In this solo episode of the Jefferson Fisher Podcast, host Jefferson Fisher presents a practical, three‑step framework for handling difficult conversations and explains how to adapt the approach depending on whether the goal is to deliver bad news or discuss a sensitive topic. He begins by emphasizing that small talk belongs elsewhere; instead, he advises opening with gratitude for the other person’s time, then requesting their help (“I need your help”) to shift the dynamic from adversarial to collaborative, and finally closing by sharing one’s own feelings and inviting the counterpart to do the same. Fisher contrasts this collaborative script with a more direct style for pure bad‑news delivery, where speed and bluntness are recommended. He illustrates the framework with a concrete scenario about confronting a friend over a hurtful comment, and then answers a listener’s email about speaking to a supervisor who dismisses his ideas, applying the same steps. Throughout, he frames difficult conversations as opportunities for deeper relationships and personal growth, urging listeners to welcome rather than avoid them. The episode ends with a call to subscribe, follow the podcast, and join his communication newsletter.
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Today we're talking about how to have a difficult conversation. What is it about difficult conversations that, well, make them so difficult? And how can you make them a little easier in your life? Welcome to the Jefferson Fisher Podcast, where I'm on a mission to make your next conversation the one that changes everything. If you enjoy learning tools that improve your communication, I'm going to ask you to subscribe to this channel and please leave a review. If you have any topic suggestions, just throw them in the comments. When it's time for that difficult conversation, number 1, don't begin with, how are you? How are things? Difficult conversations are not the time for small talk. The only thing that should come out of your mouth is thank you for making the time to talk with me. Number 2, follow that up with, I need your help. I need your help knowing how to feel about this. I need your help knowing what to do about this. When you say I need your help. It takes it from opponents to teammates. And number 3, end with how you feel about the conversation. I feel better having talked with you. I feel more settled after discussing this. And the key is you then end it with, so how about you? When you say, how about you? You are getting them to connect with you to say, how do you feel about this conversation? Do you feel better about it? Or do we need to continue to talk? Now, when I get questions about how to have a difficult conversation, it typically revolves around having to deliver bad news, meaning there is something negative that you need to say to someone and you know they are not going to like it. You know, they're going to get upset. It's going to bother them. It's going to ruin the mood. It's going to ruin the atmosphere or possibly ruin the relationship. Or you see it with how to address a sensitive topic. Maybe it's something that's been laid heavy on your heart and you don't know how to start. Or something that's been bothering you and you know it's for the best that you talk to this other person about it and you just don't know where to begin. You remove the difficult from difficult conversations when you break it down into bite-sized pieces that are going to connect you to that other person. Now, typically in my life where I see difficult conversations is when I have to deliver bad news to a client. You know, not every case is perfect and not every client is a good client and not every case is a good case. The law applies to the facts. So sometimes you have to tell them, I'm sorry, but the law doesn't allow this or the law is against you on this case. So that just is part of normal life and how you handle that conversation, meaning not just what you say, but more importantly, how you say it. Can mean the difference between making what comes after the difficult conversation easier or just more difficult. Now, the strategy does change slightly depending on whether you need to deliver bad news or simply discuss a sensitive topic. When it comes to strictly bad news, the faster you get that bad news out, the better the conversation is going to go. For example, if you have to fire someone, The first thing out of your mouth should be, "I have bad news." Or you need to say something that's hard for them to hear, you tell them that. "This is going to be hard to hear. This is going to be a difficult conversation. This is not going to be fun for us to talk about." You give them a pause and then you deliver the bad news. In that moment, directness is also kindness. All right? And when it comes to sensitive topics, it's much easier to follow Steps 1, 2, and 3, where you're going to say, thank you for talking with me. I need your help. I feel better about this. So let's go through an everyday typical conversation where you need to say something that's hard for them to hear. So let's assume you need to have a difficult conversation with someone and let's make it about something they said, a comment they made at a dinner with friends last week. You've tried to let it go, but it's just not happening. And you know that you need to talk with them about it. If you're following rule number 1, what you're not going to do is begin with, "So how was work? How was work today?" when you know good and well that's not at all what you really care about. Because what's worse is when you make them talk about work and then you just drop the hammer and say, "Oh, that's nice. Listen, you remember what you said last week?" That's a safe way to set this up for failure. Instead, what you're going to do is set aside time and say, "Hey, when you have a moment, can we talk about something?" Next, you're going to go to rule number 2: I need your help. I need your help knowing how to feel about a comment you made at dinner last week. I've tried to let it go. I have dealt with it and, and just kind of simmered on it in my mind, and I need your help with it. Then have that conversation. Tell them what they said. Tell them how it made you feel. And that's the difficult part, is that you have to express your own thoughts, and nobody can do that for you. But what makes it easier is when you lead with, I need your help. People love to be helpful. They want to be helpful. Rather than coming in and making them defensive and going into attack mode, when you can say, I need your help, it doesn't feel like you're sitting on two separate sides of the table, right? It makes you feel like you've instead scooted up a chair beside you and said, let's sit together and look at this problem that's on the table in front of us and let's work through it together. And when you're able to have that conversation and say what you need to say and get it all out, or maybe you just need to hear their perspective of what they meant by their comment last week, it's going to make it better and bring you closer together because it's the difficult conversations that allow you the chance to dive deeper into your relationship and grow and build. And then after you've had that conversation, number 3, you're going to end with, I feel X. I feel better. I feel relieved. I feel more settled. I feel better knowing your perspective or where you are coming from in it. And then you ask, how about you? Or how are you feeling? What do you think? Get that connection just a little bit closer to wrap it up in a bow and say, hey, we just went through something that was a little difficult. We went through something that was not easy, and let's walk out of it hand in hand. Let's walk out of it together. Whatever it is, you have that meeting of the minds to say, I feel okay about this. You feel okay about this? Got it? Good. All right. I'm going to take a question from a follower. This one comes from an email. In case you didn't know, I have a weekly communication newsletter where I send out one communication tip right to your inbox, totally for free. And in response, you can ask questions like the one I'm about to answer. Right now. Put this here. Um, I have my other phone. This is the one that I typically use. This one comes from Derek in Oregon. Derek says, hey Jefferson, love your content. Thanks, Derek. I have a difficult conversation. I have to speak with— I'm not going to say his name— my supervisor, my manager, about an issue. I always feel like he puts down my ideas and does not take them seriously. I'm afraid that if I address this with him It's going to make me look bad. Derek, I got you. That makes a lot of sense, and I'm sorry that you're in that position. I wish that your supervisor made it a lot easier to have these kind of conversations. This is what I want you to do. Number 1, set aside time for this conversation. Don't just knock on his door and say, hey, do you have a few minutes? That's not the way to go. All right, Derek, I want you to set aside real time. That means ahead of time you say, Hey, later today or tomorrow or this week, can I set aside 30 minutes to talk with you about something? That's the way you do that. And then when it comes time to, you're gonna follow number 1 and say, thank you for setting aside the time to talk with me. Number 2, you're going to begin with, I need your help. I need your help with knowing how to feel about something. Or you can tweak it to say, I need your help and really your insight if you ever felt like this before, or if you came across this feeling before. Even if it has to do with them, they've been in that position before. Everybody has. Okay, everybody has, Derek. So you're going to say, I need your help, and they're going to kind of straighten up, say, all right, this person needs my help, or maybe they need my insight, and ask them, I have had issues with expressing my views in meetings or wherever it is, and I can't help but feel like my contribution is not wanted. I don't know how to feel about that. And then just go quiet. Don't keep rambling. Don't— if they ask for an example, go ahead and give it to them, but don't keep talking and over-explaining. Keep it short and put it in their side of— put on their side of the net. All right, once you have that discussion, then number 3, you end it with, I feel better about that, thank you. But you're— or ask them, how do you feel about it? Is there anything else that I can do? And you have that one-on-one, that heart-to-heart to say We've set aside time for this. I need your help with this. And maybe they will, hopefully, if they're serious and this is a place that you need to be and work and have a professional career in. And hopefully this manager is someone who's going to accept this conversation and understand that they can help you, help you, that they have felt this way in the past and they can offer a great way forward. And that's how to have that difficult conversation. The biggest thing is just don't be afraid to ask them in a way that sounds like you're learning. When you come at it from an angle of wanting to be a student rather than an expectation of they should behave this way and you should behave that way, just soften that and say, look, I'm trying to learn here. I need your help here. I have ideas that could benefit this company or benefit this team, and I don't feel like they're being appreciated. How can I be better about that? And then listen. When you stop trying to prove something and start trying to learn and listen instead, magical things can happen in your life. And so when you talk with that supervisor and you have that discussion with him and you end it with, great, I feel better about this. How do you feel about it? He says, oh, I feel good. I feel X, Y, and Z. If, if this person is serious and wants to be a good manager and this is where you need to be in your life. That's how I would handle that conversation, Derek, and I wish you all the best. One of the biggest things that I want you to keep in mind about difficult conversations is that they are a catalyst for more real in your life. Real, genuine, authentic things in your life. Here's what I mean. The deeper relationship you want to have with someone, the greater tolerance you have to have for difficult conversations. If you only want easy, if you only want surface-level conversations, I'll show you a surface-level relationship. Think about the times or the closest people that you have in your life. These are the ones who have been with you, that have rolled up their sleeves and been in it with you from day one or at critical moments in your life that were not easy. They've been with you through the hard, the difficult. They've had those hard conversations with you. So don't think that difficult conversations are something to dread. Often difficult conversations are the very thing that you need to succeed, the very thing that you need to go to the next step. Sometimes it is that difficult thing that you have to say that makes all the difference. You can change your life by that next sentence. You can change everything by the next conversation. The right sentence to the right person can change everything. So keep in mind that the difficult conversations are ones to welcome, not shy away from. If you want to support this podcast and improve your communication, I ask you to subscribe to this YouTube channel as well as follow the podcast on Spotify or Apple or wherever you listen to your podcasts. Thank you so much for listening to the Jefferson Fisher Podcast. And as always, You can try that. Follow me.
