Capital Investment Advisors

#160 – How To Have Difficult, Yet Productive Conversations With Douglas Stone

In difficult conversations, do you notice you or your conversant trying to “win” the discussion instead of listening to each other’s perspectives?

Today on Retire Sooner, Wes Moss is joined by Douglas Stone, author, speaker, and lecturer on negotiation at Harvard Law School, to talk about navigating difficult conversations. Whether the subject of the conversation is financial, medical, or an interpersonal conflict, there are some discussions that can feel awkward, tense, or become argumentative.

Stone explores some ways that can be effective to start such conversations, engage empathy around the emotions and identities tied into them, and reach a mutually understood outcome. Wes also brings up blind spots we can all have in the way we talk to others and what we can do about them. They also explain productive ways to receive feedback and wrap up the episode with how liberating it can be to accept your own limitations with other people.

Time-Stamped Show Notes from the Video

  • [00:00:50] Douglas Stone explains the Harvard Negotiation Project. Most negotiation research was focused on transactional negotiations like buying a car, not interpersonal conversations. The gap in the literature led Douglas to study difficult conversations and write a book on the subject.
  • [00:03:05] Wes and Douglas explain how conflict arises, the emotions involved in difficult conversations, and how to give advice effectively.
  • [00:13:55] Wes and Douglas talk about how difficult conversations involve identity and how important it is to distinguish one’s role in conversation.
  • [00:25:42] Wes and Douglas go over ways to navigate conversations around money.
  • [00:36:11] Wes brings up blind spots in self-awareness, and Douglas explains how encouraging feedback can help improve communication.
  • [00:42:03] Douglas imparts advice for actively listening, asking questions, and problem solving in difficult conversations. Wes relates this to how advisors want clients to understand advice given and make it work for them.

Read The Full Transcript From This Episode

(click below to expand and read the full interview)

  • Wes Moss [00:00:00]:It’s a good thing that Doug Stone wanted to come on today’s show because I don’t think I could have convinced him or negotiated otherwise. His articles on negotiation and conflict resolution have appeared in The New York Times, the LA Times, and he even helped run something called the Harvard Negotiation Project. Just the name alone is intimidating. In fact, Doug negotiation at Harvard Law School. In addition to being a managing partner at Triad Consulting Group, he’s consulted for Fidelity, Honda, HP, IBM, and Microsoft. He’s appeared on many TV and radio shows, including Oprah. Back in the day, as my kids would say, and was a keynote speaker at the 2006 World Negotiation Forum in Brazil. He co authored a New York Times bestseller called Difficult Conversations: How to Discuss What Matters The Most. We all have to have difficult conversations all the time. We’re either about ready to have a difficult conversation, we’re in the middle of a difficult conversation, or we just finished a difficult conversation. Would it be nice to learn some skills to figure out how to make these inevitable conversations just a little bit easier? And I think Doug really does a good job of that today. I’m Wes Moss. The prevailing thought in America is that you’ll never have enough money and it’s almost impossible to retire early. Actually, I think the opposite is true. For more than 20 years, I’ve been researching, studying, and advising American families, including those who started late, on how to retire sooner and happier. So my mission with the Retire Sooner podcast is to help a million people retire earlier while enjoying the adventure along the way. I’d love for you to be one of them. Let’s get started. It’s a brand new day on the Retire Sooner podcast. And we’re here with Doug Stone, who is not a guy you want to get into a rough negotiation with because it’s going to be hard to walk away winning. Would you call you the creator of the Harvard Negotiation Project? Tell us about the Harvard Negotiation Project. And I want to dive into difficult conversations, which is one of your books, one of your bestsellers, because we’ve got these constantly when it comes to money and early retirement, whether it’s advisor to a family they’re working with or just me with my sister or my mom talking about, hey, mom, you’re spending too much. Or hey, dad, you’ve got to do something differently. Those are tough. So how did you get into the negotiation business?Douglas Stone [00:02:42]:

    Yeah. So you mentioned the Harvard Negotiation Project. So that was founded by my colleague and mentor, Roger Fisher. And I began working there in the 1990s, and Roger was one of the first people to study negotiation as a subject, as an academic subject. And then when I got there and negotiation tends to be very transactional. It’s like buying a car, buying a house. It’s not so much negotiating with your spouse or your business partner or your elderly parents. And so there was this gap in the literature where we’d really begun to study like across the table nuclear arms negotiations. But very few people were studying the negotiations that people have every day in their lives. Just the interpersonal conversations at work and at home, across the backyard fence and so forth. And so we wanted to do that. And we just looked at the grouping of conversations that people tended to find difficult. And when we told people, hey, we’re going to write a book about difficult conversations, the first reaction was, well, there’s nothing to say about them. They just are hard. And then you have them and then everything’s terrible, which that’s people’s experience of them often. And so we were thinking, well, is there anything that we could help people with? Is there a way in? And it turned out, at least from our point of view, there was. We’ve been researching and studying difficult conversations.

    Wes Moss [00:04:18]:

    Well, let’s start with that because you’re right. My initial impression, of course, before listening and reading some of your work is that you’re right, it’s kind of no way around it. They’re hard because they’re difficult and that’s it. There’s no way to sugarcoat an unpleasant topic or a money topic. That is where you’re trying to help somebody or tell somebody. Maybe this is where the rubber meets the road here. So first of all, again, you’ve written on how to have these conversations. Why are we firstly so bad at having difficult conversations?

    Douglas Stone [00:04:50]:

    So difficult conversations cause stress. So one thing that’s important to mention here is that anything that’s hard for someone qualifies. People often say, well, what qualifies as a difficult conversation? It’s just a conversation with my teenager. It’s not like there’s billions of dollars on the line or world peace or something. But if it’s hard for you, then it’s a difficult conversations. So it’s just whatever’s hard for you. And the things that commonly make conversations hard for people are things like there’s kind of strong or complicated emotions involved or we’re very worried about hurting the relationship with the other person. Or maybe there is a lot at stake if not materially, there might be a lot at stake in the relationship. And sometimes conversations are hard because of what we fear it might say about ourselves. So if you have to, for example, you have to negotiate with your elderly parent about taking the keys away because of their driving. In one sense it’s about your parent and it’s about safety and all that. But there’s always some way in which a conversation is also about us. Am I doing the right thing? Am I doing it too soon? Am I hurting my parent? Should I have done this earlier? So a lot of what makes conversations hard is the inward conversation about well, what will this mean about how I see myself if it doesn’t go the way I want it to?

    Wes Moss [00:06:25]:

    So what first comes to mind is the thought around. And again, this can be an advisor to a client or family you’re working with. It can be to mom, it can be to a sibling. And I recall in the financial advice profession, it’s let’s call it one part planning, one part investing, one part thinking through other investments that relate back to spending. So think of a family that’s been a great they’ve been great savers. They’ve been super diligent for a lot of years. And then they get into a situation where they maybe start overspending housing. I’ve seen this happen a lot in the last year, particularly with interest rates have gone through the roof where somebody went into a project and then it got really expensive and interest rates went way up and all of a sudden now it’s constraining, let’s say. And that’s kind of a tough conversation to have. It’s like, wait a minute, if you’re going to continue down this path and this could really mess up the longer term plan, that’s not super easy to say, is it? Because I’m not wanting to hurt their feelings. That is, I’d say, one of the harder things within the financial profession. And again, this goes back to family. It’s like, hey, you’re spending too much. I have this little bit of an internal guilt of judging somebody on their spending. What is that?

    Douglas Stone [00:07:43]:

    Exactly. So that’s a great example of the kind of conversation that’s hard partly because of how it will make us feel about ourselves, right? Like, you know the words to say the words, are you’re spending too much? Here’s why. Right? Like the words themselves aren’t hard to figure out. But the emotion around that can be difficult. And what we often do is we think, I need to give them this advice, but in a way that will not hurt their feelings or make that I want them still to like me. I want them to be happy. And those are reasonable goals, right? Of course we don’t want to hurt people’s feelings. But in a conversation where the main gist of the conversation is that you’re saying something that might be upsetting to someone, the useful thing to do, paradoxically, is just to recognize that my job is I’m going to share this information with them and I’m going to share it as clearly and respectfully and empathetically as I can. And their job, they have a role in this conversations and their role is to have whatever reaction they have. And so I can’t control their reaction. And if I sort of convince myself that I actually don’t want to or need to, then I share the news. They react however they react. They might say, that’s outrageous. You don’t understand my life. Or they might say, you’re horrible. You’re so mean. Whatever they say is kind of their right to say that, and it’s fine. And in a weird way, it’s actually good. Like you want to know what their reaction is. And then when you hear it, rather than saying, that’s not true, I’m your financial advisor. You just have to trust me, do this. Which is what I’m not saying that you do this, but I’m sure that some people do this in some context, they’ll just say, no, you have to do what I say. It’s very common in the medical community. A doctor will say, here’s the medication you have to take, and the patient will take it. They won’t like it, and then they’ll stop taking it. And the doctor will say, oh, you didn’t understand me. You have to take this medication. And what they’re not doing is talking to the patient about why aren’t you taking the medication? Does it make you feel lousy? Are you having trouble remembering to take it? Are you worried about your self image around taking it? And if you understand the reasons they’re resisting, then you can actually discuss it and engage it. So in the financial question, let’s take an example where someone is, I don’t know, they’re spending too much.

    Wes Moss [00:10:32]:

    How about this? Here’s one not saving enough. Like, hey, you guys are making a lot of money, but you should at least be maxing out your 401Ks.

    Douglas Stone [00:10:42]:


    Wes Moss [00:10:43]:

    Yeah, but I can’t because we’ve got some college expenses right now. I don’t know if I want to do that. Well, you really should be just you probably wouldn’t miss it. So let’s use that as an example. You’re not saving enough, right?

    Douglas Stone [00:10:58]:

    So that’s a great example. So in any particular conversation, the other person might say, oh, well, so we could try to figure out how to do that, but let’s assume there’s some pushback or block to them wanting to do it from the person’s point of view who’s giving the advice. The key thing you need to understand is what is the nature of the resistance? And sometimes it’s obvious, like, yeah, we’re saving for college. We can’t put money in this. And then it may just be a math problem of doing the math and saying, like, well, actually, here’s how it would work out. But often it’s not something that’s quite so tangible. Sometimes someone might be thinking, well, I saw the model of my dad and my mom. They saved their whole lives, and they were kind of miserable, and they never spent money on themselves, and so I’m just not going to make that mistake, or my parents made the opposite mistake. I don’t know whatever it is, but there’s some sort of psychological barrier to them doing it, and just explaining the math isn’t going to address that. For example, if someone’s spending a lot of money, let’s say, because it helps them feel less depressed when they buy new things, explaining to them that they’re spending too much isn’t going to address the sort of root cause.

    Wes Moss [00:12:26]:


    Douglas Stone [00:12:26]:

    And so what we need to do as advisors or financial advisors or doctors or friends or parents or children when we’re engaging with folks is really to it’s not enough just to know that we’re right on the numbers. We want to know the resistance and we want to understand the resistance even if it makes no sense, like to us. So even if it’s just wacky, it’s important because if you’re going to persuade someone to take your advice, they’re going to have to overcome their resistance and you’re going to have to help them. And you can’t do that unless you have a clear understanding of what it is.

    Wes Moss [00:13:03]:

    I’m thinking about other if you’re naturally what are the top five difficult conversations? I immediately think of work, laying somebody off, firing somebody, that’s a really tough one. I think of something with a health conversation. So doctors, I guess, have to do this all the time, but communicating there’s something wrong with your health. This is a difficult conversations. Here’s what you should do. I don’t know if I want to do it. Then there’s the marital, this back and forth of having conversations with a spouse or someone who’s a partner and it’s a relationship issue. And then parents, right. I think you’re starting to slip here and it feels like maybe we need to go to the doctor. Let’s think about some of those, maybe some examples of the difficult conversations that we all are going to go through in our lives.

    Douglas Stone [00:13:58]:

    So one of the interesting things we found when we were writing the book, originally the first title of the book was The Ten Hardest Conversations and How to Have Them. And we thought like, well, there must be ten or 20 or whatever. We’ll come up with a good list of ten and they’re the kinds of examples that you’re talking about. And so we thought, well, we’ll write a chapter about each one. And as we were doing that, what we noticed is that we were writing the same thing in each chapter. Like the content was different, but the advice was not always exactly the same, but fundamentally the same. And a really helpful to us observation that we made when we were working on it was that whatever the substance of the conversation, whether it’s a conversation with elderly parents or kind of the sandwich generation or with your teenage kid or with your boss at work, there are some similar dynamics that sort of make conversations hard. And the kind of framework that we observed was that conversations operate at three different levels at the same time.

    Wes Moss [00:15:08]:

    All right.

    Douglas Stone [00:15:08]:


    Wes Moss [00:15:09]:

    So you’ve got three conversations during any happening at any one time. Let’s walk through those.

    Douglas Stone [00:15:16]:

    Yeah. So in any topic. So let’s say you’re talking, let’s say the example of someone giving financial advice that you’re spending too much. So part of that conversation is going to be difficult because the financial advisor has this opinion and the person, the client has this different opinion and they don’t agree about it. And so they may have different perceptions about what’s going on and different stories about what’s causing the problem and so forth. So it’s all about the substance and that’s important. And there’s some key mistakes we make around that and there’s some things we can do to get our way out of those mistakes. But then there’s another level that we call the feelings conversations. So not every conversation, but many difficult conversations will have some element of feelings in them. My feelings, your feelings, feelings of anxiety or fear or anger, frustration, joy, all the whole range of feelings. And around that, it’s very common in our culture to kind of assume that, well those aren’t that’s not what any of this is really about. Those are just things that are getting in the way. And in fact that’s sometimes true. But it’s often the case that actually feelings are not the things in the way. They’re actually part of the whole relationship. They’re central. So if I’m frustrated that my advisor is not really listening to me, that’s a feeling that I have. I’m feeling frustrated. And that’s not incidental or beside the point. That’s part of their relationship that needs to be worked through. And then at the kind of most basic level, there’s what we call the identity conversation. And that’s the conversation that we have with ourself, about ourself. So any conversation that feels difficult to us, even if it really seems like it’s totally about the other person, has the potential to threaten how we see ourselves. And so one of the challenges of what makes conversations hard is that those three levels are kind of going on at the same time the substance, the feelings, and then questions about our identity and how we see ourselves. And it takes a little bit of practice to get used to thinking your way through.

    Wes Moss [00:17:41]:

    Navigating all of those. Again, if you haven’t seen this or our listeners haven’t seen it, there’s a new, relatively new series in 2023 on Apple TV called Shrinking and it’s a wonderful cast. It’s essentially three psychologists or therapists and the senior guy in the productive is Harrison Ford and he’s gruff, but kind of a lovably gruff character. And it’s a very funny show. So they’re therapists and they’re supposed to be really great at talking to people. One of the ironies of the show is that they have this difficulty communicating with each other. He’s got really early stage Parkinson’s as his character. You don’t really see it, but it’s starting to concern his colleagues. He bumps into one of them, his car bumps into somebody and then they want to ask him to stop driving even though he’s passed the Parkinson’s driving test. And he went back and passed it again. But they’re so nervous to ask him to stop driving to work and it’s this super awkward conversation in the kitchen. Hey Paul, can you hey, would you like me to pick you up from work, they’re begging him to put down the keys and it makes it so hard. Let’s use that as an example.

    Douglas Stone [00:19:03]:

    No one wants to come out and say it. So I think that’s a great example of a few things. One is one reason that’s hard is because the people who notice what’s going on but they don’t want to say it, they’re afraid of upsetting him, and then they’re afraid he’ll be upset with them. And that’s one of those places where you have to sort of distinguish between your role in a conversation and the other person’s role. So in that conversation, if I’m noticing that my colleague is having trouble driving, I have to kind of give up the desire that we all have to kind of control the conversation from the other person’s point of view. My job in that conversation is to say what I have to say and how you say it matters. By the way, it’s much better to say I’m worried about you than to say you’re not a good driver. Because we can argue about if I say you’re not a good driver, you say, yes, I am. And now we’re just arguing about it and nothing is going to go anywhere. But if I say, Gosh, I’ve been really worried about your driving and I’m just nervous for you and nervous for others. You can’t disagree with it. I’m just sharing how I feel about it. So how you say it matters, but also just accepting the limitations of sort of relinquishing the fantasy that we can control the other person. Turns out it’s hard to do that, but once you do it, it’s incredibly liberating.

    Wes Moss [00:20:34]:

    Say that again. So this sounds like one of the key elements to turning a difficult conversation into something that’s more palatable. Say that part again.

    Douglas Stone [00:20:44]:

    Yeah. So it’s very common in a conversation like this to think, my goal is to tell them to stop driving, get them to stop driving. And also I want them to be happy about the conversation and I want them to like me, and I don’t want them to be upset or annoyed or cry. That would be terrible. I don’t like it when they cry. So those are all it’s fine to hope for those things, right? But really, the second half of that list is stuff that you can’t control. So what we have to do is think about so I have control over what I say and how I say it. So my job is to say those things as well as I can, to be empathetic and to listen and to be generous and so forth. But to also, to be clear, like it’s if you ask somebody, if you started to have problems driving, would you want people to be clear in their conversation with you or would you want them to beat around the bush? Almost everyone says, oh, well, they should be clear. And then we’ll have the conversation, but when we’re on the other side, we’re thinking, but if I’m clear, they might get upset. But being clear is part of your job. Getting upset is their job. So we have to give them the space and the room and the freedom and the dignity to be able to get upset and for that to be appropriate. Like, this is a very upsetting conversation. From their point of view, if they’re not upset, maybe it’s because they’re not really understanding it. So it’s normal for someone to be upset. So from our point of view, we have to judge whether we’ve had the conversations well, not based on how the other person reacts, but based on whether we have said what we want to say and whether we’ve heard the other person as we want to hear them.

    Wes Moss [00:22:35]:

    Full disclosure I am affiliated with Capital Investment Advisors, which is a full service and a fee only financial planning and investment management firm in Atlanta and Denver and Tampa and Phoenix or wherever you are. And if you’d like to take your retirement planning or retire sooner, journey to the next level, Capital Investment Advisors would love to help. You can find our team and schedule a time to chat right at Are we supposed to harden our own feelings around upsetting someone? Is that part of this or is that maybe the wrong term?

    Douglas Stone [00:23:16]:

    No, it is, in a sense, it’s an awkward, kind of slightly disturbing thing to accept, which is that we can’t control the other person and that sometimes in life, doing what most of us think would be the right thing may involve hurting somebody, at least in the short term. And that that’s okay. It’s like a parent who has a teenager who’s been crashed a car twice now because they’re driving drunk and you’ve decided, let’s just say, to take the keys away for six months or something. The teenager is not going to say to you, wow, dad, you are such a good parent. Like, I’m so impressed at how responsible you are with me and you just took the keys away and that was great. And you’re teenagers going to go crazy and they’re going to say they hate you. They’re going to try to find ways to drive anyway. That’s their role. Your role as the parent is to take the keys away and to try to have conversations with them about why they’re drinking, why they’re driving drunk. What’s going on with that?

    Wes Moss [00:24:23]:

    So is that a learning part of this? Is that turning a difficult conversation into learning? Even though a 16 year old still they’re not going to agree. They may, when they’re 26, say, wait a minute, they were right ten years ago, or maybe when they’re 36. But we’re trying to then teach somebody or make it a learning experience.

    Douglas Stone [00:24:42]:

    We’re trying to teach them, but it’s a learning conversation in the other way too, which is we’re also learning from them about them and about the problem. So if you say to your parent absolutely should not be driving and there isn’t any ambiguity about it, it’s harder if there is ambiguity but let’s just say there’s not. And you say well so there’s nothing for me to know. Like I know all I need to know. They shouldn’t be driving and that might be true. So why do we need to listen to the other person? We need to listen to the other person to learn what that means to them so that we can work with them to try to problem solve around their resistance. So if they don’t want to give up the keys because they’re afraid they’re going to starve to death because they won’t be able to get to the grocery store that’s important to know. So okay we can work on that. If they don’t want to give up the keys because their whole life they’ve been the one that kind of is in charge and drives people around and they’re a great driver and that’s part of their self image. That’s a different kind of resistance. And so depending on the nature of their resistance we would engage differently around problem solving and what to do about it. And so you can’t know their resistance in advance. You just have to discuss that with them.

    Wes Moss [00:26:02]:

    So talk to me about the thought around a neutral third party conversations. So maybe give us an example of a difficult conversation or difficult situation where that we want to introduce this. I think you call it a neutral third party.

    Douglas Stone [00:26:16]:

    Yeah. So let’s imagine a married couple and I don’t know, they’re in their mid fifty s and they suddenly one of them is thinking hey we’re spending too much. We’re going to run out of money. Or just very anxious about that. And the others thinking we’re fine and we’re living nicely and we’re living well. Let’s say we’re on the side of the person who thinks we’re running out of money. It’s very common to start the conversation by saying hey you’ve kind of gone crazy with the spending thing. You really got to stop it’s too much. And that’s normal language. There’s nothing wrong or evil about that language. The problem with it is it’s completely in the frame of I’m right and you’re wrong. This conversation is about you being wrong. So we’re basically saying hey I’m casting a movie. Do you want to be in my movie? The movie is about how you’re so wrong and I’m always right. A person’s going to be like can I have a different part in this movie? So then people say, well if you’re not going to start by saying you’re spending too much, should you start by saying, hey I’m crazy, I get all anxious about money, there’s something wrong with me. Well that’s not so great from my point of view. So if I start from either of our points of view, it’s going to be problematic in some way. So what to do turns out a really effective way to start a conversation is the way a friend who’s friends with both of you and who understands both of you would start the conversation. And there’s a key trick to use to figure out how to do that. And it’s the word different. So if the friend is neutral and cares about both of you and understands both of you, they wouldn’t judge either side. They would simply say, you see it this way, you see it this way. And those are different approaches. So the problem is the difference. And you’re discussing the fact that, hey, we have this difference, what are wes going to do about it? That conversation has a very different feel than you are irresponsible and spend money or you can’t enjoy life and you’re so stingy and so forth. So it’s a way of starting the conversations that describes the problem, but not in a way that judges the other person.

    Wes Moss [00:28:39]:

    So you’re starting out by saying, look, we’ve got a difference of opinion here. So is that empathy? Is that what that is? Or I guess it’s empathy and understanding of being able to see their side first.

    Douglas Stone [00:28:53]:

    Yeah. So empathy would be the next move. So if I’m in that conversation, I might say, hey, we have a difference here. You like to spend this, I like to spend this. Now, we’ve described what the topic is, the difference, and what to do about it. And by the way, even people who are very argumentative, when you say we see this differently, they’re not going to say, no we don’t. There’s nothing to argue about. Like, clearly you do see it differently, so they’ll be on board with that. And then the next move from my point of view is to say, so given that we see it differently, I want to understand better why you’re doing what you do and how you see it. I want to then share how I see it and then let’s problem solve together. So I like your instinct, which is empathy is right up front. So when people say, well, once you define that there’s a difference, who should start, who should talk first? And my advice is, if possible, let the other person talk first because they’ll enjoy that, but also it’ll actually be good for you because you’ll start to understand how they see the world and why they’re doing what they’re doing. And that’s helpful and it makes it more likely that they’ll listen to you when you share your perspective.

    Wes Moss [00:30:12]:

    How about emotions, though? I mean, the reality here is that almost all of the examples we’ve been giving, whether it’s financial or it’s health related, it’s autonomy related, or again, some sort of rift in a relationship, maybe relationships going wrong, they’re all kind of emotional conversations.

    Douglas Stone [00:30:32]:

    Yeah, absolutely.

    Wes Moss [00:30:33]:

    What is your take on how to control that? Or. Is it wrong to try to if it’s an emotional conversation, it’s emotional conversation and that’s okay.

    Douglas Stone [00:30:44]:

    Yeah. I think there’s a common tendency to want to frame the emotions out of the conversation. So people it would be very easy to say this is a conversation about money. It’s a conversation about our bank account and savings and investments. It has nothing to do with I feel sad, I feel happy. It’s not about emotions. It’s about almost the opposite of emotions. It’s about just very objective things. And obviously there’s truth to that. It is about those things but it’s often also about the emotions. So if you’re saying that I’m spending too much, if I feel like, look that’s possible, but you don’t seem to care about how I see this, you’re just coming in and shutting down the bank account and telling me you have to stop. From my point of view, part of the conversation is about the money. But a big part might be about how I feel treated in this conversation. Do I feel like you’re listening to me? Do I feel like you care about me? And often the fact that I feel like you’re not listening and you don’t care is the thing that’s driving me to keep spending because I’m thinking, well I’m mad at you so I’m not going to listen because you’re not listening to me. And that’s just counterproductive. So often the fastest, most efficient way to deal with the conversation is actually to talk about the emotions. To say, I want to feel like you care about why I’m spending this money or that you care about the childhood as raised. And that has had a big impact on how I experienced this money. As Wes, you know, probably better than most people on the planet isn’t just an objective topic. Right? It’s fraud. Right? It can be tied to their deepest fears and their greatest joys and the way they are raised and whether they feel like they’re being faithful to their when I was in my 20s, my father was very let’s say tight with money to use the sort of negative phrase. But it was his experience living through the depression. So when I was raised wes, never, we went out to dinner one time between zero and once a year.

    Wes Moss [00:33:04]:

    Once a year?

    Douglas Stone [00:33:05]:

    No, once ever. And it was just he was, my father’s just he, he viewed it as unethical. Like it’s whoa, to spend $20 going out to dinner when you could spend $2 at home is just unethical. And I’m a kid so I’m thinking, okay that must be true. And it kind of persisted into my twenty s. And I’d go out to dinner with my friends and I would say, well I’m not going to order so I won’t have to pay. And I’ll just eat a sandwich afterwards. And they would be like, what is wrong with this guy? He’s insane. And in a way I was. And in another way, in my mind, I was trying to be sort of loyal to my father. Like, I was doing what I thought, like, my father’s watching. This is what he would want me to do, and I’m being a good son. Well, going out to dinner with your friends has nothing to do with being a good son in any objective sense, but in my mind, it did. And it wasn’t until I got a better sense of that that I was able to say, okay, actually spending money at dinner isn’t impacting my father.

    Wes Moss [00:34:10]:

    Is it unethical. I love that you say it’s like preposterous that you would do that. It is a really strong emotion. What about blind spots? You talk a lot about that. Do we all have them, and how do we correct them? How do we find them? What are they doing to us?

    Douglas Stone [00:34:27]:

    Well, wes all have blind spots. And the hilarious thing to me about talking about blind spots is, including me, my reaction is like, sure, everyone has blind spots. I mean, I don’t have them, but everyone else seems to have them for sure.

    Wes Moss [00:34:40]:

    Kind of like asking of somebody whose fault it was to get in an accident. It’s never the person’s fault, yet somebody has to be at fault of these accidents.

    Douglas Stone [00:34:49]:

    Right. Or it’s like when you’re driving, whatever speed you’re going is the right speed, and everyone is going faster is going too fast, and everyone’s going slower is going too slow. But blind spots are that way in the sense that they’re blind spots. So when someone says, well, you may have a blind spot there, you think, no, I just checked. I don’t have a blind spot there. But you can’t do that. That’s the challenge. So common blind spots in communication have to do with things that we think we know. So blind spots tend to be about ourselves, like the way there’s something we’re doing that is impacting other people that we’re not aware of. And so when people tell us that, like, that you raised your voice or you, whatever it is, we think, well, I was there, and I know myself. I’m with me 24 hours a day, and I don’t raise my voice.

    Wes Moss [00:35:48]:

    I did a system check and turns out after a full scan, no blind spots here.

    Douglas Stone [00:35:54]:

    Yeah, exactly. But blind spots are precisely the thing the system check isn’t going to check. Right. So, for example, like, right now, actually weirdly, I have access to my facial expressions because I could see myself, but in general, in life, I don’t. And my facial expressions are often going to be communicating things that I’m not aware of. And so when someone says, you seemed really upset with me, and I say, I wasn’t upset, and in fact, I think I was really quite friendly. Why am I thinking I wasn’t upset? And they’re thinking I was? Part of it is that I don’t have that information. It’s a blind spot. My facial expression, which may be giving away the fact that I really am actually upset even though I’m trying to hide it, I don’t see my facial expression. And so the only way to kind of engage with that is to hear is to learn it and to hear it from other people and to try to make sense of it again.

    Wes Moss [00:36:55]:

    What do we do about it?

    Douglas Stone [00:36:57]:

    So one thing that’s useful is to start to notice patterns. And so, like, on your 7th divorce, it’s probably something that you’re doing as well as the other person. So the first time we get feedback, we might say, oh, well, that’s just them being too sensitive or whatever. Maybe the second time. But if we get similar feedback consistently from different people, one way to think about it is, like, just other people are crazy. But another way is maybe I’m doing something that’s in a blind spot of mine that I just am not aware of, and I need to start taking that feedback seriously.

    Wes Moss [00:37:39]:

    It’s funny. I actually do have a blind spot that I think I kind of know of, that it’s not totally blind because obviously I’m bringing it up is a level of sarcasm where, let’s say I have a sibling that’s told me this. I’ve had a couple, let’s say, colleagues that have mentioned again, here’s the pattern that they don’t know when I’m being serious or not. When I’ve heard that feedback, and it’s happened several times over the last many years, I’m like, Come on. You know when I’m being serious and when I’m being sarcastic. Come on. So it’s like I’m looking around the room. Do you feel that? I’m asking Mallory and Marissa here. Do you feel like sometimes you don’t know if I’m being sarcastic or not? Really. Anyway, so, yeah, there you go. There’s a blind spot. What do I do about it?

    Douglas Stone [00:38:36]:

    What you just did is exactly what to do about it if you can, which is there’s an overwhelming tendency to want to say just what you started out by saying, like, oh, no, you can tell, or, I wasn’t being sarcastic, or obviously I was, but instead of doing that, just try to get that feedback. And it’s important, the fact that I gather that your colleagues couldn’t hear it, but I gathered they said so.

    Wes Moss [00:39:02]:

    They’re shaking their head yes. Like, absolutely.

    Douglas Stone [00:39:04]:

    Wes first of all, that’s a really good sign about the relationship that you have with them, because sometimes people won’t give you the feedback because they think you won’t listen or they’re afraid to or whatever. So if they’re saying yes, then the thing to do there is to say, let’s talk about that. Give me some coaching. And you have an important role in the conversations, which is to say, I feel like I’m just being relaxed or funny or natural, or that when I make jokes that are sarcastic, it’s kind of a sign of intimacy. All that is true from your point of view. For example, if it is true, it could also be true. So the fact that they’re not getting it doesn’t mean there’s something wrong with you or that you’re doing something bad. It just means they’re not getting it. You want it to come out this way, they’re not picking it up. So let’s figure it out and it’s just a thing to work on together.

    Wes Moss [00:40:01]:

    The Retire Sooner podcast audience are listening. They’re about ready to go have a difficult conversation. I feel like we’re all on the precipice of a difficult conversation. It’s kind of like a recession. We’re either going into a recession soon or we’re coming out of recession or we’re in the middle of a difficult conversation.

    Douglas Stone [00:40:21]:

    Sorry to interrupt, but that’s an important observation, which is people often equate the looming difficult conversation with something that they’ve done wrong in their life. Or like I’m too old to keep having to have these conversations. Like, okay, I was fine when I was 20, but I’m 40 or I’m 60. You don’t age out of these things. And they’re not a sign that there’s something wrong with your life. It’s just a sign that you know people. Like if you know people and you hang out with people and you work with people and you’re in relationships with people, you’re going to have difficult conversations. And the question isn’t are you going to have them? The question is, can you have them skillfully or are you going to just keep avoiding them or messing them up or whatever? Sorry.

    Wes Moss [00:41:07]:

    So how do I prepare? So I’m about to go do this tough conversation, so I’m dreading it. What do I do to prepare?

    Douglas Stone [00:41:16]:

    So there’s two things. When people say, like, sure, if I had 4 hours to think through it, I could do that, but I’m actually ten minutes away from their house and I’m driving over to talk to them, what do I do? I give two pieces of advice. One is I remind people that there’s almost no chance that you’re going to listen to them well just because that’s your natural tendency. In a difficult conversation. The most skilled listeners, the best financial advisor, the best therapist, the best friend, all the skills go out the window because you’re stressed out and you people often feel like they’ve got to get their point across. So listening becomes really hard in a difficult conversation. And it’s only going to happen if you literally remind yourself right before the conversation, okay, when they start talking, I need to be paying attention. I have to stop listening to myself and stop what we call reloading, right? Like, oh, they’re talking. So I can use this time to reload my arguments. So that means I’m not listening. So we want to pay attention and we want to not just listen, but we want to dig into the hard places when they say, when you did this, it made me really uncomfortable. Our natural tendency would be to say, okay, I heard you say that, but I don’t want to talk more about that. So I got it. Let’s just move on to the next thing. It’s much better to say, wow, I didn’t realize that. Tell me, when you say I make you uncomfortable, what am I doing? What is it? And how are you feeling uncomfortable? Why do you think this is happening? Like, stay with the heart, stay in the hard place with listening and with questions. And people will also think, well, if we keep talking about it, it’s going to make it worse. They’ll think I’m worse and worse as I ask them questions, but asking them questions about it, they already know how they think about the whole thing, so that you’re not changing. They’re not going to think it’s worse. They’re just going to feel like you care about it and you’re starting to understand them. And that’s super helpful, that’s one. Okay, the second thing, again, if you only have a couple of minutes, is to step back and ask yourself, what are the identity issues for me here? Sometimes it’s sort of obvious, but sometimes it’s not. So if you are going to tell somebody that they’re spending too much money and you’re thinking, again, this is about them, so why would I be upset about this? Well, there’s some identity issue for us in the conversation, and getting a real handle on that is incredibly empowering. So thinking. I guess what it is for me is if I say, hey, you’re spending too much, maybe they’ll be mad at me. Or maybe they’ll storm out. Or maybe they’ll say, wow. I came to you because I thought you were the kind of advisor that really was going to understand what was going on. But obviously you’re just like the others. So we need to think through, what if they said that? What would that mean to me? And what does it say about me? What doesn’t it say about me? Right? They don’t get to decide how we see ourselves, but they might have information that’s useful to us. So we want to be sort of open to taking in what they have to say, but we don’t want to exaggerate it. And often in difficult conversations, if someone has a momentary flash of like, oh, well, I’m mad at you, or you’re just like the other person that I didn’t think was doing a good job, we think, okay, well, they’re not allowed to say that. But if you think it through in advance, like, well, what would that mean if they did say it? People have thoughts like that that’s out in the world, so someone could think that about me. That’s normal. So maybe there’s something I can learn from that, but it doesn’t mean I’m a bad financial advisor. So you just want to make sense of it. You want to think it through in advance, try to imagine how to make useful sense of it without exaggerating. Like, oh, they’re right. I’m terrible at this job. How is it that I keep screwing everything up?

    Wes Moss [00:45:40]:

    Yeah, you’re giving yourself some conviction. So some vitamin C boosters of conviction as you go in.

    Douglas Stone [00:45:47]:

    Yeah, and it’s not based on psyching yourself up, just like, rah rah. It’s based on the truth. Yeah. People have opinions about me, and I can deal with that, and I can learn from that. I can also disagree with them. We can talk about them.

    Wes Moss [00:46:03]:

    So it really is about understanding both them to understand you, you to understand them and then problem solve together, which is really kind of a nice roadmap for that. What about, as we wrap up here today, what about I haven’t asked you about thanks for the feedback, but it’s interesting to me. Would you also say, tell me about that we’re giving someone feedback? Is it also I guess that’s part of the difficult conversation sometimes.

    Douglas Stone [00:46:32]:

    Yeah. So we wrote Difficult Conversations in 1999, and I should mention, by the way, just because it’s on my mind that we’re revising it now for a third edition, which will be out in August. That’s cool.

    Wes Moss [00:46:46]:


    Douglas Stone [00:46:46]:


    Wes Moss [00:46:47]:

    Three editions. That is a big deal.

    Douglas Stone [00:46:49]:

    Yeah, I know. It’s a privilege to be in that position. So my colleagues and I would go around giving talks on Difficult Conversations. We do lots of consulting organizational, corporate, family consulting on those topics. And often what we do is we start by making a list. We say, what are your difficult conversations? What are the examples? And we’ll write them up on the flip chart paper. And in any group of people, one of the things will be we have trouble with feedback because it’s hard, right? There’s no easy way around giving and receiving hard feedback. And so we thought, well, maybe that’s a maybe feedback is a topic we could dig into. And we started looking at it, and we found that there were a number of really good books on how to give feedback, and there were zero books on how to receive feedback. And at first we were like, well, that’s because you just sit there and listen and someone gives you feedback, you don’t read a book about it. And then we thought, well, that’s clear. That can’t be true because clearly it’s a skill. Like receiving feedback is a thing you can be good at or not so good at. And so we decided to examine that whole question not from the point of view of the person giving the feedback, but from the point of view of.

    Wes Moss [00:48:10]:

    The person receiving oh, you got it. Okay, so how do we receive feedback? I love this. I need the Cliff Notes for our listeners.

    Douglas Stone [00:48:19]:

    Well, in a sense, the Cliff Notes are similar to the Cliff Notes for difficult conversations. So we receive feedback by first being aware of. There’s sort of standard moves that we make to not agree with feedback. Again, not because we’re being shallow or difficult or annoying, but just because this is what people do. But when someone gives me feedback, if it’s hard feedback for me to take, it’s very easy for me to think, well, that feedback’s wrong or that feedback’s out of date or that feedback was based on that one thing I did, not the real ways I did. So like, there’s lots of what I’ll call excuses and sometimes those things are true and sometimes they’re not. So there’s no rule that says notice all your excuses and then throw them out and take the feedback. If that were true, then the book would be one page long. It would be a very powerful page. But it turns out it’s not true. So how do we figure out what’s the feedback that is right and helpful and what feedback just kind of doesn’t fit us or is based on wrong information? And the only way to do that is to have a conversation about it and to listen to the feedback and to try to dig into it. A common pattern is people. So this is just a nearly universal tendency which when I started noticing it, I was kind of astonished by. People give incredibly vague feedback and they don’t realize it. So people give feedback with labels. They use like adjectives and words. So they’ll say things like, I observed you in that meeting with the client and you just need to be more professional. There’s more professionalism or you need to be a little more assertive or you need to be a little more empathetic. And the person giving the feedback knows exactly what they mean in their head. The person receiving the feedback has almost no like those words contain almost no information, as it turns out.

    Wes Moss [00:50:26]:

    Okay, so I’m getting this. So the key to feedback receiving is saying, look, I need some specifics. I want to understand this as opposed to glaze over it.

    Douglas Stone [00:50:37]:

    Yeah, exactly. And it’s a little bit like receiving. I don’t know, you’re old enough to have had to ask for directions. I guess you’re under 30. Don’t know what those words mean. But in the old days you used to have to say, hey, how do you get to this place? And some people will say, we’ll just go over that way. But it’s really useful to have them say it’s the third right turn. But that third right actually doesn’t seem like a real road. It’s like a dirt road. And if you see the gas station on the corner, you’ve gone too far. That starts to be helpful in getting there as opposed to just you’re going to head down and then go over that way. So you want to inquire. But at the same time, it’s important to recognize that your interest in understanding the feedback doesn’t mean you have to agree with it. So you might or you might not. You might say, wow, that’s really very interesting, and I think I really understand what that feedback means and why where you’re coming from. Let me share why I actually don’t think that I should move in that direction. So understanding it well doesn’t mean you have to rush off and take it. Maybe you do, but if you’re kind of hesitant or you experience some resistance, it’s useful to share that, to kind of talk it through.

    Wes Moss [00:52:07]:

    I think about directions. I think of two things, I think. One, oh, you can’t get there from here. Kind of the person who’s like, I don’t really want to give you directions. Yes, you can’t get there from here. And then I think of the I think it’s a country music song that basically it’s billy curlington selling peaches or collard greens or something on the side of on his truck. And the girl pulls up and asks for the interstate and he says, way up yonder past the caution light there’s a little country store with an old Coke sign. Got to stop in and ask Miss Bell for some sweet tea to take a left at the interstate and then take a right and then you’ll come right back to me. I think that’s Billy Curlington or Currington.

    Douglas Stone [00:52:58]:

    Good lyrics. I’ve been trying to write country songs, by the way, so I’m very pleased to hear good country lyrics.

    Wes Moss [00:53:05]:

    Yeah, that’s a good one. It’s a classic lyrical ballad, anyway. All right, well, listen, I got to go. This is awesome. Thank you. We’ll let you get back to your day. And exciting, though, that you guys are doing the third edition of A Difficult Conversation, that’s 23 years worth of that book continuing to sell.

    Douglas Stone [00:53:26]:

    That is true. So we’re very pleased about that. And I should also just say I’m delighted to have been on the podcast, and I really admire the work you’re doing. As I mentioned to you just before we went on the air, it’s one thing to give people good, sound financial advice, but it’s even more helpful to give them financial advice that is informed by life advice and, like, what people care about in their relationships and their activities and all that. And so you all are doing a great job with that, and that’s a real service and benefit to people.

    Wes Moss [00:54:05]:

    Well, we’ll continue to try to do that. So, Doug Stone, thank you so much, man, for being here. And I feel a little bit better to go have a difficult conversation, because, really, a day doesn’t go by when we don’t have to do that. So thank you for making us all a little bit better at that. And thanks for stopping by the Retire Sooner podcast.

    Douglas Stone [00:54:25]:

    My pleasure. Thanks.

    Mallory Boggs [00:54:28]:

    Hey, y’all, this is Mallory with the Retire Sooner team. Please be sure to rate and subscribe to this podcast and share it with a friend if you have any questions, you can find us at You can also follow us on Instagram and YouTube. You’ll find us under the handle @RetireSoonerPodcast. And now for our show. Disclosure: this podcast is provided to you as a resource for informational purposes only and is not to be viewed as investment advice or recommendations. This information is being presented without consideration of the investment objectives, risk tolerance or financial financial circumstances of any specific investor and might not be suitable for all investors. It is not intended to and should not form a primary basis for any investment decision that you may make. Always consult your own legal, tax or investment advisor before making any investment or financial planning considerations. Please refer to the full disclosure in the podcast description for any additional information.

Call in with your financial questions for Wes to answer: 800-805-6301

Join other happy retirees on our Retire Sooner Facebook Group:


This information is provided to you as a resource for educational purposes and as an example only and is not to be considered investment advice or recommendation or an endorsement of any particular security.  Investing involves risk, including the possible loss of principal. There is no guarantee offered that investment return, yield, or performance will be achieved.  There will be periods of performance fluctuations, including periods of negative returns and periods where dividends will not be paid.  Past performance is not indicative of future results when considering any investment vehicle. The mention of any specific security should not be inferred as having been successful or responsible for any investor achieving their investment goals.  Additionally, the mention of any specific security is not to infer investment success of the security or of any portfolio.  A reader may request a list of all recommendations made by Capital Investment Advisors within the immediately preceding period of one year upon written request to Capital Investment Advisors.  It is not known whether any investor holding the mentioned securities have achieved their investment goals or experienced appreciation of their portfolio.  This information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. This information is not intended to, and should not, form a primary basis for any investment decision that you may make. Always consult your own legal, tax, or investment advisor before making any investment/tax/estate/financial planning considerations or decisions.

Previous ArticleNext Article