing mindset that you are either completely good or completely bad. Accept a balanced view; don’t fall into denial or overestimation, as either hinders growth. To improve self‑image, imagine where you’d like to be in three months or ten years and gain perspective.

Ground Your Identity

Be aware of identity issues.
Consolidate your identity with new information (we are more impacted by bad news than good news, so we must learn to integrate positive feedback better).

To improve awareness, identify what triggers identity concerns in conversations. Once you know the sensitive parts, check facts and evidence that support a healthier self‑image. This is about getting a clear picture of who we are—our weaknesses and strengths.

Accept that you are not perfect and can make mistakes.
Intentions are complex.
You have contributed to the problem; assess your responsibilities.

Regaining Balance

We must manage our own feelings but not try to control the other person’s response. You can’t know whether they had tea or coffee this morning. Measuring success by whether the other person is upset is a poor indicator; it’s better to prepare for a range of possible reactions.

Sometimes you need to pause the conversation and take a break. Ruminating on the same problem endlessly is exhausting and unproductive.

Remember Their Identity Too

Raise Identity Issues Explicitly

As with feelings, stating identity concerns clearly helps clarify the situation. However, it is not always appropriate—e.g., with a stranger or when discussing sexual matters with a colleague.

Ask for Help

For severe events (accidents, assault, aggression, etc.) it is difficult to cope alone. Seeking professional help is advisable.

Create a Learning Conversation

What Is Your Purpose? When to Raise It and When to Let It Go

You cannot spend all your time and energy on difficult conversations. There are times to talk and times not to talk. There is no simple rule like “not before 8 a.m.” or “never discuss X when Y.”

We will never know with certainty whether raising an issue is a good idea—like Schrödinger’s cat, you never know until you try.

Three Types of Conversations That Don’t Make Sense

Meta‑conflict – the real conflict is internal; the meta‑conversation leads nowhere.
Alternative solutions – a different approach (e.g., changing behavior) may resolve the issue without talking.
Lack of purpose – if there is no clear goal (solving the issue, changing a behavior, clarifying ideas), arguing is pointless.

Do Not Try to Change Someone

When you try to shape or attack the other person’s story, you provoke defensiveness. People are more likely to change when they feel free.

Letting Go

Even if you improve at handling these conversations, there will always be moments when you cannot win or lack the patience to continue.

Liberating Assumptions

“It’s not my responsibility” – recognize your contribution scope is limited.
“They have limitations too.”
“This conflict does not define who I am.” – identity should not be undermined by a single dispute.
Letting go does not mean you no longer care.

Getting Started: Begin with the Third Story

The most stressful moment is the beginning of the conversation. This is where you can influence its direction.

Why Typical Openings Don’t Work

We usually start from our own perspective. The other person often lacks that perspective; otherwise, the conversation wouldn’t be difficult.
We trigger their identity immediately.

How to Start Better: The “Third Story”

The “third story” is an invisible narrative that belongs to neither party. It is the perspective a neutral third party with no stake would have—similar to a mediator’s view. There is no right or wrong; it is simply another point of view.

Extend an Invitation

Describe the problem in a way both parties can accept. Agree that both need to act to solve it, without imposing. Be persistent and present the other as a partner.

Summary

Explore each other’s story to see the different points of view.
Share the impact on you.
Take responsibility for your contribution.
Describe your feelings.
Reflect on identity issues.

Learning: Listen from the Inside Out

The most common complaint in difficult conversations is that the other person “doesn’t want to learn.” The advice is to spend more time listening to them. Listening must be authentic. When you acknowledge the other, summarize what they said without judgment.

When prompting the other person to speak, avoid turning statements into questions like “Isn’t it you who did X?” Ask open‑ended questions and request concrete details.

Acknowledgment is not agreement. It means you have heard the information. Agreement involves judgment or positioning.

Expression: Speak for Yourself With Clarity and Power

Being a good orator does not automatically make you handle the conversation better. A larger vocabulary does not help.

Do not fear titles. Failure to express yourself does not give you control over the relationship. Feel entitled, not obligated.

Help people understand your view, share your information, and explain how you reached your conclusions.

Conclusion

The book is interesting but far from perfect. It repeats many ideas and could be written more concisely. While reading, I felt it was a patchwork manual—useful snippets of information but lacking a strong foundation.

The start is good: it identifies three parallel conversations. However, learning how to exploit this concept feels like a cookbook with incomplete recipes.

The authors treat all difficult conversations as if they were the same, ignoring the role of context. Sometimes both parties find it difficult; sometimes only one does.

The book lacks empirical “experiments,” such as “group A vs. group B.” It relies on a few examples where the author rewrites what was said, as if that alone would mechanically change the outcome. How do we know? You can’t ask the same person to marry you twice.

In the introduction, they claim “we get positive feedback, but also negative feedback that things did not improve.”

For me, at least, the book helps analyze conversations better. However, the tools are often too vague and unstable to be truly useful.

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Gaëlle Candel