EntreLeadership - The 3 Mistakes People Make in Hard Conversations (and How to Avoid Them)

Episode Date: February 2, 2026

Most leaders don’t mess up tough conversations—they avoid them.  In this episode, you’ll learn how to face difficult conversations head-on with a clear plan that protects trust, fixes problems faster, and strengthens your team instead of damaging it.   Next Steps:   ·      🎥 Watch the training and use the template to prepare for your next hard conversation: https://ter.li/tiy692 ·      📞 Have a question for the show? Call 844-944-1070 or send us a message: https://ter.li/ask-us ·      📚 Learn about the EntreLeadership System™: https://ter.li/system-p ·      💻 Get EntreLeadership Elite™ for your business: https://ter.li/elite-p ·      ✉️ Sign up to receive tactical tools, advice and resources in your inbox every week: https://ter.li/enl ·      🏢 Attend EntreLeadership Summit: https://ter.li/summit ·      🎤 Attend EntreLeadership Master Series: https://ter.li/masterseries  ·      📖 Order Dave’s new book, Build a Business You Love: https://ter.li/b4kru2   Listen to More From Ramsey Network: 🪑 Front Row Seat with Ken Coleman 🎙️ The Ramsey Show 💸 The Ramsey Show Highlights 🧠 The Dr. John Delony Show 🍸 Smart Money Happy Hour 💡 The Rachel Cruze Show💰 George Kamel   Ramsey Solutions Privacy Policy Learn more about your ad choices. Visit megaphone.fm/adchoices

From the headquarters of Ramsey Solutions, this is Entree Leadership. I'm your host Dave Ramsey with over 30 years of experience leading in the trenches right alongside you. Most leaders hate having difficult conversations with a team member. But trust me, avoiding the hard conversations doesn't protect your team. It paralyzes it. So the best leaders out there don't run from this. They lean in. That's why today, John Falcons from the Entry leadership team,

And one of my board members, Brendan Wochko, will show you exactly how our team has the kind of tough conversations that solve problems, grow trust, and make the business stronger. All right, thanks, Dave. Well, Brendan, we have this conversation all the time about difficult conversations. But I know all of your work on that really kind of started with a story, didn't it? Your own experience. Yeah. It's like a fun, not fun story, right? It's fun now.

It's fun now. It wasn't in the moment. Right. Yeah, so like one night my wife and I are sitting on the couch, you know, at her house. It's totally normal. She gets a text message, right? And I kind of barely notice she got the text message until, you know, when I did notice, she's kind of like staring at her phone.

And, you know, something about that moment, you could kind of just feel like the air drain out of the room, right? And she didn't say anything to me. She just kind of turns and looks. I grabbed the phone. I look at it, and my wife had gotten a text message from a woman named Anne. Okay. And I had fired Anne's husband that morning.

And it was just like the text message was just like, hey, that's all it said. So you didn't really know what was coming next. Right. You know, and, you know, like you get the three little bubbles that are telling you on the text message thing, the person on the other end is sending like a really long message. Yeah. And so at this point, my wife and I are both like, you know, sitting there like staring at her phone, like what the heck's going to happen next?

What's the next message that's going to come through? Right. And when the message came through, it was like not what we expect. And she basically said, hey, I know her husbands have just walked a really tough road together. Right. But I feel like it was handled really well. And I just want to, you know, communicate that I'm grateful for that and want to know if we can still be friends. Yeah.

Okay. That could have gone a very different direction. It could have gone a very different direction. And there were like a bunch of lessons in that, right? Like, I think at that point of my leadership experience, I was like 10 years into my into leadership at that point. And what was interesting is I kind of walked away from that that evening. And I was like, how is it that I've been doing this leadership thing for 10 years?

And I've walked through a bunch of uncomfortable conversations, but I've never had one in 10 years that actually went that well. And so it really caused me to kind of dive into that and say, what was different this time? And I think the thing that I took from it, you know, in the big picture, was the reason why uncomfortable conversations are so hard for leaders is because it's a very unmodeled skill. Yeah.

It's very difficult to model for other people what's never been modeled for you. And when it comes to uncomfortable conversations, I feel like they're probably the hardest skill in leadership. Not because they're actually hard. It's because there's just not a model. Nobody's told you how to do it. There's a lot of feelings around it. So walking into uncomfortable conversations is really hard.

So what you're talking about, it's never been modeled for you. a lot of people don't have that model. That's in fact what you've created. Right. Right? This idea of having a written plan. The plan itself is really, it is a written plan. That's the important thing. Yeah.

And lots of leaders can be really resistant to the idea of actually walking into an uncomfortable conversation with a written plan. Why do you think that is? I think the main reason that they get uncomfortable with the idea, because they're worried that if they walk into a conversation like that with a written plan, it's going to look like they don't know what they're doing. But no, what I tell leaders all the time is, you know, the only thing that's worse than not looking like you know what you're doing is actually not knowing what you're doing. Right.

So, you know, if you're going to have an uncomfortable conversation, you know, there are some people that walk into them very confident. And honestly, most people that walk into uncomfortable conversations confidently don't realize they're probably doing them very wrong. And the people that walk into uncomfortable conversations actually uncomfortable, the good news is they're. is they probably have a really high potential to do it right. Yeah. Because they're so nervous in the moment, they don't know what to do, and they bob and weave and waste time and confuse the other person and make a mess.

Yeah. And it's just better to walk in with an actual, you know, with an actual script. So that's what we learned here at Ramsey. Like we've got hundreds of leaders here at Ramsey. Now, I'm gonna start real quick. When you say script, yeah. Do you mean literally like you walk in and I'm gonna read this to you

as we go through this or, Or do you mean something? I think it depends on your level of nerves. Okay. Right? Like if you're paralyzed nervous, you could walk in there and use it, use it like a script and literally just read it. Yeah. But I would say for people that have, you know, some reps underneath their belt and they're, you know, they're not losing a full night of sleep before, you know, having an uncomfortable conversation.

It's more of a guide. Yeah. Okay. Okay. They're not just making it up on the fly. They've got something to follow. But the plan does a good job of helping you figure out, like, what's the intensity of the conversation that you have to have? Like, how do you keep it short? So, you know, when you think about an uncomfortable conversation, like, what are the ingredients of a great one? Like, you got to create a ton of clarity. That's one thing that people really get wrong is they don't do a good job of, like, actually clarifying the problem, making it crystal clear. And then they also honestly really struggle with the amount of time. time that they spent. So, like, I do this by nature. I'm like a coach by nature. So I want to sit down with somebody and, you know, give them all the examples of, you know, how I've made similar

mistakes and what they could do better and talking about all the dimensions of the problem. And, you know, hey, leadership is tough. And the, the truth is, is that the person on the other end of the uncomfortable conversation, like they're, if you're not careful, they're, they're just back in their amygdala, the fight or flight response. And all they're doing is just scanning the conversation for the words you're fired. Okay. And so you've got to have some good strategies to like overcome that. And the best strategy for that is keep the conversation short. A lot of people think that that's undignified, but the best way to create a dignified, uncomfortable conversation is for it to be short and very clear. It sounds to me like, and I think my experience is, is what you're fighting

against is all of those emotions. And you got to be very concise, very targeted to get those important words through to the person, right? You're, you're, you're not just winging it. Right. Right. It's got to be super intentional. How do you start? How do you get that conversation started? Well, and I think actually starting is one of the most important points because people, people get very awkward. It's awkward on the other person's part and it's awkward on your part. Like if you put yourself in the other person's shoes, you know, they're getting like some ambiguous meeting called. They don't know what it's about. You know, they might... Quick update or something. Yeah, quick connect.

Yeah, quick connect. It's called on their calendar or whatever. They're like, oh, you know. And so they don't really know what it's about. They're walking in with some nerves. You know, you've got some nerves to. And the biggest mistake that people make is they just start with small talk. They'll be able to, you know, talk about the weather or like, hey, how's, you know,

how's the family doing? The deal is, this is like, if you don't want someone to have that fighter flight response to an uncomfortable conversation, like right off the bat. The moment they sit down, you have got to address the elephant in the room. Yeah. And you basically, like the way that I start them is somebody will sit down and I'll say, you know, let's call the person Bob. You know, I'll say like, hey, Bob, thanks for sitting down with me. I just want to let you know up front that, you know, this is what we're about to have is a pretty uncomfortable conversation, but I want to let you know that nobody's going to lose their job today.

Level set. Right there. In one sentence, you've managed their expectations that it's going to be an uncomfortable conversation and you have told them that the outcome of the situation is not like the worst case scenario. You're kind of helping them regulate keeping them out of that fight or flight response. Yeah. And there's ways if they go to the fighter flight response to kind of yank them back from it too. That's a super good point. And I know you've got a ton on this, but one other thing I want to make sure you hit is this idea of hurt versus harm. Yeah. Talk about that a little bit because I think that's critical. Yeah. So I think one of the reasons why leaders tend to avoid uncomfortable is because they're afraid of, like, abusing their authority.

And so the thing that I felt that I felt, like, really equipped me to do a better job at uncomfortable conversations is the day that I realized that, like, hurt and harm aren't the same thing. Okay. And so a lot of people were like, well, that sounds like a distinction without a difference, right? But there actually is, there is a difference. I'm listening. Like, hurt.

Hurt is, when you address someone's behavior, like, I observed you doing a thing. Okay. You're not calling them as a person into question. You're not calling their character into question. You're not calling their identity into question. You're not like, you're not like, it's, it's not like a low dig. Okay. You're just talking about the behavior that you observed.

Okay. Now that's going to hurt. Like there's no, there's no version of like accountability and consequences that doesn't sting a little bit. Right. Right. But if you focus on the behavior, at worst, you're going to hurt them. But if you go down the road of like talking about them as a person and who they, are, that's harm.

And the reality is, it's like, once you kind of, I call that the lightning rot of conflict. The lightning rod of conflict. The lightning rod of conflict. Like, if you accidentally go, you know, say something that's harmful, the reality is,

is like right then and there, the relationship's kind of over. Okay. Or the, at best, relationships just damaged or changed, right? That's one of the things that I see leaders make huge mistakes on because they wait too long to have an uncomfortable conversation.

They're all emotionally loaded. They're at a nine of 10, you know, instead of a two of 10. And they just like almost kind of go for the jugular. They get into like identity stuff. Right. You know, you're not good enough at your job, you know, and I don't think you have the skills to do this. And, you know, they get into stuff that's like really personally judgmental instead

of doing the thing that the person needs. Yeah, because that's not help. Not only is that bad, it's not helpful. No. Yeah, I remember early on in my career, I had a CEO tell me, he said that he said that he felt like he was asking me to be three inches shorter. He said that like the things I'm asking to do, I don't feel like you're capable of doing.

And that was the first conversation. Oh, wow. And, you know, what do you do with that? Well, the problem is you can't. Right. Like, when you frame that up some way, it's like, well, like, you're right.

I can't change my height. So you're telling me right off the bat the first time that I can't do it. Right. Like, of course I'm just going to check out. Of course this is going to end poorly. Yeah. So that's harm. Right.

And so you want to keep feedback focused on people's actual behavior. Okay. Awesome. If there's just one thing that you would want people to take away just thematically over the whole thing, what would your advice be? Just like, don't wing it. You know, I've seen lots of uncomfortable conversations go well. I've seen lots of them go poorly. Almost every time they go poorly, it's the result of winging it. Okay.

You know, walking in with a written plan, you know, is the best way to show dignity to the other. person. And if you can keep dignity high, you're highly likely to have a good, uncomfortable conversation. Way better odds. Yeah, way better odds. I appreciate that, Brendan. And I know you've actually developed a lot of material on this, haven't you? Oh, yeah. So make sure that you click on the link in the show notes to get all the resources Brennan has developed on this if you want more help. Look, if all this gives you heartburn, I know it isn't easy, but it is part of the job. And when you do it the right way, your team gets better. Problems get solved. Expectations get clear. either step up or step out, both of which are wins. But the real magic happens when your team doesn't

just survive those tough talks. They trust you more because of them. That kind of trust is the foundation of a strong culture, one people want to be a part of. If you want more content to help grow yourself and your business, be sure to like this video or podcast and subscribe. I'm Dave Ramsey. Thanks for being with us on Entree Leadership. You know,