EntreLeadership - A Master Class on Handling Hard Conversations

Episode Date: July 22, 2026

🎯 Figure out your business's next steps in a free consult call with an EntreLeadership® team member: https://ter.li/cjk4u0   When emotions run high, most leaders react. The best leaders get curious.  In this episode, Jefferson Fisher and Dr. John Delony reveal how to slow down, ask better questions, and navigate difficult conversations without damaging trust or relationships.   Next Steps: ·  Help us make the show better. Take this quick survey. 👉 ⁠⁠https://ter.li/og0jwycp⁠⁠ ·      📋 Get the framework for handling difficult conversations. ·      📞 Have a question for the show? Call 844-944-1070 or send us a message. ·      ✉️ Become a better leader in six minutes a week. Get tactical tips sent to your inbox every Friday. ·      📌 Don’t wing it. Get a coach that helps you lead and grow with confidence.  ·      🏢 Attend EntreLeadership Summit. ·      🎤 Attend EntreLeadership Master Series. ·      📖 Order Dave’s book Build a Business You Love.   Connect With Our Sponsors: ·      Go to Belay Solutions or text ENTRE to 55123 for their free resource! ·      Go to Christian Healthcare Ministries and use code ENTRE for a 50% credit toward your first month of membership. ·      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

If you're leading people, you're going to have hard conversations. There's no getting around that. But you can't treat every conversation the same way. Sometimes a person needs coaching, and sometimes they need support, and sometimes they need a kick in the pants. The real challenge is figuring out what's actually going on beneath the surface so you can lead well in the moment. So today, Entree Leadership's head coach, John Falcons,

is sitting down with communication expert Jefferson Fisher. and relationship expert, Dr. John Deloney, to talk about how good leaders handle hard conversations. Let's get to it. Well, Jefferson, thanks for being here today. Thank you for having me. And Deloney, it's always nice to have you stop by. And also with you.

So, Jefferson, you spend a lot of time helping people have effective conversations and communicate effectively. Right. And Deloney, you're helping people with healthy relationships. Is that a fair way to say it? Is that good? If that works. I've watched some of your show, so I was struggling how to describe you.

You've called in like five or six times. That's true, that's true. So effective communication and healthy relationships, two big pressure points for leaders. And that's our audience. These are small business owners, people leading teams. One of the things that we hear in our coaching program is people, a lot of times, are walking into conversations, and they're not exactly sure what they're dealing with. Right.

And some of those conversations, they need to give the person, the conversation and a kick in the pants, but sometimes that's not what they need. Right. And so I'm just imagining through your show and through your work as an attorney, you've got to kind of decipher what you're walking into and what you're dealing with and where to take the conversation. So I'm curious, how do you do this? First of all, is that valid?

And if so, how do you do that? How do you determine what kind of conversation you need to have? Well, it's going to depend on the context, but largely, I always like to take the position of not taking it, taking it. it personally, right? Whenever you're taking something personally, you're picking up what nobody's asked you to carry. So people who are confident leaders, what I like to say is they, good leaders respond to conversation, great leaders leave room for it. So often it is leaving enough space to have the conversation. Rather than coming in pushing your own timeline, you're kind of having to

assess of what's happening. And you really do that by making sure that however they're feeling, they know that they can bring it up to you. So how do you say do they need to kick in the pants or do I need to ask the question of what's happening? I would always lean in favor of not the kick in the pants yet because most likely there's something going on much deeper behind the scenes because the issue that you're having is generally not the issue that's actually happening.

Not the one on the surface. You got it. Yeah. What do you think? When you're talking to folks on your show or in any conversation because I know you've led big teams all. Also, Delaney. I'm thinking of, and I don't know the coach's name or the athlete's name, but I'm thinking

about the most recent March Madness. And it was in the women's division. And there was an exchange between a coach and a player that went viral, where the coach was in the player's face. And from afar, it looks like coaches destroying this person. But when the commentators were reading her lips and decoding what she was saying, she was very strongly saying things like, I believe. believe in you and this, I can't want this more than you.

And during the interviews, they talked about, we have built a relationship so deep, I know exactly what she needs when she needs it. And the coach, I mean, the player, I love it. She was like, she's coaching me exactly as I've asked her to coach me. And so, because people are getting mad at her, how dare you yell at your player or whatever. And the player was like, that's exactly what I needed.

But all of that, took, that exchange was built over years of grinding out a relationship together. And so I think a good leader knows their team. And here, Dave knows he can have a quiet conversation with me. That's all I need. And I'm with Jefferson. Almost every time I've had a kick in the pants conversation, that was about me as a leader trying to flex.

Then it was about solving a problem. Okay, so that sounds good. And I don't disagree with y'all, but let's think of some different scenarios. But I'm gonna push a little harder because let's think of some different scenarios. We've got our sales team here. Salesperson comes into your office,

and you realize, oh, they just need training. They don't know what they're supposed to do. How do you have that conversation with them? Well, they say that the kindness thing you can do is be as direct as you can be. So there is an alignment there of, you can have all the respect and kindness you can possibly offer and be direct and also be assertive.

So if that salesperson's coming into your office, I want you to begin with, I'm telling you this because. I'm telling you this because. Because you're giving them the headline of what the conversation's gonna be about rather than making them having to guess on the outset. And truth is, if they already know

that they're not meeting their metrics or whatever it is, there's no surprise. So maybe you put a label at the beginning of the conversation, saying this is a conversation that I know is no surprise to you. This is a conversation I'm not looking forward to having, but I need to have it. And so it's this element of,

we're gonna do something hard, but we're gonna do it together. And at the end of it, we get to choose and decide what action steps are we going to have in place because I'm for you. If you act from, I'm against you and this and you need to meet me, they're going to do that resentfully. What does it mean to be for somebody when they're not doing well? Yeah, so let's put it in, let's use that same framework I just said. Okay. If you sit down and you know I could be upset with you, I could choose to, like John said, I could have the ego and flex and have everything about my own.

on pride. Or I could say, look, I'm telling you this because I believe in you and I believe that there are a lot of people that can be in this position and I want it to be you. And so even if you let's, or you could even go a little bit higher and take it as remove the personal from it. The sales role is a role that demands X, Y, and Z. And the expectations are X, Y, and Z. And the person who's going to fill that role is somebody who needs to show X, Y, and Z. and I hope that person's you. So far, it hasn't met where we need it to be. And if we don't change it,

then we're going to have to fill that with somebody else. But you see how I'm saying, I want that to be you. That's how you're forced for somebody. That's how you're forced somebody. So I get it now. Thank you for going further. So what if you start into this conversation, Deloney,

and you realize, oh, something massive is going on with this person? You know, maybe it just, maybe in this scenario, it just wasn't clear that they were, you know, maybe mailing it in a little bit. But maybe you go into the conversation and you realize, oh, they just found out that, you know, their mom has cancer. Or their spouse just told them last night that they don't, they're not sure they want to stay married anymore. Like that, to me, as a leader, that feels a little bit different than this conversation, right? What have you done and what have you seen work well in that kind of scenario? I think the challenge for leaders, especially nowadays, everybody's been talking about mental health and emotional health

and what's going on outside of the workplace for the last decade now. A lot of leaders try to be like off-the-clock therapists, and they try to take care of their employees and make sure they're warm and cuddly, which I like that sentiment, but what that does to the rest of your sales staff, they know, oh, you get special treatment, or we have different sets of numbers.

Right. And so I think it's important to remember, like, you've got to separate the work outcome I need from the personal experience. And if there's a context-specific thing, if this person's crushing it forever, and then you've seen them just fall off a cliff, man, that can be a life-saving intervention there. I'm going to give you two weeks off. I'm going to pay, like we do here, I'm going to cover 10 counseling sessions for you. But what you're doing is you're handing it to them saying, I'm going to give you some tools. It might be space. It might be resources, whatever.

but it's your job to take care of your life outside here. I can't solve that for you. When you're here, here's the demands of this job that I hired you for. And those can be really uncomfortable things. And sometimes if you've got the bandwidth, if you're a small business, I can't afford for somebody whose wife is about to leave them to take six months off. I don't have that many personnel, right? And so I might have to have a hard conversation about, I'm for you, I support you,

I've got to have somebody selling this or this business goes under. At a place like this where you have a thousand people, you can call your sales team together and say, we're all going to pick up some slack because so-and-so's wife has cancer and he's going to be gone until she's better. And depending on skill, you can do some of those things. But you can't divorce

what's going on somebody's life from the job I hired you to do. There's a context, but it's not an excuse to not do the work. Yeah, I love what you're saying, though, about not having two sets of numbers because one of the things we talk about that just destroys unity

is what we call sanctioned incompetence. So if the team doesn't, know that this thing is going on, they're just looking at you going like, you're a leader that's letting this person skate. Right. Right. You're just sanctioning them mailing it in. And so an important conversation for a leader to have is when you come up with a hey,

here's what we're going to do together, then you help, they help inform what you tell the team. We've come up with this agreement. I'm not going to go out there and spill your dirty laundry out there, but I've got to let the team know that you and I are working together on this. What are you comfortable with me telling them? And if they say nothing, they can't know anything, then we're going to have to have a different conversation.

But if they say, tell them I'm struggling, my wife's sick, I'm okay with that, then we're going to go have that conversation. Right. But you're going to give, I want the employee to help participate in the story we're going to tell the team too, because everybody kind of needs to know if I'm asking him to pick up extra slack. So I know working in the legal trade. Legal trade.

That's the nicest way I've ever heard of course. positive interpretation. My brother is a corporate attorney, so I feel like that gives me license to make all the lawyers jokes. Any lawyer joke possible. That's right. You have free license. We'll get right back to our episode,

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comaI slash Ramsey. That's NetSuite.aI slash Ramsey. Now, let's get back to the episode. Not everybody's telling the truth all the time. Yeah. And I get that it probably sounds like I'm just harping on the negative stuff. But I want to talk about both sides of the equation because both sides of the equation are reality for a lot of people leading a small business.

And we hear through coaching, like this person did this or this person did that, what do you do maybe even in the courtroom to try and determine if somebody's sheep, shooting you straight. Well, in the courtroom, you know if somebody's lying, because you have the receipts, you have the evidence. You generally know. Is that the whole thing about you never ask a question you don't know the answer to? That's somewhat partially good advice.

Sometimes you do want to ask that question. But let's say I do have the evidence and you have the receipts or you have the numbers to know that that person is not telling you the truth. So what I do is rather than pulling it out and saying, show me, here's what I have, you're a liar, okay, I'm going to give them a chance to reveal their integrity because then that's a whole separate issue. So I know if they're going to be just trying to make themselves a little good or they're actually lying. So what I like to do is, one, I slow the conversation down. Yeah, how do you know that? You just said, I know if they're going to do this or that. How do you

know? Well, because generally, I'm going to know, one, I already have the facts of what the actual facts are. Okay. So first is establish your baseline of facts. Number two, how do you know just generally if somebody's lying to you, generally, you're not going to know just from looking at their face, right? You're going to have to have some kind of baseline of information. I thought maybe you could do some lawyer tricks and just like be able to tell if they're lying. Well, a lot of times you are able to know if you ask a very easy question. Like were you, you know, did you go to the store the other day? And you're like, did I go to the store?

Like I don't, what store? Like this very blanket easy questions. Right. Hey, something's off here. Yeah. We all have this kind of sixth sense of whether or not somebody's being honest with us in that. Now, let's say you do have the metrics and the numbers. So what I like to do is I'm going to slow that conversation down.

I'm going to slow it down because somebody who's lying to you wants you to take their lie, hook, line, and sinker. They like the quick agreement. But if you were to tell me a lie, and I said, give it five to seven seconds of, huh, you know, that's really. they don't like sitting in it, okay? And if you ask them to say it again, usually a lie can't be repeated like the truth can. A lie is going to be turned just a little bit. Maybe they're going to blame somebody else.

Maybe they're going to try and dismiss or distract you somewhere else. But the biggest thing is you just don't move from it. So don't chase the lie and start trying to point it. They know exactly where they're trying to take you. Okay. So slow it down. Slow it down.

Yeah, ask them to repeat it. and if you need to pull out the receipts. Then what do you do? What do you do when you, whether you pull the receipts out? You let them go. Yeah, yeah, you let them go. You have to have a policy of,

these are the values of where we work and our business, and part of this value is having open, transparent, honest, and if I can't trust you, right? Like what Delaney was saying a minute ago between the coach and the player, there has to be a baseline of trust here. And if I, that's broken, you know, in husband and wife, marriage context, that has to be long time to repair. In the business context, you generally don't have that. It's on to the next person.

So, Deloni, I'm thinking this stuff a lot of times, it happens in real time. Sometimes it just happens unannounced. You just walk into it and you're like, what am I dealing with? Where have you seen leaders over the years get this wrong most often? Anytime you feel emotional or you feel something's under threat, whether it's your ego, whether it's your business, whatever, you don't make good decisions. The greatest example I had of this, I resigned from a position and took another job. I went out there and I realized I'd made a huge mistake.

I came back and begged for my job back. And the guy who I was talking to was a friend of mine, but he's also my supervisor at the time, and he's become a great mentor. Our conversation went over three days. I came back and we sat, we talked for a couple hours, and he said, you've put me in a really awkward position,

and I'm going to need to think about it tonight. I came back the next day, and he was ready to tell me that day, you can't come back. We talked for another hour, and he said, I'm about to make a rush decision. Let me come back tomorrow.

I came back tomorrow, and he said, I'm going to take a chance on you. He said, you bailed on me. But what he showed me in real time was, what's important here is not my ego. What's important here is not winning. What's important here is getting this decision right for our future team, and I need some time.

And he kept slowing the thing down. And it didn't get in a one loss or an exchange, or I've got to be right, or I'm the boss here. You let, it was none of that stuff. And so I think slowing down, and when I feel emotional, I'm going to stop the conversation. Let's come back in an hour, or let's pick this back up tomorrow,

go make an appointment, and we're going to come back tomorrow with this. Because the odds of making a good decision when your emotions get up. It's almost zero. It just plummet. It becomes one loss, right? Yeah. Where have you seen this,

go wrong, go poorly with folks. Well, most of the time, it's when you think that you've had it all figured out. Like, you know why. It's because they don't care. It's because they're lazy. And you're telling yourself, really, it's a self-fulfilling prophecy.

Nobody cares as much as I do. Nobody, I can only trust myself, so I'll just do it myself. When it's the conversation you're avoiding is the result that you're choosing. So if you don't choose to have the hard conversation, then you're choosing not to grow with them.

And if you think that they're lazy, well, then you're going to see everything that they do and say is lazy, rather than asking that layer underneath. Because, yeah, as soon as you make it about you, you've lost in a big way. Can I ask you a marriage conflict question that might apply here? Yeah. We're going to hijack your interview for a second.

That's great. So whenever couples... Yeah, we don't need you. Whenever couples are going at it, one thing I'll suggest they do is say what happened, and then the next sentence is, the story I'm making up about this is. Correct.

And then I'm going to respond with the story I'm making up makes me feel this way. And what I've done is I've owned it and I'm not coming at you with accusations. You didn't pick up the towels last night because you're always lazy and you don't care about this house. Yeah.

It is, hey, their towels were left out last night. The story I'm making up is it was more important for you to go watch the show than it was to do this. Does that work in a business? If I sit down and I say, you haven't hit your numbers, the story I'm making up is this is not a priority for you.

And I'm given the employee an opportunity to say, yeah, I've got all this other stuff going on, or my wife's got cancer, or I'm not good at sales. But it gives them another, I don't know if that works in a business context. I think it definitely does, because it's that whole element of what,

the story I'm telling myself is X. Then the next question of what I know to be true is, why, you know, what is also true. And so once we go to this, what I know is they're still showing up, They're here doing this. They're here doing this. And how am I, what are they called, painting by numbers?

Am I just doing this to paint my own picture? But I think that's absolutely applicable in the business context. Yeah, I would distill down what you both are saying is you have to start with curiosity. Yeah, yeah. Because if you don't start with curiosity, you're starting with your own story, which might be completely wrong. Yeah. And just to re-hyjack the interview, you and I both know, vast majority of businesses, there's family involved.

Yes. And whether they're working in the office or not working in the office, the couple is in the business. That's right. It starts their home. Yeah. So I'm actually glad that you hijacked that, ask that question. And it is a huge pain point for people because you both,

you have to deal with yourself and then you have a team of people. So there's a lot going on in this space. So I appreciate both y'all being here. and invest in the time to have the conversation. Thanks for having. And if this is something that you want to help with, we've got a download that you can get in the description in a link below for how to handle uncomfortable conversations.

And before I forget, you're coming to Summit and speaking at Summit again. That's right. I'm excited. That's awesome. We're going to run it back. Yeah, run it back. I think last time you were the highest ranked speaker. Is that right?

That's awesome. Yeah, it is awesome. And, Deloni, you're going to be there too. I'll be there too. Yeah, you'll be there too. So we appreciate that also. I wasn't the highest-ringed speaker. Jefferson beat me.

And I'm still in therapy about it. Thank you, gentlemen. Thanks for having us. Great leaders know how to challenge people, support people, and hold people accountable without losing their cool or assuming the worst. The key is to slow down long enough to understand what's really going on,

not just react to the behavior in front of you. If you enjoyed this conversation and want to hear more from Jefferson and Deloney, they'll both be at our next Entree Leadership Summit, May 23rd through the 26th, 2027 in San Diego, California. Go ahead and save your spot by clicking the link in the description. You don't want to miss this. If you enjoyed this episode, be sure to like and subscribe for more real world leadership content.

I'm your host Dave Ramsey, and this is Entree Leadership.