EntreLeadership - The Right Way to Fire Someone

Episode Date: September 7, 2026

📝 Shape what comes next for the EntreLeadership show by participating in our 2026 audience study. After you complete the survey, you can enter for a chance to win a Standard ticket to EntreLeadership® Summit 2027.   The longer you avoid a performance problem, the harder it gets to fix.  In this episode, head coach John Felkins and Vice President of Entreleadership Jason Williams break down how to have tough conversations early, coach with clarity, and know when it’s time to let someone go.     Next Steps: ·      📖 Had the hard conversation and things still aren’t improving? Check out our guide to implementing a performance improvement plan. ·      🎥 Watch our video The 3 Mistakes People Make in Hard Conversations (and How to Avoid Them). ·      🎯 Not sure what to do next in your business? Let’s figure it out together. Book a free 30-minute consult call with the EntreLeadership Team. ·      📞 Have a question for the show? Call 844-944-1070 or send us a message. ·      📚 Order Dave’s most recent EntreLeadership book, Build a Business You Love. ·      📧 Get EntreLeadership’s free weekly newsletter: expert advice and practical tips from the same playbook we used to build Ramsey Solutions into a $300 million company. ·      🌎 Attend our world-class leadership conference, EntreLeadership Summit. ·      📝 Stop guessing. Get a plan built for your business and someone who holds you to it. Find out which coaching option is right for you. ·      📈 Bad hires. Strategies that never get off the ground. Sixty-hour workweeks. Sleepless nights. EntreLeadership Master Series is where you trade all of that for the exact systems our Executive Team used to scale to $300 million. Don’t wait until seats are sold out.   Connect With Our Sponsors: ·      Go to Belay Solutions or text ENTRE to 55123 for their free resource! ·       See if Christian Healthcare Ministries Groups are the right fit for your organization. ·      Visit NetSuite today to learn more.   Listen to More From Ramsey Network: 🎙️ The Ramsey Show 💸 The Ramsey Show Highlights 🧠 The Dr. John Delony Show 🍸 Smart Money Happy Hour 💰 George Kamel   Ramsey Solutions Privacy Policy Learn more about your ad choices. Visit megaphone.fm/adchoices

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Listen, this is a big deal. We want this show to be what you want it to be. So let us know. Firing someone is one of the hardest things you'll do as a leader, but it's also part of the job. And too many business owners don't have a clear plan or process for this. They avoid the hard conversations, let things slide, then one day they pull the trigger and fire the person out of nowhere.

That's not real leadership. And you do a real disservice to the person you're letting go. Because if they didn't see it coming, it means you didn't lead them well long before that moment. So today our head coach, John Falcons, is sitting down with VP of Entree leadership, Jason Williams, to talk about what should happen before you ever fire someone. And if you do have to let them go, that it's done with clarity, intentionality, and dignity for everyone involved. Let's get to it.

Well, Jason, thanks for being here. Thanks for having me. We have a topic today is not a super fun one. I know. Firing people and why folks get that wrong. Let's start right off the bat. People do this in such horrible ways. We've even got a video of a guy that fired hundreds of people on Zoom.

Watch this. This isn't news that you're gonna wanna hear. Ultimately, it was my decision and I wanted you to hear from me. It's been a really, really challenging decision to make. This is the second time in my career I'm doing this, and I do not want to do this. The last time I did it, I cried. This time, I hope to be stronger. But we are laying off about 15% of the company.

if you're on this call you are part of the unlucky group being laid off your employment here is terminated effective immediately can you believe that

it's unfortunate that I can believe it but yeah I mean that guy's an idiot I mean I'm sure he didn't think through all the things that he was supposed to be thinking through as the leader of an organization that size that's firing that many people. Yeah. That's such an impersonal, like, what a jerk.

Yeah. Like, just a jerk. Yeah. And you think, like, that's a corporate America kind of thing. But I have to confess, we've actually had somebody at our event. You know, I think Dave was talking about core values or something like that. I honestly don't remember the exact lesson, but I remember the exact line. And it was, hey, if you knew when you were hiring this person, what you know about them today,

why do you keep rehiring them? This dude gets all fired up at a break and he goes and fires his team member. I can't remember if it was just over the phone or it might have been over text. Yeah, I remember that story and that's just, that's also like, that's really tone-deaf

to this whole process that we're about to talk about. Yeah, you should never, ever surprise people. Why do you think people get this wrong so often? It's uncomfortable. It's uncomfortable for everybody. It's obviously uncomfortable with a person that is being fired. But it's also uncomfortable for the leader.

At least I'm been uncomfortable. I think if you're not uncomfortable during this situation, you're a little sadistic. And so I think when we get uncomfortable, we make really bad emotional decisions. We don't think through things. There's just unintended consequences that happen when we don't take the time to plan out what an exit from a firing or termination looks like. Is that kind of the big high-level plan to walk somebody through? Or are you talking about like this person and I are going to sit down and we're going to have this conversation?

I got to have a plan for this conversation. Or is it both? I think it's both. I think there's a couple different situations that we can talk about, which is, you know, there's kind of an abrupt firing. You know, somebody does something really wrong. Yeah. And you need to do something about it right away. Yeah.

Or there's the performance idea where you've walked with this person and it's not a surprise because you've had really clear conversations. This is what it takes to win here. You're not winning here. this is how I'm going to help you, and I really want you to win, but it's not working out. You said there's sometimes it's a quick thing. Like what falls in that category? When are you going to just go to somebody's office, you know, go to the office and be like, we got to deal with this today? I had a really hard conversation, a really hard situation where a team member on a previous team, not an entree, was, had violated integrity.

They were a salesperson, that salesperson had a number they had a hit for the month. And if they didn't hit that specific number, they weren't going to get a commission check. And so they actually fudged a purchase order from a customer. Knowing that the purchase was coming, but not in the time frame they needed. And they really wanted that commission check. And I get it. You know, you got bills to pay, but they fudged. And the customer called me and called our company and told us about this.

And that's obviously a huge lack of integrity that's stealing, essentially stealing from the company that they're doing business with, but stealing from our company. And so after a really quick conversation with the leadership team, I said, hey, it's time for this guy to go. And I drove to meet him. I called him the night before. He knew I'd add multiple conversations with him over that day, said, hey, this is what I got a phone call about, tell me about the situation. And I called him that night and said, where will you be tomorrow morning? And where, when will you start? And he's had a day that started early, about 6 o'clock in the morning. I'll be in this parking lot. And I said, okay.

great, I'll meet you there. And I drove from Chattanooga, Tennessee to Knoxville. And I met him in a parking lot. That seems a little sketchy. It is sketchy. I got out of my car. And the business that he was going to call on was closed. And so I got into his car and just had the conversation with him. Looking back on it, that wasn't really well planned by me. Because there's some danger in that. You're putting, you're in a very emotional situation. So I would say the times that firing happens fast, it's when there's a moral or an integrity issue. Okay. They violated a core value that is significant.

They've done something like stealing from your company or stealing from somebody that you do business with. Those are the types of reasons why you'd fire somebody right away. I know we were talking earlier about sometimes why leaders get this wrong is because they're avoiding the hard conversations. But let's hit some tree tops on other reasons why they get things wrong. Feels like it's easy to wait too long. Is that a thing?

And by the way, I know those are a curveball. experience that yourself. Like, have you put it off too long sometimes? I have. Putting, like, putting hard conversations off is, is my natural. I'm a person that likes to be liked. And so, you know, having this uncomfortable conversation when the problem is a two out of ten is the time you should be having it versus letting it fester and then it becomes a six or a seven out of ten. And then there's a lot of stuff you have to unwind. So the earlier that you can have conversation, whether it's about somebody's performance or someone's attitude, those are really, they're much easier to handle when you do it earlier. I know as a leader we have to have this, we have to kind of get ourselves

in the position where I can go have this uncomfortable conversation, but I promise you it'll be a lot less uncomfortable if you do it when it's a two out of ten versus a six or seven out of time. Yeah, yeah, because the stakes are just going up the whole time. It's going up. Yeah. And you're shortening your time frame because the rest of the organization is suffering when someone is misbehaving or someone's not producing. And so you feel a lot more pressure when you let it, let it go by too long. Yeah. Maybe Ramsey is a little bit. unique in this way, but we kind of have a unique perspective on the leader's participation in this process versus HR's participation in the process. Can you kind of unpack your experience

with that and why you think it's important to do it that way? Yeah, at Ramsey, the leaders do these uncomfortable conversations, including leading up to termination, and HR is there as a massive support. So that's the way Dave set us up from the beginning. Dave didn't want HR running our company. And so we really do everything possible as the leader to take the ownership of this. And I do that as well. And I empower my leadership team, which you're a part of, to do that is to have these uncomfortable conversations and use HR as a resource. You know, hey, I've never experienced this before. You know, can you help me walk through? Like, how should I be thinking about this? And that's what they, that's their main purpose here. And then when we get to a point where

we are about to terminate somebody, we will go and make sure, have we checked all the boxes? Is there anything else that we've been missing in this conversation? And we have a group of people that are there to help us. I know that, and maybe you referenced this earlier, we have a very clear process leading up to the point where somebody is going to get let go. You and I both have participated in that process and led people through.

And how big of a part of that process going well is clear expectations? Oh, I mean, unclear expectations are usually the root cause of the reason why we're at the situation we're at. You know, that like I as a leader have to set clear expectations for my people. And then I get to hold them accountable. And so when clear expectations are not set, that causes a lot of these uncomfortable conversations, causes a lot of performance issues, causes a lot of reasons for somebody to misbehave or not do the things that we're asking them to do.

It's weird to me, honestly, because in the times where I, had this conversation, these kinds of conversations, I kind of feel like I'm being clear. You know, I'm saying things. I'm walking away and I'm like, I communicated that. But it doesn't always land with the person the way that I want it to. How do you fight against that? Yeah, one of the things that I've learned, it's not something that I did have done naturally, but one of the things I've learned, and I encourage everybody to do this, is to ask the person to repeat to you what you just said. Hey, John, I'd like to talk to you about your performance. you're missing X, Y, and Z.

After you're done with that, say, what did you just hear in that? And I think that's a really good is having somebody reflect back, and then you can correct. You know, I also, in some of these uncomfortable conversations, I need to make the assumption that this person may not be actually intaking everything because there's emotions involved. And so you need to get them to a place where they can clearly articulate back to you what you're talking about. And then you can correct them. You know, oh, those are great. And you actually missed a little bit of here. Or actually, I didn't mean to be as, and it means you to take that as harsh as the way you said.

it. And then the other thing is following up with writing. Send a quick email after you have a conversation if you and I were having one of these conversations. Hypothetically. Hypothetically. Hypothetically. And then you were to repeat back to me what we talked about. I would just send a follow-up email and just say, hey, John, here's what we talked about. You know, I'll look forward to checking in at our next one-on-one, which is usually a week from now. And that's a, those are things that you want to create clarity. You want to clear expectations, make sure everybody's on the same page. We'll get right back to our episode. But first, as your business grows, and Everything gets more complex.

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Dot A.I. slash Ramsey. Now, let's get back to the episode. When you start to say some of this stuff and people start to get the sense like, oh, this conversation is going to affect my job, like my being here, all these emotions flood in. but when you ask that question that you just recommended, it brings the person back to the conversation.

It does. Like, tell me what you're hearing right now because I want to make sure we're on the same page. And that's really, when I think about it, you're really serving that person well by doing that, aren't you? Yes, by not doing that, you're setting them up to fail. One of the things that I learned really early at Ramsey

is that we don't set people up to fail. If someone is not producing the results, getting the outcomes that we want, have a bad attitude, whatever the situation is, we never want to set somebody up to fail. And not letting them understand and articulate. You know, we hear with two ears, but it takes a different thing in our brain to actually re-articulate what I just heard out of my mouth.

And so letting them have, what you just shared is that moment to be able to process the information, verbalize the information. That's super important. And it gives you a better chance to have a good outcome because that person actually is no longer in defensive mode. They're like, okay, this is what I have to do. They start to come into reality a little bit. And then you can start building a plan together.

We don't, especially in performance stuff, we don't have performance conversations without the hope that they're actually gonna make it. Yeah, that's what I wanted to talk about next, because I was thinking back to the guy that got the call from our client at the break, right? And he just gets let go, and he's totally blindsided by that and surprise.

And that is what we want to avoid. Talk a little more about the conversations leading up. Because if we're not gonna surprise the person, they have to have a same thing. that, oh, this isn't going well, and I might get fired, but also we've got to give them a path, right, to avoid that. How do you do that? Yeah, we use uncomfortable conversations here. I know you've had Brendan on the show, and he does such a great job of unpacking that. But in summary, as you continuously have conversations that ramp up in intensity and ramp up and focus,

at the beginning, I'm starting on the same side of the table as you. You know, today, we're going to go wrestle this problem. There's a problem with your performance. Let's just use the performance. You're you're not producing the work that we need you to produce for this reason, this reason, this reason. Tell me what I just said. You say it back. Say, I'm on the same side of your table. Like, this is a problem. Let's go attack this problem together. How can I help you? Like, I'm here to support you. My hope is the outcome is that this person will be able to turn around the performance, create the outcomes that help the business. And we all work together for a long, long time. The reality is that may not happen, but I always start helping that person. And then it,

if the person continues to not produce the outcomes, that's where we have more and more intense conversations where eventually I'm gonna have to move across the table from them and I'm gonna have a conversation like, hey, listen, John, we're just, you're just not getting it. I've tried to help you, what am I missing? What are the things that are causing you to not win in this area? And we use data and we use objective outcomes.

And eventually that may lead to John, I just have lost hope. And we put them on a performance proven plan and we really get really specific about it. Yeah. You know, I have felt like, I appreciate that. And I have felt like some, sometimes when I'm in that process with a team member, it's a, it's a lot. It takes a lot for me to show up in that meeting. I don't know, frankly, why it's so hard to understand what we're talking about. But I've always felt like at the end of the process, two things. One, I want to

serve that person as best I possibly can because I hired them or I, you know, I'm responsible that they got hired. So I want to serve them. Well, and the other thing is maybe this is a little selfish, but the truth is I want to be able to wake up the morning after they're let go. And no, I did everything I could to spell it out for that person. I mean, I can't agree with you more. I think these conversations are super draining. You get, you know, I wouldn't, you know, a lot of people will say there's HR guides and these things that say, wait till the very end of the day. You know, those types of things, I don't want to do that.

I've had a whole day. I've been wrestling and battling and meetings. and battling for good reasons, but like, we're going to battle here. You know, we're trying to change things in the world. We're trying to help people. And waiting to the end of the day, my energy is not going to be in the right place. My headspace is not going to be the right place. And then so I try to pull it earlier in the day.

But at the end of that meeting, when I have an uncomfortable conversation, especially when it's getting close to the end, I'm drained. Because it takes a lot of emotional energy for me to go to a place where I am not trying to be a people like, a person that's liked. Yeah. I'm trying to have a really good service-minded conversation with this person. And then you're right, the mentality of I don't want to have any regrets. I want to put my head on the pillow that night and say, I did everything I could to help this individual.

And for whatever reason, they have not been able to do what we've asked them to do. And a lot of these people are great people. It's not like, you know, most of the people that I've had to let go in my career, they're not bad people. There are people that I'd go have a drink with afterward. They probably wouldn't want to do that with me. But that's the situation. But they're good people. They just haven't been able to perform for the expectations.

that we need in that particular role. So putting my head on the pillow, I've done everything that can to serve that person, waking up the next day, okay, it's a new day, let's go with the team that I have today. Yeah, it kind of just making that a clean transaction and not having regrets, I think, is important. All right, so we've talked a lot about how not to do it

and what's hard about it, but let's go through the treetops of five things that really are the right way to do this, process and when do you know what's the trigger for you number one i want to attack something quickly when do you know it's time to to go active on hey i need to have a rough conversation as as their leader that should be having a regular meeting with this individual um you should start to see that as early in the process as possible yeah and if you're giving them specific coaching and that's what we expect at our leaders our leaders are coaches they're they're there to help a person become more than they have been in the past.

We try to help them understand that they are more capable of things. If they're not receiving that coaching or if the results aren't turning around, that's when we start to amp up the pressure. And I say we have that first uncomfortable conversation, which is, hey, I've been trying to coach you in this area. You've verbalized back to me what we're trying to do. You've said, hey, these are the things that I'm going to go try to accomplish. You're not accomplishing that.

I need to have a conversation about what is causing you to keep, keeping you from that. So number one, hit it early. I think you said earlier when it's a two out of ten. Yes. That's step number one. Step number two, expectations. What's important about expectations with people? Yeah, you have to be really clear.

And it goes back to having people reverbalize back to you what you've said. If they don't have a clear expectation, it's like playing darts blindfolded. That's not fair to the person. You want to make sure that that person has very clear understanding of what my expectation is, what the organization's expectations are so that they can go out and try to do the work to win. Step number three is coaching. Talk a little bit about our perspective around leaders, our coaches, and also the documentation that you're suggesting or that is even required.

Yeah, there's definitely some legal things that you need to make sure you document. You know, unfortunately, we're in a litigious world where, you know, team members are going to feel like they're mistreated. And my goal and our goal at Ramsey is to not mistreat anyone, to be really clear and to have these conversations early. A lot of times the problems happen when you don't start early. You go really close to the end of where you as a leader, you're done with it. And you're just like, get this person out of my site, get them out of my building.

And that's not a good thing either. But as a coach, we're coaching consistently across. And then those conversations are amping up and you're always documenting. Part of that documentation is me sending you a follow up and saying, hey, John, we had this conversation. Here's the expectations. I look forward to talking next time. But sometimes it goes to, hey, John, here's a performance improvement plan. we're going to lay it out and tell you exactly what the expectation is going forward,

and you have these many days in order to be able to turn that around. Yeah, so that's great because number four is the performance improvement plan. Talk a little bit again. When do you use the performance improvement plan? For performance, that's around, you know, we always say you have to have a KRA, and their KRA is a description of what winning looks like for their role. And that KRA can have a lot of numerical, objective outcomes that you're trying to drive. A performance improvement plan happens when that person is not, is falling short of one.

or more of those things. That really helps. And so you really walk out. Here's the thing that we need you to move. Here are the behaviors that we see that you're not displaying. And we want you to be moving in this direction. And I'm here to coach you and to help you. What resources do you need?

What extra help do you need? Do you need a different tool or something like that? And you give them those resources. You get the individual to commit to that plan. You know, sometimes it's as short as 30 days, but typically it's a 60 or 90 day plan. And at the end of that performance approval plan, you will, we always write, or I always recommended writing, you know, if you fail to, if I start to

lose hope that you can actually make this turn, then we'll have a different conversation, which will lead to your termination. So they need to know at that point that their job's on the line, that if we don't see this improvement, the end of this might result in you leaving. I'm rooting for you. I'm going to help you. I'm going to give you resources, but the end of the day, you may be looking for a new job because you can't turn this around. Yeah, we call that the emotional firing, right? Because you want the person to actually accept. experience the full weight of, oh, I'm at risk of losing my job. Like, that has to not just hit them in the head.

It's got to hit them in the heart so they understand what's on the line. If you do this right, when you get to the performance improvement plan, as a leader, I almost tell them, I don't know that you can make this. Yeah. I've tried to coach you. Why do you do that? Well, you say, I think it goes back to the emotional firing that you're talking about is I've been coaching you very consistently.

You've known these outcomes and it hasn't moved them to. direction and I will say I have lost some hope that you can do this I'm still rooting for you I still want you to win but I don't know that you're going to make it yeah and at that point you can as a as the owner or the leader you can make a decision like hey if you want to leave today you know here's something that we're going to do for you as an organization yeah severance potentially or some kind of a package or you can say hey if you want to fight through this I'm going to walk next to you and help you fight through this I do still have hope that you're going to turn it around because if I had zero hope then we wouldn't go to performance improvement we would just say

hey, today's your last day. Yeah. But that's the other thing is part of that emotional firing is you start to as the leader, start to tell them you're losing hope. I, as the leader, I'm losing hope that you can actually turn this around because we've been trying now for weeks, months, maybe even years. Right. When I have done that, I have liked doing it on a Friday and tell the person.

I really want you to go home this weekend and maybe even talk to your spouse about like what's going on because we don't want them surprised either. We can't control that. but, you know, I want them to have that conversation. And then I tell them, like, you got to come in Monday and either say, you know what, I want to go do something else or be that new person on Monday. Like you have the grace period is now over. Like you have to start to live up to this stuff.

Yeah. That's tough. It is tough. And that's a great point because we have staff meeting at 830 on Monday mornings. And so typically if we have this conversation on Friday, it might even be Friday. lunch, like I told you. It can be earlier in the day because my energy is better. I like it early and then a lot of times I'll tell them like, hey, go take the afternoon. Go connect with your spouse. Talk to a friend, you know, your parents, depending on the situation for the individual.

And then I say, hey, let's meet at 8 o'clock on Monday morning. You tell me what your decision is. Is your decision to be all in? Are we going to go attack this thing? Or is your decision to say, hey, I just don't think I can make the turn either. And that's okay. We're going to leave, we're going to leave in a better place if that's the case. Yeah. So that leads us to the fifth point the last thing, why is, I mean, everything that you just talked about, we've talked about this whole thing, why is clarity and dignity in that final conversation? Like, if you have to let the person go, why is that so important? They're a person. Yeah, they, uh, every person is created in God's image in my, in my worldview, my belief. And, uh, and that's what we believe here at

Ramsey. So treating that person as a person that is loved, they're loved by their family, they're loved. Many times they're loved by their teammates. And, um, and so, we want to really be clear with them with happening and we want to provide dignity for them. You know, you hear these stories of like someone getting a shouting match with their leader and them storming out of the office.

Well, you also hear sometimes the stories of like someone getting terminated and then them getting walked out of the building in front of their team. That is not treating people with dignity. So at least in our location, if we're going to have a conversation like this, we try to find a place away from their teammates so that they can have a chance to

to really process what's happening. And then a lot of times, you know, people here, we have death. So a lot of times our HR team will stay after. And if they choose to leave or if we choose to let them go, depending on where we are on the process, we'll ask, you know, do you want to come back after hours and collect your stuff? Because we don't want you to have to carry your box out in front of people.

That's like something from the office. Like, what is that? Yeah, we're not going to do the walk of shame. No, you know, and that's a thing. we want to make sure that that person understands that we regard them as a person that is loved and that we want to care for. Yeah. I know. I mean, as I sit here and I think about this

and as I've walked through it, there's a lot of moving parts. And so I'll say to y'all, if you want some help with this, you want more resources. We have a performance improvement plan guide. We'll leave a link down in the description, and you can click on that and have a map for doing this if you need to. Jason, thanks for joining us today. Thank you for having me. Some firing decisions are immediate.

They lie, they cheat, they steal, they violate a core value, they're done. But most of the time, you've got a responsibility as a leader to step in early, be honest about where someone stands, and give them a path to actually improve. When you have a clear process, you can make these decisions with confidence and integrity. And by the time you do have to let someone go, no one is surprised. So don't avoid the hard conversations. That's how you serve your team well, even in the toughest moments. And if you need some help having those kinds of conversations, we've got a video that'll

walk you through it. Just click here to watch that next. If you enjoyed this episode, be sure to like and subscribe for more great leadership and business content. I'm your host Dave Ramsey and this is Entree Leadership.