A Master Class on Handling Hard Conversations

Summary

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EntreLeadership Podcast Summary

Episode: "A Master Class on Handling Hard Conversations"

Release Date: July 22, 2026
Host: Dave Ramsey (Ramsey Network)
Guests:

• John Felkins (EntreeLeadership Head Coach)
• Jefferson Fisher (Communication Expert, Attorney)
• Dr. John DeLoney (Relationship Expert)

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Episode Overview

This episode focuses on the nuanced art of leading difficult conversations within small businesses. Dave Ramsey and head coach John Felkins are joined by communication expert Jefferson Fisher and relationship expert Dr. John DeLoney. Together, they unpack leadership strategies, the necessity of discerning context, and striking the right balance between challenge and support in tough discussions. The conversation deeply explores real-world, actionable frameworks for fostering honesty, accountability, and growth among teams.

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Key Discussion Points and Insights

1. Understanding the Nature of Hard Conversations

• Every Leader Faces Them:
  • "If you're leading people, you're going to have hard conversations. There's no getting around that." (Ramsey, 00:06)
• Not Every Situation Requires the Same Approach:
  • Leaders must distinguish if a person needs coaching, support, or a more direct confrontation.

2. Assessing the Real Issue

• Get Beneath the Surface:
  • “The issue that you’re having is generally not the issue that’s actually happening.” (Jefferson Fisher, 02:48)
• Avoid Taking Things Personally:
  • "Whenever you're taking something personally, you're picking up what nobody's asked you to carry." (Fisher, 01:57)
• Respond, Don’t React:
  • "Good leaders respond to conversation. Great leaders leave room for it." (Fisher, 01:57)

3. Relationship is Key to Effective Communication

• Trust is Built Over Time:
  • DeLoney shares a viral coaching moment from women’s March Madness as an example of relationships dictating how hard a leader can “push” a team member. (03:02)
  • “That exchange was built over years of grinding out a relationship together.” (DeLoney, 03:20)
• Tailoring the Conversation:
  • Strong relationships enable leaders to know exactly how to deliver feedback.

4. Directness with Kindness

• Clarity is Kindness:
  • “The kindest thing you can do is be as direct as you can be.” (Fisher, 04:45)
• Set the Conversation Context:
  • Lead with “I’m telling you this because…” to remove guessing and uncertainty.
  • “Maybe you put a label at the beginning of the conversation…” (Fisher, 04:56)
• Be for Your Team, Even in Correction:
  • "I'm telling you this because I believe in you ... I want it to be you in this role." (Fisher, 05:47)

5. Balancing Compassion and Accountability

• Navigating Personal Crises:
  • Leaders have to differentiate between ongoing poor performance and performance dips due to personal crisis.
  • “You can’t divorce what’s going on in somebody’s life from the job I hired you to do ... but it’s not an excuse to not do the work.” (DeLoney, 08:36)
• Consistency is Crucial:
  • Avoid “sanctioned incompetence”—don’t let personal crises lead to different performance standards if the rest of the team doesn't understand the context. (09:08)
  • “One of the things we talk about that just destroys unity is what we call sanctioned incompetence.” (Felkins, 09:08)

6. Truth and Integrity in Tough Situations

• Detecting Dishonesty:
  • Have your “receipts” (evidence) before a confrontation.
  • “Rather than pulling it out and saying, ‘show me, here’s what I have, you’re a liar’ … give them a chance to reveal their integrity.” (Fisher, 12:22)
  • Use silence and slowing down to invite honesty: “Somebody who's lying to you wants you to take their lie hook, line, and sinker ... if you give it five to seven seconds of 'huh,' ... they don't like sitting in it." (Fisher, 13:47)
• Zero Tolerance for Dishonesty:
  • "If I can’t trust you ... in the business context, you generally don’t have that [long repair time]. It's on to the next person." (Fisher, 14:44)

7. The Power of Slowing Down and Emotional Self-Regulation

• When Not to Make Decisions:
  • "Anytime you feel emotional or you feel something's under threat ... you don't make good decisions." (DeLoney, 15:33)
  • Share of a personal story where a leader took three days to make a decision, modeling patience and composure. (15:33-16:54)
• Pause to Ensure Clarity
  • Suggest calling a timeout when emotions run high: "When I feel emotional, I must stop the conversation." (DeLoney, 16:54)

8. Start with Curiosity, Not Assumptions

• The ‘Story I’m Making Up’ Technique:
  • “Hey, you haven’t hit your numbers. The story I’m making up is this is not a priority for you.” (DeLoney, 18:37)
  • Fisher notes this is effective in business, not just marriage, when combined with an evaluation of what you actually know to be true. (18:46)
• Question Your Narrative:
  • “Am I just doing this to paint my own picture?” (Fisher, 18:56)
• Curiosity First:
  • "If you don't start with curiosity, you're starting with your own story, which might be completely wrong." (Felkins, 19:15)

9. Family Dynamics and Business

• Most Small Businesses Are Family Businesses:
  • Recognize implicit roles and overlap; relational skills learned at home directly apply to business. (18:56-19:41)

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Notable Quotes & Memorable Moments

• “Whenever you’re taking something personally, you’re picking up what nobody’s asked you to carry.” — Jefferson Fisher (01:57)
• “Good leaders respond to conversation. Great leaders leave room for it.” — Jefferson Fisher (01:57)
• “[Kicking someone’s pants] was about me as a leader trying to flex than it was about solving a problem.” — Dr. John DeLoney (03:31)
• “The kindest thing you can do is be as direct as you can be.” — Jefferson Fisher (04:45)
• “I’m telling you this because I believe in you and I want it to be you in this role…” — Jefferson Fisher (05:47)
• “You can’t divorce what’s going on in somebody’s life from the job I hired you to do ... but it’s not an excuse to not do the work.” — Dr. John DeLoney (08:36)
• “Sanctioned incompetence … destroys unity.” — John Felkins (09:08)
• “Rather than ... ‘here’s what I have, you’re a liar,’ … give them a chance to reveal their integrity.” — Jefferson Fisher (12:22)
• “Anytime you feel emotional or ... something’s under threat … you don’t make good decisions.” — Dr. John DeLoney (15:33)
• “The conversation you’re avoiding is the result you’re choosing.” — Jefferson Fisher (17:05)
• “If you don’t start with curiosity, you’re starting with your own story, which might be completely wrong.” — John Felkins (19:15)

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Important Timestamps

• 00:06 — Introduction: The inevitability and challenge of hard conversations in leadership.
• 01:57 — Fisher: On depersonalizing conversations and the “leave room” principle.
• 03:02 — DeLoney: March Madness coaching relationship anecdote, building trust.
• 04:45 — Fisher: The power of direct, kind, and honest conversations.
• 05:47 — Fisher: How to be “for” someone when giving corrective feedback.
• 07:27 — DeLoney: Handling team member crises; balancing compassion and business needs.
• 09:08 — Felkins: The concept of “sanctioned incompetence” and its risks.
• 12:22 — Fisher: Techniques for navigating dishonesty and promoting integrity.
• 15:33 — DeLoney: Story about patience, ego, and making wise decisions under stress.
• 18:37 — DeLoney & Fisher: Applying “the story I’m making up is…” technique in the workplace.
• 19:15 — Felkins: The primacy of curiosity in effective leadership conversations.

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Episode Tone and Style

Conversational, honest, and actionable. The hosts and guests combine humor, self-awareness, and empathy with practical leadership wisdom. They model a commitment to growth, candor, and unity—emphasizing that the hardest conversations, if handled with skill and care, are the foundation for the strongest teams.

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For Further Learning

The episode closes by directing listeners to a complimentary download for handling uncomfortable conversations and announces that both Jefferson Fisher and Dr. John DeLoney will be featured at the upcoming EntreeLeadership Summit in 2027.

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Summary prepared for those seeking actionable insights without listening to the full episode.

Transcript

[A]

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 Felkins 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.

[B]

Well, Jefferson, thanks for being here today.

[C]

Thank you for having me.

[B]

And Deloney, it's always nice to have

[D]

you stop by and also with you.

[B]

So, Jefferson, you spend a lot of time helping people have effective conversations and communicate effectively.

[C]

Right.

[B]

And Deloney, you're helping people with healthy relationships. Is that a fair way to say it? Is that good?

[D]

If that works.

[B]

I've watched some of your shows, so I was struggling how to describe it.

[D]

You've called in like five or six times.

[B]

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.

[C]

Right.

[B]

And some of those conversations, they need to give the person in the conversation a kick in the pants. But sometimes that's not what they need.

[C]

Right.

[B]

And so I'm just imagining through your show and through your work as an attorney, you gotta kinda 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 that? 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?

[C]

Well, it's going to depend on the context, but largely I always like to take the position of not taking 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 good leaders respond to conversation. Great leaders leave room for it. So often it is leaving enough space to have the conversation. And 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 a 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 than behind the scenes. Because the issue that you're having is generally not the issue that's actually happening,

[B]

not the one on the surface.

[C]

You got it?

[B]

Yeah. What do you think when you're talking to folks on your show or in any conversation? Cause I know you've led big teams.

[D]

Also, Deloney, 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. And 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 in you, and I can't want this more than you. And off. Like, 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. 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. 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 than it was about solving a problem.

[B]

Okay, so that sounds good.

[A]

Yeah.

[B]

And I don't disagree with y', all, but let's think of some different scenarios. Yeah, 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. They need training. They don't know what they're supposed to do. How do you have that conversation with.

[C]

Well, they say that the kindest 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 going to do something hard, but we're going to 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 in this and you need to meet me, they're going to do that resentfully.

[B]

What does it mean to be for somebody when they're not doing well?

[C]

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 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 gonna have to fill that with somebody else. But you see how I'm saying I want that to be you. That's how you be forced for somebody.

[B]

That's how you force 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.

[A]

Right.

[B]

What have you done and what have you seen work well in that, that kind of scenario?

[D]

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, 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 is 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 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, 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, 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 gotta 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 in 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.

[B]

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. You're just sanctioning them, mailing it in.

[D]

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 gonna go out there and spill your dirty laundry out there. But I've gotta 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 gonna have to have a different conversation because. But if they say, tell them I'm struggling, my wife's sick, I'm okay with that. Then we're gonna go have that conversation. Right, but you're gonna give. I want the employee to help participate in the story. We're gonna tell the team, too. Cause everybody kind of needs to know if I'm asking them to pick up extra slack.

[B]

So I know working in the legal trade.

[C]

The legal trade, that's the nicest way I've ever heard of.

[D]

Positive interpretation.

[B]

Yeah.

[A]

Yeah.

[B]

My brother is a corporate attorney, so I feel like that gives me license to make all the lawyers.

[C]

Any lawyer joke possible.

[D]

That's right.

[C]

You have free license.

[A]

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[B]

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 shooting you straight?

[C]

Well, in the courtroom, you know, if somebody's lying because you have the receipts, you have the evidence. You generally know.

[B]

Is that the whole thing about you never ask a question you don't know

[C]

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 look good or they're actually lying. So what I like to do is one, I slow the conversation down.

[A]

Yeah.

[B]

How do you know that? You just said, I know if they're going to do this or that. How do you know?

[C]

Well, because generally I'm going to know. One, I already have the facts of what the actual facts are.

[B]

Okay.

[C]

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.

[B]

You can do some lawyer tricks and just like, be able to tell if they're lying.

[C]

Well, a lot of times you are able to know if you ask a very easy question, like, were you. 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 question to go. Hey, something's. Something's off here. 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.

[A]

Yeah.

[C]

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.

[B]

Okay, so slow it down.

[C]

Slow it down. Yeah. Ask them to repeat it. And if you need to pull out

[B]

the receipts, then what do you do? What do you do when you, whether you pull the receipts out?

[C]

You let them go. That's what you. Yeah, yeah, you let them go. Like, you have to have a tolerance. You have to have a policy of. These are the values of where we work in our business. And part of this value is having open, transparent, honest communication. 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 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.

[B]

So, Deloney, 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?

[D]

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. 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. But 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. 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 gonna 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 gotta be right or I'm the boss here. It was none of that stuff. And so I think slowing down and when I feel emotional, I must 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.

[B]

Because the odds of making a good decision when your emotions get up is almost zero.

[D]

It just becomes one loss, right? Yeah.

[B]

Where have you seen this go wrong? Go, go poorly with folks?

[C]

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. It's nobody cares as much as I do, 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 gonna see everything that they do and say is lazy rather than asking that layer underneath because yeah, as soon as you make it about

[D]

you,

[C]

you've lost in a big way.

[D]

Can I ask you a marriage conflict question that might apply here?

[C]

Yeah.

[D]

We're gonna hijack your interview For a second.

[B]

Yes.

[D]

Let's do it. So whenever couples.

[C]

Yeah, we don't need you.

[D]

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 were. Because you're always lazy. You don't care about this house. It is. Hey, the 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, hey, you haven't hit your numbers. The story I'm making up is, this is not a priority for you. And I'm giving 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.

[C]

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 Y. 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 do they call painting by numbers? Am I just doing this to paint my own picture? But I think that's absolutely applicable in the business context.

[B]

Yeah. I would distill down what you both are saying is you have to start with curiosity, because if you don't start with curiosity, you're starting with your own story, which might be completely wrong. And just to re. Hijack the interview, you and I both know, vast majority of businesses, there's family involved.

[D]

Yes.

[B]

And whether they're working in the office or not working in the office, the couple is in the business.

[D]

That's right.

[C]

It starts at home.

[B]

Yeah. So I'm actually glad that you hijacked that, asked 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 investing the time to have the conversation.

[C]

Thanks for having me.

[B]

And if this is something that you want 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.

[C]

That's right. I'm excited.

[B]

That's awesome. We're excited to have it.

[C]

We're gonna run it back.

[B]

Yeah, run it back. I think last time you were the highest ranked speaker.

[C]

Is that right? That's awesome.

[B]

Fair. Yeah, it is awesome. And Deloney, you're gonna be there.

[D]

I'll be there too.

[B]

Yeah, you'll be there too. So we appreciate that also.

[D]

Thanks. I wasn't the highest ranked speaker. Jefferson beat me and I'm still in therapy about it.

[B]

Thank you gentlemen.

[C]

Thanks for having us.

[A]

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 wrong 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 23 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.