Difficult Conversations: Book Summary & Review

Difficult Conversations book cover

Difficult Conversations” (1999) is a communication skills book that teaches readers how to have constructive, respectful, and effective conversations exactly when it’s most difficult to have those conversations: when the stakes are high when you are very emotional, and when the last thing you would want is to talk.

Bullet Summary

  • Accusations are masked feelings: express the feelings directly instead
  • Starting a performance review by asking people how they’re feeling or how they think they’ve done is awkward
  • If you think it or feel it, you are entitled to say it. Speak for yourself and you can speak with the power
  • You can’t move the conversation in a positive direction until the other feels heard and understood


About The Authors: Douglas and Heen are the founders of Triad Consulting Group, a corporate education and communication consulting firm founded by members of the Harvard Negotiation Project.

I have found their work to be of very high quality, including their latest “Thanks For The Feedback“.

What Are Difficult Conversations?

Difficult conversations are all those conversations we’d rather avoid.

They include complaining to a neighbor about their barking dog or asking for a salary increase at work.

The authors say that underlying difficult conversations are three deeper conversations, which are:

  • What happened: usually involving the facts, what should happen, and where the blame lies
  • Feelings: the feelings and emotions involved, that most people try to cut out
  • Identity: some conversations can go to our personal core. Are we good people? Are we competent?

#1. Stick to The Facts: What Happened

The authors say that the common mistake is to stop what has happened at a superficial level.

What we should do instead is to understand what interpretations of those events are and what is important to each party.

For a good resolution, the parties involved should move from their own views of the fact to a curiosity about the other person’s view of the events.

For example, you could prod:

You: OK, and does it inconvenience you when I leave you the window open?
Them: Totally!
You: OK, and how od you feel when I leave the window open. Does it feel like I’m being rude?

From then on you can then explain you don’t mean to “hurt” them or inconvenience them so that the conversation can move to two human beings understanding each other.

Don’t Assume

The second common mistake is that people often assume to know what the other party’s intentions are.

But our assumptions are often wrong because we base them on our own feelings.
So if we are hurt, then we tend to believe the other party’s intention was to hurt us, and that’s often just not the case.

Also, there’s a certain tendency of going with the worst possible option, which certainly doesn’t help in conflict resolution.
The simple solution is to ask the other party what was their intent.

Avoid Blame, Talk Contributions

And the third mistake is to assign blame, which can quickly escalate the situation and take us further from any resolution.

The authors say we should instead focus on finding out how we all contribute to the situation.

Telling first our own contributions can help the other party move away from the natural tendency of blaming.

Here are four common contributions in difficult conversations:

  1. We avoided it for too long: We often contribute to a problem by avoiding it for so long, allowing it to grow
  2. We avoided the person: Behaving in any way that makes it hard to talk to. Moving quickly, avoiding contact, being generally unfriendly
  3. We assume righteousness: We all form opinions based on past experiences and references, but there are no right or wrong, just intersections of different needs and personalities
  4. We assume we’re good: We often assign ourselves positives roles in the issue which is comfortable for us but not useful

To expand your views on the contribution try to look at yourself from the other party’s shoes and then look at the whole situation from a third party perspective.

#2. Do Share Your Feelings

Expressing emotions openly is difficult for many of us.

We tend indeed to avoid being too open about how we feel.

This is dangerous, the authors say, because unexpressed feelings tend to fester, find their way back into the conversation in nasty ways and prevent us from listening properly.

The solution is for all the parties to share their feelings openly and clearly. Don’t mistake them for facts, this is important, but don’t pretend that feelings are not there. Both their feelings and your feelings.

#3. Detach Your Identity From The Conversation

Some conversations are very tough because they inherently touch our own sense of worth.

A job review for example, or talking about how to fix a big mistake.

The most difficult conversations threaten our ego and sense of identity by calling into question our competency or even whether we are worthy of being loved and appreciated (for more details on the importance of feeling worthy of love read Brene Brown – Daring Greatly).

The authors say it’s a human tendency of thinking in terms of all or nothing that can make the identity level of the conversation so touchy.
We tend to think we are either great and everyone loves us, or we are terrible and unworthy.
The solution is in adopting the “And Stance” and ditching the “all or nothing” paradigm.

You’re not bad because you have done a mistake.
And you can keep interacting and working on things: an issue, a refusal or a mistake does not spell the end of anything.

The authors say that there’s a relation between how easily we can admit our own mistakes and our own mixed intentions and how balanced (and strong) we will feel during the conversation.
And once you can adit admit your mistakes and emotions, chances that your difficult conversations will go well will immediately rise.

My Note:
The identity side will always hit harder those people who have a fixed mindset. Read here how to develop a growth mindset and how to develop an antifragile identity

#4. Letting Go: Do You Really Need The Conversation? 

The authors say that while many of us tend too often to avoid difficult conversations, sometimes it does indeed make no sense to have the conversation.

They suggest that working out on your own the three levels of the conversation and drafting a “contribution map” without having the difficult conversation.

That will give you more insights and will also give you a better idea of whether it makes sense to have a conversation or if it’s mostly an issue that you have within yourself only -an identity crisis for example-.

Mastering Difficult Conversations

Douglas and Heen provide a lot of practical advice and real-life examples.

#6. Tell The Story From Third-Party Perspective

They say most people start by describing the issue from their own perspective, which automatically raises the defensive barrier from the other party.

The best way to go instead is with a “third story” perspective to describe the issue in neutral terms.

Example: Discussing Open or Closed Window

For example, in my case, my neighbor always opens the window of the common building entrance area.

I hate it during the cold reason as it’s expensive for the heating and unethical.
This would be stating the conversation from your own perspective:

Your Own Perspetive: you always open the window open and it’s very cold in here

A third-party approach instead would be:

Third Party Style: you prefer having the window open why I prefer having it closed during the cold season.
I would like to find out why you want it open, explain why it’s important for me to close it and find possible solutions.

#7. Do Listen

Listening is one of the most important bits of difficult conversations.

And it’s exactly what most don’t do.

Once the other party feels heard, it calms them down, makes them more likely to hear you, and exponentially increases the chances of effective problem resolution.

The key to being a good listener is very simple: be genuinely curious and genuinely concerned about the other party.
Ask questions, ask for examples, and paraphrase what they said to make sure you understand.

You cannot move the conversation into a more positive and constructive stage until the other person feels heard and understood.

#8. Express Your Opinion As Legitimate

Each party must understand that their own views and feelings are just their own and there’s no wrong or right.

Also, personal views and feelings are no less -and no more- legitimate and important than any other party.

Don’t present your views as if they were the only truth, use the “and stance” and avoid any exaggeration such as “you always” or “you never”, which are a surefire way of raising the other party’s defensive walls.

#9. Accept There Are Some Difficult People

The authors rightly point out that the other party has likely not read Difficult Conversations, so they might remain focused on blaming and arguing about right and wrong.

They provide and detail some great tools, including:

  • Reframing: for example means taking the blame and accusation of the other party and reframing them in more positive terms for the discussion, for example as contributions.
  • Naming the dynamic: if the other party goes off track, for example by interrupting or refusing to admit their own feelings, call attention to that behavior and raise it as a point of discussion. The naming of the dynamic technique will make the other person aware of their own behavior.

You could for example tell them:

You: “it’s not okay to only look at my contribution.
I feel like I’m trying to look at the issue from both perspectives. Is there anything I’m doing to make it hard for you to look at your own contributions in the situation?”


#10. Find Common Ground Solutions: Mutual Persuasion

Remember that you both need to agree on the solution and that they have to persuade you as much as you need to persuade them.

Ask them what would persuade them, and tell them what would persuade you.

When the parties cannot find a solution working for both, they must decide whether to accept a smaller solution, deal with the consequences, or walk away.

Difficult Conversations book cover


Difficult Conversations is possibly the best book I have read on effective communication (and indeed it ranks first in the “best communication skills books).

I was excited when I first started listening to it because that’s the feeling I get any time I have “struck gold”: I get excited at how much I am going to learn -and share with you-.

The only caveat we add is that you do NOT want to share your full truth with sneaky people, manipulators, gaslighters, and what we refer to here as “turkeys”.
In that sense, postulating that anyone is a worthy recipient of your full honesty is plain naive self-help.

Overall, I highly recommend “Difficult Conversations“.

Also, read:

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