Book Review – Difficult Conversations – How To Discuss What Matters Most by Douglas Stone, Bruce Patton and Sheila Heen

Managing Difficult ConversationsIn my own opinion this is a timeless book. Why? Because it discusses a topic that we all face in various aspects of our lives. Whether at work, in our relationships, with our children or even when shopping we will all have to face difficult conversations. Having difficult conversations is a fact of life. The book, Difficult Conversations – How To Discuss What Matters Most by Douglas Stone, Bruce Patton and Sheila Heen is a classic and an international best seller too. There are lots of books about difficult conversations but this one is different for a number of reasons. To start with it is based on extensive research at the Harvard Negotiation Project of which Bruce and Douglas are members and the techniques discussed in the book are not surface level gimmicks that you can apply quickly without a good understanding of how they work. Rather they are behaviours which require us to think deeply and work hard to change the way we respond in conversations we see as difficult.

Let me state this upfront, my review here cannot do justice to this book. It’s one you should definitely read but be warned, it is not a small book. It has 311 pages of reading content, three sections with 12 chapters and a fourth section which answers 10 questions. Below I have briefly reviewed each section of the book to give you a tiny flavour of what to expect if you do decide to read it.


This first part of the book has just one chapter. This part of the book helps us to understand clearly what is involved in a difficult conversation.

Chapter 1 – Sort out the three conversations

The focus of this chapter is to help us understand that a difficult conversation is actually three different conversations. I like to describe difficult conversations as having three different components which are:

  1. The ‘what happened’ conversation
  2. The ‘feelings’ conversation
  3. The ‘identify’ conversation

Each of these conversations are described in some detail and when you really look at it, they do make sense. Every difficult conversation has an element of what happened, evokes strong feelings and affects a person’s identify in terms of what the conversation means to the people involved in it.


This part of the book has three sub-sections which have their own chapters. Each sub-section is labelled according to the components of a difficult conversation introduced in the previous section. But it moves beyond understanding the different types of conversation to moving into a learning mindset where we want to engage the person in a positive way to understand their own point of view and begin to think about more appropriate ways to handle the conversation.

The What Happened Conversation

Chapter 2 – Stop arguing about what’s right: explore each other’s story

In this chapter we learn about the first way to handle a ‘what happened’ conversation. Since these conversations typically focus on arguments about what happened and things such as I’m wrong’ you’re right, the advice given here is to explore each other’s story to understand each other’s point of view, the differences in opinion and what may be leading to the argument. While this doesn’t solve the problem, it does at least allow each party in the conversation to understand where each person is coming from.

Chapter 3 – Don’t assume they meant it: Disentangle intent from impact

Misreading people’s intentions and thinking that when we explain our true intentions the problem is solved but yet get worse are explained here. Have you ever been in a conversation when you said something and after the person you spoke to responded, you said, ‘but that’s not what I meant.’ Then you explain what you meant, and the person is still upset at what you said leaving you confused and now upset. It’s those kinds of scenarios that this chapter deals with. It also gives us some advice about how to respond in these situations.

Chapter 4 – Abandon Blame: Map the Contribution System

Imagine you are working with on a project with someone. You do your part, but the other person doesn’t, and the project falls flat. What do you do? Of course, you blame the person for their irresponsibility and hold them accountable for the failure of the project. This is a typical ‘what happened’ conversation. But there is another way to approach such situations which is described here, and it’s called ‘Contribution’. Instead of focusing on blame, you explore the situation with the person, how each of you may have contributed to the problem and what to do to ensure it doesn’t happen again. That’s the lesson you will learn from this chapter.

The ‘Feelings Conversation’

Chapter 5 – Have your feelings (or they will have you)

In this chapter there are two key lessons in my opinion. Firstly, recognise the importance of feelings because they are often the heart of difficult conversations so don’t ignore them. The second lesson then is how to handle feelings in a difficult conversation. Some things you will take away from this chapter are:

  • Unexpressed feelings can leak into a conversation.
  • Unexpressed feelings make it difficult to listen.
  • Unexpressed feelings affect our self-esteem and relationships.
  • Accept that feelings are normal and natural.
  • Recognise that good people can have bad feelings.
  • In any difficult conversation your feelings are as important as the other persons too.

The ‘identify’ Conversation

Chapter 6 – Ground your identity: Ask yourself what’s at stake

This chapter makes something clear, difficult conversations threaten our identify and three common areas where they do so, according to the authors are expressed in these questions:

  1. Am I competent?
  2. Am I a good person?
  3. Am I worthy of love?

Since the identity issue is something that is common to most of use, we need to know how to manage them, especially in difficult conversations. The second half of this chapter provides some solutions. Summarily these solutions are:

  • Step 1 – Become aware of your identify issues.
  • Step 2 – Complexify your identity be moving away from ‘I am perfect’ and ‘I am worthless’ to get a true picture of who you really are.

Among other advice given, what stood out to me was this one – find the courage to ask for help.


This section contains the remaining six chapters. The previous sections focused on understanding difficult conversations and adopting a learning mindset to learn in the conversation. This section outlines actions we can take to manage difficult conversations properly and there are five key actions to take.

Chapter 7 – What’s your purpose? When to raise it and when to let go

The opening paragraph in this chapter summarise what it is about, and it’s quoted below:

“You can’t have every difficult conversation you come across. Life is too short. The list is too long. So how do you decide when to have a conversation for the first time or the fifteenth? And how do you let go of the issues you decide not to raise?”

I’m sure you get the point; this chapter is about deciding what conversations to have and which ones to let go of. There is no straightforward answer to this dilemma, but we are told about three types of conversations that don’t make sense, probably the ones you shouldn’t bother about:

  • Is the difficult conversation more about what’s going on inside you than the other person?
  • Is there a better way to address the issues rather than talking about it?
  • Do you have purposes that make sense? There’s no point having a conversation if you have no clear outcome to get from it.

If you are going to have the conversation, according to the authors here are three purposes that make the conversation worth having:

  1. Learning their story
  2. Expressing your views and feelings
  3. Problem-solving together

Chapter 8 – Begin from the third story

So, once we know which difficult conversation to have this chapter moves on to how to begin the conversation and the advice is, begin from the third story. Here you learn how to do that. There are examples of how not to begin, compared with the best way to begin. There are also examples of specific conversations which include delivering bad news and making requests. The two general steps given to start a difficult conversation are:

  1. Begin from the third story
  2. Extend an invitation

Chapter 9 – Learning: Listening from the inside out

A major part of handling a difficult conversation appropriately is to understand the person both at a verbal and feeling level. That takes proper listening, what the authors have described here as listening from the inside out. So how do we listen from the inside out? Advice on how to do that includes:

  • Forgetting the words and focusing on authenticity
  • Becoming more aware of your internal voice
  • Use the three skills of inquiring, paraphrasing and acknowledging.

Chapter 10 – Expression: Speak for yourself with clarity and power

The step in the previous chapter was about understanding the person but handling a difficult conversation effectively cannot stop there. The other person needs to hear your story. You must express yourself too. Be mindful though, according to the authors, expressing yourself in a difficult conversation is not about persuading, impressing or trying to win the other person over. Rather the goal is to, ‘express what you see why you see it that way, how you feel, and maybe who you are.’

This chapter teaches some key lessons about expressing ourselves in difficult conversations. To start with, we should all remember that we are entitled to our own opinions and to express them too. Yes, that’s one of the lessons. And when expressing yourself, start with what matters most, clearly state what you mean and don’t make your story simplistic. We are presented with three tips to tell our story with clarity which are:

  1. Don’t present your conclusions as the truth.
  2. Share where your conclusions come from.
  3. Don’t exaggerate with “always” and “never”.

Chapter 11 – Problem solving: Take the lead

Most likely you will have to take the lead to problem solve during a difficult conversation because the other person probably has not read this book and won’t understand the techniques you are trying to use. This chapter is for when you find yourself in that situation (if you’ve read the book of course).

Two techniques explained to try and get the other person to look at the conversation from a constructive perspective are reframing and listening. If reframing and listening are not working then you will need to explicitly state what is happening in the conversation. Once you’ve been able to sort that out then it’s time to problem solve and this involves:

  • Including the other person.
  • Gathering information and testing your perceptions with the person.
  • Inventing options to solve the problem.
  • Identifying standards that apply to the issue.
  • If you still can’t resolve the issue, then consider alternatives.
  • Lastly remember that these things take time.

Chapter 12 – Putting it all together

This is the last chapter and it’s a summary of the five steps involved in handling a difficult conversation. It does a great job in using a detailed example to illustrate how the five steps work and concludes with a summary checklist of the five steps. As a reminder the five steps are:

  1. Step 1 – Prepare by walking through the five conversations.
  2. Step 2 – Check your purposes and decide whether to raise it.
  3. Step 3 – Start from the third story.
  4. Step 4 – Explore their story and yours.
  5. Step 5 – Problem solving.

Ten questions people ask about difficult conversations

This part of the book explores ten questions that people ask about difficult conversations. The questions are:

  1. It sounds like you’re saying everything is relative. Aren’t some things just true, and can’t someone simply be wrong?
  2. What if the other person really does have bad intentions – lying, bullying, or intentionally derailing the conversation to get what they want?
  3. What if the other person is genuinely difficult, perhaps even mentally ill?
  4. How does this work with someone who has all the power – like my boss?
  5. If I’m the boss/parent, why can’t I just tell my subordinates/children what to do?
  6. Isn’t this a very American approach? How does it work in other cultures?
  7. What about conversations that aren’t face-to-face? What should I do if I’m on the phone or email?
  8. Why do you advice people to “bring feelings into the workplace”? I’m not a therapist and shouldn’t business decisions be made on the merit?
  9. Who has time for all this in the real world?
  10. My identify conversation keeps getting stuck in either-or: I’m perfect or I’m horrible. I can’t seem to get past that. What can I do?

This is a very valuable book but not an easy one to read. It’s not brain candy. Reading this book will take some effort and it will make you think about yourself also and the way you handle difficult conversations. Having said that, developing some of the skills described in this book can greatly improve our relationships both in and out of work. So, my verdict is, go read it.

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