About To Have A Difficult Conversation? DO NOT Do This!

In this interview‑style segment, Jefferson Fisher shares practical communication tactics for handling tough conversations, whether in the workplace, personal relationships, or dating. He warns against the “compliment sandwich” and advises leading with the hard message, explicitly labeling the interaction as a difficult conversation so the listener can brace themselves. Fisher emphasizes transparent phrasing—especially in text—by asking “Did you mean…?” to surface unspoken expectations and avoid misinterpretation, while also detaching personalization to keep feedback objective. He promotes a learning mindset, urging people to approach dialogue with the goal of learning rather than proving a point. The conversation also touches on subtle conversational power moves, such as the “Well, maybe so” response, which encourages the other party to elaborate and defuse tension. Throughout, Fisher’s tone is conversational and advisory, offering concrete language examples and framing the advice as universally applicable across personal and professional contexts.
Chapters
Let's say that you're about to have a really difficult conversation. What are some of the things you absolutely should not do that most people do when they're going to have one?
Begin with the fluff. This compliment sandwich, what do they call that?
Yeah.
It's a— the compliment sandwich is a little hard to chew and almost impossible to swallow. It's this idea of when you give the Hey, look, we've really enjoyed your time here. We think you're just— I think you're such an awesome person and you're so great, Cody. So listen, and then they deliver the bad news. Well, that just means whatever they said before wasn't true. They said the word "but," meaning everything that came out of it didn't mean anything. It's like saying, I love you, but that's got to go. Like everything— it doesn't matter what they said before. It's always the end. And so what you do is you leave them to kind of just twist in the wind, and it's not nearly as genuine. So instead, what you have to do is lead with the difficult. Trust me, it will make it easier. It only gets harder if you start with the easy and gradually progress to the bad news. When somebody says something like, this is gonna be hard to hear, versus me saying, hey, Cody, Listen, you know how it's been really hard here lately? And, you know, we've looked at this economy, you know, and the economy, like, whatever it is, you're just— you keep on going. Versus me saying, Cody, this is going to be hard to hear. Cody, this is going to be hard for us to talk about. This isn't going to be fun. You're not going to like this. Or just as simple as, this is going to be a difficult conversation. All of a sudden, Cody's going to ready herself and go, Okay, it's kind of this, all right, lay it on me. Everybody you could possibly say that to has that same power. When you try and babyfoot it around and start with the icing, you're being disingenuous. And what you're saying is, you're not emotionally resilient enough to handle it. I'm too afraid to disappoint you because I want you to still like me. But in truth, The kinder thing is to say, I'm telling you this way because I like you. Or even if you prime the conversation of, Cody, I'm telling you this because you can take it. I'm telling you this bad news because I like you and I have to give it to you. Then you give the bad news. That's going to be a whole lot better to start your difficult conversation every single time, whether it's a sensitive conversation, whether it's you need to fire somebody, whether it's you need to talk about a difficult subject, you label that conversation to let them know rather than them having to try and figure it out of like what's— they're waiting for that hammer to drop.
Yeah, you know what else is fascinating is every time you do that, you want to nod back. Like if you say, Cody, this is going to be a difficult conversation, my initial reaction is like, okay, yep, yes, it will be. Like it feels like truth. You've already got me having confirmation verbally or physically. So it's interesting.
And you always think the worst.
Yeah.
If I were to say, Cody, I got bad news, you're going to think somebody died, or you might be thinking you're getting fired, or you might be thinking what— you're going to think the very bottom of it. And if it is the bottom, then you expected it.
Yeah.
And if it's not, most of the time it's not as bad as you think. You go, oh, okay. Oh, that's it? Okay, I can handle that. Like, it's this reverse psychology of you, uh, I can handle that. That's not nearly as bad as I thought it was going to be.
Jefferson, you talk the most about interpersonal relationships and not maybe as much about relationships.
Yeah.
But if there's a young man or woman out there wanting to have better conversations with the opposite sex, what is the most applicable advice you have for communications from all the things that you talk about?
Well, that's not easy.
I know.
For when it comes to real relationships that you're wanting to build, one is transparency. Like, the number one killer is the assumed or unspoken expectations. Let's put it in everyday life. Most of the time we text, right? That's how we communicate. When you read into somebody's text and the voice that you hear it in, and you expect it to be ugly or not nice, and it's a fine, oh, okay. Oh yeah, fine. All right. Good night. Like it's one of those as simple as, oh, okay, I guess they hate me. As soon as you get to that point in your life or any time in that conversation, you are already setting yourself up for failure in communication in the long run. You have to voice what those expectations are. So even if you were to, let's say, text that, if you can quickly text back, did you mean for that to be short, or did you mean for that to sound upset? And they go, no, no, no, I was just in the middle of X, Y, and Z. Or, well, I just didn't like that you said this. Oh, okay, and let's address it. It's— this goes back to this fear of wanting to say the, the hard thing instead. Just complaining about it and then later calling them a narcissist.
Yeah, exactly. It doesn't work out well, but it's all over the internet, right? So what's better, to say, did you mean, Jefferson, to say, to sound upset, or did you mean, Jefferson, to be short, or to say, I took it as short? Like, no, it should always be on them.
That— did you mean for that?
For that.
I'm not saying you.
Yeah, so don't put their name in there.
Don't, don't personalize it.
Good one.
Detach it. Detach the personalization so that way it's not feeling like it's a you.
And you don't want to take it on yourself because that sounds a little too— I don't know what to say. I feel like you are being short. That would not sound as smooth.
That wouldn't be dismissive. That might be too much. There's nothing wrong with that. I mean, that's perfectly fine. But the did you mean is giving them the grace of the fact that they did not.
Without internalizing it.
And so it's not even you. It doesn't get to the point of me feeling like that. It's just simply, uh, hey, I'm giving you a quick mirror here. Did you mean for that to sound upset? Did you mean for that to sound rude? Or between me and my wife, it's, did you mean for that to sound short? Because we're on the go and we're doing things, and sometimes it's like, okay, well, I guess she's mad. Uh, but it's— no, it's just I'm dropping off the kids, or I'm running this errand, I'm on the phone with a client, I'm texting you while I'm on the phone. And so a lot of the times it's just the did you mean, because most of the time they did not mean.
It's wild though how those few words change so much.
They change everything, yeah.
I know, so you really gotta pay attention. You gotta read the book, you gotta read it twice. It's an incredible book. I think you've already sold hundreds of thousands of copies. You have people over the world learning how to communicate with a little bit more kindness on both sides. And it's not manipulative, I really love. We're not in the era of some guys that are, you know, that I knew historically who taught about seduction and communication. This seems to be in a very wholesome way. Might be your Beaumont roots.
That's probably— you're probably right.
You think so?
Probably right. Well, thank you, Cody.
Um, if you had to leave people with one thought, like your favorite part of the book that you want them to take with them today, what would it be?
Have something to learn, not something to prove. Whenever you're in a conversation with a friend, with a spouse, significant other, anytime at work, living room to boardroom, have something to learn, not something to prove. When you set out to prove them wrong, you will most likely get less in return. But when you set out to ask the question internally of where is this coming from? What do I have to learn here? Your conversation is always going to go a lot better, and you're going to have better communication and a better relationship, and that means a better life.
So good. I actually always watch out for the guys with the slow Southern drawls because the people who have done the best deals against me, who have just beat me up more than anything, have been smooth-talking Texans.
You got to watch out for that.
You got to watch out. I remember—
they're up to no good.
They're up to no good. Well, they're also— they always— one of my favorite guys in the world, he's an incredible dealmaker. I won't say his name 'cause he'll get embarrassed, but he's got a real slow Southern drawl and he'll always say, well, you know, for a kid from, I won't say, I'm just a guy from Texas and I don't really understand that. Could you explain it to me? And then I'll explain it to him and then he'll proceed to just shred me.
That's how you know he knows.
That's the giveaway.
That's the dead giveaway that he already understands it.
I'm just kind of slow. Can you explain that to me again? I'm like, oh fuck, here he comes.
My favorite is to use is maybe so. Like somebody says something, no matter if it's an idea or it could be something mean or condescending, or typically it's some kind of idea. I'll go, well, maybe so. Like that right there to me is my favorite power move to do because there's nothing you can do with it. And what happens is the other person will actually start talking and like saying my point for me in many ways. But yeah, you just kind of slowly go, well, Maybe so.
It's also the well. That's a good dear friend of mine, Joe from Kentucky. That's what he does. He goes, well, yeah, he just kind of leaves it.
Well, it's a great attitude to have.
It really is.
It goes back to just being in the pocket of, no, I'm not really going to be upset about this. Well, maybe, maybe it is, maybe it isn't. I don't know.
We all need to be a little more Southern.
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