Flourishing Culture Leadership Podcast
“Moving Through the Tunnel: A Harvard Expert's Guide to Difficult Conversations“
August 25, 2025
Sheila Heen
Intro: Hi, I’m Al Lopus, and welcome to our summer encore series. We’ve pulled together the episodes you’ve loved most over the past 10 years, conversations packed with timeless wisdom, practical tips, and the kind of encouragement every leader needs. Whether it’s your first listen or favorite worth replaying, these episodes still hit home and might just be the spark you need this summer. So, let’s jump into this encore episode and see what insights await.
Welcome: Welcome to the Flourishing Culture Leadership Podcast, your home for open, honest, and insightful conversations to help develop your leadership, your team, and build a flourishing workplace culture.
Al Lopus: Sheila Heen is founder of the Triad Consulting Group and has been on the Harvard Law School faculty as a lecturer of law since 1995. Sheila has spent more than 20 years with the Harvard Negotiation Project, developing negotiation theory and practice, and she specializes in particularly difficult negotiations where emotions can run high and maybe relationships even become strained. And Sheila is the coauthor of the New York Times’ bestseller Difficult Conversations: How to Discuss What Matters Most.
Sheila, welcome back to the Flourishing Culture Podcast.
Sheila Heen: I’m delighted to be here.
Al: Great. Well, let’s dive right in with an excerpt from your book. And our listeners know that our organizations have to change to meet tomorrow’s challenges, and you write “the ability to handle difficult conversations is a prerequisite to organizational change.” And you say that because “the combination of globalized competition and technological development have really been creating rapid change and adaptation as necessary for organizational survival.” So, that causes the ability to manage difficult conversations, you say, it’s foundational to achieving any significant change. It's hard to change without having the ability to manage difficult conversations. So are today's leaders really paying attention to these words, Sheila?
Sheila: I don’t know if they’re paying attention to those words, but I do think that they’re paying attention to the challenges, right? Because the observation that things are changing incredibly fast, and it kind of doesn’t matter whether you’re in a local market, basically with one office serving local clients, or you're really starting to have regional or national or global reach. Social media and the Internet means that change finds you wherever you are. And what's interesting is that I think that for many decades, leaders have been aware of sort of the technical capabilities and skills that you need in our organizations. But in the last 20 years, I think we've come to appreciate that getting anything done really requires us to develop those skills in collaboration and in influencing other people and in working on problems across cultures, across differences, across functions.
Al: I love when you say change finds us. Boy, it certainly does.
Sheila: It does. And so I think that leaders are really thinking about, “Gosh, how do I develop the skills as I face bigger and bigger challenges and as the people are not collaborating or able to solve those problems the way that I need them to?” I think often it feels a little bit like a mess, and leaders are sometimes a little bit at a loss about what to do about it.
Al: Yeah, boy, that’s really challenging. How do we develop those necessary skills for collaboration? And as you say, change finds us. And in your book, Difficult Conversations, you talk about decoding the structure of a difficult conversation. I think that's really going to help our listeners. And you've identified three kinds of conversations that can get messy, and I think we all know what that means. And so, in our case, in a workplace culture, talk us through that.
Sheila: Yeah. So one of the things that I think has been both most surprising to me but also most reassuring is that if you look at what people are thinking and feeling in the midst of any difficult conversation, in other words, what is their internal voice doing? what we've discovered is that it actually doesn't matter who you're talking to or what you're talking about. In other words, it doesn't matter what the conflict is about. The same kinds of things show up in people's internal voices. So what this means is that every difficult conversation has the same underlying structure. And if you understand that structure, it actually gives you some landmarks that can help you find your way through the thicket to the other side, and also to bring other people with you as you go.
So the three things that show up very reliable in our internal voices, we call them the three conversations. They're really conversations we're having with ourselves. So the first one is what we call the “What Happened?” conversation, and this is the story that we're each telling about what's going on. And that story actually itself has embedded in it three key pieces, because my story about what happened or is happening or should happen includes what I'm pretty sure that I'm right about; whose fault it is that we're having this problem—which often, I'll be pointing the finger at somebody else, but it's not easier if I'm pointing the finger at myself: if I feel like I should have known better; I can't believe I let this happen, etc.—and then the third piece of my story is that I need some explanation about other people's intentions or motivations. In other words, why are they being this way? Are they clueless? Are they being controlling? Are they difficult? Do they just not get it? So my story has to include an explanation about why it is that they don't see that I'm so right about the things that I’m right about.
Now, that's sort of the most obvious piece, because that's often what we're arguing about, either explicitly, or if we're in a really polite culture, it's what we're complaining to other people about. But beneath that, our internal voice is busy with at least two more things. The second is what we call the “Feelings” conversation. And this is where I'm trying to figure out, what do I do with all the strong feelings I've got? because I'm not really supposed to be showing them at work. And so to the extent that I feel frustrated, exasperated, discouraged, disaffected, betrayed, confused, sad, fearful, guilty, I've got to figure out what to do with those feelings. And in the meantime, those feelings are often leaking out into the conversation through tone of voice and body language and facial expressions and all of that.
And then, finally, the third conversation, which is sort of at the deepest level, is what we call the “Identity” conversation. If a conversation feels difficult to you, if it's keeping you up at night and causing anxiety, chances are there's something the situation seems to suggest about you that feels like it's a state, right? Am I not a good leader? Am I not valued around here? Am I a good person or a bad person? Am I competent or incompetent? Am I worthy of love? I think at the heart of it, those questions are part of what is fueling sort of the strong feelings, and then, the stories that we're telling about what's going on.
Al: Yeah. It’s so much about a reaction to these conversations. I love the three steps: what's the story we're telling ourselves about the conversation, the feeling part—and some people react to feelings quicker than others, but, as you say, it really does leak out in the conversation—and, boy, and then, it is all about our identity. Am I saying or is this conversation causing me to think about something that I may not like about myself, even. Is that kind of the identity part?
Sheila: It can be, and it can be a fear, like, what if they're right, that I don't know what I'm doing, or that I'm not being fair, or they feel I'm not being straight with them? And I think of myself as such an honest person; that’s really upsetting. So sometimes we feel fearful that, gosh, maybe they're right. Maybe I'm not being as fair as I should be. Other times, we're pretty darn sure that we are being fair, and the fact that we're indignant and that there's someone out there in the world that believes that we are not fair is just as upsetting. So it's not, I don't think it's any easier when we feel unjustly accused.
Al: You know, recently I’ve had a difficult conversation, and I admit it didn’t go all that well. And reflecting on it, yeah, I’m sure I could have done a much better job. And that’s the beauty of these podcasts: I get free advice.
But you have a term I really like called moving through the tunnel of a difficult conversation. So coach me perhaps, or at least our listeners, about moving through the tunnel and having a conversation, a difficult conversation.
Sheila: Yeah. It’s a great question. I think that often it can feel like we're in a tunnel. It might be hard to see the light at the other end of that tunnel. But it's almost like we have blinders on. So the tunnels are such that, generally speaking, if you're picturing one, there's only one way out. Now, if we're talking about a labyrinth, maybe it also feels like there are so many options here, and none of them really feels promising, or it's hard for me to choose. But either way, what I'm trying to find is a way out to the light. And I think that often we feel like, well, I either can't find it, or I can't see my way through where they're really going to cooperate. Like, what are the magic words to get them to see and to agree that I'm right about this, or to get them on board with what I think is the right thing to do? And that kind of thinking, actually, will end up getting us stuck because chances are this isn't about figuring out the perfect right words to get them to go along with you and your story about what's going on. Instead, it's probably about doing some reflecting on your story first and changing your purposes in the conversation.
I'm curious, Al. The conversation you're thinking about, what did you feel like your purpose was in the conversation?
Al: Yeah. My purpose. Yeah, it was a difficult conversation. I had to express some bad news that somebody’s interested in working with us, and I didn’t see a spot for them. So, yeah.
Sheila: Yeah. And so identity wise, what were you worried that might suggest about you?
Al: That I was disappointing the other. And I can see what you’re saying. I clearly had the blinders on, that, okay, this was what I was going to say. I didn’t really think about setting it up. I didn’t think about the other person’s emotions. I didn’t think about how to get them on board, to use your term. So that was a bit of a situation.
Sheila: Yeah. And I also think that often when we're in what we would describe as a bad-news conversation, like a decision has been made by me or by others, and I need to deliver that news. I think that one of the traps that we fall into is that we think, “Well, I just have to figure out some way to deliver the news and have them not be upset with me, or hurt.” And there are some conversations where if they're not upset in the conversation, we're not being clear. We’re holding out false hope, or we’re being so indirect that they’re not understanding, “Actually, there is a problem,” or “This is a final decision.” And that really puts us in something of a bind.
Al: Mm-hmm. Yeah. That’s good, Sheila. Thanks.
Sheila: I know, it’s not good news. That’s the bad news.
Al: Just tell them—make sure—yeah—just, it is bad news, and communicate that, right? Just say it, right?
Sheila: Well, what’s funny is that if we ask people, or ask ourselves, if someone has bad news for you, how would you like them to handle it? What would your answer be?
Al: I would love them to say, “You’re very wise, and of course, you’re right.”
Sheila: In other words, they change their mind about the bad news.
Al: I might not be the only person that would like that to be the outcome, but, you know. I don’t know. What do you do with that?
Sheila: Well, so, if someone has bad news for me—of course, in my ideal world, they don't have bad news for me. They realize that they should have good news for me. But let's imagine that I'm living in this actual world where they still have bad news for me—and most of us would say, like, “Okay, just put it up front. Be straight with me. Be willing to hear the impact on me or sort of my reaction to it, and that that's what shows respect or compassion.” But then when we're on the other side of the conversation, we feel like we tiptoe around it, we're not clear about it, and I think that we don't follow our own advice, and I think it’s often because of that identity thing of, I don’t want to upset people or hurt their feelings, etc.
Al: You know, you talk about and write about creating a learning conversation, and maybe that fits into this discussion. So in the context of workplace cultures where we have these kinds of conversations we need to communicate, communicate effectively, walk us down the path of a learning conversation. What does a learning conversation look like?
Sheila: Yeah. So this takes us from sort of that tunnel to a better conversation, and the key shift is a shift in purposes. So I think that initially our reaction is, I know what I'm right about. This feels like a mess. I'm going to stick pretty close to what I think I'm right about. And my job or my purpose in the conversation is to explain to you why I'm right, for whatever reason you don't like that conversation, or don’t agree. So I think that I need to shift my purpose from demonstrating or arguing about what I'm right about to, instead, my purpose in the conversation is just to understand why we see it differently. Be clear, maybe about what I see, especially with a bad-news conversation, but I don't have to pretend I don't have a view. Instead, though, I need to understand why you might see it differently or what the impact on you might be. And at the end of that conversation, we're actually in a much better position. There may or may not be something to decide, but we actually understand each other a little bit better.
And that learning conversation takes me from sort of a message-delivery stance to a purpose that includes my view about this and your view about this, and then we'll see where we're at at the end of it, and that actually helps the relationship. Even if we still don't agree at the end, it both helps my understanding of what's going on—I have a more complete picture—and it sets us up to actually be able to solve a problem if there is a problem that is solvable between us. In the meantime, we're each going to learn something, definitely about the other person's perspective, but sometimes also about our own. Our own perspective may shift a little bit because, oh, I didn't realize that, or oh, that's new information to me, or gosh, I haven't thought about that risk that you're pointing out. And that really partly involves me having a conversation with myself first about letting go of, this isn’t necessarily about what I’m right about; it’s about why we see it differently. And that’s going to actually help me learn something along the way.
Al: Yeah. I like that. So the learning conversation, asking that question: Why do we see that differently? Boy, that's very helpful.
I know you have a passion for helping leaders and Christian organizations flourish, and I've heard you speak to Christian leaders, and this is an area that you care about, just from your own personal faith and working and serving Christian organizations. And you've also seen how cultures in Christian organizations can be, can I say, a bit shallow because everybody wants to be nice, and we've got this Christian-nice thing where we don't want to be critical or disrespectful. Yet as a result, unresolved problems fester and never get resolved. Of course, Christian organizations aren’t the only ones where that’s the case. But what advice do you have for these situations? How can we address this issue?
Sheila: I think you've really hit it on the head. And I think because we want to be nice and we want to be kind, we end up actually handling conflict in a way that ultimately makes things worse, totally unintentionally. So what happens is that often those cultures tend to be very indirect because, “I'm not going to give you the feedback directly, the way that you handled this,” or “the thing that you left undone,” or “The accountability here isn't there. You didn't follow through and that had an impact on me, and I ended up staying late and having to fix it for you.” But I don’t come back to have that conversation with you, or if I do, like, “You were supposed to give it to me over the weekend, and you didn't.” Rather than saying, “Hey, I thought you were going to get that for me over the weekend, what happened? Let's talk about it,” instead, I'll just say, “So, Al, how was your weekend?” And you’ll say, “Oh, it was really busy.” And I’ll say, “Okay, great.” And then we don’t talk about it. But I have to do something with my frustration, so I’m going to talk to somebody else about it, and I’m going to vent to them because, by the way, they saw me there late, and said, “Hey, how come you were there so late?” And I’m, “Oh my gosh. Al did not come through, again.”
I’m not having an honest conversation with you, partly because I don’t want to be mean or too hard on you or make you feel bad or something, or I don’t want there to be tension between us. But instead, that is festering, and when it happens again, I’m even more frustrated. You are not actually getting the feedback to know that it’s frustrating me, and in the meantime, I’m triangulating that to someone else. So now other members of the team know that you’re a problem. They have their own things to add. Or maybe they’re hearing you complain about me and my unreasonable deadlines. But you and I aren’t actually having the conversation directly.
So I think that the polite cultures, which really grow from a well-intentioned desire to turn the other cheek or cut each other a little bit of slack, they end up, over time, actually meaning that we’re not doing the kindness to actually sit down to understand, “Hey, what’s going on? because this isn’t working so well, and let’s sort it out between us rather than triangulating it to everybody else, and then distorting the organizational culture because all the conflict is underground or behind closed doors.”
Al: Yeah. I like that, Sheila. We're really not being kind by not going direct, and letting all this fester. I love what you're saying. It's the Matthew 18 principle: go direct. Just deal with it head on. Yeah.
Sheila: And then, people develop reputations, right? So new people join the organization or volunteer to join the team, and somebody fills them in on what it’s like to work with Sheila, or what it’s like to work with Al, which is also not kind or fair. But we’re really trying to help that new person know how to navigate because it’s kind of a minefield.
Al: Yeah. So it’s the polite culture where people don’t deal with that. But it’s really, as you say, it’s not being kind, it’s not really being polite, because it just creates a festering of bad feelings, doesn’t it.
Sheila: It does. At least in my experience.
Al: Last year, Patrick Lencioni’s talk at the Global Leadership Summit, he said that it’s the responsibility of a servant leader to have difficult conversations. Yet, so many times, leaders demonstrate, or maybe it’s a lack of desire or even a lack of courage, to address issues directly. So it’s not just in the workplace, but leaders really have this issue, too. What advice do you have for leaders to help them follow through with important, yet maybe difficult, conversations?
Sheila: Well, I think it does have to do with the story you're telling about your role, which is related to identity. So if I think of my role as, I’m the person that gets everybody fired up and enthusiastic, and people love working for me, etc., that’s a great identity to foster. But it actually may make it harder for me to give people direct feedback or to work things out. So often, the way that we tell the story of who we are as a leader makes it harder rather than easier, and so often, it involves a shift in how I'm telling that story about what being a servant leader or what being my style of leader means, and thinking about the responsibility I have to the people around me to be upfront with them. And my job is to equip them to work well together to get the job done, and to see opportunities to adapt and to grow and to continue to innovate or support each other. And in order to do that, my job as a leader is to have the courage to name the issues and bring people together to say, “Hey, this isn't working as well as it needs to or as well as it maybe could. How could we improve it, and what could we each change?” And if that's my role as a leader, a servant leader to the team or to the organization, that's actually pretty aligned with me catching these conversations and spotting things early and bringing people together in a mindset of learning and growth and change.
Al: Well, I like that. A servant leader, clearly it’s their job to help people work together but to catch it early if there is an issue and name it, and then just ask, “How can we improve this?” really does get over some of the barriers that people have to having a difficult conversation. You make it sound easy, Sheila.
Sheila: And everybody listening knows better than that.
Al: So, when leaders, their teams, and departments fail to navigate through difficult conversations, what do they jeopardize, both for themselves and then also for the organization?
Sheila: Oh, golly. What don’t they jeopardize? I mean, I think that probably we could take 10 callers, who would call in and give us different versions of how things go awry when the conversations that need to happen and the issues that need to get engaged and addressed and worked through don't get engaged and worked through. So people will describe organizations that don't innovate because nobody wants to—it’s a blaming culture. And if people feel like, “If I do something differently or try something new, and it doesn't work, I'm going to get blamed. So I'm definitely not going to try anything new.” People will describe cultures where people are just totally unengaged. If you have a team member who is difficult to work with, whether that means—there are 10 different versions of that. They don't follow through or meet deadlines. They yell at or get upset with other team members. They themselves are blaming. People could come up with different versions of what makes them difficult. And if that's not getting addressed, people get discouraged. They feel like it doesn't feel fair that I'm carrying your workload for you, or that I'm having to work around you. And then for the people below those people, when their bosses don't get along, it has a ripple effect across the organization. And then people spend a ton of time with either work arounds or trying to make sure that they don't get blamed when things don't work. And so then that has an impact on the bottom line. It has an impact on the constituents or the community or the people that we're trying, the clients and customers, we're trying to serve. And then we don’t have the ability to figure out how to solve those problems, because we don't have the forum or the skills or the track record to think like, “Well, whatever comes up, we'll address it, and we'll be able to fix it.” The transaction costs just get really high, and then you lose a lot of talent.
We could go on and on. You got another hour? We could talk about all the—
Al: Yeah. I was going to say—
Sheila: We should write a book on how the way things go wrong.
Al: It hinders innovation; it really causes people to be unengaged. I mean, you’ve just listed just really critical things. There are work arounds, and so that causes problems with getting things done. Productivity, you know, problems don't get solved. That's a lot for all of us to think about, the consequences of not being able to have these kind of difficult conversations.
Given these likely losses, are there some simple things leaders can do to notice the real dangers and consequences of difficult conversations before the fire starts to get out of control?
Sheila: So, partly, I like the “fire getting out of control” image because I do think that is how it feels, whether it's a low-level, burning in the background kind of thing, or it, then, erupts onto the surface. Partly one of the things to pay attention to is, what kind of problem do I have? And chances are, if things have been festering for a while, you've got two layers of problem. One is on the team, whatever the issue of the moment is. What strategy are we going to go with? Are we going to debut a new product line or service this year or not? How do we fix the delivery date? Are we going to land this next client, and who's going to jump on board to help make that happen? So those are the business issues that we're trying to actually get done.
And the mistake that we make is that we think it's just about those business issues, but chances are, if you're not having the conversations you need to have, you've got another layer under those issues, which is how people are feeling treated as we go about the daily work that we're trying to do together, encounter the challenges, and do or don't successfully navigate them. So then you've got a feeling sort of conversation going on beneath the surface, and you're not going to get to the heart of it unless you address the “how people are feeling about how we're working together.” And so often, I see leaders try to improve engagement or morale by giving a pep talk—it's about sort of business goals—rather than sitting people down to say, “Hey, let's talk about what's going on and what's causing people to feel disengaged or discouraged.” So you're trying to solve a feelings problem with a business talk.
Al: So, feelings actually kind of get involved in these conversations?
Sheila: Can you believe it? Sounds like you’re feeling sort of incredulous.
Al: Oh, I’d rather not talk about feelings, Sheila.
Sheila: I know. Well, yeah. It’s interesting because actually feelings are part of what makes successful businesses and, by the way, successful faith communities thrive. When people feel like they are fully accepted as human beings and challenged to step up to the plate and excited about what they're doing and curious about what they might be able to accomplish, you are going to get the very best out of them. They are going to bring their best selves to work. And if you're not paying attention to that stuff, their best selves are staying at home, and they're coping while they're at work. And that means that you are squandering a huge percentage of the capabilities and talents that they could be bringing.
Al: And I’m kind of joking about that, but there’s a lot of leaders in the world that listen to this that are really thinking oriented, intuitive thinkers. And as we work with engagement, people that are getting and connecting people's emotions to the work they're doing, and so really being emotionally intelligent, being able to connect people's feelings, and make sure that they're well taken care of is really important in creating that kind of a workplace environment. I appreciate the whole conversation because for many leaders, it's like, let's put the feelings away, and let's just kind of deal with things on a thinking basis. But boy, that really, as you say, it doesn't really engage people. People are leaving part of themselves at home if you're not addressing that.
Sheila: Yeah. And I think that we get scared away from opening that “can of worms” of feelings because what we're worried about is the way in which feelings get translated into sort of emotional blame, arguments, heated arguments, etc. And I think that instead what we're suggesting is that having a sort of reflective conversation about how we're each feeling, and what's working and what's not, and the ways in which I sometimes feel frustrated or confused, and what could we do that would change that for me, and how are you feeling about how things are working? Where do you feel stuck or at a loss or whatever or anxious? I think really it's a problem-solving conversation that can be quite professional and direct, and it doesn't mean that we're both escalating to be emotional, which is, I think, what people sometimes picture and worry about.
Al: Mm-hmm, yeah. Exactly. For a leader who's listening and maybe thinking, “I like what you guys are talking about, but our situation here at work is so complex, we don't even know where to begin,” or maybe the conflict is so strong that people don't know where to begin, what's the first step? What do you say to that, Sheila?
Sheila: The thing that helps me is actually to focus on that piece of what happened that makes a shift from blame to what we call joint contribution. So the situation feels really complex, complicated, long standing. The thing that helps me is sitting down to think, okay, how did we get here? What is the contribution system? In other words, everybody involved contributed something, meaning we each did things or failed to do things that are part of the picture that got us here. And none of us did anything wrong, maybe. But the fact that I haven't addressed this for six months or a year has meant that it sat and gotten worse. I didn't mean to do that. I wasn't paying close enough attention, or I was distracted by other things, but it's definitely part of what hasn't helped. You've probably got a number of players who have done or failed to do things along the way that got us here. It's not that contribution isn't even. It's not 50/50. And we sometimes have some other factors, like the cost of supplies went up, or we had a new competitor open up shop. So that isn't somebody, necessarily, but it's a factor that has changed the picture for us. And figuring out, what do we each contribute that got us here, is part of what helps me take apart and take a close look at what, then, would need to change for us to address the problem so that we'll be in a different place a week or a month or a year from now, because if we can figure out our contributions, that tells us what we could change and see if we get a different result.
Al: Yeah. I really like that because it really breaks it down to something that's actionable that each person can perhaps own or realize, “Well, I can see why that didn't work so well,” just listening to the outcome of what that caused the person to feel or how that caused the person to feel. Joint contribution, okay. There's a term for us today.
Sheila: Yeah. It’s a way to enhance accountability. I’m accountable for the choices I’m making and the impact they have on the team or the business. But without the cost of blame.
Al: I like that. You know, Sheila, we work with literally hundreds of churches, parachurch organizations, Christian-led companies, and we know a flourishing workplace culture equates to significant life-giving outcomes that lead to greater trust and unity and collaboration and even productiveness, effectiveness—I mean, there's a whole bunch of words we can use—where even people feel enjoyment coming to work. What are the essential outcomes that leaders and their teams can experience through these learning conversations? Why would we invest in that?
Sheila: I think that you're right, that it's the experience of coming to work, in part, that changes, which is you come to work feeling confident that, “Hey, whatever happens today, I'm not in this alone. And the people around me, we are all on the same team, and we'll figure it out. And I'll be listened to. If I'm wrong and somebody has a better idea, it's not that big a deal. That's great because that means I've learned something, and we're going to actually solve the problem in a way that's even better than if I was left holding the bag and trying to figure out how to solve the problem by myself.” So not only is it incredibly relaxing and transparent a culture, but we'll end up spotting problems earlier and finding solutions that are actually—they capitalize on the diversity of perspectives and ideas that people are bringing to the table. And so then you end up becoming, not only do you get better outcomes for clients, but clients love working with you. Customers are incredibly happy. And you start to be a talent magnet because people are like, you know, every interaction I have with this organization is so positive, even when something goes wrong. That's the kind of place I want to spend more time.
Al: Yeah. In today's environment of low unemployment, clearly, that's one of the benefits of healthy culture, of a flourishing culture, is that you become a talent magnet, and you're able to grow as a result of attracting talent. And creating that experience—I like the way you describe that—where we're not alone; together we can figure things out; where we're transparent as we work together. We can spot problems earlier. We have better outcomes. I love your thought there.
And we've done a lot of research around what the drivers are for employee engagement in Christian organizations, and Healthy Communication is one of our drivers, one of our eight distinctive drivers, of employee engagement. And we kind of think of healthy communication where we value diversity—and you've already talked about the importance of diverse thinking—and also experience an environment of mutual accountability, innovation, and unity. So give us a favorite story, Sheila, of a leader that you've worked with who's really succeeded at tackling difficult conversations that has caused you to smile and say, “Yeah, that's what I'm talking about.”
Sheila: Well, it's funny because I can't particularly take credit for any of it, but one of the fun things about doing the work that I do is that I get to hear lots of stories about the ways in which people have turned things around. And I just was told last week—actually, I was on the West Coast—and a guy came up to me. He said, “I read your book a bunch of years ago, and I had a really, really hard conversation coming up. And of course, you were on my mind,” because he knew I was going to come—he was coming to this talk I was giving. So he said, “That prompted me to actually go back to the book and then prepare for this conversation differently. And I had a feeling that it was a bad-news conversation, and I was going to be”—not fired because he's a contractor, too, but he's a regular contractor. It's most of his work to this organization. And by the end of the conversation, he had handled the conversation so well that the other person said, “You know what? We were going to fire you, but we’ve changed our mind because you handled this conversation so well.” And I just feel like I don’t know why things weren’t working before, but based on this conversation, I feel like, gosh, if we just continue to talk it through, we’re going to be able to fix it. So let’s give it a shot and see whether we can turn things around. He was laughing as he was telling me this, but that’s a fun thing to hear about.
Al: Yeah. Isn’t it? That’s great. Well, okay.
The biggest mistake I made in that conversation I referred to earlier is that I didn’t pull your book out.
Sheila: I’ll send you your own personal copy.
Al: I think I’ve got one already. I just need to pull it back out.
Sheila: Yeah, you probably do.
Al: Yeah, I think I do.
Sheila: I need one that says, “Al, turn to page 42.” If you give it to your spouse or to the people closest to you, they will underline the relevant parts for you, and they’ll have all sorts of Post-its for you to look at.
Al: Yeah, yeah, great.
I have to ask. In all the years you’ve lectured, you've consulted, you've written about this topic, okay. Here's the personal question. So how has your commitment to helping people mastering difficult conversations changed you, Sheila?
Sheila: Well, I think partly I have been humbled, because as long as I've been doing this, when I get frustrated, this is still where my internal voice goes, “I'm still focused on what I know I'm right about and what's wrong with the other person and why this is their fault.” And so that instinct, when we're in conflict to go there, doesn't leave. And recognizing that, “You know what? I’m doing all the things that I spend my whole life trying to help people not do, and here I am, again,” is definitely humbling. But it’s also true that I have watched people turn around teams that are disaffected and in trouble, businesses and communities that are struggling, and I've watched them find and navigate a way through. And so when I feel low, I think that I think to myself, “Well, gosh, this is nothing compared to what I've seen other people do. Get it together, Sheila. You can figure this out, and you just need to actually follow some of your own advice and see whether you can do it and find your way through, because I've been inspired by the people that I've watched do the same.”
I do think I probably tackle those conversations earlier, so I have more difficult conversations, but I have them earlier in the process before they get as bad as I maybe let them get, say, 15 years ago. And so over time, actually, that means I have fewer of them that become some kind of crisis. And that, I think, is really a relief for me in my life.
Al: I love that. That’s great advice for all of us. We all know that we should tackle these conversations earlier. Somebody said that leadership is about moving to the problem quickly and not backing away from them, but moving to issues and the problem quickly; just as you say, tackle these things earlier.
Well, Sheila, this has just been a great conversation. I have loved having the conversation about difficult conversations, and I love how we all react when we're in a difficult conversation, where our instincts take us. There are ways that we can move through it, as you've just taught us. And I appreciate that very much. And how it really isn't polite to wait to have difficult conversations. We need to go direct to those that we're having these situations, and we need to go direct even earlier than maybe we want to. So this has just been great.
I’m curious. Is there anything you’d like to add that we haven’t talked about?
Sheila: The one thing that we haven't talked much about is just separating intentions and impact, and remembering that we’re quick to attribute negative attention to someone else, like, “They were just trying to undermine me,” or “They're jealous of me,” or “They're trying to intimidate me or control the situation.” But much of the time, this is a whole room full or organization full of well-intentioned people trying to do their best, and yet, having negative impacts on each other and frustrating each other. So if I can give them the grace of thinking, “I don't know why you did what you did, and I'm suspecting it wasn't intentional. I don't know. But the important part is the impact that I see it having. Let's talk about that, because that seems like something we should address.” Separating those two things, intention from impact, I've seen really make a difference in the reaction you get and sidestepping a little bit of the defensiveness that you can otherwise get.
Al: Yeah, I like that. What you’re saying is just take the attitude, well, they’re really trying to do their best. And with that attitude, you can really get to the core of it quicker, don’t you think?
Sheila: I do think. And sometimes people will say, assume good intentions. I think that's a reasonable default because more often than not, people have good intentions or no intention. Like, they're not paying attention. They're not trying to hurt us, in other words. But I would also say that's not always true. But what to remember is that you don't know for sure, and the problem you're trying to solve is the impact. So you can stick to the impact, whether or not they have good intentions.
Al: And Sheila, where can we find more about your work and your books?
Sheila: Yeah. So one of the blessings of having a very unique name in this day and age, which I maybe didn't like as a kid, but now it's really coming in handy, is that if you Google “Sheila Heen,” you will very quickly find our website. So Triad Consulting, or triadlearning.com. Also, diffcon.com. They all go to the same place. And we have a nav at the top of that website called “Help Yourself,” and that's a place where you can find additional reading, reader's guides, preparation worksheets, and additional resources.
Al: And to put a final bow on our conversation, Sheila, is there one final thought or encouragement you’d like to leave with our listeners today?
Sheila: I think often we are thinking of the difficult conversations and maybe difficult people in our lives and trying to figure out how do I get them to “fill in the blank,” change in some way. And of course, the only person that we have any control over is ourselves and trying to figure out, well, can I invite them into a different kind of conversation that might enable us to change things? And if not, I can't control them. So all I can do is give them the best invitation I know how to do. It’s rarely too late to do that, and I’ve seen people turn around decades of frustration and estrangement or damage, just by being persistent about that invitation.
Al: Invite them into a conversation and be persistent. Sheila, that's great advice.
So, ladies and gentlemen, Sheila Heen, founder of the Triad Consulting Group, a Harvard Law School lecturer, and author, and a New York Times’ best seller of the book Difficult Conversations: How to Discuss What Matters Most. Yeah, thanks, Sheila, for sharing your wisdom, your insights, and your great stories, and, even in my case, some personal advice. Thank you, and thanks for investing yourself in everyone who's listening today and certainly benefiting from all you've shared. So thanks, Sheila. I appreciate it very much.
Sheila: It's always a pleasure, Al.
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