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Book Summary: Difficult Conversations

Difficult conversations are a normal part of life. They include anything you find hard to talk about - like asking for a raise at work, to confronting disrespectful behaviour in your family, and everywhere in between.

Usually, these conversations seem like a no-win situation. If you tackle them head on, somebody will get their feelings hurt or a relationship will turn sour. If you avoid them, whatever is causing you to think about confronting the situation continues to fester.

But what if there was a different way to approach these conversations where they actually make your relationships and performance at work stronger? That's exactly what we'll explore in this summary of Difficult Conversations, the book from the people behind the Harvard Negotiation Project.

In this summary you'll learn the 3 hidden conversations we have inside of every conversation, and a 5-step strategy for making the most out of every interaction we have.

Conversation #1 - What Happened

The first conversation within a difficult conversation deals with what happened. Most of the time it involves some sort of disagreement about the facts.

We disagree about the facts, most of us end up in an argument rather than searching for answers. Usually because we believe that the other person is the problem. They are selfish, naive, controlling and irrational. This might surprise you, but the other person in the argument believes the exact same thing about you.

This causes both sides to enter the conversation with the goal of pointing out why the other person is wrong, and it never ends well. There are some good reasons why this happens.

First, we have different information about what happened that led up to the difficult conversation. It's rare that either side in a difficult conversation has a strong handle on all of the relevant facts.

Second, we have different interpretations about the facts that we both know about. If you want a good example of this in action, look at the headlines from Fox News and CNN on any particular day to see completely different conclusions based on the same set of events.

Third, our conclusions about why things turned out the way they did are greatly influenced by self-interest.

We'll get into how to get to a shared understanding of the facts in a bit, but for now what you need to internalise is that your view of what happened is incomplete, and part of the conversation needs to be about getting a better handle on it.

Conversation #2 - The Feelings

In a difficult conversation, it's impossible to deal with it properly without considering your feelings, and the feelings of the other side. In fact, they are often at the heart of the issue. You and your counterpart will both be wondering whether or not your feelings are valid and appropriate, and whether or not you should bring them up. The answer is that yes, you should. If you don't, one of three things is likely to happen.

First, unexpressed feelings can 'leak' into the conversation. No matter how hard you try, your feelings will let themselves be known. Your body language will change, your tone of voice will betray the words that are coming out of your mouth, or you might even completely disengage from the conversation altogether.

Second, sometimes they don't just leak into the conversation, they burst directly into it. Keeping it bottled up inside can eventually lead you to explode during an emotional part of the conversation, leading you to say something you later regret.

Third, unexpressed feelings make it difficult to listen to what the other person is saying. Good listening requires you to be genuinely interested in learning about what the other person has to say, which is next to impossible when you have feelings about that person you're not dealing with.

Conversation #3 - The Identity

Finally, the last conversation within the difficult conversation is what it means to us as a person - our identity. There are three core identities that each of us question within difficult conversations:

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

The answers to these internal dialogue questions determine whether or not we feel grounded during these conversations, which greatly impacts our ability to 'show up'. Most of us have an 'all or nothing' approach to these questions. For instance, we are either 'the most competent', or 'not competent at all'. Truth, of course, lies somewhere in middle for almost all things. Keeping an open mind about this during the conversation will greatly help you feel grounded.

Accepting the following three things about yourself will help you find that middle ground:

  1. You will make mistakes. This will help you accept the legitimate aspects of the other person's story about what's going on.
  2. Your intentions are complex. Sometimes your intentions will be selfish, and sometimes they will be altruistic. Understanding this will help you when legitimate accusations about your past behaviour comes up.
  3. You have contributed to the problem. You need to be able to take responsibility for what you've contributed to the problem.

Finally, you also need to keep in mind that the other person in the conversation will have a complex identity conversation going on in their head as well.

Now that we have the 3 conversations within the conversation covered, let's move into the 5 steps you can take to have a difficult conversation that goes incredibly well.

Step One: Prepare by walking through the three conversations

Your goal in the first step is to prepare for the conversation.

Sort out what happened

Here you need to figure out where your story about what happened came from. What information do you have? Are past experiences colouring your view of the situation? Then, determine what the impact the situation has had on you, and what their intentions might have been. Quite often, we get the intentions of the other side wrong. Finally, you need to figure out how you both contributed to the problem. Figuring out how they contributed is usually the easy part. Figuring out your contribution is usually a bit tougher.

If you are struggling with it, you might consider how a dispassionate observer would view the entire issue, or put yourself in the shoes of the other person.

Understand the emotions

Here you need to explore your emotions about the issue so that you can put them on the table. Are you feeling angry? Hurt? Shame? Fear? Self-Doubt? If this is a difficult conversation, there is some emotion that you are dealing with, and it's critical for you to identify it.

At the same time, your goal here isn't to vent. It's the frame the feelings so that they help your counterpart understand where you are coming from.

Identify your identity issues

Lastly, you need to identify your identity issues as they relate to the conversation. Consider what's at stake in this conversation for you, about you. What do you need to accept in order to be better grounded in this conversation?

Step Two: Check your purposes and decide whether to raise it

Next, we move on to the purpose of the conversation. Consider what you hope to accomplish by having the conversation. Once you've done that, here are some questions to ask yourself to determine if the conversation is worth having.

First, does your purpose make sense? Make sure it's possible to produce the outcome in the conversation. Sometimes, when you are forced to articulate the outcome, you'll realise that you can't actually accomplish it. Or that the short-term gain isn't worth the long term cost. Typically, there are three purposes that make sense: (a) learning their story, (b) expressing your views and feelings, and (c) problem solving together.

Second, is the real issue inside you? Sometimes what's difficult about a situation has more to do with what's going on inside you rather than the other person.

Third, is there a better way to address the issue rather than talk about it? Sometimes the more appropriate path is not a difficult conversation, but a change in behaviour.

If you get beyond those questions and are still ready to go, there are some liberating assumptions you should take with you into the conversation:

  • It's not my responsibility to make things better, it's my responsibility to do my best.
  • They have limitations too.
  • This conflict is not who I am.

Now that we are ready, let's jump into having the actual conversation.

Step Three: Start from the Third Story

As the authors point out, the most stressful moment of a difficult conversation is typically the beginning. But this is also where the greatest leverage in a difficult conversation lies, so it's important to get it right.

Our typical openings don't usually help, because we begin 'inside our own story'. We describe the problem for our own perspective, and trigger the kinds of reactions we are hoping to avoid. If they agreed with our story, we wouldn't need to have the conversation in the first place, right?

The right way to do it is to begin from the Third Story. This is the one a keen observer would tell, who has no stake in the problem. Think of this person as a mediator, and think about how they would describe the issue at hand.

First, they would describe the problem as the difference between your stories. No matter what else you might think and feel, you can at least agree that you and the other person see things differently. There's no judgment about who is right or wrong, and each side gets to feel like their story is a legitimate part of the discussion. Remember, this doesn't mean giving up your point of view.

Second, share your purposes. If the other person is going to join you in this conversation, they need to know what they are agreeing to do.

Third, invite them to join you as a partner in sorting out the situation together. A great line to use is "I wonder if it would make sense...?" This allows the other person the choice to join the conversation or not.

Now that they have joined you in the conversation, it's time to explore each other's stories.

Step Four: Explore their story and yours


As you begin to listen to their side of the story, your mindset is critical. The authors suggest that you start with a stance of curiosity. There are three skills that you can bring into the conversation to help you do that.

The first is inquiry. Ask questions, but only to understand, not cross-examine. In particular, ask a lot of questions that will help you understand the three 'conversations within the conversation' from their side.

  • Can you say a little more about how you see things?
  • What information might you have that I don't?
  • What impact have my actions had on you?
  • How are you feeling about all of this?
  • Say more about why this is important to you. What would it mean to you if that happened?

The second skill is to paraphrase for clarity.

The third skill is to acknowledge their feelings. Here are some phrases you can use to help:

  • "it sounds like you are really upset"...
  • "this seems really important to you"...
  • "if I were in your shoes, I'd probably feel confused too"

Remember, acknowledging is not agreeing. You can still disagree with them after you acknowledge them. Once you feel that you understand their story, you can move on to telling yours.


The other person also needs to hear your story. There are a few guidelines to keep in mind while sharing your side of the story.

First, don't present your conclusions as the truth. Say what you mean and avoid easing into the issue, but don't make it seem like you've closed your mind off to their side of the story.

Second, share where your conclusions come from. This is where your feelings and past experiences come to mind.

Third, don't exaggerate with "always" and "never". It's typically not true, which only hurts your credibility and gets the other person even more defensive about their side of the story.

Here are some concrete suggestions on what ground you might cover while sharing your story:

  • Explore where each story comes from "my reactions here probably have a lot to do with my experiences in a previous job"
  • Share the impact on you "I don't know whether you intended this, but I feel extremely uncomfortable when..."
  • Take responsibility for your contribution "there are a number of things I've done that have made this situation harder..."
  • Describe feelings "I'm anxious about bringing this up, but at the same time, it's important to me that we talk about it..."
  • Reflect on the identity issues "I think the reason this subject hooks me is that I don't like to think of myself as someone who..."


Most people coming into these difficult conversations will not be as skilled as you are, and so it's natural that they will get off track. When the other person heads in a destructive direction, your job is to reframe an unhelpful statement into a helpful one. For instance, you can say something like "I can see that you're feeling really angry about what I did, which is upsetting to me. It wasn't my intention. Can you say more about how you felt?"

Step Five: Problem Solving

Of course, the whole purpose of having a difficult conversation is to solve the problem, which you can do better together than either of you could do on your own. There are three things to keep in mind as you go through this step.

First, you should invent options that meet each side's most important concerns and interests. This should be obvious.

Second, if there are no obvious solutions that immediately spring to mind, look to standards about what should happen. There might be a precedent set for these types of disagreements that you can rely on.

Third, talk about how to keep communication open as you go forward. Make sure you utilise all the difficult conversation skills you've learned as you take it across the finish line.


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