Communication breakdown: Here's how to have better "Difficult Conversations"

Author Douglas Stone reveals how understanding intent and emotional intelligence can lead to better tough talks

By Mary Elizabeth Williams

Senior Writer

Published August 27, 2023 1:59PM (EDT)

A man and woman sitting across a speech bubble (Getty Images/Klaus Vedfelt)
A man and woman sitting across a speech bubble (Getty Images/Klaus Vedfelt)

The world has changed dramatically in the near quarter of a century since the first edition of "Difficult Conversations: How to Discuss What Matters Most" appeared. Did people even argue about before social media? Have tough conversations just become tougher? Well, yes and no.

As the newly updated version of Douglas Stone, Bruce Patton and Sheila Heen's bestselling guide to more productive communication recognizes our understanding of power dynamics has evolved. And the ways in which we can talk to each other — and misunderstand each other — have changed. But certain dynamics of human interaction remain consistent. We all have different ways of looking at things and we all share a need to feel heard and seen.

I talked recently to one of the book's authors, Triad Consulting founder and Harvard lecturer Douglas Stone, about what's changed about having challenging conversations, what good intentions aren't good enough and why the first person you need to negotiate with is always yourself.

We don't always understand that difficult conversations are not necessarily fights, are not necessarily conflicts. You and your co-authors break it down so well in the book. Explain to me, what is a difficult conversation?

For me, the key is just the word difference. When there's a difference, we're going to have trouble communicating. How you handle that difference could result in a conflict. It could damage the relationship. Or if both people are handling it well, it can go fine and you can problem solve and move into a better place. 

There can be conflict and a difficult conversation, but there doesn't have to be. So our definition of a difficult conversation is literally anything that you subjectively experience as difficult. We've gotten some pushback on that, like, "There must be something more technical to it." And there really isn't.

If a person subjectively feels worried about a conversation, or they're up at night, and they can't figure out, it doesn't matter. It doesn't matter if it's something that will have big consequences, or just returning something without a receipt and feeling, "Do they think I'm trying to get away with something here?" That's not a very important conversation, but if it feels hard for somebody, it's a difficult conversation.

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It's called "Difficult" for a reason. Some things are just going to be hard and to understand that is really key because we are avoidant in our culture.

When I teach this material, I often begin by saying, "The good news is, by the end of the day, you will have some skills that will help you have these conversations more effectively, and that will make it more likely that the conversation will go well. But no matter how skilled you become, there's nothing that turns a difficult conversation into an easy conversation or a fun conversation."

It's really a matter of being more effective, having more information going back and forth and hopefully reducing some of the stress and anxiety that we feel. But all the problems in life don't disappear just because you acquire some skills.

You start the book with the question, "What happened?" How do we get that clarity? Even if we can't agree on what happened, we can understand that maybe there are different accounts of what happened.

In working with many, many people on their conversations, one of the most interesting things was that we started to see patterns in ways conversations were going wrong. One of our categories is the "What happened?" conversation, literally meaning our recollection of who said what, who did what and what that means. It's basically everything other than emotions or identity issues, which are the other two categories. In terms of understanding what actually happened between us, if there is some conflict or issue there, there are roads that we go down that are not useful. 

"We often go through life without ever getting the feedback that the way we see things is just a way of seeing things."

One of them is that we assume, "I know what's happening in my life. We had a conversation, I remember what it was. When I describe it to you, it's not that hard to figure out." Of course, the other person is feeling the same thing, that that they see the world their way and that they're right. We often go through life without ever getting the feedback that the way we see things is just a way of seeing things. 

There's two broad reasons for why two people could look at exactly the same thing and see completely different things. One is that we're we're taking in different information. No matter what we're looking at, we might be looking at different parts of it. Or I might have access to information that you don't have access to, for a variety of reasons. Another big piece of that is that we're going to interpret what we see in our own particular way.

Two people might overhear a conversation and one might say, "Well, that was a racist comment." The other person might say, "It didn't seem like a good comment, but I didn't think it was racist." Both people have noticed the same thing. They're just filtering it differently. They're making meaning out of it differently. We do that all the time. 

If I'm looking through the filter of "The world is unfair," it's very easy to see lots of things that are unfair, and I'm right about those things as I see them. If I'm looking through the filter of, "The world is as fair as it reasonably could be," I'm going to notice a lot of things that are remarkably fair, given how complicated the world is. Those are two very different orientations toward the world. And there's a million of those kinds of orientations that are inside of us, and are going to impact how we make sense of our lives.

You talk a lot about intention, and this is where I always get screwed up, because I'm positive I can read everybody else's mind and everyone can read mine and knows what I really meant. How do we rephrase leaping to intention, which is a real stumbling block? 

I would say that it absolutely matters how it's received. It also often matters what the intention is. Not always. We feel more patient if we're driving, and we're being blocked because someone's being loaded into an ambulance, than if someone's double parked their fancy sports car because they felt like looking at the scenery. It's the same impact on us, which is we can't drive for being blocked. But we know there's a different reason, there's a different intention behind each of them. Both intentions and impacts matter. 

"Just having good intentions doesn't fix anything."

But it's really important to observe that just having good intentions doesn't fix anything. If I make a joke and my intention is to break the ice, and the other person is saying, "That joke was actually inappropriate and sexist," and then I say, "No, it's fine because I meant it as a good thing," that doesn't fix the problem. It might help to know that my intention was to use it as a social lubricant. But whatever the whatever the impact is, is still the impact.

If we're doing something that's discriminating against a group of people, and we're saying, "We were doing for this other reason, so it's fine," we have to look at the impact and solve that as well. People are too quick to feel that their own good intentions just fixes the problem. 

The word that comes up so much in this book is feelings. I love Antonio Damasio, and his work acknowledging that feelings have value, that they drive a lot of our decision making. Those things matter. 

Damasio, at least from my perspective, was really the person who made that case, that it's not like, there's rational thought over here, and then there's feelings over here. That division isn't a real division. There's no such thing as rational thought with no feelings, and then just feelings. All the rational calculation in the world doesn't get you very far. We need to care about things, we need to want things and be afraid of things and have values. 

How do we then balance that? I am a great believer in the power of emotion to guide us to compassion, to empathy, to listening, to conflict resolution and to intelligent, informed decision making. 

We can make a case that feelings are integral to decision making, in a good way. It's also true that feelings, handled a certain way, can result in bad decisions. There are lots of examples where we make decisions based on emotion in the moment that seem right. And then the next day or a year later, we look back on it, and we think, "Oh, that was not a good decision."

But the answer there isn't to throw out feelings. We can't do that. The answer is just to start to notice our own patterns in terms of what how emotions impact decision making. When you notice, "I tend to make worse decisions when I'm really stressed out and anxious or fearful," then you can try to correct for that, try to postpone the decision or whatever you have to do. Feelings can lead us in a direction that we don't want to go. The answer isn't, therefore don't listen to your feelings. The answer is actually listen to them more, get better understanding of how they impact your life. And then, try to move from there.

Another thing is to listen. The hardest thing for most of us to do is to just shut up. 

"Listening is both the most important piece of all of this, and the hardest."

Listening is both the most important piece of all of this, and the hardest. One reason I know that it's the hardest is because it's also the hardest for me. When I'm teaching this, students will say "When will listening become my default? When will it start to get easier and I'll just get better at it?" My slightly cynical answer is "Well, really never." If someone's attacking you, you're never going to think, "The thing I should do here is say, 'Tell me more about that.'" It tends not to feel natural. 

Often, I remind myself right before the conversation, there are going to be moments during this when you're overwhelmed with a desire to disagree or to interject or to flee. The thing to do when you feel those things instead is time to ask a question or to say, "Tell me more about that," to lean into what they're saying. 

Towards the end of the book, you answer the questions of "What if...?" and "What about...?" I think about power dynamics a lot, the inequities and the emotional labor and the heavy lifting more vulnerable people have to do. You can be respectful and you can be listening, but if the other person is holding more of the cards, you maybe have put in exponentially more work.

That's one of the topics that we're adding to the third edition. That's very much on our minds. We felt that we did not sufficiently address it in the previous editions that we had. 

In our revisions, we talk to both sides of that. We say to the people who tend to be in the more powerful position, "Be aware of this dynamic that that you might be putting in X amount of time, and this other person's putting in 10X. That's a big difference, and do what you can on your end to try to even that out." And we do in the book acknowledge that there are situations that are just structurally unfair. 

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What we sometimes hear is people will say, "It's unfair, therefore, I'm not going to have the conversation." That will sometimes be a good choice. But what we're also making the case for is saying, even as it's unfair, what you can do is just the best that you can do, given the cards that you do have, given whatever leverage or power you have in the situation. Try to put it together as well as you can. At the same time, you can be working to make society just more fair, generally in structural and systemic ways.

Sometimes people are treating it like it's an either/or, like you can stick up for yourself individual situation, or you can try to change the system. The book is more about the individual conversations. But that doesn't in any way preclude us from trying to make systemic change as well.

By Mary Elizabeth Williams

Mary Elizabeth Williams is a senior writer for Salon and author of "A Series of Catastrophes & Miracles."

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Conflict Debate Difficult Conversations Douglas Stone Emotional Intelligence Interview Psychology