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

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. But trust me, avoiding the hard conversations doesn't It paralyzes it. So the best leaders out there don't run from this, they lean in. Today, John Falkins from the Ontrei Leadership Team and one of my board members, Brendan Woachko, will show you.

Exactly how our team has the kind of tough conversations that solve problems, grow troubles. And make the business. 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.

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 noticed 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 she didn't say anything to me. She just kind of turns and looks. I grab 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 it 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 uh, you know, like you get the three little bubbles that are, that are telling you on the text message thing, the person on the other end to send in like a really long message. Yeah. And so at at this point, my wife and I are both like, you know, sitting there like staring at her phone, like what the heck's gonna happen next? What what's the next message that's gonna come through? Right. And uh when the message came through, it was like not what we expected.

And she she basically said, Hey, I know our husbands have just walked a really tough road together. Right. Uh but I feel like uh uh it was handled really well and I just wanna, you know, communicate that I'm grateful for that and uh wanna know if we can still be friends. Yeah. Okay. That could have gone a very different direction. Could have gone a very different direction. And um and and there were like a bunch of lessons in that, right?

Like I I think I think at that point of my leadership experience I was like ten years into my into leadership at that point. Okay. And what was interesting is I kind of walked away from that that evening and I was I was like how is it that I've been doing this leadership thing for ten years. And uh Uh I've walked through a bunch of uncomfortable conversations, but I've never had one in ten years that actually went that well.

Yeah. And so it it really caused me to kind of dive into that and say, what was different this time? And you know, I think the thing that I took from it, you know, in in the big picture was The reason why uncomfortable conversations are so hard for leaders is because it's a very unmodeled skill. Yeah. That's a it it's it's very difficult to model for other people what's never been modeled for you. Yeah. 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. Yeah. There's a lot of feelings around it. So walking into uncomfortable conversations is really hard.

But that's 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. This this idea of having a written plan and the plan itself is R really i 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 why do you think that is?

I think the main reason that they get uncomfortable with the idea'cause they're worried that if they walk into a a conversation like that with a written plan, it's gonna 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. Yeah. Right. So, you know, if you're gonna 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. Uh and the people that walk into uncomfortable conversations actually uncomfortable. The good news is there is.

They probably have a really high potential to do it right. But 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 it 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 you uh I'm I'm gonna stop 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 are you do you mean something I I think it 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 I would say for people that have uh you know some reps underneath their belt and they're they're uh

Uh you know, they're not losing a full night of sleep before g you know, having an uncomfortable conversation. It's more of a guide. Yeah. Okay. Okay. Um They're not they're not just making it up on the fly. They've they've got something to follow.

But the but the plan does a good job of like 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 when you think about an uncomfortable conversation, like what are the the ingredients of a great one? Yeah. Like you gotta create a ton of clarity. That's that's one thing that people really get wrong. is uh they don't do a good job of like actually clarifying the problem, making it crystal clear.

Uh and then they they also honestly really uh struggle with the amount of time that they spend. So I like I do this by nature. I'm like a coach by nature, so I wanna sit down with somebody.

and, you know, give'em 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 yeah, if you're not careful, they're they're just backing 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 gotta have some good strategies to like overcome that. And the 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. It sounds to me like and I think my experience is is

What you're fighting against is all of those emotions and you you gotta be very concise, very targeted to get th those important words through to the person, right? You you're you're you're not just winging it. Right. Right. It's it's gotta be super intentional.

How do you start? How how do you get that conversation started? Well, and I I think actually starting is one of the most important points because people people get very awkward. It's it's awkward on the other person's part and it's awkward on your part. Like if If you put yourself in the other person's shoes, Um You know, they're they're they're getting like some ambiguous meeting called. They don't know what it's about. You know, they they might

Quick uh update or something. Quick connect. Yeah, quick. You know, it's called on their calendar or whatever and they're like, Oh, you know. And uh so they don't really know what it's about. Yeah. They're walking in with some nerves. You know, you've got some nerves too. And the biggest mistake that people make is they just start with small talk. They'll be like, you know, talk about the weather or like, hey, how's you know, how's the family doing? The deal is is like

I if you don't want someone to have that fight or 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 basic like the way that I start'em is somebody will sit down and now say

you know, let's call the person Bob, you know, I'll I'll 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 gonna lose their job today.

Right there, in one sentence, you've managed their expectations that it's gonna 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. Yep. You know. And there's ways if they go to the fight or 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 wanna make sure you hit is this idea of hurt versus harm. Yeah. Tal talk about that a little bit, because I think that's that's critical. Yeah, so I I think one of the reasons why leaders tend to avoid uncomfortable conversations is because they're afraid of like abusing their authority.

And so the the thing that I felt uh that I felt like really equipped me to do a better job at uncomfortable conversations is the 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 it it's it's not like a low dig. Okay. You're just talking about the behavior that you observed. Okay. Now that that's gonna hurt.

Like there's there's no good there's no version of like accountability and consequences that don't doesn't sting a little bit, right? Right. Um but if you focus on the behavior, at worst you're gonna hurt them. But if you go down the road of like talking about them as a person and who they are, uh, that's harm.

And the reality is is like once once you kind of I I call that the lightning rod 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 r at at best the relationship's 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, like they're at a nine of ten, you know, instead of a two of ten.

And they they just like almost kind of go for the jugular. They get into like identity stuff. Like, you know, you're not good enough at your job, you know, and I 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. Yeah. Yeah. I I remember early on in my career I had a CEO tell me, he said that he felt like he was asking me to be three inches shorter. He he he said that like the things I'm asking you to do, I don't feel like you're capable of doing.

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

You're right, I can't change my height. So you're you're telling me right off the bat the first time that I can't do it. Right. Like of course I'm just gonna check out if of course this is gonna end poorly. Yeah. So that that's harm. Yeah. Right. And so you wanna keep you wanna keep feedback focused on people's actual behavior. Okay.

Awesome. If there's 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. Uh almost every time they go poorly, it's the result of winging it. Okay. You know, it walking in with a written plan. you know, i is the best way to to show dignity to the other person. And if you can keep dignity high.

you're highly likely to have a a good uncomfortable conversation. Way better odds. Yeah, way better odds. Yeah. 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 of the resources Brendan 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, and people 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. 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.