Difficult Conversations

By Douglas Stone, Bruce Patton, and Sheila Heen

Rating: 10/10

Best Line #1: In a difficult conversation your primary task is not to persuade, impress, trick, outwit, convert, or win over the other person. It is to express what you see and why you see it that way, how you feel, and maybe who you are.

Best Line #2: Guessing the wrong intention is hazardous to your relationships.

How Many Difficult-yet-Production Conversations Have You Seen?

Every single one of us, regardless of our station in life, have (or need to have) difficult conversations.

Do we know how? Where did we learn? As a kid, a lot of my exposure to such conversations came from parental disputes, bad television, and worse radio. A lot of fingers would be pointed, brows furrowed, and voices raised. Doors would be slammed. Callers would hang up. People would talk over one another to a point where their statements occurred simultaneously at an ever-increasing volume.

In other words, I never saw a difficult-yet-productive conversation unfold until I found a way to have them myself. Everything else was just shouting matches. Arguments. Adults acting like children. And why not? Isn’t that how it’s done? Indeed, my most vivid memory of such things comes from watching a preview for A Few Good Men that culminated in the great line from Jack Nicholson:

Suffice to say, this scene is not the exemplar of the exchanges our authors encourage. But it is definitely the sort of exchange that every screenwriter wants to recreate. It is also the exchange that every social media troll and politician wants to spark. Hackneyed versions of this movie clip play out every day and it perpetuates the idea that this is how adults behave.

It will take a tremendous amount of non-publicized work for us to turn that tide.

Over the course of the week, I reviewed a few ways we can start that work with the articles provided here:

Each article stands on its own but there is a running theme that I don’t want to lose. I write a lot about techniques, principles, and mental models. Out of all the information that I have shared, the tactics on how we productively engage in difficult conversations is far and away the most important and beneficial thing I can offer. Nothing else has consistently helped me as much as this.

Difficult Conversations Don’t Solve Problems. They Minimize Them.

What is the goal of a difficult conversation? Why have them at all? Some people will do anything possible to avoid them. In the workplace, my staff occasionally want me to address an issue with another coworker. I always rebuff and tell them to address the issue themselves. If the issue is so important, it’s worth their own time to settle it—not mine. More times than not, the staff member abandons the effort altogether. It says a lot.

For me, I don’t want to become the “fixer” of every interpersonal problem. That doesn’t strengthen the team. For them, they don’t need to voice complaints unless there is a willingness, on their part, to do something constructive about it. If they aren’t willing to have a difficult conversation about the topic with their co-worker, then it isn’t really a problem and I definitely don’t need to do anything about it as the manager/director.

Or so I thought.

Then I remembered a very important model from our previous book Influencer. In one of my favorite posts, I shared the two-part model the authors provide to explain how people decide what to do:

People won’t attempt a behavior unless (1) they think it’s worth it, and (2) they think they can do what’s required.

When dealing with my employees and their interpersonal issues with other staff, my approach was only half-right. In charging them to confront the issues themselves, coworker to coworker, I created a test for them, a gut-check that would determine whether or not the employee thought the issue was so big that it warranted the conversation. That effectively addressed Part One of the aforementioned equation.

Yet, I was doing a significant disservice to my team by not factoring Part Two of the equation. I wrongfully thought that my staff knew how to have those conversations. Doesn’t everyone? Of course not! I know and I still fail. So I’m now revising my approach. I still want my staff to confront their own issues, for the sake of my personal sanity and their personal growth, but I must make sure they are equally equipped with the tools to do what’s required.

More importantly, I must manage the collective expectation. No one should enter a difficult conversation thinking they’re going to solve the problem. This is the biggest mistake I see. We put so much pressure on ourselves to break the logjams and “win” while the other party presumably “loses” or, at minimum, accepts a marginal victory. This win-lose problem-solving approach just escalates things. It turns the whole situation into a debate. Such debates are fun but not very productive.

Outside of high school, no one ever wins a debate.

So lower the stakes and everyone will feel relief. Lower the stakes by shifting to a different form of conversation. No more debates, no more trials a’la A Few Good Men. Try instead the three forms of learning conversations that our authors provide.

Three Types of Conversation

The central framework of the book identifies three conversation archetypes. I thought these were a bit inaccurate at first. But there is much more depth in the book than I expected. Everything conversation can indeed fit into these categories.

It’s neither forced nor shallow. And the fantastic aspect of the thesis here is that the authors distinguish between the assumptions and goals of the conventional, argumentative, message-driven standpoint compared to the much-better mutual learning, conversation-driven standpoint. It lines up in a way that makes more sense every time I read it.

Type 1: The “What Happened?” Conversation

These conversations are about understanding a situation from other points of view and eventually landing on a diagnosis. From the argumentative standpoint, we usually use this conversation to convince someone what really happened, tell people what they did wrong, and try to make someone take the blame. From the conversation standpoint, we explore the variations of truth in a very Rashomon fashion and come to shared understanding.

I think these conversations are the most common of the three. Especially in the workplace. And when done right, it usually leads to fantastic new solutions for teams. When done poorly, we end up with territorial disputes and the same blame game.

Type 2: The Feelings Conversation

True to the title, these conversations are all about emotions. In the worst situations, we mask our true feelings and yell at each other. Far too often, we don’t just talk about how we feel and why. Instead, we project the emotion on someone else. We “let them have it” so that they can feel the same way. Misery loves company.

I think the trickiest part about feelings conversations is that we try to turn them into logical arguments. As if the feelings themselves weren’t enough. As if adults can’t share their feelings without some justification. But what’s the worst to me is the lack of reciprocation.

So often, what happens in the feelings conversation is that one party shares their feelings and the other doesn’t. It leads to a horrible imbalance if you’re not expecting it. The person who shares their feelings can often feel like they did something wrong. The other person, who doesn’t reciprocate, then hides and allows the awkwardness to grow.

It’s a shameful practice. In the future, if you share your feelings but the other person does not, it’s a red flag. I wouldn’t continue the conversation until they do.

That may sound harsh but the reality is that a feelings conversation is supposed to be about acknowledgement on both sides. A recognition that there are complex emotions at hand and, together, we must share them in order to parcel them out before moving into problem-solving.

On a sidenote, I must confess: my hyper-logical Spock-lite mind makes this the hardest conversation type for me.

Type 3: The Identity Conversation

This is the stuff of the extremes I reviewed in Wednesday’s post. This conversation creates false dichotomies of the all-or-nothing kind: either we’re good or we’re bad. We’re competent or not. We’re loveable or unloveable. This is the most subtle of conversation types but it gets to a lot of the corrective conversations we have. I see this most often in parenting, teaching, and coaching. It usually starts with some sort of criticism.

The message is conveyed, the conversation doesn’t go anywhere, and the affected party walks away thinking they must be awful. Or in another instance, a person makes a generalized statement like “You people are all the same.” This sort of thing erupts in an awful back-and-forth as the affected party defends not just their identity but that of the associated group.

The key to this conversation, to avoid argument, is to stop associating a given problem with a given person. Be hard on the problem, not the people. Recognize there are contributing factors out of any person’s control. Better yet, be a strong, humble adult and recognize that you play a part on the problems too. With the identity conversation, there’s much more at stake than egos. Attacking identity can lead to horrible attitudes and even more horrible actions.

The more I think about this framework, the more I realize that these conversation types are not static. Your exchange with another person can shift in and out of all three types in one discussion. Stay nimble enough in the moment and you can feel it happen.

The Seven Commandments for Making Difficult-But-Productive Conversation

Regardless of the conversation type, there are mistakes we must avoid and tactics we must utilize. These “seven commandments” reek of “listicle” fluff but I think this is a rare occasion where the plain words truly speak themselves. I’ve gleaned these from various points in the book and I firmly believe these “commandments” will work every time even if they are slightly contradictory.

    1. Speak up! Don’t silence your fears at any point. It is more courageous and helpful to mention them.  
    2. Speak when you’re ready. You’re not obliged to be uncomfortable. Stay true to your feelings and wait until your calmer, cooler head can prevail.
    3. Don’t ease into the conversation. Don’t “beat around the bush”. Doing this just creates doubt for the other party and turns the problem into something unnecessarily uncomfortable, almost taboo.
    4. Don’t Treat Your Conclusions As Truth. I’ve done this far more than I care to admit. I build some logical fortress around my argument prior to entering a conversation and, as a result, concede no ground to the other person. It makes me look foolish. Stubborn. Too opinionated. Entering the conversation with a question instead of a conclusion, treating your knowledge as imperfect, makes you far more flexible and—frankly—more enjoyable to be around.
    5. When someone isn’t getting it, ask how they see it differently. Please never ask this question again: “Why aren’t you getting it?” It never works. Acknowledge their point of view instead. Ask them what they see.
    6. A difficult conversation isn’t about what’s true. It’s about what’s important. Facts hardly matter in these moments because you’re sharing your feelings around those facts. That’s where the progress awaits. Don’t debate the truth anymore than you have to. Don’t debate at all. Uncover the values first. They’re hidden just underneath the feelings.
    7. Recognize joint contribution to a problem. Simply put, no more blame games. We all have a part to play. Difficult conversations are all about confronting complex issues. If you come prepared to acknowledge your faults, you’ll gain the other party’s appreciation. If you acknowledge the broader systemic faults, outside the two of you, you’ll gain their alliance.



Again, these “seven commandments” are really capable of elevating your exchanges. When coupled with the detailed insights from the authors’ framework, you can really understand how complex these conversations are. And also how much better we can be when we practice a few simple techniques from the start.


I received a wonderful comment on another book review yesterday. The reader said that I did a great job explaining the book without spoiling it. This, in turn, compelled the reader to buy the book.

This made me very happy; it’s exactly what I hope to accomplish with these reviews. I’m always trying to dance on the fine line between oversharing the book’s value and overshadowing what it can do for you. Make no mistake: I am trying my best to convince you that these books are worth your money and time. I do this by providing a good, hearty sample of their brilliance.

So with that said, I’m going to just tease the most valuable element of this week’s book. It involves the authors’ techniques for reframing a discussion. With the fantastic framework of conversation types firmly established, the reframing method is the elegant leverage point for shifting difficult conversations into something completely different, better, and wholesome. I’ve used it a few times already and it’s fascinating to see how people react.

This isn’t the stuff of “spin” but it may feel that way when you read it. Then, when you try it, you’ll find the reframing isn’t just for the context or the “messaging”. It’s for the mindset. The technique actually puts you in a completely different frame of mind, so much so that the “difficult” part of the conversation isn’t so bad after all. 

In closing, we have so much to learn from one another. This book shows us how. 

Here’s a link to the book on Amazon.

Mental Models and Principles

  • Intent versus Impact
  • 3 types of conversation: what happened, the feelings conversation, and the identity conversation
  • When we are unsure of someone’s intentions, we too often decides they are bad.
  • When stuck in a stalemate, step away from discussing what is true and shift towards discussing what is important.
  • Feelings are an integral part of conflict
  • Listen beyond the argument for the emotions; where do they sound hurt, angry, or offended. Acknowledge those feelings and respond to them.
  • Three components for identity: you will make mistakes; your intentions are complex; you have contributed to the problem.
  • Don’t try to control their reaction
  • Everyone has a hypothesis, an assumption, about your intentions.
  • “This is your fault” really means you did something wrong and you should be punished.
  • Listening to them helps them listen to you.
    • Truth – to – different stories
    • Accusations – to – intentions and impact
    • Blame – to – contributions
    • Judgments and characterizations – to – feelings
    • What’s wrong with you – to – what’s going on for them?
  • The Difficult Conversation Checklist
  • Prepare by Walking Through the Three Conversations
    • Sort out What Happened
    • Understand Emotions
    • Ground Your Identity
      • What’s at stake for you about you? What do you need to accept to be better grounded?
  • Check your purposes and decided whether to raise the issue
    • Purposes: What do you hope to accomplish by having this conversation?
    • Deciding: Is this the best way to address the issue and achieve your purposes?
  • Start from the third story
    • Describe the difference between your stories.
    • Share your purposes
    • Invite them to join you as a partner in sorting out the situation together
  • Explore Their Story and Yours
    • Listen to understand their perspective.
    • Share your own viewpoint
    • Reframe, reframe, reframe to keep on track.
  • Problem solving
    • Invent options that meet each side’s most important concerns and interests
    • Look to standards for what should happen.
    • Talk about how to keep communication open as you go forward.