The Nice Boss Trap

Ryan Calkins and John Moore talk through what happens when the instinct to be understanding slowly slides into avoidance, and why the thing that feels like kindness ends up being harder on everyone. A real conversation for anyone who's been letting things go and wondering why it's getting worse.

Most leaders don't start out trying to be a pushover. They start out trying not to be the boss they hated (the one who rode them for being a minute late, who never seemed to care about the person behind the job). That's a reasonable instinct. The problem is where it leads.

Ryan and John have both been there, and in this episode, they talk through what actually happens when "understanding" becomes "avoiding", and what it takes to find the balance.

They get into:

• How letting small things slide stops being a leadership strategy and starts being a culture problem. Because one person going a minute late becomes five minutes, and then everyone's watching to see what the rules actually are
• The real reasons leaders avoid hard conversations: fear of not being liked, fear of damaging relationships they've spent years building, and sometimes just not knowing how to start
• What nobody teaches new leaders when they get promoted, and how the absence of that training leaves people improvising in situations where it matters most
• Why clarity is actually the kinder move, and how Ryan thinks about delivering bad news in a way that's honest, respectful, and doesn't leave people guessing
• What showing up for your people actually looks like: not just the words you use, but how present you are when it counts

The episode closes with a question worth sitting with: who is paying the price for the conversations you've been putting off?

"Leading ain't easy, but you don't have to do it alone."

Leading Ain't Easy was created by Ryan Calkins and Erny Epley, and is hosted by Ryan and John Moore.

• Ryan is the founder of Reframe & Rise, where he works with veterans who transitioned successfully but still feel something's off; helping them find alignment, not just a better job title.
• John is a certified life and career coach with 20+ years of experience helping people navigate transitions, find purpose, and lead with intention — drawing on backgrounds in corporate leadership, counseling, and entrepreneurship.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development, and joins the show as an occasional guest.

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Transcript

Ryan Calkins 0:00

Leading ain't easy, the show that cuts through the noise and gets real about leadership. I'm Ryan Calkins, Marine Corps veteran and founder of Reframe and Ride, and I'm here with my good friend and fellow leader, John Moore. As we unpack the highs, lows, and hard-earned lessons of what it actually takes to lead with character in today's world. It's not another highlight reel or fluffy leadership pep talk. We're talking about the stuff most people don't: the doubt, the pressure, the people problems, the pivots, and the personal growth that it demands. Because the truth is, leadership looks good on paper, but in real life, leading ain't easy. Welcome back to Leading Ain't Easy. Today we wanted to focus on something that every new leader kind of experiences. And it's the cost of being the easy leader where a lot of people don't necessarily start out trying to be soft. They start out trying to be relatable and approachable and understanding and not be like the boss that they hated being under. And somewhere along the way, that understanding turns into avoiding and inconsistency and just really puts you in a position where you you start to get taken advantage of.

John Moore 1:21

I like that word of inconsistency because it does. It really and how it makes it inconsistent is because you're trying to please so many and you're not keeping up with whom you're pleasing and what you're giving out and what you're saying is okay to do. And so now you can't even remember who you told what to, just to keep everybody happy. And it happens, it really does. It happens. So I thought you promised me to be off next week and then come to find out. It's like, oh hell. So yes, this is an awesome topic. I can't wait to get more into it with you.

Ryan Calkins 1:50

I mean, I know for me, at least when I when I first started, it was a lot of well, I don't even want to say it's when I first started. I think it's just something that I have always, even later in my career, I don't want to say struggled with because I learned how to maneuver with it. I guess early I struggled with allowing small things to slide. Like it just, you know, I was picking and choosing my battles, but I think I still do that, but it's more intentional, I think, to where it's like, I'm not gonna bother you with this because we have this big picture thing that's really happening, where I think early in my career it was kind of letting things go in a way to where, oh, well, if I don't bother John with this, maybe he'll just stop doing it.

John Moore 2:43

He'll just figure it out on his own. And I think for me, when I started in leadership almost 30, well, almost 25 years ago ago, um, I think it was trying not to be like the bosses I had. So taking a little of this, taking a little that, and saying, I don't want to be anything like them, but then not really pulling the good part about them because I was only dealing with the bad. I didn't think about the good parts, right? Which was, you know, proper management, proper leadership, you know, accountability, all those wonderful things, right? And so when I when I got this topic, when you assign the topic, I was thinking, I said, yeah, that that was me too. I think we've all struggled with it, but the simple fact that we are trying not to be what we all experience and we're trying to be something different, but then we're also not paying attention to that, that, that difference that we're missing is really not trying to be so nice and pleasing to everyone, but steadfast being leadership, being the steady course, being the one that keeps things steady, because being a leader is that, to be honest with you. It really is that. What do you think about that?

Ryan Calkins 3:46

No, I agree. I think part of the, I don't even know if it's a niceness trap per se, but it was a lot of saying yes to everything. One, because I guess I was overconfident in my own capacity, but it was also not wanting to let other people down. So it's like, yeah, I can do that. Yeah, I'll take care of that. Yes, I'll do this, yes, I'll do that. And then I don't know, as it I think it's harder to say yes and agree to something and to have to pull it back than to just not grant it immediately or whatever it is. And then if you have the means to do it, come back, it's like, yeah, I can do that.

John Moore 4:27

But then it makes me think about does it make me unapproachable? Does it make me be understanding? Does it make me being that nice person, you know, you know, what are the pros and cons about it, right? Does it really give me that intentional, like you said, that intentional pause that I really want to bring to the to the forefront because I'm really trying to be different than what I was brought up in? I don't know, it's such a struggle sometimes it can be because you really are trying to balance these two things out. And even with like what you just said about, you know, maybe they'll just they'll fix it. Maybe that they will start to come on, come to work on time. I won't have to tell them that they're late, they'll figure it out, right? I'll make these little innuendos where our bosses were like, Tardies, we're not gonna have it. We were read up. You know, it was just, you know, done. It was just straight up. But us trying to be nice and and not trying to rock the boat and trying to have everyone to like us, I don't always know if it really gets us where we really want to be at the end of it as well. No, it well, it it doesn't.

Ryan Calkins 5:26

I mean, I don't know. Like part of me with the uh the like, you know, say you came in late, right? And I'm like, well, John knows he came in late. Like, why do I need to tell him? He he knows what he did, like he'll fix it, right? And having bosses that get on you for that, it's like, dude, I was a minute late. Are you really gonna, you know? And I don't know. It's like I you had mentioned it where uh the stuff about the boss that you focus on, you focus on the negative. And in hindsight, it's like, yeah, he was a hard ass, but he did a lot of these things that were effective, even though it may not have been the best approach. And then it's like, okay, well, how do I take what he did that was effective, but not have to be a dick about it?

John Moore 6:12

Exactly. Because there is balance, to be honest with you. Uh, and what we have lesser than we than they had back then, there were there was more at stake back then, I think. Now it's more lesser at stake. I think we have a little bit more of a juggling where we don't have much at stake. So yeah, you could, you really could do more. But back then it was like we had to be on time. We had to do all these things because that was the accountability component. It was, it was bigger than just you're late. It was what late represented, if that makes sense, right? It was bigger than you didn't finish the the project or you didn't finish whatever was, you know, due to you, or you didn't have good quality scores. It was all of what it represented, right? It was a bigger, your character, your your discipline or lack of, right? So it was it was bigger than what it is now. Because kids now, they don't even think about it that way. Are you just bitching about one minute? But it's about your character. You know, I I don't wanna, I don't wanna have to question you. I want to know that you're gonna be on time. I want to know I can depend upon you, right? And unfortunately that wasn't explained back then, but then it was because the the the bosses would, in some shape or way, they would make it known that it's not just about being late. It's about you're gonna be a man of your word, be a man of your word, right? You're gonna be on time, be on time. If you're not on time, how can I trust you? You know, it's these other bigger components to it. Have you did you have those experiences? Was that a philosophy for you as well?

Ryan Calkins 7:40

Well, I mean, when so when I started working, uh my very first job was a uh it was a busser at a restaurant, like many people. But I was we had two bosses. There was the one that was the the total a-hole that would ride you on everything, and then there was the other one that was super chill. And whenever you had a problem, you go to the chill one, you know? Yeah. And I don't know. I mean, I appreciate it then because if I was late, it was like, oh, I could just, hey John, I'm a few minutes late, you know, I'm getting this in. You're like, yeah, you know, no problem. Blah, blah, blah, blah, blah. And then things go on. If I if you're not there, I have to go to the other guy. He's like, well, why okay? I'm gonna document that. I'm like, okay, well, now this is documented. And I don't know, like in the moment as the employee, obviously I want to go to the person that is more relaxed and understanding when things happen. And I think looking back, a lot of times I feel like you learn more from the experiences where you have somebody that is pressuring you. And I'm not saying that you necessarily want to be in those situations, but I think that forced uncomfortableness and really being pushed to do things helps you grow more than somebody that lets things slide because you don't grow from that. You know, you continue to do what you do and operate with the same bad behaviors.

John Moore 9:03

But what do you think the drawbacks, and I know, you know, we all know this, but I want to hear your standpoint. What do you think the drawback is by letting things slide and letting the person figure it out themselves? What do you think the drawbacks would be?

Ryan Calkins 9:16

Well, the drawbacks for me personally were when I was that same chill supervisor, one minute of somebody showing up late would turn into two minutes, and then it was three minutes, and then it was like 10 minutes. But not just that, it it's it, I was put, I was creating uncertainty in staff and making them unreliable for myself by not staying on top of the things that seem minuscule and and unimportant. But when they they build up, it's not just a tardiness. It's I can't trust you to show up on time, but now I can't trust the quality of your work because it's like, oh, well, I ran out of time, so here it is. Or, you know, it's showing up to a meeting that that I don't know, it's just it's it doesn't end up being one thing. It ends up compounding, and then it if it's one person, it's easier to to maintain, but it's usually not. It's that one person that who's taking the most advantage that is the biggest problem. But when you step back and look, it's like everybody is doing little bits and pieces here and there. And it's a it's a much bigger problem than just one bad employee.

John Moore 10:29

And and my point in asking that, and you did a great job, thank you, is people are watching. So you got to think about it's you say it's uh it, you know, it accumulates, but it also is a domino. Everybody else is watching and they're gonna start doing because you know the first thing someone's gonna say, well, John was late. You didn't say anything to John, and then so-and-so was late. So then, of course, they're watching, so therefore they start the behavior. So that's why I I can honor the old bosses, if you will, the old guard, because they had a secret to the sauce. I wish that they were more um transparent about it. So we would have had, and maybe they were in in their own way, but it would have been nicer. So therefore, when we came up in leaders, we would have had a better understanding as to why they did what they did, instead of just saying, Dan, you you're a real asshole. You know, you're just really bad, right? But it makes it make sense now because we've seen it. We've seen how people take advantage, we've seen how other people were watching, and it just keeps on ripple, just ripples and ripples. Now your whole team is a problem. And and that's why those control mechanisms, and I know people want to don't want to hear that word, but it's a true thing. Those control mechanisms make sense because people will start to take advantage, no matter what. They will, they'll start taking advantage. What do you think about that?

Ryan Calkins 11:44

No, I think that's the case. And I think part of it is you're trying to protect the relationship by being more lenient or or helping people, and it just leads to a very, I don't know, it's kind of uneven standards to the point that it creates the confusion and the problems. And it's like, okay, well, does this really matter? It it ends up being more problematic for you as a leader and a manager when you're allowing a bunch of different things to continue to occur.

John Moore 12:17

But then the the let's go back to some of the reasoning. I think we kind of opened opened it up this morning and this this this evening, thinking about some of the reasonings behind why we're trying to be the nicer bosses because sometimes people don't know how to deal with conflict. They're fear of it, um, the fear of not being liked, right? Um also then there's some other thoughts about the fear of damaging the relationship. They could be at a place for 20-something years, they know all of these folks, they they treat them like family, all of these wonderful things. And now I'm the big boss, and now I have to discipline you. That's huge. And and I think this is where a lot of businesses, and I've said this in previous um podcasts, is that that's what that's where they go wrong, is that they don't really train up the new leaders to give that sense of understanding and give that sense of, again, uh new leaders training so you can understand the difference between when we were working together and we were going to have lunch together, then now I can. And this is the reason why. Not only does that person know that's being promoted, but they know how to articulate that to their friends and let them know, no, I'm not trying to be funny, no, I'm not trying to be some kind of a way because I'm I'm a boss now, is that I just can't. Now I have access to stuff that I can't share with you guys. So none of that's really taught. And it really, really needs to be taught because I think that we would have better leaders. I think we would have more structured leaders, more intentional leaders, right? We would have uh long-term leaders that wouldn't get burned out and stressed out, right? Because I believe there's a balance of being a um a nice and kind, you know, I've said this to you and when I first met, started doing your podcast. Uh, I think that there is a balance of loving on your staff, but also being a disciplinarian or what a manager, what a leader, whatever you want to call it, in our roles because it has to have that balance. We can't just be one way because it's just impossible. When you're dealing with human beings, unfortunately, their flaw, like I'm flawed, people are going to take advantage of situations. So the best thing you can do is cut it off at the at the head so that therefore we don't have those issues.

Ryan Calkins 14:18

Yeah. I mean, you have to have standards and and guardrails on things, and and people need to know what boundaries that we're operating within.

John Moore 14:26

At the beginning. Yes. Yes. Versus mid-drift after something's happened. Now I'm trying to put up guardrails. Now it's this big scenario. It's like this whole culture change. It's like that's not how you were. It's just yesterday. So now why are we changing now?

Ryan Calkins 14:42

Yeah. And with the with the leadership development and the and the uh having hard conversations with people that you mentioned, it was, I think it's something that you continue to struggle with uh until you receive, like, I don't even remember where I was when I when I had it, but uh there was a specific training called Crucial Conversations that I think was really beneficial in helping to have those the direct conversations that that help to coach and it sets up scenarios where you know you you do a lot of role play and you have an employee and then a coach that's sitting there and kind of going through everything. It's like, well, you said this, and that caused this person to get defensive and da-da-da. And it sounds very, you know, like tedious or even well, duh. Like obviously you know how to talk to people, but it gets tricky because, you know, one misquote or or misstep, and it's like it can shift the entire conversation.

John Moore 15:40

You you uniquely made me think about when I was coaching uh a new leader and I was sitting in a room and he had to uh write up a staff member. And I remember, and I might have brought this up before, but I remember him going in with the staff member. And I mean, she said something and he was like, Yes, you did. You know, and they were just going at it. I was like, No, you can't do that. Because once I didn't say that then I said afterwards. I said, Because you once you do that, now you're putting yourself in a situation, right? You, you know, anything that she combats or they combat, you have them to write it on that document. We go back in HR and we have that conversation. We don't do that here. This is not the form for it, but again, no leadership training. So he was just thinking like, you know, like him and his wife. Oh, yeah, you did, you did it. I mean, he was going at it, yeah, you did it, you did it. And it was like, wow, that's not what we're supposed to do. Because unfortunately, there's a lack of training. And just think about right now, there's such a lack of training right now. People in the restaurant industry working at McDonald's, that was my first job. They don't have any skill set.

SPEAKER_02 16:45

None that developed them like how we were developed. Well, yeah. I what are you thinking? What are you thinking?

Ryan Calkins 16:57

What, what, what? Well, no, I'm just thinking it it's like I do think that a lot of people do genuinely care. And yes, I the hard part is you you just don't realize what it's going to be like down the line, you know, as things build until it's too late. And then you're like, oh man, I really screwed this up. And then, like you said, you know, it's it's hard to reel back in. And I mean, even without training, if there, there's I feel like there's certain elements of of common sense that are there and maybe people don't realize it, but I've seen it to where, you know, the whole concept with uh, you know, like yeah, the hot stove. Like you touch a hot stove, you get burned immediately, right? Exactly. Yeah, and that's the last idea. Yeah. So and and if you touch a stove and you get burned three days later, you're like, oh, well, where the hell did this burn come from? Yeah, yeah. And I've seen so many people that it's like, I have a problem with you right now. And I'm like, oh, I'll talk to him when it when it's a better time, you know. And I come in the next morning and I'm like, Boy, didn't John looks upset. I'll I'll talk to him tomorrow. And then we finally have the conversation. You're like, you're talking to me about something that happened two weeks ago. I see me.

John Moore 18:05

Remember that? You're sort of a situation. Absolutely. But it's it's it's it's still, I stay on the on on this, you know, nice leader. It's still such a wonderful thing to have, right? But at the same time, it's one of the hardest things to do because again, how do we find our balance? Well, I think how do you find that balance? Go for it.

Ryan Calkins 18:26

Well, I was just gonna say, I think for me, the the balance is in the approach. And it's always being respectful to the person that I'm talking to, even if it's a hard conversation. It's never coming from a place of being condescending or or rude or anything else. You can still be a nice person and a genuine supervisor or leader or whatever that cares about the other person having those hard conversations, but being respectful in and doing it.

John Moore 19:00

I wonder why do you think the having the conversations, why do you think that that's so difficult? Do you think it's so difficult because it's a cultural thing? Do you think it's so difficult because there is the relationship thing on the line? What do you think makes those hard conversations so difficult to have? And we want to be more on avoidance, like you were giving the demonstration before. What why do you think we do that more?

Ryan Calkins 19:27

I mean, I don't know why everybody does it. I know I just wanted to be liked and not be, because I had disdain for many supervisors and I didn't want to be a supervisor that everybody hated because I feel like uh what you you get more flies with honey, right? But it's also one of those situations where, like we talked about, if it gets out of control, you've lost what, you've lost your hive. I don't know, whatever.

John Moore 19:54

Yeah, you you've kind of lost that whole authority figure looking ish thing as well. I find it difficult sometimes when you, um not you, just saying in general, when when we as leaders uh are put in those situations where you have to have the car conversations and there are things in the way, culture, um, relationships, um, you know, whatever those things may be, right? Um, cultural dynamics, whatever it may be, you have to dance around those nuances. You're really, we I don't want it to be that way. I want it to be where we could just, you know, let's have a conversation. Let's talk about, you know, what we need to talk about. But then it's all about timing. It's about, you know, not waiting it to be so long, you know. Uh then you you don't want to do it when it just happened because it's too fresh and everybody's emotional. You don't want to be too far out. It's just a lot of dancing around, you know, a conversation that we really should be able to have. But it's a lot of uh nuances that, you know, are put in the way.

Ryan Calkins 20:52

It's just uh, I don't know. Uh obviously a lot of people are more approachable than others, and you tend to talk quickly to the ones that are approachable. It's like, oh yeah, you know, I screwed up, I won't do that anymore. And then you have the other ones where you know it's going to be a challenge.

John Moore 21:09

You're right.

Ryan Calkins 21:09

Because everything that you talk to this person about is a challenge.

SPEAKER_02 21:13

Yeah, yeah.

Ryan Calkins 21:14

Like it could be the smallest thing in the world. Like when you're done using the dry erase markers, can you put the lids back on so they don't dry out? And they'll be like, Yeah, yeah, yeah.

John Moore 21:23

Why do I do that? It's not my responsibility. Well, you used them, didn't you? It's like just a billion-dollar company. You can buy more markers. Exactly. Oh, we don't have enough money to buy new markers. Well, it's not about that. It's it's about putting the damn top on the market, right? But yeah, it's it's it's it's so interesting why we make it sometimes hard. And we just spoke about some of the factors that are there, but I think sometimes we make it harder on ourselves than actually it actually is. Do you think that too, or do you think it is just hard?

Ryan Calkins 21:52

I think it's hard. I I I think that I have made things harder on myself by you know my own practices and And trying to avoid difficult conversations and things. Um, I think that getting that that training that I had helped tremendously. And the the more you do it, the the more comfortable you get. But I think also realizing through going through all of that that the only person I well, I'm not gonna say the only person I was hurting was me, because I was also hurting everybody else by not having, you know, consistent accountability on things. And it it may seem small, but there's a reason that that those are there. And I think it helps to just to maintain order and expectancy. And when somebody shows up, it's not like, oh, I don't know what to do. It's like we do know what to do because we've been operating in this way. And, you know, in the well, at least in the Marine Corps, it was if you're 15 minutes early, you're on time. If you're on time, you're late, you know. It's like, well, yeah, that's a little extreme, but I also understand to to show up. And I know that I've mentioned on this show before about joining uh performance review meetings where the boss that was doing my performance review was typing away on a on a computer while we're on the screen together. And it just it was one of those things that like really pissed me off that I didn't even want to have.

John Moore 23:18

And you felt like he wasn't paying or she wasn't paying attention. What?

Ryan Calkins 23:22

No, it I mean, he clearly was trying to to multitask, but you're never really present with somebody when you're focused on writing something else.

SPEAKER_01 23:32

Like true, I don't know.

Ryan Calkins 23:34

And it was just one of those things that used to drive me crazy. And I had a conversation with him and told him, like, I I think it's disrespectful. I think everybody else that it happens to, and like performance review meetings should be ones that you keep no matter what. I understand like project meetings or other things that maybe reschedule, but if you're if you dedicate time to somebody for a performance review, don't reschedule it. And it was another thing with that same person where it was like, oh, well, I'm busy, I'm gonna bump John the next week, and then I'm gonna bump the next week. And it just makes people feel like they don't matter, you know? And it still bothers me when people do that. Like I last week I had an interview for an ambassador position for a an organization focused on veteran entrepreneurship. And uh it was a volunteer spot, and it was something that I wanted to do because I went through one of their programs and found it really beneficial. I went through the individual interview and that was fine. And then we had a group interview, and there was a regional manager, whatever her title was for how she was doing the program, but she's on a treadmill and sort of paying attention and is like, oh, you know how it is with entrepreneurs, like we multitask. And I'm like, I don't know, it feels really unprofessional to me. Like, I even for a volunteer position, I would still show up and be present for the person that's there, and it just the whole thing was very off-putting.

John Moore 25:02

No, I agree 100%. I I would have felt the same. It's funny you brought up the um performance review and the keep putting it off, keep putting it off. I have someone uh that I work with that, I mean, I think we can't count now how many times they keep putting it off, keep putting it off. So we start trying, you know, your mind starts to think, what's really behind that? What's what's behind the putting it off? Is it um I would appreciate someone saying we're trying to work on, and I've heard this before, we're trying to work on getting you some money. It's just taking us a little longer. Can you be patient with us? Tell us that, right? Versus we have a performance review, we have a review, which is also supposed to be a part of a merit, you know, uh increase that we keep putting off. And I think this has been months that they keep putting it off, keep putting it off, keep putting it off. And that's not cool. I mean, just think of what it does to the person themselves. You know, they're thinking, I'm not important enough to give me a proper review, right? I'm not important enough that you could take out the time. And, you know, whether it's a hard conversation or not, you're not getting money, or you are getting money, or you're not gonna get this. Or, you know, I rather you have it with me than have me in my mind and my head thinking all these crazy things, right? It's just sad. I think sometimes we do more hurt and damage in the states of avoidance than we do with just facing the matter.

Ryan Calkins 26:24

Yeah. Yeah. Well, you just I mean, you just have a level of professional responsibility to others. And I think the the way that you show up, like, I don't always wear a suit and a tie or anything else, but when I have a performance review for somebody, I show up in a full suit because it matters to me to be there for them. Like it's about them, it's not about me, you know? And like I could wear, I don't know, a t-shirt and shorts every single day and go into the office. But if I'm showing up to have a professional meeting with you about your performance, out of respect for you, I want to dress up and be present and professional for you.

John Moore 27:09

So, where did you get that discipline? Do you think that was from being in the service? Where do you think you got that discipline from?

Ryan Calkins 27:15

I think part of it, well, I think part of it was was being raised and and having, you know, grandparents' influence. I mean, they were both retired, the ones that I was living with, but it was still, I think it was just a different time to where it's like when you have work to do, you show up and you do your work and then you play after. And I I am not at all going to say that I am a professional that that never plays and jokes around because that would be a lie. But when it comes to being there for other people, like so I I was in a fraternity, I know big surprise, right? But when I got there, it was very loose, um just kind of in in approach and everything else. And one thing that I tried to do was bring some some order and respect to what we did. And we would have, you know, events and things that uh pledges would go through. And I made it a point to it's like, we're not here for us, like we're here for them. So when people would show up, you know, and and other brothers would be out of sorts, like there were guys that I had to send away from events. I'm like, hey, try next week, you know, you gotta go. I'm not gonna go into the detail details on everything on why, but I gave them the boot from events was just unheard of. And I mean, I was president at the time, so I could do that. But and it was just trying to like my whole thing is like we're trying to teach these incoming kids about brotherhood, right? And bring them in and have them join a brotherhood, but we're gonna show up and just be unnecessary a-holes. It's like, no, like I'm not doing any of that. Like, we are going to show up. We're here for them. We need to be focused on them when it's their time, and then we can go back to doing whatever we want to do. But anytime that we have an organized event for these guys, they are the focus and it's for them.

John Moore 29:12

No, I like that. I and I and I do like the fact even you bringing back up your grandparents, because um, I I think we've lost a bit of that type of investment, like not only in the simple fact of we're here for them, or when we're doing a uh merit increase, we're doing a uh performance review, whatever it may be, that it is to engage with them and then you give them the uninvited attention. I think we've lost that. I think it, I think people are just so more fearful about, oh my gosh, she's gonna freak out on me because she's not gonna get a raise, or oh my gosh, she's gonna freak out because whatever, then than anything else. And I think we make it more, like you said, we make it more about ourselves and we make it about them. How about, or how is she going to respond? How am I what is the best way that I can say it? This is gonna be bad news that she understands I'm not liking to give you this, you know, this news, you know, versus it being in the negative. How can we turn this sucker around, right? How can we make bad news sound more palatable than not? And I just find that some people, one, don't have the skill set, two, we're not trained. Everyone is not a leader, and that's okay. That balances this earth. You know, we have leaders, we have followers, we have, you know, all these different roles that people play. But it's it's it's really interesting when you think about how when it winds up to you having to perform and do it and you can't for whatever the reasons, whether it's fair, not fair, whether you're trying to be, excuse me, being fearful or not being fearful, or you're trying to be the nice boss, and you don't want people, whatever it may be, it just seems like it's always something that hinders us from being able to do what we could, what we could do and what we should do, which is like you said, show up.

Ryan Calkins 30:58

Yeah. Show up. I think a lot of it is also just you know, people I don't even know if it's being selfish. I I think it's just people like don't want to have the conversations and they have a ton of stuff on their plates, and all they're thinking about is I want to get through this conversation with John so I can get back to what I'm doing and do this next thing. And I'm like, okay, but this is important too. Yeah, like this is a priority. This person that you are responsible for, like, show up and dedicate that that hour or whatever time it is. Like, it's I don't know.

John Moore 31:35

Do you think from that and that standpoint spar is another makes me think about another thought or question? Do you think that is more of a leadership issue, or do you think that's again goes to training issue where um the the prioritization is not really there, or that we even think about prioritizing our staff in those kind of environments?

Ryan Calkins 31:57

It might be a balance of both. Like I I don't know if my care for others is necessarily, you know, training, like leadership training that I received. I think it's just a genuine care for the people that I'm responsible for, that I want to be there and be there professionally and give them what I would want on the receiving end of a conversation, or what I would expect somebody showing up to give me a performance review. And I think it's just for me, it's a personal, this is what I would want. So this is what I'm going to provide for somebody else.

John Moore 32:39

So do onto others as you would want them to do onto you kind of approach more, right?

Ryan Calkins 32:45

Yeah, I mean, I I guess it's the applying the golden rule in a way to yeah.

John Moore 32:50

Yeah. And I don't think there's anything wrong with that, but I also find that this is why I asked the question again, you know, me on the training side, I think it should be trained more that way. That we put it into the prioritization of things, you know, that we make this is what employees complain about the most, is that they're not important. Just what you're talking about. They're not important. Now, here the person's trying to be their best manager and be fair and be nice, they make them important, but then the employee, no matter what, still feels like they're not important. So it is again trying to find these balances between these things. One wants to be liked, one wants to be treated with respect. And that's real, that's real, that's real happening today in any work environment as it happened 30 years ago, it's still happening today. People want that balance. They want to be respected and they want to be considered. And right now, that's still happening. I mean, when you think about what's happening in the workforce now, uh, it's it's tremendously different. Morales are different, the the whole approach is different. Somebody was just telling me how uh they conduct uh different types of um health fairs, those things are different. I mean, everything is just changing. Just changing. So it makes you, you know, think about the whole if I'm gonna be a fair or I'm gonna be a nice boss, is there really anything you get out of it? You know, at the end of the day, do you really get something out of it or is that not the whole purpose at all? Is there anything you get out of you personally get out of being a nice boss? Being a nice boss, you know, do you get anything out of it? Because at the end of the day, sometimes you do and sometimes you don't.

Ryan Calkins 34:27

Well, I think the alternative is being a dick, you know? And I well, I don't know. I mean, for some people, I I I think that they're fine with that, you know? And they can show up, they don't care about anything. And I'm not even gonna say that I need to be liked anymore. But if I showed up every single day and and I treated others in a way that I didn't want to be treated, I would go home and struggle with it. And it's not even a matter of like not being liked, it's just like, man, I can't believe I was like that today, you know?

John Moore 35:05

Well, and then I'm looking at, you know, thinking about, well, being liked less, being trusted more, but being, but being trusted more in that same thing, you know, I'm trying to figure out is there this balance? I'm I'm not gonna be the nice boss, but am I gonna be liked less? Am I gonna be liked more? It's like, well, what's gonna happen here? I don't know.

Ryan Calkins 35:26

I I will say that my goal and intent is always to be liked. Okay. With the caveat that I know not everybody is going to like everything that I do. Or trust. And what I've always tried to do is deliver things that people aren't going to like in a way that is clear, that they understand, even if they don't like it, they know why it's happening. And I try to be clear with everything and intentional in what I do, and I share as much as I can without, you know, getting in trouble.

SPEAKER_01 36:02

Yeah.

Ryan Calkins 36:02

But I I I I think people feel I don't know, less trusting when they're receiving bad news, they don't know why, and they feel like something's intentionally being hidden, right? But when you can be as clear as possible, it can also make bad news more palatable.

John Moore 36:24

Absolutely. I agree. And timing is everything too. Remember your example, you could just you talking about something that happened two weeks, three weeks ago. You know, you try your best to like I was saying about the timing of it, you don't want it to be too far off, but then you also don't want it to be too short. You want to make sure that the timing is perfect and the best way that it can be perfect, because again, it that comes with the respect, that comes with the prioritization of you know, giving of whether good news or bad news. I think all of those things had to be considered. Um, funny we even said that about time because it made me think, hey, it's amazing how things trigger you. And I'm and this is nothing to be celebrated, you know, to make a joke about, but when we would terminate people, unfortunately, we would do it on Fridays. And we would do it on a certain time. We would do it at two between two and three. We would not do it like, you know, after, you know, time when they would go to work, you know, like after, excuse me, it wouldn't be their time to like five o'clock to leave for work. We would do it beforehand. There was a method to the madness about it. And it was supposed to be about respect. We weren't gonna fire someone and then everybody would see you. We did it on a Friday because it was less people around, you know, those kind of things. So it was about timing. It was about, you know, what it appeared and what it looked like. Have you ever seen that in your world? Yeah. Like on a Friday, too.

SPEAKER_02 37:47

I'm trying to remember when I got fired.

Ryan Calkins 37:48

I don't know if it was a Friday. Oh Lord, not you. Not you, crazy. But I don't remember what day it was. That could have been Friday.

John Moore 37:56

Yeah, it's a Friday. We always do it on Fridays. Always Fridays.

Ryan Calkins 38:00

Well, yeah, I mean, you do it on Friday because it it's safer anyway, right? No, we didn't even think about the safety. We really was thinking about less people at work. Because then they can go home and and ruminate all weekend and be angry without it being a weekday.

John Moore 38:15

Not do the postman thing. Yeah, but yeah, we would do it on Fridays. And it was always around three o'clock. That morning we're working on the document, we're getting the document together. I mean, I could do it like clockwork. We're getting that document together, we're we're making sure that it's being examined by HR. We have everything together, we have all of our points together, we're presenting it at three o'clock. We've cut off all their access at three o'clock. So when they go back to their desk, they can't go back to, you know, send, you know, uh, what's the thing's called? Viruses or, you know, get their last documents shut down at three o'clock. We sent that booking in. I mean, boom, boom, boom, it's done just like that. Unfortunately. It's nothing to celebrate, but when you were thinking about it, I was like, yeah, that's we we were very considerate about how we even, you know, terminated or laid off people. We're very, very considerate in that way. I don't know what you want to call that considerate, but we were kind of respectful.

Ryan Calkins 39:13

So did you guys like fire people and then go camping for the weekends so nobody knew where you were?

John Moore 39:17

Not me, because I didn't believe in celebrating after that. It's a terrible thing to let people go. No, it's not. It's not a good thing at all. Um, and some people, some respond, some don't respond.

Ryan Calkins 39:29

You know, space, right?

John Moore 39:31

No.

Ryan Calkins 39:32

Oh, you gotta watch that. They were cut up? No, it's uh, you know, Mike Judge, the guy that did Beavis and Butthead.

John Moore 39:39

Yeah, but they were cut up when they got terminated or something. What happened?

Ryan Calkins 39:42

No, they uh it was just uh they brought in these consultants to evaluate this tech business, and they were talking about layoffs, and they're like trying to read this guy's name that they couldn't, and they were like, Yeah, well, it doesn't matter, he's fired. I don't know. Yeah, you gotta watch it. Like the whole thing is just it's it's about working in an office environment and and all of the stuff that comes along with it. Oh, yeah, and it's stands the test of time. It's the same things that have been occurring for 30 years, and it is a fantastic and hilarious movie.

John Moore 40:15

Wow.

Ryan Calkins 40:15

But you gotta watch it and then we'll talk about it.

John Moore 40:17

All right, cool, cool, cool, cool. I'll do so. But yeah, I mean it's it's just um you know, we we we wanna be we want to respect our employees as best as we can. Do we always do our best? I don't think we do. I think we could do better.

Ryan Calkins 40:30

Yeah, I mean I think you have to want to do better. You have to want to and it it's all on the individual. I mean, it the way that you treat back to the golden rule, I guess, but it's you know It's all about how you treat people and you will want someone to treat, you know, and somebody else said that too.

John Moore 40:48

Um she just said that to me. She said that uh this young man was gonna be terminated, and he asked, he said, if anyone terminates me, could it be this person? And so that person said, Well, why? He said, Because you would do it with the utmost respect where others would not. And I was just like, Wow, the you first you know, again, people are watching, you never know who's watching what. You're they're watching how you interact with people, they're watching your disciplines. And I and I remember her saying that, and that that came up as well. It's it's about you know, people are watching and how how we conduct ourselves, and I think that's also important too. So that respect level should be there.

Ryan Calkins 41:26

I agree.

John Moore 41:28

Very good, very good conversation.

Ryan Calkins 41:30

Yeah, so the the things that we really hit on was the uh avoidance is what actually damages relationships, and that clarity in itself is a a kindness, and you can maintain a professional kindness by being clear in in your messaging and the conversations that you have.

John Moore 41:52

Clear and transparent and um also respectful. Absolutely.

Ryan Calkins 41:59

So I guess for for our listeners, is is are there any conversations you've been delaying with your team? Um should have already occurred.

John Moore 42:08

And and what are what are the feelings as to why you're delaying and why you're avoiding? And we have to get past that sense of avoidance because it's creating more of a problem than it is of a helper, if you will.

Ryan Calkins 42:19

And who is paying the price for that avoidance?

John Moore 42:21

Absolutely. At the end of the day, remember we want to make sure we give them the utmost respect, even sometimes when we don't believe they deserve it.

Ryan Calkins 42:29

Yeah, that's true.

John Moore 42:30

Yeah.

Ryan Calkins 42:32

And you're not being a good leader by making things easier for everyone.

John Moore 42:40

Honestly, you're not. It feels like you are, but you're really making it worse for yourself and you're making worse for the environment, because again, people are watching.

SPEAKER_02 42:48

True.

John Moore 42:49

So until next week, leading ain't easy.

Ryan Calkins 42:52

But you don't have to do it alone. Thanks for tuning in to Leading Ain't Easy. If something in today's episode resonated, please do us a favor and share it with someone else who leads or aspires to lead. Because honestly, none of us have this figured out, but we can all get better together. If you're a leader or professional feeling quietly stuck in your career, visit ReframeRise.com. It's a career and leadership coaching firm where I work with veterans and other high achievers to realign their work and lead with purpose. Again, that's ReframeRise.com. And if you're looking for leadership tools, training, or support for your transportation department, check out Bust Pro Network, where Ernie helps school transportation leaders across California build safer, stronger teams. Please subscribe wherever you listen, leave a review, and let us know what topics you'd like us to tackle in the future. And remember, leading ain't easy, but you don't have to do it alone.