The Jefferson Fisher Podcast - 3 Steps to Say the Hard Thing

Episode Date: April 7, 2026

Join me on Supercast for ad-free episodes, bonus content, and monthly AMAs:⁠ https://jefferson.supercast.com/⁠ There’s a conversation you’ve been avoiding—and it’s already costing you more than you think. In this episode, I’m breaking down why not saying the hard thing is shaping your relationships in ways you don’t even realize. When you avoid the truth, you keep everyone stuck in a version of reality that isn’t real. I’ll walk you through a simple, practical way to have difficult conversations with clarity, confidence, and respect—without overexplaining or softening the message. Order The Next Conversation Workbook: https://www.jeffersonfisher.com/workbook Thank you to our sponsors: Cozy Earth. Upgrade Your Every Day. Get 20% off at cozyearth.com/jefferson or use code JEFFERSON at check out. Monarch Money. 50% off your first year at https://monarchmoney.com/jefferson Notion. Try Custom Agents now at https://notion.com/jefferson  BetterHelp. Click https://betterhelp.com/jeffersonfisher for a discount on your first month of therapy. Order my book, The Next Conversation, or listen to the full audiobook today. Like what you hear? Don’t forget to subscribe and leave a 5-star review! Suggest a topic or ask a question for me to answer on the show!  Want a FREE communication tip each week? Click here to join my newsletter.  Join My School of Communication Watch my podcast on YouTube  Follow me on Instagram  Follow me on TikTok Follow me on LinkedIn Learn more about your ad choices. Visit megaphone.fm/adchoices

There's somebody who's listening to this right now and needs to have a conversation that they've been avoiding. And I'm going to tell you, and the point of this episode is, if you're choosing not to have the conversation, then you're choosing the result that you're getting. There's not going to be some aha moment in this episode. What this episode is going to give you as a perspective and the courage to say the thing that you, that you've been avoiding, that angst, that thought that you want to say something, and all of a sudden it just makes your stomach churn. I have had difficult conversations like you so many times in my life. And the perspective that I'm going to give you is one that I use every day when I have to give hard advice. I need to give a hard truth to my legal clients. Or I need to say something

to a judge or to a jury. And there's a process in which you, you know, you know, you know, you know, which I go through in my mind that I want to share with you. So listening to this episode is going to give you the, I want to put some air in your balloon. I want to put some air in your lungs that's going to encourage you today. All that more coming up. Welcome to the Jefferson Fisher podcast where I'm on a mission to make your next conversation, the one that changes everything.

Wherever you're listening, it would mean a great deal to me that if you would press the button that says subscribe, press the button that says subscribe, or love you like or comment. What it does is tell wherever you're listening that this is good quality content. And that's my promise that wherever you're listening, if you listen to these episodes and subscribe, I'm going to make you a better communicator. Thank you very much. Before we keep going, I want to take a moment to tell you about Cozy Earth. Not only is Cozy Earth one of my favorite sponsors of this podcast. I'm also wearing their shoes, their house shoes, in particular, right at this very moment. That's how much I like Cozy Earth. Not only do I like

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And now let's keep going. It's a hard thing, knowing that you want to say something, and all of a sudden you feel it in your body, just something pressing against you that goes, I don't want to say that. I need to say something, but I can't. What are some categories of things that we often avoid? Maybe that's you right now listening.

One is boundaries. Say, hey, I'm not okay with how things are, and I need to put up a boundary, a wall. I need to draw a path here to do something else. Maybe it is something sensitive and hard, like hard news, something that's going to be sensitive to talk about because there's a lot of places where you can get burned if it doesn't go right.

The other is the truth. That to me is probably one of the hardest ones. The truth. It is absolutely true. the truth will set you free. And many times there are things that even listening, you think, man, if I shared that with somebody, they wouldn't, that would change everything.

That would change everything if I actually told somebody the truth. Let me give you what I have learned in my own life. By avoiding the conversation, you are changing the relationship. Let me say that differently. People think that the natural default is, oh well if I tell them this if I have the conversation I'm going to change the relationship it's it's backwards all right you avoiding it is changing the relationship because now you're

not allowing them to live in the reality of the relationship instead you're just allowing them to continue to exist in this alternate reality that you now have a truth a reality of what's really happening in your life that you're not choosing the share and here they are living in the alternate, the multiverse, because you can't get it out. You haven't gotten it out. And I know, trust me, I know that is way easier said than done. So if it is you with boundaries or hard things and change or something that you know, just even listening to me, you're feeling nauseous in your stomach because there's a truth that you need to get out, by avoiding the conversation, you are choosing to accept the result of it. And maybe you go, yeah, Jefferson,

That sounds great. I'm just going to continue to live in this. I'm okay with living in this result. If that's you, I'm going to push you a little bit, all right? I'm going to push you a little bit. In the same way, I'd want myself to be pushed, and that there is a finite amount of time that you're going to be on this earth like everybody else. and I would much rather you live in the truth in the reality of what is rather than living in the yeah it would have been nice ifs and so how do we start to compartmentalize us into some sections that are workable for you I want to give you my mindset when I go into a difficult conversation when I am about to have to deliver hard news to somebody or give them the truth I usually have the mindset of they want me to tell them this, even if it's hard. They're going to want me to tell

them this. But if I put myself in the position of on the opposite end of the chain, of knowing that hard news is about to come to me, I want to know it. I want to know it. Like when somebody goes, you want the good news or the bad news? What do we almost always say typically? Just give me the bad news first. I need that anxiety out of my life. What do I don't know? Ignorance is bliss. That all that mentality is I need to know the information that's going to affect my life. And so if I get in my head that I'm about to have a hard talk with the client, maybe it's that they don't have a case. Maybe it's that the case law, now that we've done some legal research,

it's not in their favor. They're probably going to lose the case. Or I need to give a percentage of, hey, if you want to move forward this, you have about a 69% shot of the court. And maybe if we go to an appellate court and we submit this and we argue this, then maybe so. But I have to give you the full spectrum of, what your truth is because how wrong would it be if I just said, no, this is a great case.

You're good. Everything's golden. And they get all the way up to the very end of trial. We've already gone everything. And they've lost it and say, why didn't you tell me? And go, yeah, you know what? I was going to tell you, but, you know, I didn't think you could handle it. There, right there. It's that I didn't think you could handle it. In reality, if I do some self-reflection in that, it's that I didn't, I couldn't handle it. it. I couldn't handle it. I couldn't take giving that piece of information that they needed to know. And so I take it on myself to feel their feelings for them. Listen to me. Stop feeling other people's feelings for them. That has to do with, I'm afraid I'm going to disappoint them. I'm afraid I'm

going to upset them. I'm afraid they're not going to like me as much. I'm afraid they're going to have some kind of negative feeling towards me. The answer is yes and. Yes, they will, and they get to choose what to do with that. Yes, they're going to be hurt, and they get to choose what they're going to do with that. Let them decide what to do with that information rather than you avoiding it for the hope that they're going to continue living in the multiverse. So if I am going to give somebody difficult information in my law practice, it is,

I'm going to give you the difficult news at the first. then you get to decide. You want to continue the case, not continue the case, you want to do this, you want to do that. You have agency. Before we continue, I want a quick word from Monarch. Tax season is one of the only times I actually stop and look at everything, what came in, what went out, and then I start to catch myself thinking, where did it all go? I don't want to just look back. I also want to make progress. That's why I use Monarch. It shows me where my money's gone and where something like a tax refund can actually make a real impact. Pay down debt, build savings, what actually moves the needle.

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the all-in-one tool that makes money management simple. Use code Jefferson at Monarch.com for half off your first year. That's 50% off at monarch.com code Jefferson. And now let's keep going. having a hard talk with somebody, trust and remember that they have the agency to choose what they want. Whether it's in a relationship, they get to choose. Do they want to stay in the relationship? Not stay in the relationship. They get to choose that. Rather than you not giving them the truth just for the sake of afraid they're going to leave. Or I want this kind of something to happen at the workplace or the job. And so I try to control the narrative in a way that's going to protect their feelings, so to speak. Rarely and ever in history has that gone well.

And it's probably not going to go well for you either. And I mean that. Whenever you try to couch things in a way that it's, I don't want to disappoint them, you're feeling their feelings for them, and you don't get to do that. That's not something you get to do. They get to do that. So your role in this is that you speak what you need to speak. What is the truth? What is the boundary, the change, the hard topic? You get to say that. That's your part in this dance. Their part is getting to decide what to do with that information rather than you trying to control it. You can't do both. Can't have your cake and eat it to.

So what's my mindset? Number one, when I go into these hard conversations of knowing I'm trusting them that they can do with this information, what they want to do with it, but I'm going to get it out. Because if you continue just to store up conversations in your head, you get to store up these things where you know you could be more honest and transparent, but you're not. It's just living in your head rent free. And that rent is going to come do no matter what. So I have this mentality in my mind of that I'm going to trust that they can handle what I'm going to tell them. And the truth is they can. They can. You're not going to like it and it's going to make you uncomfortable. But the truth is they can certainly handle it. And when you're choosing not to tell them, you're deciding for them that they can't handle it. And that's that's not your job. You can't do that. Number two, what I try to emphasize is the quicker I can get to the end of the line, meaning quicker I can get to the truth. rather than starting all with the context. You know what this is like when somebody's trying to tell you a story

about something and they go, okay, remember that time, that day, remember when I told you this and they start backwards. And what that does, when you start backwards, it injects anxiety into the conversation. Ever heard somebody start that slow roll backwards

and you're neatly thinking, okay, where are you going with this? What's happening here? Okay, what am I, are we breaking up? Are we something wrong? Did I do something wrong? And you're continually looking the whole time. What did I do?

What is happening? What is wrong? Because we always go to the default of the negative. Rather than allowing that anxiety to continue to breathe and to create panic and put more strain and stress on a conversation that's already going to be stressful for you, start with the end. You start with something that just can kick open the front door. so to speak. And so what I, phrases I like to use, rather than trying to sugarcoat, is something as simple as, I need to have a difficult conversation with you. You see how much

cleaner and more direct that is than me going, okay, hey, you remember that time, you know, and this is, okay, let me back up. You remember then, and I'm just losing them. But if I can start out with, this is going to be a difficult conversation. Hey, this is going to be hard for us to talk about. I need to tell you something that you're not going to like. I need to tell you something because it's the truth. You hear how as soon as I get that out front, it's like a snap. They're in it. They're engaged.

They now know this is the label I can put on this conversation and this is the room that I'm in. They don't have to worry about X, Y, and Z and things that are totally outside of it. Have you ever had somebody, you know, text you that we need to talk? And it's just immediately pitting your gut. and then they start talking later, and they mentioned something, and you're like, oh, that, oh, okay, like, that, oh, geez, okay, why didn't you say so?

Like, because the whole time, you've had that pit in your stomach. So when you can get to the beginning sooner, it's going to go better for you. How does that sound? That means I'm going to say, I need to tell you something that you're not going to like, this is not a case that I'm going to be able to continue to move forward. You see how I'm getting right to the point,

right after that. So I'm going to label the conversation. This is going to be hard for us to talk about. Pause. Give them a second to breathe. And most likely they're going to kind of nod and give eye contact with you. Deliver the line. Whatever it is. The boundary, the change, the sensitive topic, the truth, that's what you do. Then you can deliver the context, but don't do it right away. So you have to give time for things to breathe in difficult conversation. patients. Like you, if I were to take a bottle of soda and just shake it around and then try and open it, terrible things. But if you open it, allow it to breathe, allow things to settle, probably a bad example. But it emphasizes that point of there are certain phases of the roller coaster of a hard conversation.

And you have to give enough time to allow that to sit and to sit. settle and that does not mean that all of that is going to require you to talk. Silence is a great way of allowing things to breathe, especially in hard conversations. So if you label it, this is going to be a hard conversation. I need to let you go. Pause. You don't go, I need to let you go. Because, you know, all these things you've done and all these things, it's just a pause.

They're going to allow that to breathe. there might be shock, there might be anger. Whatever it is, they get to decide that. You don't try to curb that into what you want. That's going backwards. So once you have that in mind, I want you to let it breathe. Then give context, because most likely they're going to ask questions of why or how come or how does this start or what's my options.

What do we do now? There's always going to be a question that comes from that. That's where you are able to succinctly, clearly, give context, right? So that's, that's two. Putting a label on that and getting to the point way sooner. Before we keep going, I'm going to take a moment to tell you about Notion. You know what eats up more time than the actual work? All the little things around the work. It's the status updates, the task assigning, the quick questions that somehow never stay quick. That's what I've been using Notion and especially their new feature called Custom agents. Now, I can say personally,

I viewed Notion both in my law firm and media company for several years now, and I felt like I used Notion before anybody else had heard of Notion. Notion is an AI-powered, connected workspace for teams. Notion brings all your notes, documents, and projects into one space that just works. It's seamless, flexible, powerful, and actually fun to use, which I can attest to. With AI built right in, you spend less time switching between tools and apps and more time creating great work. And now with Notion's new custom agents, the busy work that seem to take hours, or really never happen at all, let's be honest, runs itself. One of my favorites is a status update agent.

Every week it scans what I've been working on, pulls all the key updates, and turns it into a clean report automatically. No chasing notes, no rewriting the same thing every week in trying to memorize it. It's just right there. Custom agents automate repetitive workflows right inside of Notion. And unlike most AI, they don't wait for you to prompt them. some way. Instead, they run on schedules and triggers like real teammates with specific jobs. So try custom agents now at notion.com slash Jefferson. That's all lowercase letters,

notion.com slash Jefferson to try custom agents today. And when you use our link, you're supporting our show, which is pretty cool. Notion.com slash Jefferson. All right, let's keep going. Three, this is my encouragement to you. And it's simply this. the very thing you're avoiding is the very thing that's going to reveal the actual reality of the conversation whatever you're avoiding is what's preventing the reality of the conversation

and I want you to be in a place where whatever the conversation is it needs to be something that you know is going to continue to move your life forward I know way too many people and I've spoken to a lot of people who are avoiding a conversation because they're afraid of what their life is going to look like afterwards.

And my word to you is this, I'd be much more afraid of what my life is going to look like if I don't have that conversation. So wherever you are in life, whatever the topic is, if it is somebody you're married to or in a relationship with, or if it is a son, a daughter, an uncle, a mom, somebody, a co-worker, a boss, a supervisor, whatever it is, be way more concerned with your life of not having that conversation than having it because when you are avoiding it, that's when you're actually changing the whole thing.

It's not the opposite. So what can we do? There's a conversation most likely if you're still listening to this that you're avoiding right now. And if that's you, I just need you to nod wherever you are. Just nod to yourself. And I want you to start formalizing in your head. It helps to write it down. What's the goal of the conversation? How can I get to the beginning as fast as I can't? How can I make sure there's enough time? How can I set time to allow the conversation to breathe for this? When Sierra and I need to have hard conversations, you know, sometimes we have to do it usually before the kids are awake or after

the kids are in bed. Usually we like to have them in the mornings because that's when we're kind of energizing ready to go, not exhausted and our batteries already, you know, at 2% emotionally and mentally. So making sure you have enough time to have these conversations is going to do you a whole lot of good, all right? I'm telling you, on the other side of the conversation is a world that's going to be much better for you. Don't feel other people's feelings for them. They have the agency to do that. Your job is to communicate. Their job is to understand. And if you don't have understanding, if you've only just said it, if you've only just talked to talk, that's not real communication. There are two parts to it. There is the speaking and there is the understanding. Just because you said it does not mean they understood it. So be very careful of thinking just because you said it out loud, it automatically results in communication. They need to understand it as well. So give enough time for that to happen. You with me? All right. I believe in you.

Go say the hard thing. All right, try that and follow me.