in: People, Podcast, Social Skills

• Last updated: September 30, 2021

Podcast #559: How to Handle Difficult Conversations

Asking for a raise. Disagreeing with your boss. Telling your neighbor that their dog’s barking is bothering you. Talking about money with your spouse. Debating politics with a friend. These are all difficult conversations fraught with anxiety, anger, and awkwardness. Many people just avoid them, but my guest says that with the right framework, you can handle even the most pitfall-laden exchanges. Her name is Sheila Heen, she’s spent twenty years developing negotiation theory and practice as part of the Harvard Negotiation Project, and she’s one of the co-authors of the book Difficult Conversations: How to Discuss What Matters Most. Sheila starts things off by sharing the most common difficult conversations people encounter professionally and personally and the most common unhelpful ways people deal with them. She then explains how every difficult conversation actually has three hidden conversations going on, how people confuse the impact of what others say and do with their intentions, how you can acknowledge your contribution to a problem without assuming the blame, how to share your emotions without being emotional, and how to generally move a conversation from being about combative confrontation, to being about exploring each other’s stories. 

Show Highlights

  • The most common types of difficult conversations
  • The ways we deal with difficult conversations that lead to more problems
  • Why unknown contexts and background info can hamper our point of view 
  • The 3 convos happening below the surface in the midst of any difficult conversation 
  • How to get a better of what’s really going on in any uncomfortable talk 
  • Disentangling intent from impact 
  • Figuring out the “third story” — not our own and not the other party’s 
  • How to talk about feelings in the midst of any difficult conversation
  • How does our identity (or how we see our identity) play into how we conduct these conversations?
  • Are there instances where information should be withheld?
  • What to do when honesty and niceties in conversation aren’t reciprocated 

Resources/People/Articles Mentioned in Podcast

Sheila Heen's "Difficult conversations" about what matters the most.

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Read the Transcript

Brett McKay: Brett McKay here and welcome to another edition of the art of Manliness podcast, asking for a raise, disagreeing with your boss, telling your neighbor that their dog’s parking is bothering you. Talking about money with your spouse, debating politics with a friend. These are all examples of difficult conversations fraught with anxiety, anger, and awkwardness. Many people just avoid them. My guest today says the right framework you can handle even the most pitfall Laden exchanges. Her name is Sheila Heen. She spent 20 years developing negotiation theory in practice as part of the Harvard negotiation project and she’s one of the coauthors of the book, difficult conversations, how to discuss what matters most.

She will start things off by sharing the most common difficult conversations people encounter professionally and personally and the most common unhelpful ways people deal with them. She then explains how every difficult conversation actually has three hidden conversations going on, how people confuse the impact of what others say and do with their intentions. How you can acknowledge your contribution to a problem without assuming the blame, how to share your emotions without being emotional. How to generally move a conversation from being about combative confrontation to be about exploring each other’s stories. After the show’s over, check out our show notes at Sheila joins me now via

Sheila Heen. Welcome to the show.

Sheila Heen: I am delighted to be here.

Brett McKay: So you are a coauthor of a book called difficult conversations, how to discuss what matters most. Now, this book originally was published in 1999, so that was 20 years ago. You came out with a 10 year anniversary in 2010, 10 years ago and both times New York times bestseller. It’s still selling well. I see this book brought up in conversations with friends, in articles on the internet and I think that speaks to the idea that difficult conversations is a perennial problem for a lot of people.

Sheila Heen: Well, it is. If you’re human and you’re in relationships with other people, guess what? You have difficult conversations, or you’re not having the ones that you need to have and that’s not actually a better solution

Brett McKay: And your work, dealing, talking about difficult conversations and talking to people about this issue. Like what are some examples of the most common difficult conversations that people encounter professionally or personally?

Sheila Heen: Our second book was about feedback, because giving and receiving feedback basically in conversation with other people or in relationship with other people, the things they’re doing that drives you crazy or that are making it harder to work together or live together or be their friend or be their family member. Those conflicts between us, our particular type of difficult conversation that really every person on the planet that we’ve ever met and worked with struggles with. So that’s definitely a really big category. Another big category is just talking up and down hierarchy in any way. Telling your boss that they’re wrong. Trying to figure out how to handle a client whose expectations feel unreasonable or a scope creep is sort of a chronic problem.

Also any conversations across difference or across culture tend to be challenging? There’s like an extra layer of challenge, although we would probably say that any conversation between two people, including identical twins is in some way cross-cultural because of the stories that we form in our heads about what’s going on and what we expect of each other. Those can be different. Actually even in the same family as anybody who’s got family conflict can probably attest to, so that those kinds of talking across values and stories about who we are and how we are is a big category as well.

Brett McKay: All right, so the categories you see, so feedback is always uncomfortable because you have to tell someone you’re not so great at something potentially and that’s awkward to hear, telling someone someone’s wrong, you think they’re wrong or bothering you or annoying you. That’s another awkward conversation. And just talking across different values or cultures is another type of awkward or category,

Sheila Heen: I think that’s right. And so any sort of disagreement or conflict in the relationship causes a set of conversations that either we feel like we should have or we’re avoiding. Anytime it feels there’s emotion involved. So strong disagreement, strong emotion. And then of course you’ve got sensitive topics that tend to end up implicating strong disagreement and strong emotion, right? The classic politics maybe particularly right now, religion, etc. Like deeply held views where it’s actually pretty upsetting to learn that some people really don’t see it the same way that we do.

Brett McKay: And how do people, most people manage or handle difficult conversations that actually leads to more problems?

Sheila Heen: Well, one of the most common is that we avoid them, right? So instead of talking to the person who I’m frustrated with, I have to do something with that frustration. So then I instead will vent to someone else. And once I feel better venting, somehow I feel like that I’m relieved of the responsibility or maybe the energy right. To go back to have the conversation directly. So we triangulate the problem rather than talking to the person directly. And then it’s sort of festers. It festers both for us emotionally. And it festers often in the system of relationships, like in the family or at work. And the problem with it festering is that the next time they do exactly the same thing, which I promise will happen, now I’m reacting not just to what you just did, but the fact that this is the 17th time you’ve done that and you should know better.

And so my reaction is really cumulative, which then appears to you if I let you see it. And sometimes I can’t help it, to be an overreaction. And in some sense it is an overreaction to what just happened today, but it’s not an overreaction to what’s been happening for 17 years. So that’s part of the problem, which is that we’re trying to sidestep them. The other way to go of course, is that we decide we’re going to step up and confront them, and explain to them why this is what the problem is. In other words, why you are the problem and what you need to change. Because if you change, then we won’t have a problem. And that doesn’t tend to go very well either. So one of the metaphors, and my colleague Doug Stone came up with this one actually, I have to give credit where credit is due.

It’s like you’re standing there holding a hand grenade and my choices are, I can either throw the hand grenade and confront you with what you need to change, but I think, well that’s probably not going to go well, but holding onto it once the pin has been pulled isn’t a solution either, and there isn’t a diplomatic or tactful way to deliver a hand grenade. So part of it is that we try to get out of it by finding exactly the right words that will mean that they’ll either agree that we’re right or they won’t be upset or mad at us because it’s more comfortable for me to secretly be mad at you than to know that you’re mad at me. For many of us, I think, I don’t know, what’s your experience with this?

Brett McKay: No, I think the former’s typically the approach that I take, avoiding, I’d rather avoid it. I think it’s for a lot of people, just cultural, I grew up in Oklahoma, so it’s sort of the Midwest, you from Iowa, like Minnesota nice, Iowa nice, right? You just don’t talk about the problem and then you sort of festers and then you sort of, you vent about it to somebody and then you don’t actually address the problem.

Sheila Heen: Yeah. And I’m really glad that you brought up the way that upbringing affects this, because I do think that in families we sort of learn by osmosis how conflict is handled. And it’s interesting because if you look at the research about how kids do in adult life and sort of the relationship between that and how they saw conflict handled in their own families of origin, there are some striking results. So there are families where the kids never saw the parents argue or the family members argue and you’d think, well that’s wonderful. That’s idyllic, right? But then they don’t know how to handle conflict. Conflict feels like a huge deal because it just isn’t done. And if you are upset with me, it’s catastrophic. Then you have kids who see their parents have conflict and then they go in a different room and then they come back out and they’ve made up somehow.

And so even if what we saw wasn’t upsetting, not sure what happened in between. I’m not sure really we want to tell the kids what happened in between sometimes, but they’re not sure. How do you get from, I’m so frustrated with you to now everything is fine. And then you’ve got a third category who are kids who see their parents have a conflict or estrangement, violence, abuse, anger, et cetera, rupture in the family. And obviously those aren’t great things to learn. And so really the kids who do the best are sort of in this fourth category, which is they saw the conflict and they saw it happen within boundaries of, I know you so well. I know what I could say right now that would really hurt you and part of me really wants to hurt you, but there’s a boundary on where I will go, even though right now I hate you.

So they see people actually have conflict, have some boundaries on how we treat each other even when we’re in conflict but not avoid it. To talk it through to understand why is it that we see this so differently and to find some kind of resolution even if it’s, well now, I still don’t agree with you but I understand why you reacted that way or why you see it that way. The kids who see that process happen are the ones who go on to tend to form the most stable relationships later.

Brett McKay: And I imagine that group’s really small because like this isn’t explicitly taught how to handle conflict, right? If you don’t get it at home, if you don’t see it through osmosis, you have to go to law school and take a negotiation class to really learn like explosively what you are doing wrong.

Sheila Heen: I’m not sure law school generally is good training for dealing with conflict effectively. But negotiation course is supposed to be right. I mean, part of the reason why there’s one piece of the puzzle and the divorce rate among attorneys is just that we take our advocacy skills home and we argue that we’re right, but there’s no judge at home to declare us the winner. So we win the marriage or we think we do, but we actually do all sorts of damage to the relationship. I think you’re right though, that that category feels sort of dishearteningly small. But I guess maybe what’s more reassuring is that we just need to expand our horizons for where you can learn it. Because I do think that you can learn it by watching others. Like if it’s not happening in your family, maybe you had a friend as a kid or maybe you had a mentor or a coach or a teacher.

And so, we’re sponges absorbing everything. We’re not sunk if members of our immediate family didn’t handle it well, because it certainly is something that you can learn both by watching people. And of course by actually deciding this is a set of skills that I need to work on.

Brett McKay: All right, so the two most common approaches you probably see, avoiding the difficult conversation in the first place or just confronting it, but doing what you guys call battle conversations, battle messaging, where you’re like, I’m right and here’s why you’re wrong. Type of conversation

Sheila Heen: For sure. I think that we go into these conversations when we decided to have them and because the whole situation just feels really messy and anxiety written and uncertain. Part of the natural tendency is, okay, I do actually need to have this conversation, so I’m going to stick as close as I can to the things that I’m pretty sure that I’m right about. Because if I wasn’t sure I was right about them, I wouldn’t have this conversation in the first place. So once they see how obviously right I am, then right, they’ll have to agree. And the problem is that that leads us into this sort of message delivery stance. Like, I’m going to deliver a message to you for why I’m right and your choices are agree or be a problem. And the problem with that approach of course, is that the other person is pretty sure that they’re right about a few things as well. And that’s why it doesn’t go anywhere.

Brett McKay: Well, here’s an example of that. So like asking for a raise, it’s one of the difficult conversations. So you go in and you have all the data’s like, here’s what I’ve done for the bottom line for the company. Here’s this… because you just follow all the advice on what you do when you ask for a raise, document, show what you’ve done, blah, blah, blah. And you’re like, here’s what I’ve done. I’m comfortable with what I know. So I’m going to present that. I think I’m right. I know I’m right. But then your boss says, well no, because you don’t know this other part of the story that’s going on.

Sheila Heen: Yeah. And so, Oh, this is a good one. So let’s just name three or four different other parts of the story that might be going on.

Brett McKay: They took a loss somewhere that that employee doesn’t know about.

Sheila Heen: Yeah. So like actually your right about all of the amazing things that you did this year. The problem is that I’m also right that we incurred a loss so that our pool is just not as big as it should be. Right? So that’s a great example of the boss is sticking to what he or she is pretty right about and they are. But we’re just talking about two different topics. Another answer might be you did actually do all of these things and that’s not the criteria we use for a raise. Like you would need to move into a different role, and although you’re fantastic at the role that you’re in, you actually don’t have some of the skills that the next role needs and pay is tied to that set of responsibilities.

So you’ve got some development to do. Right. That would be another version of why the boss is pretty clear on what they’re right about, which is how pay is tied to responsibilities and your skillset. So that’s another really common thing. And it’s not that you did a bad job, it’s just that your frame on what you need to do in the conversation is just a little off.

Brett McKay: Okay. So doesn’t matter what the conversation is about, whether it’s asking for a raise or bringing up a difficult issue in your marriage, you and your coauthors say that whenever, you have a difficult conversation, there are actually three different conversations going on at the same time. What are those three different conversations that are going on?

Sheila Heen: Yeah, so actually let me pause for a second because I should have added something to what we were just saying, which is, it feels like, well if I’m not supposed to talk about what I’m right about, am I supposed to pretend that they’re right or like what am I supposed to instead? And I think that the key shift is actually a shift in your purpose in the conversation, which is to shift from delivering a message about what I’m right about, to instead, I just need to understand whether we see this differently and if we do why?. So if I’m going in to ask for a raise and I’ve done all of my homework in all of the same ways, but my frame on the conversation rather than saying, so here’s why I deserve a raise, yes or no, which kind of backs your boss into a corner by the way. I would instead say, look, I’m looking at a whole bunch of things that I did this year. I’m happy to share them and I’d love to talk about them.

That suggests to me that an adjustment in my compensation makes sense and that I deserve a raise, including by the way, criteria for what people doing my role are paid elsewhere. So I’m curious to talk a little bit about that and learn more about how you think about compensation and the job that I’ve done. So that’s a frame that says, I want to share what I see. I need though to understand what you see so that then we can kind of think about what might make sense or not. You’re not saying that it’s not your boss’s decision, but that’s actually an invitation to a really different kind of conversation where you’re likely to walk away having learned something, whether or not you got the raise now, you’re going to walk away with a much better sense of what it would take to get the raise the next time you have the conversation.

Brett McKay: So you’re shifting from a that battle conversation to a learning conversation.

Sheila Heen: To a learning conversation. Yeah, exactly. Now we’re ready to talk about those three conversations.

Brett McKay: So when you’re having a difficult conversation, what are those three conversations that are actually going on? But you don’t know is going on.

Sheila Heen: Right, because they’re below the surface. That’s exactly right. So, one of the insights for us, and we learned this in part from Chris Argyris over at Harvard business school and his colleagues doing action science, has to do with the internal voice. So if you want to understand a difficult conversation, you have to listen beyond what people are saying to actually listen to what they’re really thinking and feeling. And often not saying to each other, maybe particularly in polite corporate cultures or a nonprofit cultures or Midwestern cultures, where we say just a tiny fraction of what we’re really thinking and feeling. So there’s a gap between what I’m saying and what I really think and feel. So then when you take a look at, okay, well then what in the world are people really thinking and feeling during these conversations? It’s like you’re x-raying the conversation and what you’ll find is a really predictable structure, because no matter who you’re talking to or what you’re talking about, in the midst of a hard conversation, your internal voice is doing a very predictable set of things.

And we basically categorize them into three buckets, which we call the three conversations that are happening sort of inside of you. And by the way, inside of the other person. So the first is what we call the what happened conversation. In other words, we each have a story about what has happened, what’s happening now in this conversation while you’re being so difficult and defensive, and what we think should happen, like what’s the solution? And that story has three key pieces to it that are sort of sub pieces of our story of what is happening. The first is what I’m right about. The second is whose fault it is that we’re having this problem because blame is always at least implicit if not explicit when things go wrong or get hard. And then the last is suspicions about your intentions, motivations or character. Like why are you being this way?

What is wrong with you that you’re so clueless or controlling or naive to be acting this way. So those are three pieces of the story that are particularly important. Below that though, there are two more things going on and we can circle back to dig in a little bit more. But I should just name the other two. The second one is what we call the feelings conversation, which is that we’re each trying to figure out what do I do with all of these strong feelings and reactions I’m having, that are often bundles of feelings and sometimes contradictory feelings. Like I feel grateful for the opportunity you’ve given me this past year to really step up and shine. And I have felt sometimes neglected along the way and now I’m frustrated and dismayed and a little betrayed that this is not going to pay off, right? And, but I’m in a corporate context.

So like what am I supposed to do with that? Because I feel like I’m not supposed to be emotional and just to check my feelings at the door when I come in the morning and stay rational and businesslike. So I’ve got to figure out what to do with those emotions, even though they tend to leak out in tone of voice and body language and all of that. And then finally at the deepest level, the third piece is what we call the identity conversation. And it really came out of our observation that, if a conversation feels difficult to you, if it’s keeping you up at night, chances are there’s something that the situation suggests about you that feels like it’s a stake. In other words, what if you go in and ask for a raise and your boss actually says, well, that’s great. All of your facts and figures for what you accomplish.

But I have to tell you, you were kind of a disappointment to me this year. Like holy cow, we’re not just talking about dollars and cents. We’re talking about who I am and whether I’m valued around here. And if I don’t get the raise, well, do they think they can take advantage of me? Do they not actually value me? Am I not the superstar I thought I was. And so it’s who we are is really on the line. And that’s part of the anxiety around the conversation. And by the way, for the boss too, right, are they somebody who goes to bat for their people or are they somebody who isn’t able to reward good work or wasn’t honest with you during the year about how things were going so that they’re not a great manager or leader. So identity is actually in play often on both sides of the conversation.

Brett McKay: Awesome. So let’s circle back and dig into these a little bit more, because like, the what happened conversation. It seems to me, in my experience, whenever you have a difficult conversation, or once you sort of come at loggerheads, it’s always around this like what happened? Who’s to blame? What was your intent? Because there’s all these differing perspectives of what’s going on in the conversation. So what can you do to get a better idea of what happened with an issue that’s there?

Sheila Heen: Yeah. Well, so importantly, the first conversation you need to have is a conversation with yourself. If I go into the conversation, still focused on what I’m right about and focused on blame and my suspicions about why you’re being so crazy, it’s not going to help. I’m not going to be able to have the conversation any differently, because my behavior of course flows from my internal assumptions and stance and thoughts and feelings. So the first conversation is a conversation with myself where I’ve really got to shift all three pieces of that story from being focused on what I’m right about, to wondering why we see it so differently. What is it that you can see that I can’t? That helps me understand why you could possibly disagree with me or what I’m saying is the issue isn’t the issue from your point of view, right?

I think we’re arguing about what the contract says. You’re actually not arguing about what the contract says. We agree on that. What you’re arguing about is what the contract means. Now that the circumstances have changed and what we should expect from each other given that circumstance. The second shift in the story is from blame to something we call joint contribution, which is to step back from the idea that it’s as simple as somebody’s fault and instead to think, okay, probably we both contributed to this and the things we’ve contributed down or failed to do may not really be blame worthy. We didn’t do anything wrong, but it hasn’t helped. And it doesn’t mean it’s 50, 50 it could be 90, 10, but if I can think about, well looking back, what do I think I’ve contributed to this problem and what do I wish I would’ve handled differently and what do I need them to do differently or what do I wish they would do differently that I think would actually help? That’s actually a much easier conversation for us to have, particularly if I take the initiative to put my contribution and taking responsibility for it up front.

Brett McKay: Yeah, the accepting contributions, that can be hard for a lot of people because you’re going into, it’s like, well, I didn’t do anything wrong. This guy, this lady, she’s the problem. But your contribution can be as simple as maybe you didn’t say something earlier like, hey, this is bothering me. And then you let it fester for a long time till it became like a bigger problem. And that was your contribution.

Sheila Heen: Totally. And that’s the thing is, that people say, look, I didn’t do anything wrong. To which we would say, that’s right, you didn’t, but you did do or fail to do some things that probably didn’t help. Right. And avoiding until now is one of the most common. It’s also like, you didn’t call right back so people had to make some decisions in the meantime, you didn’t do anything wrong. You didn’t even do it on purpose, right? You were on a plane or asleep. But partly if we want this not to happen again, figuring out what we each contribute if we wanted it to go differently, what we each contribute tells us what would have to change so that we’re not having the same conversation, next week or next month. And so contribution, we sort of lower the stakes on it. It doesn’t say that you’ve done something wrong necessarily. It just is untangling how did we get here? And if we want to land in somewhere in a different place, what would we need to change to make that happen?

Brett McKay: And this idea of trying to figure out what happened and learning how they’re seeing the issue. Like one line that really stuck out to me was reminding yourself when you’re going into one of these conversations, if you think you already understand how someone feels or what they’re trying to say and what they see about the topic, you’re being delusional.

Sheila Heen: Well put.

Brett McKay: And I think, this idea that you take a learning stance for a difficult conversation, you just start asking questions about like, you agree that something happened, right? You agree what happened? But like the meaning of what happened can be vastly different in that guy’s head then in your head. And so you start asking questions about that.

Sheila Heen: Yeah. I mean, I sometimes remind myself that if I can move from my reaction of like they’re crazy or there’s no excuse for that, to, I wonder why they’re crazy or how could they possibly be telling this story that makes sense? Because they are telling a story that makes sense to them. So there’s something, I’m not understanding that I may or may not agree with it at the end of the day, but I’m better off if I at least understand how they’re seeing it. They always have information that we don’t, right, including about their own reactions. But often they have a whole bunch of information about conversations they were in with other people or they stayed after the meeting and we didn’t, or they got invited to the meeting after the meeting where everybody talked sort of what we said at the meeting.

So they have information that we don’t about the impact that we had on them or on the team or whatever on the project. And if we walk in thinking that we have all the pieces of the puzzle visible to us now, that is delusional. So part of our purpose in the conversation is, look, I’m going to put my puzzle pieces on the table. I’d love to have yours and let’s see whether they fit together in any way. But at least we can both have a more complete picture about what is going on. And at that point we’re in a better place to figure out what do we want to change and how would we do that.

Brett McKay: And I think another key concept of really trying to figure out what happened, is you have to remind yourself that a lot of the reasons that difficult conversations exist, it’s not because someone said something, though that can be a source, but like people aren’t saying things right. So you’re left to make assumptions that make things awkward. So what you have to do is you have to craft questions to make those unspoken things explicit.

Sheila Heen: Yeah, I think that’s right. And also in the vacuum of understanding what is going on because of all that we don’t see or have access to. One of the automatic things that as human beings, our brains do, is that we attribute intentions to other people. Like we make up stories about why they did what they did. Well, they didn’t really want us to come to the meeting. They were trying to hide it or they just need to control everything or they’re threatened by me, because that helps make sense of what we see. And if you want to turn a regular conversation into a difficult conversation, here’s a little tip. If you want to go the other way, accuse the other person. Like, I know why you did that. It was strategic. You were hiding something. You were out to get me. You’ve never liked me. Right? I mean you could come up with all kinds of stories, the worst possible story about why they’re behaving, the way they’re behaving. And I guarantee you they will react to that.

Brett McKay: Right. That’s this idea of you have to disentangle intent from impact. Because that happens… if something that affects you in a bad way. You automatically want to assume like, someone did this on purpose, they’re out to get me and I’m going to do something about it. But usually sometimes people just do things and they weren’t malicious about it, but it impacted you and they didn’t know.

Sheila Heen: Yeah, It’s amazing. I don’t know about you, but it’s a rare day that I wake up and think to myself, how can I make this person’s day horrible? Right? And I’m going to figure out a way to really mess with them. And yet somehow when other people mess with us, we assume that that is in fact how they’re living their day. Like we always know that we have good intentions or at least like look, it was a joke, I’m sorry, I didn’t mean to offend you. I didn’t mean to upset you. I didn’t mean to forget to add you to the conference call. I’m really sorry. Like we always know that at worst we were forgetful or busy or distracted, but when we’re upset with someone else, part of what happens is like our brains jump from how we feel impacted, frustrated, left out, betrayed, et cetera to assuming well they meant to do that.

And so we’re not even aware that we are making that leap to attributing intentions or character. Like it’s just the kind of person that they are is the next step. And the more frustrated we are, the more likely we are to assume the worst. But people, it’s really hard to live in a world where somebody else has really different beliefs than you do about things that are important to you. Like we can talk about politics here, that just living alongside each other is upsetting. It’s even harder to live alongside someone who has a story about the kind of person we are that feels fundamentally wrong. They somehow have the impression that you are a scheming, lying, defensive controlling person and you’re thinking, I don’t even recognize that picture of me. And it’s really hard to feel that deeply misunderstood by other people.

Brett McKay: So what’s the solution there? The idea is, can you disentangle intent from impact, I guess assume good faith, right? Don’t assume that, you did this just to get at me, and then explore what was going on. Like why they really did what they did and how they felt about that thing.

Sheila Heen: Yeah. I would probably tweak that just a little bit, because people often say assume good faith and in longterm relationships you’ll get a quick reaction to that. Oh no, I know them better than that. There’s no basis on which to assume good faith. So I actually would say, assume you don’t know. In other words, other people’s intentions are invisible to us, so we have to impute them from their actions. So just assume that you don’t know. They might have been busy, they might have been well-intentioned, but actually they were trying to help in a way that actually hurt, but their intentions were good, and instead just, and they might’ve had bad intentions, but what’s important is actually speak to the impact that you’re concerned about.

Here’s what you did and here was the consequence of that, which is that I ended up having to explain to the client, yada, yada, yada. Or explained to the family the following and then we had to change the travel plans, et cetera, et cetera. That’s the problem. I don’t know what was going on with you. I don’t know whether you were even aware of the impact, but I wanted to talk to you about it because actually the impact is the problem that we’re trying to fix. Whatever your intentions were.

Brett McKay: And another tactic you and your colleagues suggest on, trying to figure out what happened is, instead of starting from your story, right, which is this happened, this guy meant to do it and it’s terrible and you don’t have to start from their story and say, okay, your perspective. What you do instead is you start from a third story. How do you figure out what that third story is?

Sheila Heen: Yeah, it’s a great question. So we automatically start from within our own story. And by the way, when I have students or executives I work with, they’re often sort of walking in the door with stronger skills on one side or another. So either and more often they’re quite good at asserting their view, explaining their persuasive, they’re articulate, et cetera. And what they actually need to work on is a set of empathy skills for understanding someone else. And also listening when you actually don’t feel like listening. Many people will say like, Oh, I think listening is really important. I think it’s really, one of my better skills, a thing that I really work on. And when things get difficult, listening is like the first skill to go totally out the window.

Partly because I’m coping with my internal voice, like in a difficult conversation my internal voice is super loud, it’s saying that’s ridiculous, that’s not what happened. You’re totally not taking responsibility for your part in this. So often people will come in with pretty good skills on explaining their view and what they need to do is work on listening to and understanding someone else’s story, what we call the second story. Other people actually have the reverse. They’re really empathetic. They’re the person everybody comes to talk to. And often what happens to them is they have a difficult conversation. They’re really great at listening to the other person’s story, and then they walk away and they think, well, hang on a second. That all made sense. And I felt it, but I forgot to say what’s important to me, like my needs and my views and my interests actually somehow got left behind or lost, because I forgot to transition back to say, okay, well here’s what makes sense to me, but here’s what doesn’t.

Or here’s what matters to me that seems like it’s left out. So that’s a big, long windup to say. Part of it is balancing those two skills, but starting the conversation from what we call the third story cannot only help you have a good conversation, but it also can remind you to do whichever of those comes less naturally to you. So the third story would be basically how does an observer, how would an observer describe the problem between you, and the key phrase is different or difference. So just saying, I think we have different assumptions about when and how well to do the dishes, how well adds my view perhaps. But we have different views about when to do the dishes, whether they should be done after dinner and cleaned up before we go to bed, or whether you’re too tired after dinner, you’d rather come down in the morning and do them.

And I wonder whether we could talk about that, that describing it as a difference does a couple of things. Number one, it names their view, their story, and my story as legitimate. Those are both legitimate parts of the conversation rather than, let’s talk about why you can’t seem to actually clean up after dinner, even when it’s your turn and I have to come downstairs to a mess, that would be totally inside my story. And in my story, I’m the good person and you’re the bad person. So that’s one of the reasons why starting in your own story proposes a conversation that the other person is like, well, I don’t want to be part of that conversation. I’m cast as the bad guy and that one. So I’m not definitely not agreeing to be part of that conversation.

Brett McKay: They’re going to get defensive and it’s not going to go anywhere.

Sheila Heen: Yeah, and we’re casting a play. Anytime we have a conversation, our story casts people as good guys or bad guys as the problem or sort of the hero of the story. And when we start the conversation from inside our story, chances are they’re cast as the problem or the villain and they don’t want to have anything to do with that and vice versa. Right? So if I start from inside your story, I’m losing track of my own. And from your point of view, either there isn’t a problem, which I don’t agree with or I’m the problem because I’m complaining too much and I’m needy, etc. And that’s why the third story is kind of the magic place you can go that creates both, look, we’re partners in this. The role I’m casting you in, is that together, let’s figure out what’s going on. And that’s actually a role that people are much more likely to say yes to.

Brett McKay: So I think it’s really useful for people who have problems managing conflict. Because like the typical approach like you said earlier is avoid it because it’s uncomfortable. The second approach is just like go agro and just like go overly aggressive and that just makes things worse. This idea of just going at it at a stance. If I’m going to try to figure out what the problem really is and how this other person is seeing the problem and how an outside observer would see the problem, diffuses that hand grenade you were talking about. Right. It’s still a little bit like it’s still a hand grenade. If you bring up the problem, someone might not react favorably, but if you come at it with say, well, tell me how you’re seeing things. They can take a step back and it takes the, I don’t know, it just makes it easier. You sort of having an actual productive conversation.

Sheila Heen: Yeah, so if you look at the research or the literature, one of the things that jumps out is that reciprocity is one of the strongest social norms that just unconsciously we tend to fall into. So if you attack me, I’m going to attack you back. If you take responsibility for your part of the problem, that’s a super strong signal to me that like, Oh, that’s what this is about. Okay, well, there’s some things I probably should have done differently too. It’s no guarantee. But by saying, hey, I think we should just try to figure out what’s going wrong here. And then we can think about whether there’s a solution. I’m inviting you to join me and to reciprocate a stance that you’re both likely to say yes to, more likely to say yes to.

And also that will actually get us somewhere, because we’ve tried the other ways to go about this and that didn’t get us anywhere. So this is probably my best shot. And part of what’s hard about these conversations is that the only person you have any control over, and we might argue that sometimes you don’t have as much control as you want to, is yourself. And you can’t control whether the other person takes the invitation. You can’t control whether they see themselves, I suppose also use the word accurately, right? Based on what we see. But they will react to however you handle it. And so you’re sort of giving it your best shot and you often have to do that persistently over time because these kinds of patterns don’t change quickly.

Brett McKay: All right, so how to handle those what happened conversation’s better, is shift from certainty to curiosity and remind yourself, if you think you know what happened, you’re probably diluting yourself. Let’s talk about that feelings conversation of a difficult conversation. Now as you said, people like in business thing, well, there’s no feelings involved, but there are feelings because like you feel awkward about having that conversation. So if obviously there’s emotions there. So what does that feelings conversation look like in a difficult conversation?

Sheila Heen: Yeah. People will say like, Oh no, we don’t have feelings in my organization’s like really? Because I just sat in on that meeting. There were a lot of feelings going on or just read people’s email conversations, right? You can tell there’s emotion behind them, whether that’s frustration or uncertainty or anxiety. And so part of it, is just being honest with ourselves about what’s going on. Like we’re all sitting in meetings having reactions. And also by the time someone becomes a tough conversation, chances are there two problems that we’re trying to grapple with. One is the surface problem, like whatever the business issue is that we need to decide or fix. But often there’s a second problem sitting under it, which is how I feel treated by you, which is you’re not even willing to see my part. You’re part of the problem, but you’re not willing to own up to that.

I can’t fix this by myself. Right? Because you just won’t say no to the client. And that’s part of what’s wrong here. And so I feel badly treated. And so if we stay on the surface and just talk about the business problem, we may or may not solve that problem. But the deeper issue is still there and it’s just going to manifest in some, whatever the next problem is next week. And so part of it is understanding that feelings are actually, what’s that issue, and at the heart of it in many cases. And so if we’re not addressing that, we’re not actually addressing the problem at its heart.

Brett McKay: So how do you address those? Do you just bring it up like, this issues made me feel frustrated or angry or is that as simple as that?

Sheila Heen: I think part of what makes people shy away from thinking that including feelings at all is like opening a can of worms it’s not going to go well, is that what they’re picturing is what we would call being emotional. And being emotional is just letting the feeling basically drive the conversation. So feelings end up getting translated into arguments, accusations, ultimatums, et cetera. Right. I don’t understand why you can’t just say no to the client. Like is that so hard? What they’re asking for is totally unreasonable, but no, you can’t say no to them. You’re going to turn around and tell us that we have to scramble and work all weekend to meet a deadline that has no, there’s no reason they need this by Monday, but you just can’t man up and have the conversation. You want to name a few feelings you hear in that?

Brett McKay: A lot of feelings there. Yeah.

Sheila Heen: But what was interesting is I didn’t name a single failure feeling, so people would walk out and say, woo. She was emotional, right? I didn’t actually name a single feeling. The feeling was just the energy that drove what I translate that feeling into, which is a bunch of incredibly frustrated, exasperated accusations and a story, right? About what I’m right about and about why you’re acting this way is because you can’t man up. So you’re the problem and it’s your fault. If I want to handle it differently, and by the way, include feelings in the conversation because they’re probably at the heart of it. What you actually did a few minutes ago is exactly direction to go, which is to just name the feelings and describe them and describe the role that they’re playing in this situation.

So I could be much more effective and actually get my point across more clearly if I simply said, so look, I’m frustrated and I’m a little bit at the end of my rope because the client keeps asking for things and insisting apparently on really short timelines. And what that means is that on a Friday afternoon repeatedly, we learned that we need to work all weekend and turn ourselves inside out to deliver something on Monday. It’s confusing because I’m not sure why it’s needed on Monday. It’s frustrating and I’m worried it’s causing burnout. It’s definitely causing burnout for me and I see it on the team, and I’m not sure what’s going on on your end. And so that’s what I think we need to talk about because the way it’s working now, the impact on the team is a real problem. And I probably should have brought it up earlier, because I’ve let it, it’s festered for a little while and I’m worried that it’s going to take some doing if we’re going to change things.

Brett McKay:                I like this example because you showcase that a lot of times difficult conversations or issues, there’s multiple feelings going on and in some cases you might have, what would you think be contradictory feelings? So I think an example in the book was, a mother who’s always calling you to like visit, right? And on the one hand, okay, you feel frustrated because it’s just like, I got stuff going on with my family and I feel like she’s being bothersome, blah, blah, blah. But the other hand, you also feel, Oh, my mom loves me and she cares about me. She wants to know what’s going on in my life. So it would probably be good. First you have to recognize the sort of complex feelings you have but also expressing those as well can help that difficult conversation.

Yeah and somehow, what I find is that we don’t have the conversation because we can’t quite figure out how to express what we really think and feel and it’s because we somehow think we’re not allowed to have contradictory feelings or contradictory views. Like mom on the one hand, it’s really good to hear from you and I love you and I’m so appreciative of the role that you play in our lives. I’m also a little bit overwhelmed and I’m worried about how some things are going with so-and-so at home, and so I’m not sure whether I can come this weekend actually and whether that’s going to be a good decision. Same time. I’m a little worried because I imagine it feels lonely for you. Do you want to tell me a little bit about that? So you can say like I love you and I don’t know that I can come and I’m grappling with worry and I’m not sure what the answer is.

Brett McKay: Well, I think what is interesting about this feeling’s conversations is that, by having it, by making your feelings explicit and getting the other person’s feelings explicit, it can go a long way to helping understand the what happened conversation, because often feelings, color what happened, right?

Sheila Heen: Totally. Yeah. The more frustrated you feel or even mood can color the way that we experience what’s happening actually. And so I think we make the mistake of thinking that there’s rationality and then there’s irrationality, there’s thinking and there’s feeling and they’re separate things. But actually what the brain research is showing us is that these two things are pretty intimately intertwined.

Brett McKay: Let’s talk about the identity conversation, this is more about like the conversation going inside your own head. So what does that look like in a difficult conversation?

Sheila Heen: Yeah. Often it manifests as a strong reaction or overreaction that sometimes we’re not even sure what’s going on for us. And I now think, by the way, since we wrote the book, I tend to think that the identity stuff gets triggered. That’s part of what drives the intensity of our emotional reactions in the conversation in many cases. And then that colors, the way we tell the story, and by the way, the way we tell the story because of confirmation bias will tend to reinforce why identity is in play, right? So what kind of person am I? What kind of parent do I want to be? What kind of boss do I strive to be, et cetera. That story we tell about who we want to be. Each of us has some things that we hold pretty tightly, and so the conversations that we’re going to find most difficult are the conversations where maybe that’s in question or maybe we let ourselves down.

Brett McKay: This made me think about like going back to the Midwest nice. Right? Your identity to be identity might be warm, nice person. If I bring this issue up or if I don’t bring up the issue in a tactful way and then like I’m not a nice person anymore.

Sheila Heen: What if I hurt their feelings?

Brett McKay: What if I hurt their feelings? Or your identity could be like, well, I don’t want to be the Patsy. I don’t want to be the guy getting taken advantage of. So, I’m going to like dig my heels in and make sure that doesn’t happen. But that could get in the way of resolving the problem.

Sheila Heen: Yeah, yeah. That’s exactly right.

Brett McKay: And do you bring this stuff up with the person you’re interacting with? It’s like, hey, this is what I’m thinking, like I want to be a guy who’s known as going up to that for my employees. I want to give you this raise, but I can’t do it. And this is making me like, do you bring that up or is that sort of something you just keep to yourself?

Sheila Heen: I think it depends on the relationship. I mean, I actually think if someone’s giving you upsetting feedback, like you’re not going to bat for me, sometimes it’s actually, I think we’re better off generally being transparent, so that there’s not a gap between what I’m really feeling or what I’m saying in most cases, it depends on the relationship and the context, but I actually think it’d be totally fine to say, the idea that I am not going to bat for you, that’s actually pretty upsetting to me. I need to think a little bit about whether that’s fair, but if it is, then that’s upsetting because I think of myself as going to bat for my team. So I think when you’re getting upsetting feedback it’s totally fine and actually in your best interest to own that. I pride myself on being fair and if I’m not being fair here, that would be really upsetting and I want to think about what you’ve said, because it’s going to be showing on your face and in your body language anyway, so you might as well just name it and own it.

Sometimes people say, I need to have this conversation. I’m really worried that I’m going to get emotional, like I’ll start to yell or I’ll cry or, and how do I make sure I don’t do that? And the counter intuitive advice is, if there’s something, an issue for you and you’re worried about your emotional reaction rather than trying to keep all of that out of the conversation, you’re better off actually naming it in the conversation because it’s like, it releases some of the pressure. So if you don’t want to cry in the conversation saying, what you’re saying is really disappointing, will actually help you not cry, because crying is basically your physiology. Trying to figure out what do I do with all these feelings because you’re not letting me put them anywhere. So naming them actually puts them somewhere that feels actually helpful in the conversation, but probably more helpful than getting emotional.

Brett McKay: All right. So we’ve talked about some things you can do to get a handle on what’s going on in the difficult conversation, the what happened, the feelings aspect of it, and also the identity aspect, where’s is this all leading to? Is it leading to a problem like resolving the problem or is sometimes the problem can’t be resolved despite all this work?

Sheila Heen: Yeah, it’s true. So I think that sometimes we think, well, I need some sort of magic words that will change the other person or fix the situation. So I think that part of where it’s all going is number one, for me, and I do think that this is sort of a lifelong journey. For me it’s helped me better understand myself and like what is going on with me here? Like why is this conversation, why am I finding this conversation or this relationship so frustrating? Why is there so much transaction cost here and what is going on with me that I need to sort out and get straight? And then what conversations do I need to have about it? And so rather than feeling stuck and victimized, it’s a way for me to better understand both problem itself, but also my own reactions to it.

And then to make a good decision. And by the way, you don’t always have to have a conversation about it. You might say, Oh well, I can now see that I’m contributing to this by not calling mom. So she always has to call me. So maybe I’ll just run an experiment. Maybe I’ll change my contribution. We don’t have to talk about it. I’ll just start to make a habit of trying to call her on, at some set time of the week and over time she’ll kind of figure that out and know that, she doesn’t need to call me today because we’ll talk tomorrow morning. I always call her on Saturday mornings, whatever it would be. Right? You can, but I can make a good decision about whether to have the conversation or what to do.

Brett McKay: Yeah, it sounds like you’re doing like a premortem, right? Like having the conversation even before you actually have it, and then you might even figure out, well I can just do this thing and just don’t have that conversation.

Sheila Heen: Well, will just try it out, and see if you get a different reaction. And then I’m more likely to have the conversation. And often these are not one shot deals. There are series of conversations over time, have the conversation or handle the frustration in the moment, in more productive ways. And they can either take that invitation or not take that invitation. But at least I walk away feeling like I’m handling this as well as I know how. So I’m giving it every opportunity to work well. So if at the end of the day, I need to let somebody go, I’m the boss and I got to let somebody go, I can be confident that I tried everything I could think of to figure out what are we contributing to their struggle that they’re not performing the way we need you to perform or whatever.

I’ve changed everything I know how, we’ve talked about it this many times. I’ve been honest with them about how serious it is. If I now have to make a hard decision, I can at least feel like I treated them well and I gave it every opportunity to work. So if the problem could be solved, then we solved it. And if they weren’t ready for that or it wasn’t a problem that could be solved, I can feel much more confident of that at the end of the day.

Brett McKay: What do you do? Say, if someone reads this book and they start implementing these tactics or these techniques or this mindset, and in their conversations with people, but it’s sort of unilateral, right? Like can you take the blame? It’s like, well, I can see my contribution and the other guy’s like, well, yeah, it is your fault.

Sheila Heen: Totally.

Brett McKay: What do you do whenever they don’t reciprocate?

Sheila Heen: I know, right? That guy is in every single person’s life. How does he do that?

Brett McKay: Right. You try to be understanding, but they are like, yeah, that is the pro… You are a jerk. Like what do you do with that?

Sheila Heen: Yeah, totally. I think that people really worry, like they read the book, the book I think, there’s a way in which it feels like common sense, which is true, I think actually. The hard part is actually doing it, and then that part also feels risky because they didn’t read this book. They’re their usual difficult selves. So do I really want to own my contribution to the problem when they’re going to take it as an opportunity to blame me and go out and repeat to other people? They even said that it was their fault. I guess partly, sure, there is a little bit of risk and when we talk about contributions, many of them are both not blame worthy but also they’re not secret. Like they knew that you didn’t call them back, and they know that we haven’t had this conversation up until now.

So it’s not like I’m giving them information they don’t already have. So if I start by saying, look, I wish we’d had this conversation six months ago and there are some things I think I haven’t been clear about. There are probably part of the picture for why we are where we are in terms of whatever, what we need and what’s going on with the client. And then you say, you be the guy.

Brett McKay: Well, yeah, it is a problem.

Sheila Heen: He’s so articulate that guy. And I say, well, so that’s definitely part of the picture. At the same time, I can’t fix this myself. So if we’re going to fix this, we’re probably each going to need to do some things differently. And there are some things actually, if you could change, I think that would make a big difference. And by the way, I can’t change them for you. So I also need you to step up to the plate. Now that assumes that I’m higher in the hierarchy. If you’re my boss and you say, yeah, so this is all your fault, you’re a screw up. I might have a slightly more differential frame, but I’m not necessarily going to change what I say. I might just rather than saying I need you to do some things differently, I might frame it as a request.

So boss, I think, if there are a couple of things that I don’t know if they’re possible, but if you were able to change them, a couple of requests I would have, I would actually be able to deliver what you need for that client much more efficiently. Because sometimes I have questions about the scope of what you’re asking for over the weekend and I’ve reached out to a couple of times, but I can’t tell to what extent there’s room for us to get clarity on that upfront. So let’s talk about that because I actually think that would help both of us deliver what the client needs. So I’m framing it as why it’s in their interest and why I can’t fix this by myself. So blame basically says it’s not me, it’s you good luck with that. And I’m not accepting that frame. So the conversation doesn’t have to be over. Even if they storm out after they say, great, it’s all your fault, I’m going to go tell the board. I can say, okay. I mean, the beauty of texts and email is that they’re never too far away. So you can always follow up and say, look, here’s the next part of that conversation. If we’re serious about actually fixing it.

Brett McKay: I think another thing, people need to keep in mind with handling these difficult conversations. You have to be patient. It’s not going to like, you can’t just bust out these tactics and like, I’m going to resolve this in 10 minutes, like this could take days, even weeks of just trying to keep going back and figuring out what they’re talking about. Even if they put up sort of, those hard walls, you have to just keep at it and slowly you’ll get something.

Sheila Heen: Yeah. I think that it feels unfair. Like I’m working so hard at this, and I think there may be a point where you need to say, do I want to work this hard in this relationship if they are not willing to change their part? Sure. But it’s also true that it’s taken a while, often to get you to where you’re at, so it’s going to take a while to change things and so it can be hard work, but it’s hard work to be in the relationship in the first place. So you’re just actually doing work that’s more likely to be helpful.

Brett McKay: Yeah. If you don’t work hard, you have to do this for that cost benefit analysis.

Sheila Heen: Yeah, you do. And also to realize people don’t change sort of deeply held views or behavior quickly. Like you don’t have one conversation and somebody says, Oh, you know what? After being a lifelong Democrat or Republican, I suddenly realize I’m on the wrong side of this. Right. That doesn’t tend to happen. So having sort of realistic expectations for what we can accomplish in this conversation, if we walk away actually better understanding each other and why we’re on such different sides of this, or why we find this so frustrating and what might help, man, that’s huge progress. And we were going to be having a hard conversation one way or another. If we had a battle that wasn’t going to be more fun. This actually has that upside that maybe we’re working towards something that’s going to be better for both of us.

Brett McKay: Well, Sheila, this has been a great conversation. Where can people go to learn more about the book and the other work you do?

Sheila Heen: Yeah, so, is a place where you can also then hop over to our website. We have a section called help yourself, where you can download, worksheets, a few white papers, etc. And also, we do exec ed at Harvard and we do in house programs through triad, to just try to equip leaders and their teams with the skills they need to have better conversations.

Brett McKay: Fantastic. Well, Sheila Heen, thanks for your time. It’s been a pleasure.

Sheila Heen: It’s been a delight. Thank you.

Brett McKay: My guest here was Sheila Heen, she is the coauthor of the book, difficult conversations. It’s available at and bookstores everywhere. Find out more information about her work at the website, also check out our show notes at, where you find links to resources where you delve deeper into this topic.

Well, that wraps up another edition of the AOM podcast. Check out our website, where you can find our podcast archives, there’s over 555 episodes there, as well as thousands of articles we’ve written over the years about how to be a better husband, better father, personal finance, physical fitness and if you’d like to enjoy ad-free episodes of the AOM podcast, you can do so on stitcher premium at, sign up use code, Manliness, for your free month trial. Once you’re signed up, download the Stitcher app on Android or iOS. And start enjoying ad-free episodes of the AOM podcast.

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