Win More, Live Better
Win More, Live Better is a podcast for sport coaches and high-performing leaders who care deeply about results, but refuse to compromise their well-being, joy, or relationships in the process.
This show explores what it really means to win more and live better on your terms. Through stories, conversations, and practical frameworks, each episode helps you sharpen your leadership, strengthen your inner game, and build systems that support sustainable performance for you and those you lead.
Hosted by Zach Brandon, a nationally recognized performance and leadership advisor who partners with elite sport coaches, executives, and high performers to help them thrive using practical tools, systems, and mindset frameworks.
Win More, Live Better
The Conversation You're Avoiding
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What conversation are you currently talking yourself out of? Difficult conversations rarely become easier simply because we avoid them. More often, the frustration, assumptions, and tension continue to build beneath the surface. In this episode, Zach shares some practical strategies for navigating difficult conversations and becoming more skilled at them.
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I think the vast majority of people are far more skilled at talking themselves out of a difficult conversation than actually having it. When we walk into these, we often rehearse what we want to say, we predict how the other person might respond. Sometimes we'll even convince ourselves that, ooh, the timing's maybe not right, so maybe it's not that big of a deal, and I can just let this thing go, and then hopefully with enough time the problem will just somehow resolve itself. And what I've come to find out, not only through my own experiences, but with others, is that usually they don't resolve themselves. Oftentimes, the conversation that can have the biggest impact on a relationship, a team, or even our own lives, is the one that we're currently avoiding. So today on the podcast, I want to talk about difficult conversations and a few things that I've learned, made most of them through the hard way, uh, about how to have them better though, and how to get more skilled at them too. Hey, before we continue, I want to extend a simple invitation. The heart of this show and really all of my coaching work is about helping coaches, executives, and leaders develop the mindset and systems to win not only professionally, but also personally. I offer a free coaching call where I can help you unpack a variety of situations that show up in my work with those that I serve. So if you're trying to level up your program's culture, looking for creative ways to develop your staff, if you're feeling stretched or burned out by leadership, trying to build a better system for how you train the mental game with your players, or you just simply want a space where you can be honest, unfiltered, and stretch, I'd love to connect. Even if working together isn't the right next step for you, my goal is to help you leave with greater clarity, a practical direction next, and useful resources. So if that sounds valuable for you or someone you know, visit the link in the show notes. Now let me begin this episode by saying that I do not think I'm by any means an expert in difficult conversations. Uh, if anything, I think a lot of what I've learned is from having conversations that didn't go particularly well at times. Uh, I've had conversations where I waited too long to engage in it. Uh, I've had conversations where I probably spent too much time trying to prove a point and not enough time trying to really understand the other person, their needs or their wants or their values coming into that conversation. Uh, and I can't tell you how many I've walked out of where afterward I thought to myself, uh, I could have probably handled that differently, or I should have said something a little bit different there. Um, and I think it's kind of one of the things that makes this topic so interesting is on one hand, like we get a ton of reps at this on a day-to-day basis, not only professionally, but also personally. Um, and the other side of this, though, is like most of us have never really been taught how to have difficult conversations. For the majority, we've learned how to communicate largely through observation and experience, with the biggest source being through our parents. So, regardless whether it was your parents or maybe some others that have uh influenced you and how you communicate now, I think for the vast majority of us, we have seen relationships where people not only communicate really well, but I think a lot of us have also seen a lot of ineffective forms of communication. The latter, for example, like for some people, disagreement uh oftentimes gets shown out uh shown through confrontation. Uh, for others, it leads to people shutting down. And then you have others where just uh their strategy is just peer avoidance altogether, where it's like, again, as I mentioned earlier, it's like, okay, if I just don't bring this up, if I give it some time, create enough distance, hopefully it just goes away. But again, I think one thing that I've learned is that unresolved problems will rarely disappear just because we stop talking about them. Now, this past week, I got a chance to attend uh a workshop with a gentleman by the name of Matthew Blades. Now, Matthew has spent nearly three decades in media and broadcasting, and he now does a lot of work with leaders and organizations trying to help them improve their communication, uh, particularly uh when conversations become difficult. And one of the things I really appreciated is he kind of set the expectation of his whole presentation at the beginning with under the kind of the quote that so much of what um we want in life is likely on the other side of a crucial conversation. So think about something that you want right now, whether it's a better relationship, maybe there's an opportunity that you're hoping to have. I think in most instances, there's a lot of times we're on the other side of that, the gateway to that is through a conversation. And yet, despite how much possibility exists on the other side of these conversations, most of us are not very uh skilled at them. What we are incredibly skilled at is avoiding them. And the irony is that we often spend an incredible amount of energy on a conversation that we're unwilling to actually have. We just have it with ourselves instead. So if you have that conversation, we start to replay. Um, I'm sorry, let me back that up. Not if you've had the conversation, but like let's say there's a situation that has unfolded where you feel like in afterwards you need to have maybe a difficult conversation with someone, whether this is an acute one-time thing, or maybe this has been an accumulation or compounding of multiple events. But what happens is we replay whatever frustrated us or whatever has agitated us to engage in this conversation in the first place. Then we start to rehearse what we want to actually say. We imagine how they might respond to us, and then we respond to the response that hasn't even happened yet. And we build this entire conversation in our head with somebody that's not even in the room. And I think it's important to understand that like most things that I try to do in these episodes, is like there's always like another side of the coin. Like there's nothing that's ever just like black and white. So within all of this, is like, I do think there is value in preparing for these like crucial, difficult conversations. There, there's an aspect of that that is valuable. If something matters, we should probably think it through a little bit and how we want to communicate and what we want to communicate. Uh, we should also consider the other person's uh perspective. And then there's on top of that, there's a point where we're no longer just actually preparing ourselves to engage in it, we're just talking ourselves um out of it. And so the the challenge though with this is like if we avoid them, it doesn't eliminate the tension. It's almost as if you could think of it like it relocates it, is one way I think about it. So instead of tension being between you and another person, now that tension is within you. Yeah, there's frustration, there's resentment, there's rumination of what happened, and you're replaying it over and over again. And there's that story that you keep telling yourself about the other person. And all of that uh starts to influence how you interact with them, even though you've maybe never actually given them an opportunity to participate in the actual conversation um itself. So lately I've been thinking about difficult conversations a lot more. Some of this was again inspired a little bit from Matthew Blades, and again, kind of taking in my own experiences or how I've helped others try to navigate them. So my hope is to share uh a couple of keys, things that I've used in my own life to try to help uh and be a work in progress with these uh crucial conversations. So the first one is to make sure that you make the problem the problem. The other person can't be the problem. Because the moment you make the other person the problem, I think there's a pretty good chance that the conversation is going to become just a fight over well, who is right. It's and it's like more like it's a me versus you conversation, which I think in most instances in most parts of life, like those don't ever uh end up well because then you have like here's my version versus your version, or here's my evidence versus your evidence. Um, and on top of that, when you attack a person, what naturally happens is people defend themselves. Um and so I think this is where it's not me versus you, but the shift being it's you and me versus the problem. We're not sitting on opposite sides of the table trying to defeat one another. We're trying to get on the same side of the table and look at something together. What are we trying to solve? What do we both want to be different when we leave this conversation? And this is where I think establishing some sort of shared outcome um on the front end is is really useful because uh we may disagree about what happened or why it happened, um, but we need to find common ground on like what we both care about. So we both care about the relationship or the team or working together more effectively or wanting the the organization to succeed, that needs to be the starting point uh because we're not trying to determine which person is the problem. We're just trying to be two people uh attempting to solve it. So I think that's the first distinction that I think is really important. The second one is you have to get underneath the disagreement. Um, it's about recognizing that what we're arguing about isn't always what we're actually arguing about. So, what I mean by that is when you really like peel back the layers, confrontation or disagreements and those types of things often comes when there's like misalignment with values, or somebody is approaching a situation or the conversation with a certain value top of mind, and the other person has a a completely different take. So you could have one person that values being, you know, direct and candidness um and and delivering like the truth no matter what. And then you have somebody else where like their first main value is like harmony and making sure that people are connected and making sure that um you know people feel seen and heard and valued and and those types of things. And sometimes those can be um at odds in a conversation, or you can walk into a conversation if you're not on the same page and you're cognizant of what the other person values, uh, it can lead to this underlying um friction. And I think this is where curiosity becomes uh really important. And I think one of the biggest mistakes that we can make is arriving into these conversations with a conclusion. Um it's almost like, you know, if we were like an FBI investigator uh and we've already completed the whole uh investigation and we didn't even give the other person uh an opportunity. So I think it's really important that we uh we we lean into curiosity in these two. Um and and I think one way to do that, one of my favorite ways to make this practical is like uh if somebody does something you didn't love, it's like, hey, help me understand blank, like help me understand what was happening in this moment, like from your perspective. Um, and that doesn't necessarily mean that you need to abandon your own, but it does uh it is a way I think to acknowledge that your perspective, your vantage point isn't the only one in the room. So that's the second one. Get the uh like tap into be clear on the values underneath for each person. The third is be willing to go first. Um, and this requires vulnerability. One of the fastest ways to lower the temperature of a difficult conversation is be willing to go first. I think within that, one thing that I've had to do in my own life is sometimes acknowledging um where I've messed up or maybe where I've waited too long. And I've had an instance where I've said, hey, I probably should have had this conversation with you a couple months ago and I didn't. And I'm sorry, but like that's on me. And I want to help I want to have this now because I want to make sure that we can create a different outcome, or we want to like um solve this in essence uh together, and I don't want to just keep holding on to this. So something like that. Um, or I I've uh seen this where it's like, hey, I've thought a lot about our last conversation, and if I could do it again, there's probably parts where I would do something differently or I would change it. Um and then even too, within all that, one other um just example that came to mind is is just acknowledging maybe the difficulty itself. So, like, hey, I don't know exactly how this conversation's gonna go, but I care enough about the relationship that I don't want to keep avoiding this. Um, and I think there's something really important when you start to um lead with that vulnerability because it almost uh it helps you communicate from a way where you're not just like coming in trying to prosecute the other person, like sticking with kind of like the the uh uh legal uh slash um investigative perspective or analogy for this. Um you're trying to like I'm willing to acknowledge my own contribution to this. Um, and I think somebody has to create enough safety for both people, in essence, to put the weapons down for these. Um, and that's really I think the only way that it can actually be done effectively. Uh the fourth one, I think we all need to get better at repairing relationships. So this kind of goes hand in hand um in in all of this, but uh, you know, I think we spend a lot of time talking about how to build relationships, but what happens when we need to repair one? Um, what happens when there's someone professionally or personally uh where a relationship's gone sideways and they've disappointed you or you disappointed them? Um someone may have said something that they wish they hadn't, whatever the case might be. I think it's a good reminder that the quality of a relationship can't just be measured by like it avoids conflict or like rupturing. Like I think um, you know, do you have the strength in the relationship to repair it or to apologize or to, you know, again, be vulnerable and say maybe where you messed up? And I think uh at the end of the day, it it's just uh a reiteration of like, hey, I don't like where we're at right now, but I want to try to figure out how we can get somewhere better. Um, and that leads me to uh the last thing that I wanted to share with this, because I think this is a helpful analogy, at least in my own life, is to think about um difficult conversations like flying on an airplane. And what I mean by that is like, let's say, you know, I live in Phoenix, I'm trying to get to New York. Um, the entire purpose of getting on that plane is to end up somewhere different than where I was when I started. So along the way, though, especially in the beginning, there's probably gonna be some turbulence. Like the plane might shake, you know, the seatbelt light's gonna come on at some point, things are gonna probably have moments where there's gonna be a minute or two of like some discomfort in these conversations. We don't have to immediately assume that because the flight became uncon uncomfortable, uh, that we're going in the wrong direction. Turbulence is sometimes simply part of just getting somewhere else. And and I think that's how difficult conversations are. Like the goal isn't to have a turbulence-free flight, but the key is to make sure that we both land somewhere differently within our relationship. Um, and I think again, I think that's a a really uh important distinction. And that better, I guess, um, destination could be like, okay, do we understand each other better? Is there greater clarity on how we can move forward? Like, did we establish a boundary? Uh like do we know what we need to do next or what happens next? And and so on. So that to me is, I think, really important. So to bring this episode to a close, very simple here. I think it's just one question worth reflecting on. What's the conversation you've been talking yourself out of? In essence, what's the conversation that you're currently avoided that could help you or someone else get somewhere a little bit better? Whatever that conversation is, my invitation, my hope for you this week is that you engage in it. You lead with some vulnerability, uh, you admit maybe where you're wrong, uh, and you just create an opportunity for repair or a chance for both of you to get to a better place. Thanks for listening.