EntreLeadership - The 5 Step Framework for Addressing Difficult Employees

Episode Date: March 2, 2026

Hard conversations aren’t optional—they’re part of the job. In this episode, you’ll learn how to handle the five types of difficult conversations leaders face with clarity and confidence—so you can lead decisively instead of tiptoeing around problems. Next Steps: 🎥 Watch our video The 3 Mistakes People Make in Hard Conversations (and How to Avoid Them): https://www.youtube.com/watch?v=UBsV1vHu7rY 📋 Get the framework for addressing your difficult employees: https://ter.li/ravdz3 📞 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

We've talked before about how to have hard conversations as a leader, but not every tough talk is the same. So today, we're breaking down the five types of hard conversations you'll face and how to approach each one with clarity and confidence. Because when you know which type of conversation to have and when, it helps you communicate the problem clearly. Keep your team on the same page and make those tough moments a lot more productive. Ramsey's chief technology officer, Brendan Wojko, joins Entree leadership's John Falcons to share some practical ways to handle these moments well. So you can lead your team forward instead of avoiding the tension. So, Brendan, we've talked a lot about how to have a difficult conversation. And we've got resources on that.

So if people want that, they can click the link in the show notes. But today we really want to get into the different types of difficult conversations. So could you help us unpack what those different types are? Yeah, yeah. Usually when people ask me about uncomfortable conversations, it's all about how to have them, like how to have a successful uncomfortable conversation. And the reality is that there's not just one.

What I found is there's five distinct kind of uncomfortable conversations. The first one is what we call first contact. The first time you actually address a problem with someone, right? And in that conversation, like, I mean, the biggest thing is just to make sure that you really clearly state the problem in a way that they understand what the problem is. Okay. You know, I always joke around and say, like, your articulation or the problem should be so clear, like your fourth grade, you know, English teacher should be proud of you. Right.

The reading level should be a low number, right? The reading level should be low, and the statement should be really short. Okay. And it should be about observed behavior. Like, John, I see that you've been showing up late to work, and that's not okay. Yeah, this is getting personal fast. Right. Yeah.

I mean, it's, you want to be really clear on the problem. The second part of it, you want to make sure that they're really clear about the problem. process you're going to walk out next. Okay. Because you're typically not having uncomfortable conversations the right way when you sit down with somebody and you kind of like swoop and poop. Like if you, if you swoop into the situation, you kind of drop a problem on their lap and then you're gone. That's not a productive uncomfortable conversation because the person, if they just become problem aware, it doesn't mean that they know what to do. It doesn't mean that they're going to get the coaching they need. It doesn't mean that the problem's actually going to get fixed.

All it means is you dropped a 10, 10 ton, you know, concrete block on them, which is you got a problem. And so in that first contact conversation, we want to make sure that we really clarify the problem. And we want to help them understand, like, what happens next. Okay. And usually in that conversation, I'll say to people, like, listen, we're going to walk through a series of, like, coaching conversations. Because it's great that in this conversation, this first contact conversation that we've made the problem clear. Yeah. But I'm actually going to separate the coaching to a different time.

And the reason for that is because, like, people just get into like an overload. You generally want to keep these conversations short because if you load in too much at one time, they're simply going to go to a fight or flight and they're not going to remember. Yeah, they're not hearing that stuff. So, you know, that first contact conversation is what's the problem? What are we going to do next? Then we walk into that second kind of uncomfortable conversation, which is coaching. And the whole point is we want to reiterate the problem, but we also want to give the person tools about how they can fix it.

The number one mistake that leaders make in coaching conversations is they make the conversations unnecessarily adversarial. Okay. Here's what I mean. It's really easy as a leader to kind of put yourself in the situation where it's like me versus you. Yeah. Like you've done something wrong and now you got to meet my expectations. Right. And that might actually be ultimately true. The reality is, like, you actually have to help the person understand, one, how people around them are experiencing them. Mm-hmm. Right? Because if I'm just saying how I'm experiencing you, it's almost immediately a me versus you thing. I'm just curious if you've ever seen this where the leader might do everything really well in

that setting to not set it up me versus you, but the person has got a lot of experiences where regardless of what the leader has done, that's how they're coming into it. Is that fair? Yeah, it's totally fair. Okay. So there's two things I do in this coaching conversation that are not obvious. The first thing is I actually want to go to other leaders and I want to, number one, check to make sure that they've all experienced that kind of same problem that I'm addressing and then get some of their feedback. Why do you do that? Well, Because really, it really melts down the me versus you. Now, now more of what it's about is, hey, this is me helping guide you through the resolution

of this problem. Okay. Right. And if you're working with somebody that reminds you of the kid that beat you up on the playground at school, all of a sudden, you know, like, again, this is getting very personal. Yeah. But yeah, it is good for that reason to kind of get that collective wisdom from a group of people, right?

You get that. And I bring that into the uncomfortable conversation. I'll say, like, hey, there's a behavior that I'm seeing, but hey, it's just, it's not just me. It's a couple of us that are seeing this. And by the way, when I say a coaching conversation, there's not typically one of them. Okay. Like you have to coach somebody through the behavior that's a problem. Right. And so I can't tell you exactly whether you should have three coaching conversations with somebody or 33. Like it's it's a little dependent on the circumstances, severity of the thing. Yeah. And their receptivity. Right. They're receptivity. But I will say like if I had to

pick between three and 30, it'd be a whole lot closer to three. Right. I don't want to be a having like unending, you know, coaching conversations with somebody. But the other thing in the coaching conversation that's really critically important, you got to really tell them where you stand. And so I use this thing called the table metaphor. What I would actually say to the person is, John, you and I are on the same side of the table and this problem that you're having is on the other side. And my role is to coach you in such a way where we can get rid of that problem and we can go back to the way that we all want things, which is things are just flowing and going normally. Right. But I'm going to ask you to do two things. I need you to share my urgency and apply my coaching.

But if at any point we kind of get off track with you either not sharing my urgency or applying my coaching, I'm going to be forced to re-evaluate where I am at the table. Gotcha. And I don't want to go to the other side of the table, but I think we both know that if I go to the other side of the table, what that means and we both don't want that. Again, the coaching conversation is I like to bring in the feedback of other leaders. have that table, put that table metaphor in place so that the person that you're talking to actually understands, like, I'm actually working for you against this problem, unless your receptivity or your action really drops, and then I'm going to have to get on the other side of the team. Right. So you're having this coaching conversation, right? That's the second type of conversation. Yeah. And you said, they got to share the urgency and they got to apply the coaching.

What happens if they don't do that? Yeah, because sometimes that happens. Hopefully you clean the situation up and no big deal. But if you got to, escalate it farther. The next thing is something called an emotional firing. Okay, talk about that. Which sounds like super intense. Yeah. Right. It's actually just giving the person the last opportunity to turn the situation around before their job's actually on the line. Okay. And so, you know, somebody will come in. They'll think that like, okay, we're going for our fifth or third, you know, coaching conversation. I got to reset their expectations. They're just bouncing along. Like this is status quo. Right. And so, you know, I'll say to the

person like, hey, listen, I feel like you're, you're either not sharing my urgency or not applying my coaching. And I, I just need you to understand, like, the heat on this situation is turning up. Yeah. You know, and usually in that first contact conversation, I will have also put some timing around this situation. Right. So let's say we set the expectation like, hey, this behavior needs to change in 30 days. Well, hey, you know, John, we're at, we're at day 25. We've had like three coaching conversations. We had an initial conversation. We're working things through. I feel like you're not sharing my urgency, you're not playing my coaching. Right.

I just need to let you know that we're now in a situation where I'm moving to the, like I'm considering moving to the other side of the table. Right. And like your job might actually be on the line. Okay. Right. And so there are some choices that we need to make. Now let me just say, you say those words, those alarm bells are going to go off in a person's head, right?

And isn't that what you're trying to do? I mean, not manipulatively, but you want them to understand how serious this is. like this is a last-ditch effort to save this situation. And they should feel that, right? And they should feel it. Now, I will say that if you start to see somebody space out and you can tell, right, they'll start to get a little disassociated or they'll start getting emotional. By the way, if somebody cries, that's fine.

Like, people are allowed to cry. People are allowed to have emotions. Right. The thing that you've got to help them with in the moment is, if the emotion gets to the point where they can no longer hear you, then you've got to kind of like step into that situation in the moment and get them back to a place. where they can hear you. So the trick for that is if you start to see somebody's like emotions get to the point where they can't hear you, the key phrase is remind them of their need for dignity. Okay. So if they start to get overwhelmed, the thing that I found is if I just say to him,

like, hey John, I know this is a serious conversation. I know it can be scary. Yeah. And listen, emotions are totally okay. Yeah. But when you and I both look back at this conversation a year from now, what I know is both you and I want to remember it as a dignified moment. Yeah. And there's something that when you say that to somebody, it allows them just kind of collect themselves and kind of snap right back into things. Like 99 out of 100 times, that little phrase works. And if it doesn't, then you've got to give the conversation maybe a little space.

Yeah. But usually it works. And so what you're really trying to help the person understand this emotional firing is like, this is a last ditch effort to kind of fix this situation. And so you're going to give them two options. Okay. You know, you're going to say, you need to make a choice between continuing to try to save your job or call an uncle, right? Calling it quits.

I don't blame you either one that you want to pick. Right. Right. But listen, if you decide that you want to try to save your job, I need you to understand we're moving out of the kind of the realm of coaching. Right. And we're going to write some things down on paper. We're going to give you a written plan. 30, 60, 90 day plan, whatever is right for the situation.

you know, let's say a 30 in this situation. I'm going to give you a 30-day written performance plan. And here's what I need you to hear. It is a zero wiggle room plan. You've got to do this. Zero wiggle room. It's a do or don't. There is no gray area.

There is no kind of. Right. And I got to be honest with you. We've been having three or four of these coaching conversations. And I really think that if this change was going to happen, it would have happened already. Yeah. By virtue of the fact that we're having this level of a conversation, I really think you should strongly consider option B, which is tapping out, right?

But I'm going to respect whatever decision you made. Yeah. Right. And at this point, I'll ask the person to, like, actually go home. I want them to get out of the office. I'll tell them, listen, find some people in your life you trust, talk to your spouse, talk to a friend, talk to a pastor, whatever you need to do. Share with them the situation and, like, kind of co-author that decision with somebody that you trust, right?

And tomorrow morning we're going to sit down first thing, and I want to hear what your choice is. Stick with it or tap out. Gotcha. Conversation over. Okay. We get back again in the morning. They're going to pick their path. Okay.

Right. So they come back. They say, I want to fight for my job. What do you need to be prepared with at that point? Right. So I've already got that performance plan written down. We're going to talk about it. But before we actually walk through the plan, I want to remind them, like, look, I respect

the decision that you made that you want to try to save your job. I need you to understand that based on our prior history, I have a very low confidence that this is actually going to work out. That sounds negative, Brandon. Like, why do you have to say that to them? Well, because all I'm doing is just telling them what I've already experienced. Okay. You don't ever want to walk into a termination conversation and people are like, what?

Okay. You know, and like this is the moment. Like, that's why we call it an emotional firing. Yeah, yeah. It's intense. Yeah. You know, like, but I want them to know where things stand. So even when they make the choice,

of the performance plan, I'm going to reiterate it. Great, I'm prepared. I respect your decision. I've showed up with the plan, but I just want to reiterate. I don't think that we're going to be able to successfully do this, but I'm willing to walk it out. Then we're actually going to walk through the plan.

The important thing, the thing that you've got to say, zero wiggle room. This is not a negotiation, is it? Because the number of times that somebody will get through a plan and they'll be like, well, I did most of it.

Sorry, dude. Like, this is a scenario, the scenario that you've put yourself in is an all or nothing situation, not the scenario I put you in. Yeah, yeah. By the way, other important tip for performance plans.

If you pick 30 days, a performance plan doesn't have to last 30 days. Like if they're not sharing your urgency and they're not applying your coaching, they're not doing what's on the written plan, we're done. We're done. 12 days in, eight days in, two days in. Doesn't matter, we can be done. Yeah, right? It's not waste time. And you typically want to put that in writing in the plan. Okay.

Right? The performance plan can be cut short in any time. Okay. So let's just pretend that we've, okay, we've gone through this whole. thing, this 30-day performance plan, it hasn't worked out. I don't know whether we're ending this at day 12 or day 30, whatever it is, but no matter when we end it, it's going to end the same way, right? So we sit down and here's the thing, because we've done all of this work, we've done the first contact, we've done the coaching, we've done the emotional firing, we've done the performance

improvement plan. There is a ton, a metric ton of clarity for this person about what is wrong and what their performance is. We've gotten the feedback of other leaders. We've been very clear about where we stand with the table metaphor, all this stuff. On one hand, to me, that creates a ton of clarity for the person. But as a leader, that's a really good insurance policy. At the end of the day, I know I've done everything I could to help this person. You can go home with confidence that you tried everything you could and you can actually sleep when you go home tonight.

Because there's nothing worse than a scenario where you feel like there's something else that could have been done. You don't want to live with that weight as a leader. And you want to serve people well ultimately. But when it actually comes down to a term, Here's the thing you got to know. Because of all that context, because of all the setup, because of all the time investment we put into things, a termination does not need to be long.

You would be stunned how short it can actually be. Because what else is there left to say, really, right? And say, John, we have had six or seven conversations up to this point. I feel like I've been articulating a very specific problem to you for the last 30 days. And I've given you plenty of opportunity and plenty of clarity around what needs to do. what needs to change in order for you to continue to be with the company. But the decision has been made that today's going to be your last day.

What everybody needs to hear is that phrase, the decision has been made is the one sentence that must be included in a termination conversation. Okay. One, because it helps bring finality to the person. But you would be stunned how many people walk through a termination and don't actually realize they've been terminated. Okay. It's because leaders get real shifty and they get nervous and they don't feel, they feel like it's an undignified thing to say you're fired.

Yeah. Which it is kind of an undignified thing. Right. That's why I say the decision's been made that today's your last day. Like I said, it's important because it gives clarity. But the other thing is there is a certain percentage of personalities that will immediately begin negotiating. Yeah. They'll say, well, can I have a different job?

Yeah. Or can I have a different set of responsibilities or whatever? And at that point, all you have to do is just repeat the decision's been made. Today's going to be your last day. Yeah. It's over. Yeah. And so really a termination conversation, honestly, if it's gone much longer than three minutes, it's too long. Okay. Now, I'll also say in a termination conversation, I'll usually have a buddy with me. I call him the wingman.

Right. And so I'll deliver the hard news. And then I'll usually exit the conversation because at this point, I'm kind of the bad guy. right and I'll leave the room and then I'll let my wingman kind of deal with the details okay like hey I need your your key fog or I need the the you know the keys to the truck yeah the logistics the logistics of it you know hey I want to let you know that your access to company email's been terminated talk to you about medical insurance you know like if there's any severance involved like talk through all those details yeah that's really for the wingman okay um and you do that immediately right after the termination or? I think that's really up to you in terms of the culture that you want to create inside

your company. I will tell you the way that we do it here is the wingman basically says like, hey, there's conversations we need to have about insurance and severance and what a separation between our two companies look like. We're going to schedule a follow-up phone call and an opportunity for you to come visit. Okay. And so, you know, it's just like how you want to do it. Right.

But the point is is keep it dignified. And the last point there that's really important is you don't want to put people through the walk of shame after they've been terminated. Okay. And so oftentimes I'll have some, I'll say to a person, you know, before I get up and leave, I'll say, is there anything important at your desk that you need before we walk together out to the parking lot? Okay. Right. Yeah. And I'll typically send somebody else to get keys or a purse or something.

And I'll let them know, we're going to schedule a time before after business hours where you can come clean out your desk and not everybody's going to be staring at you. and we'll do this the right. Really still protecting their dignity. Yeah. Because, I mean, it's unfortunate that it ended this way, but we do want to protect them and their dignity. I love it. So that's it.

All five. That's a lot, Brandon. It's a lot. But I appreciate that. It's super valuable. And I do realize, just like we're saying, it's a lot. So if you want the resources to help you go through this, make sure you click the link in the show notes.

Listen, having these conversations isn't easy, but it's where real leadership growth happens. And now you've got a strategy to start approaching these conversations the right way. Big thanks to Brendan and John for walking us through it. If you enjoyed today's episode, be sure to like, share, and subscribe for more great leadership content. I'm your host, Dave Ramsey, and this is Andre Leadership.