How To Have Hard Conversations With Friends ft. Bobby Bones

Summary

---

Podcast Summary:

The Jefferson Fisher Podcast
Episode: How To Have Hard Conversations With Friends ft. Bobby Bones
Date: July 17, 2026

---

Overview

In this episode, Jefferson Fisher welcomes radio personality, author, and entertainer Bobby Bones to talk about the art of having hard conversations—especially with friends and co-workers. Together, they unpack lessons from Bobby's 20+ years of leading his close-knit radio show, discuss the intersection of friendship and professionalism, and offer highly relatable, actionable strategies for navigating uncomfortable but necessary discussions. The episode is rich with stories, vulnerabilities, and humor, making it engaging for listeners aiming to become better communicators—at work, with friends, or in their daily lives.

---

Key Discussion Points & Insights

1. Working with Friends: Boundaries and Balance

• Hiring Friends and Relationship Dynamics
  • Bobby describes how his show was built by necessity with friends rather than professional co-hosts due to budget constraints, which “made me better” (02:39).
  • The result: long-lasting bonds, but also blurred lines between boss and friend.
  • “The hardest part about working with your friends is you got be their boss, too. And that ain't comfortable sometimes.” — Bobby (03:49)
• Boundaries Must Be Repeated
  • "The boundaries have to be discussed many times over just to even be reinstated.” — Bobby (00:30, 20:51)
  • Discussing and reaffirming boundaries is essential to maintaining both friendship and professional expectations.

2. The Foundation: Trust, Freedom, and Honesty

• Being able to “communicate openly and honestly…with millions of people listening” is rooted in “complete trust and comfortability” (04:49).
• Real conversations don’t happen without years of shared experience—and willingness to risk awkwardness or disagreement.

3. Influence of Upbringing on Communication Style

• Bobby credits his small-town Arkansas roots for his warmth, curiosity, and ability to keep conversations alive.
  • “Everybody talked to everybody…if you didn’t wave when someone drove by, that was weird.” — Bobby (06:36)
• He balances curiosity with insecurity, which he believes makes him better at his job (07:21).

4. Overcoming the Fear of Rejection

• Both Jefferson and Bobby explore the universal fear that keeps us from connecting or asking questions.
  • “I think it’s rejection. Rejection and failure. …But again, when someone does it to us, we love it. Yet we’re afraid to do it to anybody else…” — Bobby (10:10)
• The lesson: People usually want to help and connect more than we expect.

5. Mastering Questions and Deepening Conversations

• Bobby claims he’s “genuinely and generally curious” rather than a technical master of interview questions (11:59).
• The true magic: showing real interest and using intent over crafted queries.
  • “Sometimes my questions are bad, but my intent is good.” — Bobby (12:23)
• Key technique: Start with surface questions, look for shared interests or trauma to open deeper conversations (14:28–15:10).

6. Handling When Conversations Aren’t Working

• If an interview or discussion isn’t clicking, Bobby will “just start talking and entertaining myself…you’re just now part of the audience” (32:37).
• Storytelling is a reliable fallback and often rekindles participation.

7. Directness and Dealing with Hard Conversations

• Be quick and to the point—no need to sugarcoat or buffer unnecessarily.
  • “I found that the quicker we can get to the problem and get it solved, the better it is for everybody. Even if it’s wildly uncomfortable at the beginning.” — Bobby (27:40)
• Pre-frame tough talks: “Hey, you’re not going to like this. But…” (27:50)
• Follow-up with assurance and belief in the person:
  • “If I didn’t believe in you, we wouldn’t be having this conversation…But the fact that I’m having that conversation means that I do believe in you.” — Bobby (31:06)

8. Self-Care and Leadership

• Bobby distinguishes between roles: as the leader at work, he has to show up even when he’s not feeling it, but expects his team to stay home if unwell (23:16–24:05).
• Regular therapy, diet, exercise, and reading are key to maintaining his performance and managing his “fear-based success.”
• “I have complete fear-based success…It’s a superhero. It’s a superpower at the same time.” — Bobby (44:30)

9. Handling Anxiety, Insecurity, and Mental Health

• Bobby is candid about his battles with PTSD, insomnia, and a persistent belief that everything could collapse at any moment (40:05–44:13).
• His strict work ethic (never being late, constant readiness) is rooted in childhood scarcity and insecurity, not just discipline.

---

Notable Quotes & Memorable Moments

• On long-term collaboration:
  “It’s crazy to think about…It’s been over 20 years with pretty much all of them…you can’t really [have open conversations] unless there is a complete trust and comfortability.” — Bobby (02:39–04:49)

• On curiosity and conversation:
  “I feel like I’m just genuinely curious, though…kind of wonder…what their circles are.” — Bobby (07:21)

• On the power of silence in conversation:
  “If you have no fear of sitting in silence with someone, they will just talk. And so that works.” — Bobby (15:11)

• On being direct:
  “I don’t need the syrup. Let’s get to the point, and then let’s get off of it, because we just fixed it.” — Bobby (29:05–29:10)

• On the fear behind the drive:
  “All my success is completely fear-based. It’s a superpower at the same time.” — Bobby (44:30)

---

Important Segments & Timestamps

• [00:30 | 20:51] – Establishing and maintaining boundaries when mixing friendship and leadership.
• [03:49] – The discomfort and necessity of being both boss and friend.
• [06:36] – Impact of small-town upbringing on communication style.
• [10:10] – Addressing the fear of rejection in conversations.
• [12:23, 15:11] – The importance of intent and the power of silence in interviews and relationships.
• [18:02–19:04] – How to recover when things are going off-track in a conversation.
• [27:40–29:10] – How to deliver uncomfortable feedback directly and kindly.
• [31:06–31:41] – Balancing direct feedback with expressions of belief and support.
• [32:37, 34:01] – Storytelling as a rescue tactic in dead-end conversations.
• [40:05–44:30] – Bobby’s struggles with anxiety, PTSD, fear-based motivation, and mental health practices.

---

Practical Strategies Highlighted

• Reinforce boundaries regularly, especially with friends you work with.
• Model open, honest conversation to cultivate trust and long-term collaboration.
• Overcome the fear of initiating conversation by remembering how good it feels to be approached.
• Adopt direct and kind communication: quickly address issues and express belief in the relationship.
• Leverage storytelling and personal “I statements” as tools to keep discussions engaging and authentic.
• Prioritize self-care outside of work to sustain leadership and prevent burnout.
• Acknowledge and address unhelpful mental scripts; therapy and supportive relationships are essential.

---

This episode is a trove of wisdom for anyone who:

• Works closely with friends or loved ones
• Leads teams or communities (big or small)
• Struggles with the “hard talk” moments of work, friendship, or family
• Wants to deepen their communication skills with authenticity and compassion

Bobby Bones and Jefferson Fisher keep it real, humorous, and practical—a conversation that models the very civility and openness they encourage in others.

Transcript

[Jefferson]

Teens share everything that may include the bacteria that can cause meningococcal disease, known as meningitis. Even if your teen's been vaccinated in the past, they could still be missing meningitis vaccinations. Ask your teen's doctor or visit meningitis.com today. Sponsored by GSK. How do you have those harder conversations with friends, especially when you're working with them to make sure you're not damaging. Like you need to make a decision and sometimes you need to be, I need to say the boss thing. But you also don't want to damage that relationship.

[Bobby]

The boundaries have to be discussed many times over just to be even reinstated.

[Jefferson]

I remember, I think, I don't think I went a day in high school where I didn't listen to Bobby Bones, Amy and Lunchbox.

[Bobby]

By the way, what town in Beaumont?

[Jefferson]

Uh huh.

[Bobby]

Oh yeah, yeah, yeah. Our pop days.

[Jefferson]

94.1 top 40. That was like, that was the first time I was ever introduced. But I don't think I ever had a morning that it wasn't Bobby, Amy and Lunchbox. What is it like to be able to even now have like really close, I would imagine, very close friends of people you've done a lot of life with and Eddie and best friend and you have, you do the music and everything that you're still to this day are able to have really awesome conversations with and just do it for a living.

[Bobby]

I think one of the coolest things that I've been able to do is hire all my friends, just generally speaking.

[Jefferson]

Yeah.

[Bobby]

I've been with the whole show now for over 20 years, which is crazy. But also I did the math. It means I'm getting older too. Like my mortality comes out whenever I start thinking about how long we've been together. But it's awesome because my goal was to always just like work alongside people I liked.

[Jefferson]

Yeah.

[Bobby]

Cuz I saw like my stepdad, he worked at a mill. He did not really like the job that he had. He really did not like the people. He didn't have a close bond with them. So I always wanted to have something that I like, enjoyed with people I enjoyed. But it was kind of a weird way that it all happened because it was never my strategically, you know, grandiose plan to have all my friends come into the show. We had no money and so you just call the people that you know to come in and jump in with you. And so when I started that show and I was by myself and I had no co host, it was who can I hire for cheap. And who do you hire for cheap? Well, your friends don't come do it for free.

[Jefferson]

Right.

[Bobby]

And so it was such an odd way to build that show. And at the time I resented it a bit because the company wouldn't give me money to hire professional co hosts.

[Jefferson]

Right.

[Bobby]

Because they didn't know if they believed in the product. So I just grabbed all the people that I liked and that made me better. And now we've been together for a long time. Made a long time. It's crazy to think about when you think about like thinking of the numbers. It's been over 20 years with pretty much all of them, even Eddie and I. He's my best friend and we've done the radio show together for 13, 14 years, but we did television for another three or four before that. So we've been together, you know, 17, 18 years.

[Jefferson]

Yeah. And now not only do you have that close relationship, but I mean, they're also really professionals, like at a craft. Now, I think that that can be really easily overlooked of I think just any radio or television for that matter of there's a certain craft to making sure that you keep kind of the ball in the air. Or do you find that it's just pure friendship that you're able to keep things rolling?

[Bobby]

Oh, I think they've gotten really good at what they do. I also think it's a couple of hats. Like I have to wear the hat of being the boss sometimes and then I have to wear the hat of being the friend sometimes. But I think over the years there's been a great understanding of when I have to switch those hats.

[Jefferson]

Right.

[Bobby]

Because number one, I gotta make sure the ship is taken care of.

[Jefferson]

Right.

[Bobby]

And there's some difficult decisions that have to be made at times. So they are great at doing their job, but they're also great at knowing when they have to do their job at a higher level because it needs to be done that way. So I think that's been the hardest part about working with your friends is you got be their boss too. And that ain't comfortable sometimes. But at this point, we've done it for so long. It's a well oiled machine, it works and nobody's left. You know, sometimes people will message in and be like, man, sometimes you guys sound like you hate each other because we're literally arguing about something. Yeah, man, do you think we'd all be here 21, 22 years later together if anyone really hated each other? Yeah. I mean, to have the freedom to actually Communicate openly and honestly with millions of people listening through radio or podcast. That. That is something that I don't really take for granted because we've worked hard to be able to do that. And the relationship is what really allows that to happen. Because I've worked on other projects with other people, and you can't really do that unless there is a complete trust

[Jefferson]

and comfortability, and that has to do. Like, it reminds me of my hear my grandparents argue, you know, and, like, you go, God, I think they hate each other. It's like. No, they just. It's an. It's a morning thing.

[Bobby]

They have the freedom to say how they feel and not worry that the other one's gonna run away or leave or.

[Jefferson]

My grandmother will look at me and just insult my grandfather about something. You know, he doesn't take his medicine. You know, he never. And he's just. He's in a different world, you know, because there's just been such that. That bond. But I. My audience, Bobby, is somebody who really cares a lot about how they show up in communication. And what really just inspires me so much about what you've built and where you've come from is you get to have and you've cultivated a show that does model real conversation. And I find that can be lacking sometimes in the way we model relationships. I wonder if you're not all the details of your childhood, but simply a smaller town Right. In Arkansas of, like, do you find that that has influenced the way that you approach conversations, handle small talk, or ask questions? Do you find that that's been something that's driven that?

[Bobby]

I think being from where I'm from, maybe a small town, a rural area, and maybe from the south, even I feel like that is a part of it with, like, just a warmness, because I have friends that are way nicer than me, and they're from the Northeast, and they are not near as warm.

[Jefferson]

Right.

[Bobby]

Like, you understand how, like, how genuine they are after a. After a bit of time with them. Yeah. I think, you know, coming from where I come from in rural Arkansas, everybody talked to everybody.

[Jefferson]

Yes.

[Bobby]

So if you didn't wave when someone drove by, that was weird. And, you know, when I go back home, if I'm driving through and people are waving at me, I was like, wait, what? Who is that?

[Jefferson]

And.

[Bobby]

And I forget. That's just when you drive by a car, you wave at them, and if you don't, that's weird, even if you don't know who it is. Yeah.

[Jefferson]

I definitely think that in the south, from getting a haircut to ordering at a cafe. Like, they're going to learn your life story one way or another.

[Bobby]

Haircuts. Yep.

[Jefferson]

Yeah. Church. Whatever it is, you're going to find out everything about everybody. And for me, I know that is. That has been helpful in terms of being able to keep conversation, because a lot of people struggle keeping conversation in the air, kind of passing the ball back and forth.

[Bobby]

I feel like I'm just genuinely curious, though. Like, I think I see someone and kind of wonder, you know, if you cut a tree and you see all the circles. I kind of just wonder, like, what their circles are. Like, I genuinely am curious about folks, and so I think that's where a lot of mind comes from, you know, I also sometimes feel like I don't want to bother people, so there's that, because it's kind of a. It's a weird juxtaposition of being, like, wildly insecure and very confident. Because I have them both.

[Jefferson]

Yeah.

[Bobby]

Like, I feel like I don't want to bother people yet. I'm very curious. But it's like, even with my job, like, I don't think I would be good at my job if I was the most secure person ever. Like, I'm wildly insecure. But to do my job, I've got to be really. I got to think I'm really good at doing the job. So it's been. It's a. It's like an. An odd mix or like I got a screw loose, but it's the right screw.

[Jefferson]

Right.

[Bobby]

It's kind of how I feel about where I'm from as well. But I.

[Jefferson]

Sure.

[Bobby]

I think that helps with communication. Everybody talks to everybody all the time. I. If someone talks to me randomly, especially if they, like, don't know what I do for a living, because that happens a lot. But if it's just somebody random, I'm never annoyed. But I always feel like I'm annoying everybody.

[Jefferson]

Exactly.

[Bobby]

It's a weird, you know, if someone's like, hey, you know, how's your day going? And even in an elevator, I'm like, oh, this is nice. Someone's talking to me. But I would never, like, randomly, like, bother somebody, but I. It. When someone does it to me.

[Jefferson]

Yes.

[Bobby]

So.

[Jefferson]

So what's. What's the lesson there?

[Bobby]

The lesson? Well, the lesson is I. In my comedy act, there was kind of a inspirational talk, too. I talk about whenever you want help with something, like, ask people for help. And then I say, it was always weird for me to ask people for help because I thought people didn't really want to spend time with me. They didn't, they don't want to be bothered. But then when people ask me for, for help, I'd love to help because I would say, hey, tell people your goals. If you tell people your goals, they are more likely to help you. And it's the same thing where I never wanted to ask for help because I thought they were bothered by someone asking for help. But when I would, people ask me for help, I love it. I can't wait to give people help or advice or tips. So, yeah, we just worry too much about how people look at us and view us and it's kind of counterproductive.

[Jefferson]

Do you think? I find this very interesting because I love talking about this. Like, this is my nerdy talk of like, how does this happen? So if somebody in the elevator approaches you and strikes up conversation, you almost get like a boost from it when you leave of like, hey, I've connected with another human in the world, I'm here. But when it's you, you have the chance. It's very difficult because it comes to mind of like, why would they.

[Bobby]

Yeah, I don't want to bother them.

[Jefferson]

So what do you think? Like the script is that's, that's preventing that of like, is it that nobody would care?

[Bobby]

I think it's rejection. Yes. Rejection. What keeps us from doing anything and everything? Yeah, it's rejection and failure. And if I do try to connect and they don't connect, what does it say about me that I'm not good enough?

[Jefferson]

Right.

[Bobby]

I'm not, you know, strong enough, I'm not good looking enough. I'm not what's. And it's not that at all actually. But yeah, it's complete fear of rejection. Complete fear of failure. But again, when someone does it to us, we love it. Yet we're afraid to do it to anybody else because we feel like if they don't react the way we want them to, that's on us and it's really not. It's on them. They could be having ten hundred thousand things. It's not a real number that's happening in their day. That's keeping them from, from reacting the way that we want them to.

[Jefferson]

Before we get going, I want to take a moment to tell you about square. But you didn't know that. When I was a young attorney, I also owned a coffee shop and one of the point of sale systems that we used was Square. And in fact, this morning, I'm out of the country right now. With my family, we hopped into a little Australian cafe and you know what they used? Square is a nice little full circle moment for me. And they're using it for good reason, for the same reason I did. Because everything about business that you don't like becomes that much easier so you can focus more on the things that you love. It's not just a point of sale system. It adds all the things up that you don't like to do, like payment processing, invoices, everything all into one to make everything organized, smooth and easy. So if you are looking to start a new business or maybe wanting to run a business with better tools, people who use businesses who use Square online earn up to 36% more revenue, which is awesome. Right now you can go to square.com go jefferson and sign up to get 200 off your. Your square hardware, which is awesome. That's square.com go jefferson. So run your business better with Square. And now let's keep going. Have you always been somebody who's excellent at questions?

[Bobby]

Oh, I don't know if I'm even that now. I just am, like, genuinely and generally curious. I think it being true about me makes my questions better, even if they're not good questions, because, you know, I'm coming from a place of. That's how I. I really want to know. And so even with, like my interviews, I. I don't. I kind of just ask the things that I want to know.

[Jefferson]

And.

[Bobby]

And even if it's at a place with someone where it could be something that's a little personal or it kind of hits a nerve, I feel like for the most part they don't take offense to it because they know I'm coming from a place of curiosity or caring and not coming from a place to get a click. Both can be true, But I feel like it's not so much my questions, but my intent. Because sometimes my questions are bad, but my intent is good. And yeah, I just like. I like connecting with people. I feel like even. Even doing this. I've made so many friends from doing this. And you would think that this is very surface, it's professional. Nothing really matters because cameras are on. You do your thing, cameras are off. And it doesn't happen with most, but there. I've made some great friends that have started in this environment because you get really intimate doing this big time. I mean, it's. It. You're depending on me, I'm depending on you.

[Jefferson]

Yeah.

[Bobby]

It's only us doing this.

[Jefferson]

We're doing this together.

[Bobby]

Yeah.

[Jefferson]

Yeah.

[Bobby]

And so, yeah, I feel like my questions are fine, but I feel like my curiosity is high. But I think in normal life, I think that counts too. Like, you know, when you talk to

[Jefferson]

people, well, people, I think more people than you think. At least the people I hear from really struggle a lot with questions. And you're somebody who does it as a, I mean, a master of the craft. I know you could say my questions aren't that good. Well, to me, my brain sees that as. Okay, well, there's some element of this that's also a skill because it might be self deprecating. It might be like, hey, I know I'm going to get a lot of this wrong. And what that's doing is saying I'm no more important than you are and I'm lowering myself. Or maybe it's a joke, or maybe it's humor. It's one way to like break the ice. Because every interview that you give, you're looking for that way to kind of remove that polish. I imagine when you, when you're talking to some of the biggest stars, country stars out there, do you find that you have to ask a few questions to kind of get a layer deep? Like it has to be like. You're like, that's a canned answer.

[Bobby]

Yeah. I'm looking for what we have in common that can kind of put the guard down in like a jokey way. Not always. Sometimes it can be like real trauma. Sometimes it can be a television show we both like. Sometimes it can be. And I tell you what's worked for me the past few years is I did that, the Dancing with the Stars, the dance show. And if somebody comes in, it's done that show. And I mentioned to, to you before we started recording, like there's real like trauma bonding in that show. I believe it. And so I can kind of find our, our like minded entity and focus on it. And also people, when they don't feel like they're trying to get got, they open up. I'm not trying to got anybody.

[Jefferson]

Yeah.

[Bobby]

You know, sometimes people will give me great stuff, sometimes they won't. But. But my question is, I don't feel like they're good though. I just feel like again, I feel like I am genuinely curious and if something doesn't hit, I have no problem. One, sitting in silence with someone, that's the best trick in any sort of communication. If you have no fear of sitting in silence with someone, they will just talk. And so that works.

[Jefferson]

Absolutely.

[Bobby]

I've done this so many times that I also know what it's like for things not to go well. And I know I can always get it back, but I've done it wrong so many times that I know that even if it's going terribly wrong, I can get it back. I've been through some terrible ones that have turned out great. So just doing it so many times. But it's also helped in real life as well, like human conversations, like just talking to folks, because a little bit I can just turn on the. Hey, I'm curious. Just gonna ask some questions. And I find the, like, the thing we have in common. It works. Like, if I'm being, let's say, interviewed for a. Not even interview, but like, I'm doing a job interview for a TV show, I'm doing it. I'm in auditioning for something. I can just find, like, a sports team. They like a shoe they're wearing, something with their kid that I understand. Man. That is the real key to any sort of relaxed conversation is to find what you have in common with that person.

[Jefferson]

So I've heard finding something separate from the person is actually a key to that commonality. If it's actually maybe separate from. It's like the third person in the room. For example, dancing with the Stars could have been something. Or maybe I had seen something on your shelf that you were, I don't know, a Houston Astros fan or something. Where you see it, and then that's where you're able to kind of create that bond with.

[Bobby]

Yeah, especially if I know enough about it.

[Jefferson]

Yeah.

[Bobby]

You know, if I'm just like, hey, look at that fish. But I never fished, right?

[Jefferson]

Yeah, yeah.

[Bobby]

But if you got a fish, and I go, hey, I see you caught that fish. Like, my stepdad was a striper guide for many years. I can find that thing that puts us in the same place, that allows us to go to the same place together. Because I probably didn't come here to talk about fishing. But we can get there much easier if we kind of feel like we're in the same boat.

[Jefferson]

I think that then goes into upbringing, what you've been around and how much you just talk to ordinary people. I think that's where I see it. So my background, Bobby, is as a trial attorney. And so the best way I can relate the cases to the jury relating to just human elements of every day or the ways that maybe I want to get a person, I'm taking their deposition, get them more relaxed, is to use a little bit of humor and know that, yeah, I'm going to get a Lot of things wrong. So don't. That. That kind of lowers the temperature of it. You said something a minute ago. I want to make sure and pull back on is you say, I know I can get it back. How. How do. How does somebody correct course and get them back?

[Bobby]

Just keep going. There's no magic. You just keep going.

[Jefferson]

If you don't feel like there's magic,

[Bobby]

if you don't quit, it's over.

[Jefferson]

Right.

[Bobby]

It's not. Oh. If you don't quit, it's not over. And so, yeah, there have been a lot of interviews or just situations that don't go well at the very beginning.

[Jefferson]

Yeah.

[Bobby]

But I know I can get it back. Just stay in. It's just staying in and trying to find, you know, whatever you have in common with that person. It can be in a professional setting. It can even be, you know, when I was dating my wife, you know, I don't think she wanted to go out with me immediately. I don't know if you've seen us beside each other. It kind of doesn't match. But it, you know, I. And I don't think I was super smooth with her when I first met her, but I just kept trying. And so, yeah, as long as you stay in, regardless of the situation, I think you can get it back. It's just that when it doesn't go well early, we tend to go, this ain't going good. Abort mission. But I think that's the key. Well, I think that's the key to pretty much any success that I've had is just figuring it out as I go, having the confidence to go in and know that it may not work at the beginning.

[Jefferson]

Yeah.

[Bobby]

And then just staying in when it's uncomfortable. So, yeah, in this situation, a lot of times, because most people come in, it could be like, this could be a job interview. People are tight. As soon as I start, everybody's tight. People are like, I'm tense. Yeah. I'm about to do a job interview. About to have a job interview. I'm about to do an interview. But, you know, one of these. And so people come in and they're tight. So it's. How do we get each other to kind of be on the same place so we can actually get the most out of it? And it's finding whatever it is you have in common.

[Jefferson]

Do you think that having. When you're having conversations with, like, multiple people, if you have Eddie or Amy or Lunchbox in there, that helps?

[Bobby]

Nah, not really. I mean, it depends on what we're trying to do. If I'm trying to, like, be super sincere or, or if I'm sad or I would rather just do it by myself. Certain dynamics, it works wonderfully. Certain, not so much. But, you know, it's. If you're trying to have a real connection, it's hard to do it with seven people sitting around you. Just generally speaking.

[Jefferson]

Yeah.

[Bobby]

It's much easier if it's, you know, one on one. And that one on one can be me talking through a microphone to the person listening or even like to me talking to Amy. Yeah. You know, whenever you have people chirping your ear from the side, it gets to be a little bit more difficult.

[Jefferson]

I can imagine. I want to, I want to pause. I want to bring us back for a moment. How would, based on your experience in the 20 plus years you've been having this, this show, how do you have those harder conversations with friends, especially when you're working with them, to make sure you're not damaging? Like, you need to make a decision and sometimes you need to be. I need to say the boss thing, but you also don't want to damage that relationship.

[Bobby]

The boundaries have to be discussed many times over just to be even reinstated. Because there are boundaries. The boundaries are when we're at work. In a work situation, I'm going to be the boss. They're certain when we're performing, you can do whatever you want to do. But it mostly it comes to, like, everybody else is putting in their time and their effort. You just got to match that. I mean, that's really what everybody's job is. Match everybody else's effort. Don't be late, have a good attitude, those type. Other than that, you're good. Right. Show up, do your best. If for some reason you're not performing, I will tell you if I feel like someone else having to pick up your slack, I don't like that. And I will tell you so they understand that I'm going to communicate with them. The things that are good and things that are bad. When I'm the boss.

[Jefferson]

Yeah.

[Bobby]

When I'm the friend who knows. Like, you know, we, Eddie and I go a lot of places together and we're able to switch back and forth. But if there's something wrong with some content, it's never weird anymore for me to go in and go, hey, this isn't good. Also, I want to be super efficient. I'm not going to, you know, kind of dance around it, but I think generally speaking, I just kind of operate that way because we all have things we want to do outside of work. So let's get all the work things done first and let's do the best that we can do for each other so we can go be the best we can for our families. Not only that, it's. You know, there's an open rule on our show that if anything is affecting you or bothering you, don't come in. Just, just don't. Because if you can't be. You can't be good for me. If you're not good for you at home.

[Jefferson]

Yeah. So if home's not good, the conversation's not gonna be good.

[Bobby]

Nope.

[Jefferson]

It's impossible to not carry.

[Bobby]

Nothing's gonna be good. Yeah. So if you're not good at home, you do not need to come in at all. And I think that's where being a friend.

[Jefferson]

Yeah.

[Bobby]

Kind of, you know, creeps back into play. Because when you come in, you've gotta be great.

[Jefferson]

Right. And it makes you really attuned to the other people if something's off. Because, I mean.

[Bobby]

And I can tell when something's off with him immediately. But I think that's the 20 plus years of working together.

[Jefferson]

Well. But it also, I think highlights the significance of if something's off in the conversation, that's something to take care of first. Usually when you try and just push through and act like everything's fine, I tend to find that that makes things worse than improve what's about to happen.

[Bobby]

The only person who can come in sick or affected is me. Everybody else stay home. If you're affected, you need to unaffect yourself. If you got.

[Jefferson]

Why can't you.

[Bobby]

Oh, I got a lead.

[Jefferson]

Sing, you're the captain.

[Bobby]

I got it. It doesn't, it doesn't move without me. And that's okay. Like, I know my role. They're all depending on me in that. That way. So. Yeah. We have a rule. If you're not feeling good, mental or physical, you gotta take care of you before you can come in. Because you're not gonna be good for me if you're not good for you.

[Jefferson]

Well, what do you do when you don't feel good?

[Bobby]

I feel good.

[Jefferson]

Oh, so you just.

[Bobby]

Yeah.

[Jefferson]

Is it just a thing? Okay.

[Bobby]

Yeah. I gotta be the leader, so I will find time to feel bad.

[Jefferson]

Okay. All right. Got it. That's harder. Yeah, it's hard because then. Then if you're not doing it there, you're. You're outlet somewhere else.

[Bobby]

It is. But you know, I do a great job of making sure that I'm Taking care of myself outside of that room. I'm in therapy twice a week.

[Jefferson]

Yeah.

[Bobby]

Or. Or my wife. I have a therapist that my wife and I go to a couple's therapist. I have my own therapist. So I'm not going to two different therapists, man.

[Jefferson]

Same.

[Bobby]

I'm a big, big therapy guy. So I'm doing the things hopefully to keep myself mentally ready. I'm also doing the things physically. Meaning I know that my diet matters. If I don't eat good, I'm not going to perform well. I know that if I'm not exercising, I'm not going to perform well. I know if I'm not working my brain and going to therapy and talking about what's bothering me, and if I'm not reading books, I'm not going to perform well. So I'm doing all that work ahead of time that if something does come up, I think I can get through it until my next break. But they're counting on me. I have a staff of like 15, 16 people that if I don't go, I let down 15 or 16 families. So I don't take that for granted. And at times it can be extremely difficult. But in that part, I am the leader back home, though, in the home dynamic. My wife is that. My wife is exactly, to me and our family, that I am to that show. She doesn't feel good a lot of days. We have a new baby. Baby's about to say congratulations, and I know she doesn't feel good sometimes and I'm there and I try to help, but she freaking dials it in and does it. So, you know, in every organization, you got to have a couple of those. My wife is that at home. I'm that when we're out. I think everybody's that in some. Some version, some part of their life.

[Jefferson]

Yeah. I would definitely just to like, cover you and me. What they do is much harder. I'm just. That's like, way harder. This episode is sponsored by Cozy Earth. And for all of you listening, if you are adults, I need to. I need you to lean in and have this conversation with me. It is time. Yes. This is the time in your life, you may not have expected it, that you need to take bedding and towels seriously. Because when people come over to your house, are you, as a. As an individual human, you deserve nice bed sheets and nice towels. Stop using the stuff that you had in college or when you were first married or anything. Like, you deserve some of this nice stuff. Because Cozy Earth makes some of the most premium products when it comes to bamboo bed sheeting and towels that make you wish and think that you're sleeping on a cloud. So if you are like me, and that is, I'm in this season two where I got to take this kind of stuff seriously, you cannot ask for any better than cozy earth for both bedding for your bed and towels for your bathroom. That's all I need to say about that. Cozyearth.com Jefferson used to go Jefferson for up to 20% off. That's cozyeart.com Jefferson used to go Jefferson for up to 20% off. And now let's keep going. We handled questions, so we talked about the power of silence. Usually you get a whole lot more. We talked about have a genuine curiosity, maybe even sometimes when you don't feel like it. We talked about some ways that you can kind of get below the surface when it comes to hard conversations as a leader, not just friends that you've been forever with. I'm talking just anything that there's some kind of crisis. And you guys say I have to be really direct and not apologize for it because I know people who go, look, I'm sorry I got to say this, but I got to. How have you found to be direct in your communication?

[Bobby]

I found that the quicker we can get to the problem and get it solved, the better it is for everybody. Even if it's wildly uncomfortable at the

[Jefferson]

beginning without bringing personality into it.

[Bobby]

No personality at all.

[Jefferson]

Yeah.

[Bobby]

Yeah. None. How I will do it if there is something uncomfortable to talk about is, hey, you're not going to like this. But yeah, because just by me saying that, it. It almost braces them for a few words like, this is not going to be fun to talk about. But even that, you know, 0.7 seconds of setup allows them to go, okay, we're getting into something that is not comfortable. I'm ready. And sometimes it's not near as bad as they think by me saying that, but that's kind of the precursor. And then I just try to get to it and say it immediately because neither one of us want to dick around with trying to figure out what I'm trying to talk about.

[Jefferson]

Yeah.

[Bobby]

Uh, so let's figure out the problem. Let's address it. Let's get through it and get to the other side of it as fast as possible so we can get back to doing the right things. Yes, it's very uncomfortable, but it's very uncomfortable for a limited time.

[Jefferson]

Right.

[Bobby]

And I prefer it to be very uncomfortable for a limited time than kind of uncomfortable for a long time because you can do either one. I've. I've had people that I've worked for that love to dance around it. I'm gonna. We're gonna talk about three things. The first two are gonna be positive, and then the whole time, I know the third thing's about to be bad. Let's just do it.

[Jefferson]

Yeah.

[Bobby]

I don't. I don't really. I don't need the syrup because I want to figure out what's wrong, fix it, and get back to the good spot. So there's not a lot of buffer.

[Jefferson]

That's how I know you're Southern. As you said, I don't need the syrup. That's how I know. Yeah.

[Bobby]

No syrup. And there's no buffer because I don't feel like, for me, that's healthy to either hear it or give it. So it can be uncomfortable. It should be uncomfortable because whatever it is is an uncomfortable thing that we're talking about.

[Jefferson]

Right.

[Bobby]

So let's get to the point, and then let's get off of it, because we just fixed it. How awesome is it that we can fix it? And I think now, too, my people know that. They know I'm not going to come in and, hey, how's the dog? And then hit them with some bad news. If I'm really asking about the dog, they know I'm curious about the dog.

[Jefferson]

Right.

[Bobby]

That I'm not setting them up for something where I'm going to be like, well, your performance has been bad. We might have to fire you.

[Jefferson]

Yeah.

[Bobby]

So that's how I do it. It's like, all right, this is not going to be comfortable to talk about. And then I say it immediately because once it's out there, it's easier to fix.

[Jefferson]

Morten, you know, I love that approach because I. What I preach is the kindest thing you can do is be as direct as you can be. Like, the more I string you along, the more painful it's going to be

[Bobby]

for both of you.

[Jefferson]

Oh.

[Bobby]

Without you and them.

[Jefferson]

Yeah. Yeah, yeah. Do you mind if I share the version that I use for.

[Bobby]

I would love to hear it.

[Jefferson]

So it's very similar to yours. It's. I know this is. I know this isn't going to be fun to talk about, and we're going to do it together. That's what I add whenever I add the and we're going to do it together instead of the. But it tells them that, hey, you and me, we're going to, like, lock in for a moment. There's going to be an end. There's going to be a beginning. And this is not me leaving you to say bad, you good, me. I'm saying I'm separating out the problem from both of us. This is going to be uncomfortable to talk about and we're going to do it together. That's what I have found, at least. So Those from my 2 cents I have found.

[Bobby]

And I mean it when I say it, is that when I'm done saying what the issue is? Because if I were to say this is not going to be fun for us, Jefferson, but A, B and C is happening. That is not good. We need to fix it. But I believe in you.

[Jefferson]

Yes.

[Bobby]

Like, and it may sound hokey, but if I didn't believe in you, we wouldn't be having this conversation. We would just move on. I'd move on to somebody else that I think could do a better job, a quicker job, make it easier for me. But the fact that I'm having that conversation means that I do believe in you. So this wasn't good, but I believe in you. So let's make it good. So good that that works a lot. Yeah. Because again, everybody, everybody's kind of feeling like they don't want to be there.

[Jefferson]

Oh, no doubt. I, like, I'm telling you this because I believe in you. I'm telling you this because I know you can handle it.

[Bobby]

Oh, that's a good one. I know you can handle it.

[Jefferson]

Yeah. That type of stuff is like, it empowers them to go, oh, yeah, okay, whatever he's about to say, he said I can handle it. So I am.

[Bobby]

That's a good one. That's a good build up to be

[Jefferson]

able to kind of like push that a lot. But I think it, what we're talking about hits the very home of a lot of small businesses, a lot of families. Anybody listening that can apply these kind of frameworks to very difficult conversation. The other thing I wanted to make sure and push a little bit is when it, when you don't have, you don't feel like there's any chemistry with that person you're asking questions to. Let's say you're having an interviewer, you're having an interview. Let me rephrase that. You're taking an interview, you have somebody across from you and there's just no compatibility. Are there certain, like, tethers you're trying to like, please let me find something that we can tackle along with?

[Bobby]

Yeah, I just take over and start talking myself. Especially if we're Doing, like, one of these. And, yeah, let's say I'm getting nothing from you, or you may not be feeling good. Like, I don't know the reasons that we're not connecting. I will then just start talking and entertaining myself. And you're just now part of the audience. That's smart. And then it's through. A lot of that's business, too.

[Jefferson]

I mean, you have to. Yeah.

[Bobby]

You know, we got an hour we got to fill, and you're not giving me much. I know the person that's watching, you know, they're not liking it or they're.

[Jefferson]

Right.

[Bobby]

So I'm just gonna tell stories. And so you're. You're welcome to hop in, but that happens occasionally if, like, you're, like. If you're watching my podcast ever, or listen to my podcast and I'm interviewing somebody, which is Bobby Cass, by the way. Yeah. Thank you. And you hear me just start to just talk and tell stories. It means for whatever reason, we're not connecting right then.

[Jefferson]

Yeah.

[Bobby]

A lot of times, though, it does turn into.

[Jefferson]

It'll pick up.

[Bobby]

Yep. Because the person will then hear me talk about something and find something they want to talk back about and go into it. So, yeah, that's been a technique that I've learned.

[Jefferson]

I think that's really smart because sometimes you're just not vibing. You go, hey, let me tell you a story. You know, the other day I was doing this, and they go, well, I. I didn't have anything to say back then, but I do have a story, because it's much easier to relay stories a lot of times than it is to give the back and forth kind of small talk. And I think conversation can be really hard for people, but telling stories, I think is kind of timeless, so it's a lot easier to hit that default.

[Bobby]

Yeah. That's what we do if, like, we're just sitting around with friends, too. Right. We're just telling stories and everybody jumps in. So if someone is not giving me what I feel like is good for both of us, I'm just going to entertain for a while until you like something on my story and you're going to hop in and give me your version of it, or you're just going

[Jefferson]

to sit there quietly or not.

[Bobby]

And that doesn't happen often where they just want to sit there quietly.

[Jefferson]

Yeah, I can imagine. I think that when I think of radio hosts, which, when I was a kid, that's who I wanted to be, actually, when I grew up, because I was like, how awesome they just get to talk all the time. I think that radio hosts have to have a different gear. Like, they have to be able to put conversation in a different gear because you can keep the ball in the air totally by yourself. If something were to go wrong or you realize somebody, nobody's giving you anything to go, okay, I need to lock in and fill 20 minutes or whatever it is. And to talk non stop, really, with hardly any likes or ums or ahs. Is that a skill that you've learned over time or you always felt like

[Bobby]

it's helped with improvisational work?

[Jefferson]

Improv.

[Bobby]

Well, just. It's all improv, right? So lots of likes and still. But I went to American Idol, you know, I was over there for four years and I think one of the things that allowed me to stay there for more than a year was the fact that they knew if something broke down, they could just go, hey, throw it over to Bobby. And I think that was developed through doing long form content with, you know, having to fill 5, 7, 12, 18 minutes at a time.

[Jefferson]

That's hard.

[Bobby]

It's hard. It's now pretty natural for me. Like, if everything crashed around here and you're like, hey, can you kill 12 minutes? I got like four stories I can go to immediately that I've just naturally got, you know, saved up to go to. But it has helped me in that way. I mean, there was a time, I think it was my second year on American Idol and again, that's really why they kept me around. It was the week where everybody comes to Hollywood and you're just like. It's just cutting people left and right like crazy. It's literally called Hollywood Week. And the celebrities then come in and they sing as part of that. And we're like seven minutes from going on the air. And I'm not the main guy. I'm like fourth string. I'm on every episode. But I'm just like helping the, the young people pick songs and mentoring them. And they say, hey, Ryan is sick. He's not going to be able to come and do the show. And I was like, oh, yeah, cool. So we punning till next week? No, we need you to host the show. And from what I've learned is the only people to ever host that show are Ryan and Brian Knuckleman from the first season. But it was so close to the show starting. They were like, hey, we need you to hop up there and host the show and be able to fill. There was no rehearsal, but like, I was, I don't wanna Say born to do that, but I've trained to do that. I think doing live long form content on the radio has trained me to be put in those situations and be fine, even, you know, doing stand up. And I toured pretty, pretty hard for like three years where if things broke down and they did often I'm fine. Like, I've been through it and been put in situations that were really uncomfortable and I've gotten out of them. This is only mildly uncomfortable. So I'm fine. I'll get out of this one. So, yeah, the improvisational gear is pretty easy to switch into at this point.

[Jefferson]

I find that a lot of anybody's improv or comics that just have no fear at all of bombing or any. Because they've just done it enough where

[Bobby]

they can just roll with it. I think there's a lot of fear. But we've learned. I've learned that it's not good to. It actually affects performance if you're so fearful. So you're deathly afraid at first, but you survive. Yeah, it's like life. Crap happens, right. You survive. So you feel like when crap happens again, you could probably get through that too.

[Jefferson]

Right?

[Bobby]

Like that. That's a metaphor for any. For life.

[Jefferson]

Yeah, for everything.

[Bobby]

So, yeah, it's. Everybody's afraid. I don't know a single person in the creative space that isn't wildly insecure and completely scared.

[Jefferson]

That's probably true.

[Bobby]

It's just we. Yeah, we've done it for so long so many times that we're still that. But we've gotten through really hard things. We're really not scared of those, those medium hard things anymore because we've gone through it and done just fine.

[Jefferson]

Yeah. And you still, you're still here.

[Bobby]

We're still here.

[Jefferson]

You think that when you go, okay, I know that I have to fill this X amount of time. Has there been any trick that you've learned outside of just doing it forever that you know, okay, I'm going to keep maybe at all times. I just have stories locked and loaded that should I need to. I got to do it. Because I can only imagine when you're running your show, you're thinking of eight different things. Not only the question you're going to ask, but how this is looking or how they're performing. And because at some level, you're having to think about the output and to know, okay, I have to. It's like you're. You're producing it in your mind at the same time. Constantly.

[Bobby]

Yep. I feel like to do an I Story, if everything goes wrong, helps me all the time because that's what I know about I. So if it all breaks down, the first thing I'm going to go to is I see or feel this. Here's why. If I'm just describing things generically, that never works. But if I go right to the I, that's the one thing I do know about me. So I'm good. I can eye you all day in any situation. It may take me 5, 7 seconds to get my bearings, but, you know, once I'm on, I think generally the most comfortable thing is to talk about ourselves. We know it. We know ourselves in any situation. If you're like, I don't really know what to talk about here, talk about I. Because you know it. You're comfortable talking about it. You're not guessing.

[Jefferson]

Yeah. Is there something that you find hard to kind of turn off in your brain?

[Bobby]

Yeah. I mean, all. I have trouble sleeping. Yeah, I have for a couple of reasons. I think everybody says, you know, my thoughts spin. I. I go to sleep with a podcast in my ear, because if I just lay in silence, I tend to spiral out.

[Jefferson]

Yeah.

[Bobby]

So I will listen to a podcast when I go to sleep. I have trouble sleeping. I also have, like, some ptsd. You know, when I started to have any success in this job, it was weird because I think for me, I've been able to start at the bottom. And I worked in a really small town in Hot Springs, Arkansas, and nobody knew or cared. But then once I started to have a little more success and people would kind of care, then people were kind of weird. There's a couple. Then there's a couple weirdos. It's at a none. And then when I got a little. A little more popular and the show started to branch out nationally, then it wasn't that the percentage of weirdos went up, but there's just more people.

[Jefferson]

Yeah.

[Bobby]

And so I, you know, I got jumped outside of work. I had my house broken into while I was on the air. I got held at gunpoint outside of an event once. I've had multiple death threats. So I had some really bad PTSD for a long time.

[Jefferson]

Well, that makes complete sense.

[Bobby]

And I tried it all. I mean, I. I don't drink, never had alcohol or tried a drug or anything because of my family's addiction problems. So I'm always really nervous about taking anything that could trigger any sort of addiction or dependence. And so my doctor knows that my doctors. And I remember was really struggling with sleeping after the last time I Got jumped at work, and we tried everything. We tried all the holistic. Didn't work. I need chemicals, man.

[Jefferson]

Yeah.

[Bobby]

And we tried. Finally, he was like, you know, we. We can finally go. We can do sleeping pills. I'd never tried sleeping pill before. And I was like, man, I don't know. He said, you're right. But I was getting so sick because I wasn't sleeping. Yeah, you don't sleep. You don't drink water.

[Jefferson]

It still works.

[Bobby]

And so I took sleeping pills for a little bit, and, man, they work. But there were full nights. I would look at my phone. I FaceTime, like, seven people. I don't remember any of it. Yeah, I drove off with my gas. The gas pump in my car once, you know, like, just like in. In tv.

[Jefferson]

Yeah. I said, this isn't good, this.

[Bobby]

Yeah, yeah, it wasn't good. So I've tried a lot of things. I've tried mdmr, you know, a lot of therapy. It's hard to shut off at night for a couple of reasons. One, safety, but also, like, I just have this constant fear of everything crashing

[Jefferson]

down that I've built at any moment.

[Bobby]

At any moment.

[Jefferson]

Yeah.

[Bobby]

My wife is great because she constantly reminds me that if I'm fired today and I never work again, we're good. But my mind doesn't work like that. Yeah, my mind is. If we're not going as hard right now, I could end up back where I was.

[Jefferson]

That's why I was like, is it a. What they call kind of a scarcity mindset where it's like I'm. I could lose it all and I'm gonna. I don't want to go back there.

[Bobby]

That's for sure what it is. Like, we have a rule on our show. You can't be late, meaning if you're one minute late, you should go home. You get sent home. It's. It's happened on our show for 10 years at this point.

[Jefferson]

Yeah, guests, too.

[Bobby]

Oh, I've sent guests home. I have sent guests home. I give them a little bit more grace. Yeah. There's a little more flexibility. Yeah. That gets to. But I've sent guests home if they're really late. Yeah, but we have that rule, and I. I've never been late to my job once in my entire life.

[Jefferson]

Wow.

[Bobby]

But it's not a bragging thing. I'm so scared of being late, because if I'm late, the show will struggle. If the show struggles, I will lose my job. If I lose my job, I will have no money. If I have no money. I end up back in the trailer park where I started.

[Jefferson]

Yes.

[Bobby]

Right. Like it's all safety seeking, all rooted in that. Yeah.

[Jefferson]

Yeah.

[Bobby]

It's not rational.

[Jefferson]

No, but that's. But, but that doesn't make it any less real.

[Bobby]

And I can look at it and identify it as irrational, but again, it doesn't make it any less real.

[Jefferson]

No.

[Bobby]

And I can go to therapy twice a week.

[Jefferson]

Yeah.

[Bobby]

But at least I can acknowledge that it exists now. Where I don't think I could for a long time.

[Jefferson]

Yeah, well, that's. I mean, for anybody listening, like this is. That's what triggers are like, I mean, to bring your nervous system back to. Back in Arkansas.

[Bobby]

I have complete fear based success. Yeah. That's all my success is. It's completely fear based. It's a superhero. It's a super. Super power.

[Jefferson]

Absolutely.

[Bobby]

At the same time. So I'm not saying, like anybody should feel sorry for me. Like, I am so grateful that I have been able to develop that superpower instead of any of the others that, like, my family went through easily.

[Jefferson]

Could have been. Yeah. For sure. It's definitely that. It's the, the thing that you got found success is also the thing that saved you kind of that there's that paradox of it because you wouldn't be the same person without it. Thanks for coming on the show, man.

[Bobby]

Yeah, thanks for having me.

[Jefferson]

Thanks, dude.