When Your Best Employee Is Also the Problem

Ryan Calkins and John Moore discuss one of the most challenging dynamics in leadership: what happens when your most valuable employee also becomes your biggest problem. For any manager who's ever felt stuck protecting someone because of what they bring to the table, this one's for you.

Every leader has had this person, or knows someone who has. The employee who delivers (who knows the operation better than anyone, who customers love, who hits every number) and who also, somehow, becomes impossible to manage.

Ryan and John get into how this dynamic actually forms. It's rarely a leadership failure on day one. More often, it's a slow build: a new leader relies on an experienced employee to get up to speed, that employee gets more confident, and confidence tips into arrogance nobody wants to name.

• John talks through the "divide and conquer" trap when leaders hand off responsibility and never circle back to stay in the loop, and what it costs them later
• Ryan and John name what it actually feels like to be "held hostage" by an employee who has information or access that you don't
• John shares real stories from the sales world and the "indispensable a**hole" (the top producer whose behavior gets excused because the numbers are too good to touch)
• They talk through the very real fear of pushing someone out (the revenue loss, the pressure from ownership, the risk of becoming the target yourself for trying to hold the line)
• Ryan walks through how he's tried to coach high performers toward leadership instead of confrontation, and John challenges whether that works in commission-driven cultures
• They close by asking listeners to look at their own team: who's getting the longest leash, and would you tolerate that behavior from anyone else?

"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

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Ryan Calkins 0:00

Leading Aim Easy, the show that cuts to 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.

John Moore 0:57

And when this topic came up, it really kind of made me think about it. I was like, golly, have I had these instances? But it also made me think about all the history that I work with other companies. Yes, this does occur. When has it happened to you or has it happened to you?

Ryan Calkins 1:10

Yeah, no, it's tough because I'd say I think more it's been a problem for me when I come in somewhere and you first meet people, you see what they bring to the table, not necessarily who they are, but what they bring to the table. They they deliver, they know the operation, they a lot of times in the cases I've had, they've been there longer than you, they know how everything functions, they, you know, other people rely on them, et cetera, et cetera. Problems that I've had is once you start to get to know some of these people, that's where it's like, okay, well, you're doing these things, but it doesn't mean you're doing it the right way. Or you start to see things that make them difficult to work with, or other things to where it just becomes problematic. And if you come in as a superior for this person, there's a dynamic that you need that really is balancing who this person is with what you need them to do. But also when you have somebody that knows more than you do in the job, that in itself can be a problem when they are full of themselves.

John Moore 2:27

Exactly. Now, for me, as I was, as we kind of do our pre-show, I was thinking, no, I've not had this before, and I'm glad I haven't. Unfortunately, they were bad when he started being bad when they leave. But I find that uh I always, and I want to pose this question first before we get even more into it. I wonder how does the dynamic shift to where uh they know more than you or they have that empowerment. I wonder where does the controls, and I know people are not gonna like that word, the controls uh kind of either change or they have been released from the leadership that another person is now taking on such the responsibility like they do. I wonder what happens. Can you you can you think of a time when you've seen that that could have happened and how that could have happened?

Ryan Calkins 3:14

I don't know if it was necessarily leadership not doing anything. I think it's just the as people learn, they become more comfortable in what they're doing. And when they become more comfortable, they become more confident. And for some people, that confidence turns into arrogance, right? And cockiness. And I think that the longer somebody's there, when you first come in, those are the people that you rely on because you're new, you don't necessarily know everything. And this person or people are running away with everything. And you kind of uh give them that freedom to continue to do so while you get up to speed. And it's as you become more familiar and comfortable and confident, then you start to realize, okay, well, this isn't right. I don't like what this person is doing, I don't like this, I don't like that. And then it's the balance of, okay, well, this person that I've been reliant on is a problem. And how do I deal with this? Because they could still very well know more than you do and have more influence than you do because you're new. And and and again, this is my situation where I came in and I was new. For others, it could be, you know, you came up with this person and both developed over time, and and you have, or you were a manager and this person was there the same time. And whatever reason, they are starting to become a problem. I think it's just for me, it was awareness and learning more in what I was doing, and then realizing, okay, well, I don't like the way that this is happening or what this person is doing in order to accomplish what they are doing.

John Moore 4:54

And I think for me, as I'm listening to you and agreeing with you, I also look at it from a different side of it too, to where I'm looking at leadership, maybe not being new, but leadership, because you know, my mind always goes into the stressings sometimes of leadership where they're so overwhelmed and they're like, okay, good, you have that, I got this, and we kind of divide and conquer. But not knowing in the divide and conquer what you're creating. Because a lot of the time, speaking from experience, when I divide and conquer, I don't necessarily go back to figure out what did you learn? What are you doing? I'm just glad it's being taken care of. That was my fault. You know, my fault. Instead of, instead of saying, okay, so tell me what you did today, how did you fix that? Blah, blah, blah. So now I've learned, now I'm in the loop of what has happened. I was just glad, okay, you have that. I'm dealing with the executives, you deal with the staff, we'll rock and roll, we'll come back and say, okay, all was well, we had a good day, and we keep it rocking. But never did I, and I have seen leadership do this too, really get back involved in figuring out, okay, what did you do? Tell me how you did it. Tell me how you came up with that. Who were your contacts, right? Really getting into that granial part because what you're doing, and forgive me for using the word again, but you're losing of your power. You're losing of that sense of your leadership in a sense, because now they're gaining tidbits of things that you will never know. You may know stuff from the executive level, but you also need to know stuff from this level too. And you need to be able to be balanced in that. And I think a lot of the times I've seen it with my own eyes and also experienced it, that we're so happy that we have someone we could depend on, that then in turn they're just, and I know that they're doing it. I've seen the person that did it that I'm thinking about, she just was gathering and gathering and gathering. And then when it's time for you to, oh, oh, I don't have that. Oh, I didn't oh I didn't do it that way. And it's like, well, how did you do it? And then you're sitting there in the loss because they figured it out or they made that contact. And now you're like, okay, well, I need for her to, and then now you are codependent or you are you are held hostage by that employee because they have access to something that you don't. And I don't like that. Um every company I've ever gone to, I've always advocated no staff will hold us hostage. We need to cross-train people, we need to know what folks are doing because when you do that, when you allow for that information not to have an exchange back and forth, where it's from management to employee or employee back to management or peer-to-peer, you're screwed. You are literally screwed because they know they got the dime on you because if they leave, they're leaving with that information and they're leaving with that book of information. Yeah. What do you think about that?

Ryan Calkins 7:33

Well, as you were talking about that, there was an episode before where Ernie and I had discussed something similar. It wasn't the same topic, but it it was an issue that he was dealing with or had been exposed to, where somebody under him had a relationship, not romantic, just had a relationship with one of his superiors, which was making things difficult because it's like he was trying to do his job, but also being undermined in what he was doing. And it's another piece of a high performer or somebody that has sway that is able to get away with things. And it just puts you in an awkward position as a leader because it's like, well, how much can I let this person get away with and have this bad behavior because they perform?

John Moore 8:19

They perform. Or here's another one I thought of when you were talking. Um they're either of age of the staff, you're of a different age of the staff, or you have not connected with the staff. They're connected, so therefore you're like, okay, well, you tell them this, blah, blah, blah. When it's time for you to get something done, it's like hell and fire to get them done. But when they ask to get it done, they're on it and get it done rot and rot, because they like how you approach them. They like this, they like that. And because they have a different relationship than you may have. Now that's a management flaw. You need to figure out how you get that same relationship. But until you do, you're stuck. You know, you're stuck in that situation where, again, you don't have the power, you don't have the sway, you don't have the relationship that you need with your staff to get things done. So the reason I'm loving this conversation is because I want to tell our listeners that it is so important for a leader not to just um pass off things or delegate things. I learned this early part of my leadership. Don't just delegate, don't just pass things off because you really put yourself in a worse situation. Look at what you're not learning. Look at what you're not involved in, look at what you're not gaining. And then when that person leaves, whether it's in a good situation or a bad situation, you are still in the dark and you don't have that information that they had or they took with you. And then when it's time to say, okay, the next, the last two weeks, we're gonna have you sit with so-and-so and deep, you know, like download. They ain't downloading nothing. And you sitting there like, we ain't have none of that information, none of that insight that we need. And that's that's unfortunate. But that's a lot of times because somebody feels like I got the upper hand on them.

Ryan Calkins 9:58

Yeah, well, I and there's I mean, there's situations where when you confront that person, there's a very real risk that it, you know, like you're mentioning, it'll it'll lead to problems with the operation tomorrow. So when do you finally pull that band-aid off and have that discussion at the real risk of loss, as you said.

John Moore 10:19

And I think I think too to that, I think to be in that spirit of preparation, you don't get there. You have to remember that the job of the leadership is to, and I know this sounds real crazy, but you need to know everything. And you need to know it as best as you can. I've always been one to say, sit with my trainers, I want to know what they're training, I want to know how they're doing it, I want to know that what they're teaching. So if I have to teach, I train. But if you are, oh, I'm the manager and you guys are doing this, and which I've seen a lot in my career, you're gonna screw yourself because you're not gonna be prepared for those moments to where you're not able to do what the what needs to be done. And leadership above you has that expectation.

Ryan Calkins 10:58

They do. They do, but a lot of times leadership above you are the ones that are saying we can't afford to lose this person. Because they're keeping all of the stuff together.

John Moore 11:09

So it seems, yes. That's why we can't have that one person again holding us hostage. I know that sounds harsh, guys, but as you are managers and you're leaders, you will respect and understand that we cannot be held hostage by our staff. We have to figure out how do we level that playing field. It cannot be where somebody has more knowledge than you and you're left to dry and you're just sitting there with your hands like because you don't know what to do.

Ryan Calkins 11:34

Well, especially so when it becomes the the the behavioral stuff, which is typically the reason why this type of employee is who it is, right? Or so you know the thing is like nobody would allow that from an average employee. No, they'd they'd be gone. So why do we allow it from performers?

John Moore 11:56

Because they perform. And that's the sad part. I mean, the thing of it is is that so let's go back into sales when I did the mortgage industry. If somebody's a producer and they're making a hundred or one point something million dollars, they're getting anything they want. Anything they want. They're not working from home, they're working from home, they're not coming into the office and not following the policies like they need to because they're making business money, which should not be the reasoning why. And then also look at what it's doing to morale. People are thinking, well, that's lowering morale. And then you have sales folks that say, well, that's increasing morale because everybody wants to be like that performer. But then when you get multiple of those people, now you got multiple people with behavior issues, not following policy, not doing what they're supposed to do. So it's it's you gotta nip it at the butt before it gets out of control. Yes, go ahead.

Ryan Calkins 12:43

Well, I don't know. I was thinking, so like even with high sales performers that everybody wants to be like, that doesn't I I mean, I guess I'd argue that it doesn't necessarily boost morale. It may boost competition, but I feel like those that aren't at that level still see the same result that, oh, this person is getting preferential treatment, which would seem more detrimental. And it can go both ways.

John Moore 13:06

You can have some folks, like you said, that are go-getters and they they look at that and say, I'm I'm gonna, you know, do that too. And then you have the other one who's struggling and trying to get there, and they're seeing also, well, he doesn't have to be on time, or he doesn't have to, you know, sit at his desk. He's doing all those other things. So there now we're seeing this imbalance. But that's also what high performers also do. Well, right.

Ryan Calkins 13:28

But when you when you would apply punishments and reprimands to average employees, but you're not doing that to your performers. Not only does it set a bad example, but it also shows everybody exactly what your standards are, right?

John Moore 13:47

It does. But then look at the company. Now we got to go company, company culture, company dynamic. You can probably even go to HR and say blah, blah, blah. But then if the CEO is about making money, she's gonna say, well, you know what? It's all about making money. They're all doing what they're supposed to do. I let them do blah, blah, blah. I've seen it. And it's a hard, it's a hard pill to swallow because what you're saying is absolutely correct. The morale, the policy, the HR, all of these different components in it are all looking in their heads or spinning because they're trying to deal with this influx of um uh personnel policies and procedures that are not being followed. And you got one group of people that you want to chastise and you, oh, they're not on time. And then you got another group, oh, whatever, you come in. No, that's not cool. But that happens. And it's not, it's not cool, but it happens. And it's sad. But it's always unfortunately about something. If money was not involved, would you do the right thing? And the question will be, yeah, if it wasn't involved, but I'm gonna some money, so they're gonna they're gonna do what they want to do.

Ryan Calkins 14:50

So that's what leads to the one type of uh person that we're referring to as the indispensable asshole, right? That knows, oh, well, I can't be fired, I'm too important, so it leads to belittling and you know, like you said, showing up whenever you want. Like their customers usually love them because they don't know.

John Moore 15:09

Um, slapping up employees in the office, coming to work intoxicated, but you're the top producer, you're making a hundred grand in this office, and this is a small office, it's not a big national conglomerate. So, yes, this is real life, it's happening.

Ryan Calkins 15:29

And in the situations I've seen with that type of person, there's enough complaints internally that upper management will have little conversations here and there, but they never have the conversation that actually makes a difference or pushes that person out because they're too important, right?

John Moore 15:51

Because think about it, the owner or the CEO knows this name. They know they're making 1.0 million, they know they're bringing in 100,000, that one person. So you let them go, you have let go a chunk of their asset. So it really puts someone in the rock and hard space, and it really Fs that manager up a lot because they're trying to manage this employee and they can't even manage them because they're a top producer. And their lies that holding them hostage, they know you won't do anything to them. They're like, okay, I'll just find me another job. And it's like now everybody's like, wait, wait, wait, we didn't say you need to leave. We're just saying you need to come in on time. Well, I don't want to come in on time. And then they start playing the role. So my thoughts are you you try your best to again level the playing field so it does not get to that point of out of control. You gotta keep everybody on the slow and flow. It's like, okay, yeah, you're ringing, oh great, but you still gotta be here on time. Great, you but you still gotta fill out these documents, every loan or every sale, you still gotta do boom, boom, boom, like everybody else. Oh, why do I gotta do that? You see how I'm your top producer because it's policy. If you don't do that then, if you don't set those precedents and culture, you're gonna be screwed. As soon as you slip up, they're gonna get that intention in their mind thinking, but I'm a top producer, why I gotta do all of this?

Ryan Calkins 17:10

So, as a leader, how do you get over that fear of potential loss by cutting ties with somebody that is creating toxicity in your workplace?

John Moore 17:22

That's a hard one. Because think about this, you're a leader, and you're also in your ears your leadership. Again, they know that name, they know that person's a producer, and they're like, oh, you know, give Johnny a break. You know, I just heard he had a kid, you know, blah, blah, blah, making excuses for the behavior. I've seen it. What do you do? You're in a rockin' hard space. I've seen managers leave because they felt like I I couldn't get anywhere. And that's a bad situation to be in. Because you cannot manage your staff.

SPEAKER_02 17:53

You just can't.

Ryan Calkins 17:56

Right? So when that person's output is exceptional, but it's damaging everybody else, and you see it, is it a matter of having enough goodwill and trust built up with leadership to say, look, I need to get this person out. We are going to suffer a setback, but you know, we'll recover within three months, six months. I mean, what argument would you would you make to push past it?

John Moore 18:24

I think it would be, and that's a good one too. I think because the first thing that came to mind is how egregious the incident is. If it's something that's such a to a point of egregious, and I use that word specifically, if it's something that's so egregious, you will hopefully have HR and upper leadership to support you because now we're talking about lawsuits. Now we're talking about even greater loss than just the loss of the employee and what they bring in, right? So therefore you may now have the attention, but it has to be something that is just that big. If it's minute, they're not going to push it as much. Because they're still looking at dollars and cents.

Ryan Calkins 19:00

True. But most of the time, it there is no egregious event that that leads to a a termination. I mean, there there are for sure. Sexual harassment, it could have been a rape, you know, car, it could be any of those kind of things. Go ahead, go ahead. But but most of the time it's just this high performer, right? It's it's the behavior that that continues to go unchecked. And it gets to a point to where it is so bad that if you don't get this person in line, like you're screwed. So maybe it's not forcing them out, but you have to start documenting and holding this person accountable. And they will hoot and holler and go wherever they can to try to make you look bad. And then what? It's like you either get run out or they get in line.

John Moore 19:49

And I think it's more the run out than unfortunately, then they get in line because that's where the rubber hits the road. Uh and is my management skills and knowing my policies and procedures gonna uphold my decision making of disciplining a person where this person could leave us. That's something that they're gonna weigh. Because you gotta understand, unfortunately, and I know you know this, you know, people are greedy. They're looking at dollars and cents. And so this person or persons are really kicking butt and making those numbers is always making them hit a billion. I mean, I remember we were from mortgage shop, they was making one point something billion a month in mortgage loans. And all of those kids was making that money for them. So it's like, uh, they weren't trying to hear it. They weren't trying to hear it. So I mean, you you get you be you become this rock in the hard space. And so what I what I've also seen is people just acquiesce. They just feel like, look, I'm getting paid to. They don't care, I don't care. And that's a bad, that's a bad mentality we have, but it's a reality. But to your point, yeah, if it was in a regular world, yeah, of course, we'll be able to do things. But that will be in a regular world where, again, policies and procedures were followed, um, where you had the support of leadership, the people who own the company, all those good things. But when you're talking about making money and everything is about money, if it's in a sales world or it's about a money-driven, not a service type world, wow.

SPEAKER_02 21:22

You're talking about a huge defeat.

John Moore 21:26

And it feels just like how you think it, it feels awful because your hands are tied and this and this employee knows it. They know they're top producer and they take advantage of it. They do. I've seen it, I've seen it with my own eyes.

Ryan Calkins 21:41

Yeah, and then you get you get pinched for for trying to do the right thing.

John Moore 21:45

For doing the right thing. And now you're the booger. Now you're the oh, don't talk around John. He was gonna talk to HR about you. And then now you become the one that everyone is looking at as being like the outsider, and you're like, I'm just doing my job. Seen it. It's no joke. And it is sad. It is. It's quite sad.

Ryan Calkins 22:03

Well, I I have seen other leaders that they get in that position and then they become jaded because there's nothing that they can do. And they're like, well, I guess I'm gonna get this paycheck and coast from here.

SPEAKER_02 22:16

Which yeah, which is sad.

Ryan Calkins 22:20

And I I don't know. I struggle because I can't do that. You know? But I also it it's it's hard for me to just cut ties and bail too. So it's like a battle that is worth fighting, but it is exhausting.

John Moore 22:37

It's extremely exhausting, especially when there's no end. See, you're looking for an end because of your world, there's an end. Something's gonna happen, you know. No, my mind there is for sure. Okay, good. You'll buy it here, right? But sometimes in this realistic world, there is no end. And in my diverse career, I've seen sales, I've seen service, I've seen every level of it. And it's sales is the worst. They are the worst. Sorry guys, but y'all know I'm not lying. Sales is the worst. If it's about them bringing in money and it's a small outfit or a large outfit, and they're trying to make their goals, that manager will start to sit back and like, you know what, I'm getting my commission off of them. I'm not gonna care less. And won't. And you kind of get to a point in saying, I get it. Because if you're not getting the support from the leadership that you're supposed to.

Ryan Calkins 23:33

No, I agree. I think for me, that's where a lot of the kind of trying to find historical context and why things are the way they are now has been beneficial in seeing how stuff developed and being able to talk to people that have been there longer and watched it and leadership that is willing to share and knowing that it isn't a quick resolution because if you go in guns blazing, that's the quickest way for you to end up getting screwed. And I have been that person that has gone down in a blaze of glory. So, what I've tried to do since is look more long-term. How can I, I guess, strategically transition the change that I want using this person as kind of, I don't want to say the tool, but being able to slowly adapt and take what they are giving you, and I don't necessarily want to say use it against them, but kind of use it against them in a way to force the change without, I guess, direct confrontation. And I don't mean that by like, you know, kind of scooting around the edge of everything, like you're having direct conversations, but it's not like ultimatum type conversations. It's more trying to coach without being condescending, which is difficult with somebody that is full of themselves to begin with and already doesn't care what you have to say, but it's trying to find things that they relate to and motivate them. The successful attempts that I've had is using them as I guess tools to kind of foster that change in getting them on board as pseudo-leadership, if that makes sense, and exhibiting behaviors that others can model and talking up ways to progress. And it's more difficult with sales where a lot of times you don't want to get promoted because you're making a ton of money. That's not my avenue. It's never where I've been. But in operations, being able to use people that are that mindset and helping to, I don't want to say form them. It makes it sound like I'm manipulating, but it's more leveraging their skills to try and help them become better at their job in terms of leadership that is really what you want other people to emulate and not the bad stuff that you're allowing them to get away with.

John Moore 26:28

And as you're thinking, my response immediately was it's gonna be a catch-22. You're gonna have one that you are able to start to pull back their responsibilities, right? They're gonna then start seeing this is the other side. They're gonna start seeing, I'm doing less, I'm doing less. Hey, what's going on? So you might have, when you're pulling back some of those responsibilities, some of those meetings, some of those reports, whatever it may be, you want to start pulling some of those things back. That person's gonna start recognizing that. And then they're gonna be like, now I'm getting bored. Now I have anything to do. They're gonna want to go anyway. Because they don't have what they had before, which was the feeling of the carte blanche. I have access to these reports, I know this, I know that. Now, all those things are being pulled away, you know, using your example, because now you're trying to pull back their responsibilities in a sense so that therefore, because I know you're not doing your best. You're your performance, excuse me, you're you're performing at a level by doing the job great, but your uh employee performance is at a lower level. So I'm trying to pull things back from you so we can get this performance level up. They ain't gonna see it that way. We're talking about the the high performer? Yeah, thanks.

Ryan Calkins 27:40

Oh no, I didn't I didn't mean to imply pull pull like responsibilities away. I meant pull like information and kind of leverage that person to help start to share that knowledge and kind of put them into a kind of like pseudo-leadership position to where they are starting to get more positive authority, but then letting them know and coaching, like, hey, you know, by doing this, people see this, da-da-da, and trying to coach them into the behaviors that you need from this person.

John Moore 28:15

Come to be. Yeah. And and I think that that could be great. I'll still hold on to the to the catch 22 scenario because for me, I would want to pull some of their responsibilities back until they increased in their attendance and all these other things, right? Because my excuse would be the writer would be is that I have you have too many things on you that maybe it's it's too much on you and you're you're preoccupied. That's how I probably would try to lead in with it, right? So let me pull some of these things back, your reports, your this, your that, and and maybe let's get you back on a level playing field. Well, I've seen to where that could have very well been, again, the time when someone is saying, Well, I don't have anything to do now. Behavior still continues to be poor because now morale has gone down because they're not doing what they did, what they did before. They don't have access to the same stuff that they have. So it's like, that's why I say what I was saying earlier, try your best to get a hold of these things early. Even if, to your example, you're new and you're seeing these things. You know, I used to make statements and sometimes it would get in trouble, but I would say, yeah, I like to I like to manage those things. I would say that from the get-go. Because I want them to know, yeah, you might be doing those now, but I like to have my hands on those things. I like to be able to get more engrossed into it. Oh no, I used to do it, oh no, I appreciate you doing it, but at one point you're gonna transfer it over to me. Because I need for them to know I want to be in the loop too. And again, it can go either way. I've seen it. One of my good um lover to death, we're still friends, one of my good leaders, she um, I would, I would say, I could, I could, I'll pull this back up. Oh no, I could do it. And you could just see how it felt like it was just depleting her. Because she she she functioned and moved based on this chaos of all these things she had to do and which she was good in managing it. But to feel balanced, which this is the same one I said we would divide and conquer, because we would, we would divide and conquer. But I would very seldom say, okay, what did you do? Because I knew she handled it, which was always my thing. I should have knocked done. I should have been like, okay, now tell me what you did. How did it go? Boom, boom, boom, because I knew she got it. And that's great to feel like that, but it's not always good just to feel like that and leave it that way. Because it could lean up to having a person who gets cocky, who gets to having problem issues, and then you can't do anything with them. Yeah. Then now you're screwed because now you stop. So I I would really advise. I mean, let's let's talk about this. What would you advise? Would you advise like where I'm thinking I'm going in reference to being proactive when you see it, do something about it immediately? Or do you think you are going to kind of see how it plays out and then it becomes a major problem? Then we want to do something.

Ryan Calkins 31:04

What do you think? It depends because when I'm the one coming in, I usually observe for a while. Like I want to see the dynamics. I want to see how everybody reacts and responds and treats each other and who knows what, you know, both in a process uh application type of capacity, but also in how they treat other people, how they interact, what their team building is like, uh, you know, what they're sharing and teamwork and everything else. And I observe for a while and then I start to have conversations, like initial conversations on observations that I've had and work with them to talk about goal setting and stuff like that. But not like I hate to say it like that sometimes because I don't just sit down, I'm like, well, John, this is what I've seen from you the last six months. But it's more most of the observations I keep to myself, right? But I do let them influence where the goal setting and the thing that they need to accomplish comes out through that.

John Moore 32:09

Yeah.

SPEAKER_02 32:10

Um what was your question?

John Moore 32:13

More of do you think being proactive or reactive? You said you're thinking doing the goal setting, putting those things up front. Go ahead, I'm listening.

Ryan Calkins 32:22

For me, initially, when I when I first come in, it it's more reactive because I want to observe, I want to see, I want to get a lay of the land. And then from there, I move into proactive and really helping to shape how I need my team to be, how I need people to work together, the knowledge share that we need and moving together. Um also if I come in at a level that isn't, if I don't have any responsibilities for other people, then I can come in and be more proactive. But I also want to see the environment because I've, you know, been that young employee that comes in and I'm hard charging, ready to go, and then nobody else wants to move. So then I become that person. So I think that there's a balance between reactive and proactive. But anytime that I'm trying to implement change and bring whether it's cultural, whatever, you have to be proactive because being completely reactive, you're not going to get anywhere.

John Moore 33:18

Who do you think is at fault the most? This is a burning question. Who do you think is at fault the most? And I'm using that word specifically. Who do you think is at fault the most that this employee has gotten to this place? The behavior issues, the accolades, who do you think is the one that's really at fault?

Ryan Calkins 33:36

Aaron Powell Whoever allowed it to develop to begin with. I mean, it could be that person's direct supervisor, or maybe that supervisor left because of the way the employee and everything else is. I think a lot of times it's in the small companies that I've been in, it's definitely on ownership that allows things to develop and go unchecked. For larger companies, it's hard to say that it's ownership or the executive level because they're so far removed from everything that every department, division, site are completely different.

John Moore 34:13

Yeah, they run like their own islands.

Ryan Calkins 34:15

Yeah, and that they think that everything is exactly the same no matter where they go, but it's not. It's the individual general manager or whoever it is at the site that allows for that culture to be the way that it is.

John Moore 34:30

And then I also put some onus on the responsibility of the employee. I I question, was that their intention, right? To come in. You know, some people come in with a plan. You know, was it their intention to come in that way and do that? You know, some people are very observant. They can see where they can manipulate, where they can, you know, do things and make it rock and roll. I I look at it that way, some responsibility. I look at ownership of that leadership themselves, that they they saw something, they knew that something was off, but they elected to go, dang, but this is a top performer and they didn't do anything about it. And then I go on the company side. So I think there could be multiple parties that are responsible for the behavior. Um, because it's unfortunate to celebrate someone with important behavior. You know, you should celebrate someone with across the board, but I know that many times I've seen it's like, yeah, I know I'm late, but look, I made my goal. I can hear it in my ears. I can hear them saying it, but I made my goal. I made you a million dollars. Isn't that not good enough?

Ryan Calkins 35:34

But that's where you gotta coach on, okay, yeah, you made us a million dollars, but you cost us another million and other employees that are disgruntled or whatever. And I think that that's really what I was trying to get to before is helping that individual understand to raise their own standard and contribute as a team, because not only do they still mostly maintain their own numbers and what they bring to the table, they make everybody else around them better. And when everybody else is better, the team is better, the company is better, everybody is more productive. And those are the people that can end up being amazing leaders because they're already great at what they do.

John Moore 36:21

You're right. And I'm gonna kind of be devil's advocate here. And it's like, but that's not normally always. You have a competitive person, a competitive department or competitive, whatever it may be, they're not thinking about anybody else but themselves. So you come in with that philosophy, which is so freaking great, right? To take that energy, mold it now, you know, spread it out against the group, and everybody should. They don't care. I just made a million dollars.

Ryan Calkins 36:50

Right. I mean, you can still have individual rewards and benefits. So I think that you can have, I don't even want to say friendly competition. You can have it be a competitive environment, but you don't want the competition to be detrimental to the goal.

John Moore 37:07

But unfortunately, and I know I'm talking to a world that's not yours, sales, where this is might have seen more primary, and I've seen it in operations too, where you have let's say a lead who really knows everything because she's been there the longest or he's been there the longest. I've seen it there, but I've seen it more harshly and more realistically in sales, that what you're saying would be great, but it would not always work because they're only thinking of the bottom line, how much money is that?

Ryan Calkins 37:34

Well, it doesn't always work, for sure.

John Moore 37:37

And and but it's a it's a great idea. It's really a normal idea. I mean, what you're saying is great, but it's unfortunately in this world where people are driven by money, especially this generation, I see, you know, you start talking about money, oh, how can I make it? How can I make it? Um, they're gonna want to make the money. And they could give a balls about, okay, what that's doing to you and my morale, they could care less. Um, but I think it still goes back to, again, like we said, and I agree with what you're saying. I just wanted to give an another opinion and look at it. It's different industries, different philosophies, different cultures, because everyone is not of that same culture thinking team oriented. They're just not. Not even thinking about it. Self-driven, self-s and which is why the behavior is that because they're selfish, unfortunately.

Ryan Calkins 38:28

I do want to clarify that somebody being blunt isn't necessarily toxicity in itself, right? And you want people, yeah, direct, but you also you want people to disagree, and it's not insubordination just because somebody doesn't agree with what you're saying.

John Moore 38:47

I think it's how you do it. Isn't that? I think it's how you do it. Would you agree on that? Would you be because I think to your point, I agree with you, but isn't it how you go about doing it and where you're doing it?

Ryan Calkins 38:58

It is. I mean, I it I guess there's still a level of tact in the disagreement, but I guess what I'm getting at is somebody being unpleasant to work with isn't necessarily creating a toxic environment. I just want to differentiate that just some of the things that we've been talking about with behavioral stuff, like if somebody just sucks to be around, it doesn't necessarily make them a bad employee, right? Well, you yeah.

John Moore 39:22

I'm with you. I'm with you. Yeah. Well, and yes, but then also someone could assess it as that because that's their opinion of that. That's not what we're talking about right now, but someone could assess it that way and still feel like they're like, you know, they really suck. Every time we turn around, we're in the meeting, they're interrupting you. You can't even get a full thought out. Or, you know, they always are going against you, or you know, you have that too. And it's just unfortunate. But I think those, again, you have to have a proactive approach with it. And I think that I want people to, yeah, bring your ideas, but I also always want you to be respectful. I want you to be disciplined, that you're you're identifying the audience and the and the environment. Because it's not just you. Yes, you have an opinion. You might even have passion around your your opinion, but you also have to think about how people are receiving that opinion as well, or that thought. I agree.

Ryan Calkins 40:11

I guess the thing that matters the most is how that person is impacting. Yes. Like they can be unpleasant, but still not be disruptive. Well, you know what I mean. Like you can have somebody that is gruff, but they're not necessarily disrupting the team and damaging the impact of what the team can accomplish or what the company can accomplish. I think when that impact is detrimental is the point to where it's like, okay, we have to stop this now. You know, if this person leaves, it's going to suck.

John Moore 40:47

But we gotta do what we gotta do. Yeah, and that's in a more hopefully a normal service-driven, operations-driven environment. Yes. Yeah. Yeah.

Ryan Calkins 40:56

I mean, that that's all I really know.

John Moore 40:59

And I'm with you on that too, but I've just seen so often on the sales side, it's just scary. It really, really is. Because you're like, wow, they're doing what? And it's because they were bringing money in and then making commissions off that 1.2. Just think about the commissions off of 1.2.

SPEAKER_02 41:19

I don't want that. Yeah. I know that's right. Yeah.

John Moore 41:27

Just think about the damn commissions of $1.2 million that we made. I mean, we I remember our hearing numbers, oh, we made $3.5 billion. Like $3.5 billion in loans. I'm like, what? Wow. And that's one person on a team of maybe 30 people making $1.2. Stupid. Ridiculous money. So of course it's gonna be get arrogance. Of course it's gonna bring in all those things we're talking about. But no, I agree with you. I think that a person is not um, we shouldn't label or wouldn't label a person who speaks up, or there's a little um there's another word I wanted to use. It's it's not as delicate or not as savvy with their with their their their speech and tone, you know, or tonality. Yeah, I think you know, we give them a little break. But at the same time, if we see this becoming excessive or abusive, we gotta say something because it's like it will become disruptive over a period of time.

SPEAKER_02 42:27

Yeah.

Ryan Calkins 42:29

Now, for for listeners, I just want to have you take a moment, think about the person on your team that gets the longest leash and why do they get it? Have they earned the trust or have you become dependent on them?

John Moore 42:44

And what does it really make you feel like when you see it, when you observe it? How does it make you feel? Does it make you feel like the left man out? Does it make you feel like you want to accomplish that and be that person, or does it make you want to feel like the opposite? I think that's something else we need to look at our own selves to say, what are we all striving for? Are we striving for that type of lack of discipline, or are we striving to be disciplined and enjoy what we do? I think that's something else to think about too.

Ryan Calkins 43:08

And if someone else on your team behaved exactly the same way, would you tolerate it?

John Moore 43:14

Would it be from a company standpoint? You know, and that's something that we need to ask all of us. And I and I think what we were discussing, I'm asking the audience too. Think about the approach. Do we want to be proactive or do we want to be reactive when it comes to these types of things? And as we both agree on, we we want to be reactive to a degree because then we want to be proactive so we can nip it in the butt. The reactiveness is that we've learned what's happening and then we want to react to it so we can fix it. And then we're fortering in the future to make sure things are fixed so we don't have those problems that continue to persist. So think about how you want to approach it as well. Yeah. Well, hey, we enjoyed this conversation. Hope you did as well. We would love to hear from you. So please comment, like, subscribe. We would love to hear from you. Any ideas? Um, please bring them to us. You know, this is this is our form as well as your form. So until next week, leading ain't easy. But you don't have to do it alone.

Ryan Calkins 44:10

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 Refraimerise.com. And if you're looking for leadership tools, training, or support for your transportation department, check out Bus 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.