“How Can I Ensure That The Team Stays Loyal and Doesn't Leave To Go Work For Another Company?”

Dave Kashen discusses how to keep your team from leaving. He covers compensation and appreciation, clear roles and growth opportunities, and weeding out people who don't fit the culture. Managing your own fear as a leader matters too.
How can I ensure my team stays loyal and doesn't leave to go work for another company, especially when going through difficult times and like having to lay off people? For example, one of her top employees quit and she had to tell, you know, the rest of her team and she was nervous that the response is going to be like triggering a waterfall of people quitting and leaving.
And if people are unhappy, so like the dominoes.
Yeah.
Yeah. Well, first of all, it's our minds tend to make up the most negative story about what's gonna happen in the future. So it's very common when a top performer or like beloved employee or culture carrier leaves, uh, for your mind to imagine it's gonna lead to this domino and everyone's gonna quit. I've rarely seen that to actually be true. So that's first thing is just recognize that your mind's just making up a story and see how the opposite, you know, ask yourself how could the opposite of that story be true? Second thing is, you know, the question was how do I ensure people stay loyal and don't leave? You can't. That is not something you can control and have certainty around. So the question I would ask myself is like, how do I create the conditions for people to want to stay? And it's maybe a tangent, but I, you know, I'd mentioned we had our offsite and, you know, it was just 3 of us, me and Seth and Jory. And Jory's kind of runs our operations for our venture fund. And she's just been so generous and like she just gives and gives and like tries to take as little as possible, understanding our constraints and all that. And the paradox of that is like we just want to give her as much as possible, whereas like it wouldn't be hard to imagine someone in her position being like, well, I've been doing all these things for you guys and you owe me this, or like, I, you know, I'm demanding that. And funny how it creates like the opposite effect. Like, so similarly, I think part of it is being as generous as you can with people when you don't have to, right? Like, often, you know, there's a lot of leaders who basically try to, for example, like, pay as little as they can get away with, you know. And but then when someone comes and is like, hey, I have this offer from a competitor You know, then they're like, oh, okay, well then, you know, they'll go match it and maybe the person will stay, maybe they won't. But you know, it's like there's this notion that like people don't, people don't stay for the compensation, but they might leave for the compensation. Like in other words, people want to feel valued.. And so if you convey to people that you don't really value them, whether that's through compensation or other ways, like often it's too little too late when they, you know, don't feel valued and come and try to like claim the value. You know, that's really what's behind a lot of these conversations around compensation sometimes is it's really like people saying, I don't feel like you value me. And so at least like pay me in this, you know, more so that I know you value me. And that, you know, we are— leaders are, and humans are for some reason very stingy with their appreciation. And so like the, you know, one of the things to be gen— you know, I say be generous. I don't just mean compensation, like be generous in your appreciation. Hey, I noticed you did this thing. I really appreciate you for You know, the way you step up, I, I know that, you know, like catch people in the act of doing things well. And it's amazing how powerful, like the words, especially if you're, you know, boss or manager. Yeah. There's this, this like line that like your, your direct manager has a bigger influence on your health than your, than your doctor.
Right.
It's like really affects you, the relationship with your direct managers. So if you're someone's manager or if you're managing managers, like, be really thoughtful about how do you have people feel appreciated, valued. And then like most people want to feel like they're growing and developing in the ways they want to. So, you know, as a leader, your job is not just to align people with what the company needs, but also to do your best to align people with what they need and what they want and the ways they want to grow and develop, which require you to know that. So that's, you know, having conversations with the people on your team about how do you want to grow and how do you want to develop, and, and then actually like making efforts to help them develop in that way. And ideally, you know, putting them into a role where they get to develop and grow, you know, and build the skills that they want to. And I think when people feel valued and cared for and feel like they're growing in the ways they want to grow and like see a bright future ahead, they're generally, generally whether you call it loyal, you know, there's no real reason for them to want to, you know, go do something else. So, and cared for is important, like cared for as a human, not just like Oh, you know, I'm, uh, I'm gonna clean my engine parts so my engine works well, right? These aren't engine parts. These are humans. And like, humans wanna feel cared for. So actually care about them as people, get to know them, you know? And like, there is this way I see some leaders feel like they have to close their heart because, oh, what if I have to fire this person? Then that'll be harder. And you know, I'd say to that, like, yeah, it'll be harder, but it's worth it. To have, you know, every day until then, you know, the per— you know, to feel more of a sense of connection and caring with the humans you work with. So I wouldn't, I wouldn't close your heart just to, just to make, you know, it easier to let someone go if you have to. You know, it's only easier emotionally, and I think that's a bad trade-off. There's this funny line that keeps coming to my mind. This is more for like big companies, but it's like, It's like a CEO talking to the CFO and the CFO's like, what if we invest in training all our people and then they leave? And then the CEO says, what if we don't and they stay? That was clever. You know, it's like such a win-win when you invest in your people's development and growth because then you have more capacity as a team. And so that's a, that's a big thing I would think about. There's this book called The Three Laws of Performance, and the, the essence of it is that people's performance, and I might say morale as well, correlates to the future that they're living into. And that, that sort of arises in language. Like they'll tell themselves some story about the future. And as a leader, it's one of the core levers you have is to actually shift the future that your people are living into. Is why a lot of people talk about, you know, vision. It's so important to have a vision, but usually they think of like a vision statement, which, yeah, it's useful, right? In 2020, in 2030, we're going to have blah, blah, blah, blah, blah, you know, million users or, but just even more like literally when, you know, in the quiet of people's own thoughts, when they think about or imagine the next year, What do they imagine? Do they imagine it's going to be really fun and the company's going to grow and, you know, they're going to get to learn a lot? Do they imagine it's going to be frustrating and, you know, it's just going to be challenging? Do they imagine, you know, we're going to stall out? They imagine, you know, so that's, I think that's really useful to recognize so that you can try to understand like what are people envisioning and through your, you know, through conversation, that's one-on-one or team meetings or all hands, like literally paint them your most bright vision of the future that they can replace their current one with. So kind of really shifting the future that people are living into can have a big difference, make a big difference. I was just having another thought around this too. Oh, autonomy. So this is an interesting one. There was like a, a good, uh, I think it was in the Joe Hodson podcast on like empower over power. You know, think if people feel like things aren't going the way they want and they have no power to affect them, that's often cause of like frustration and ultimately people leaving. And it's interesting because a lot of leaders will say like, I want everyone to act like an owner, you know, everyone to take responsibility and act like an owner. But you know, the flip side of that is like, do they have the decision authority of an owner? And like, would you want them to? Right? And he makes his point in the podcast, like you don't want your janitor setting your IPO price.
Right?
Like that's just wouldn't, you know, that's wouldn't be wise. So ideally, one, you have like clear roles and responsibilities. So people, and then you give as much decision authority as possible within the role and responsibility. So people do have a sense of autonomy. And usually what gets in the way of this is fear. You know, leaders not wanting to let go of decisions because they're scared that the person won't make it as well as they can. And sometimes that's true. I mean, we were talking about, right? Like if you're gonna post content, you know, I don't know if we want people to know this or not, but you know, on my behalf and like, that's kind of scary, but also like if I had the control at all, we'd be, we'd be posting much less content probably, or I'd spend a lot more time. So like to really get leverage and unleash, you have to be with that fear. And then maybe occasionally I'll read something and be like, ugh, that's not Oh, that's not really right, Larry. That's not what I want to say. And like, you know, both of us would have to be with that possibility. And, you know, I certainly know your intentions are good. So like, it's not like you're going to purposely post something that is not, you know, whatever I would want to say. What was my point there? Oh, letting go. Just like, you know, that's sometimes what gets in the way of people having a sense of autonomy is letting go. But the other thing that gets in the way actually is lack of structure. So a lot of entrepreneurs are like, I don't want to be corporate. I don't want bureaucracy. So what that ends up meaning is like, there's no clear sort of mechanism for things to change. And so ironically, it creates the very politics you're trying to avoid, because if people don't know what the mechanism of to like try to influence decisions or affect, you know, change, Then they just try to get to know the people in authority and cozy up to them, have them like them so they can have influence, you know, and the Constitution of the United States is a really, well, sadly at least was a really good example of this where like very clearly laid out in the Constitution was how you change the Constitution. So people didn't have to, you know, wonder, what do I do? Oh, do I try to like You know, getting the good graces of the president. No, you need this, you know, whatever it was, three-fifths vote of Congress and blah, blah, blah. So similarly, it's like if there's really clear mechanisms, processes for how things, how to give input, how things, decisions are, you know, are made and could be changed, people actually feel more autonomous with that kind of structure. With lack of structure. And that's a big misconception. I think a lot of founders resist structure and resist policy, but then people end up feeling like stuck and they don't have autonomy, you know? And trying to think if there's like a really good example that comes to mind. Yeah, this might be a good, like, I, you know, I had a client who like, like some people, I don't know if it's a good example or not, but I'll share it and see if it is. You know, like some people on the team really didn't want to work weekends. Some people don't mind working weekends. Some people just like, you know, just liked working weekends, you know, catch up on stuff. And it was like causing a lot of tension. And so he actually realized like he doesn't want people to assume there's no weekend work, you know? And so he actually made it clear, like, I don't know if it's a policy or, yeah, I guess a policy that he communicated to people like, like you shouldn't expect to not work on weekends. Like we're not gonna necessarily like, you know, demand you work on weekends, but like we, you know, we take, we're, we're all in, we're fully engaged in our, in what we're doing here. I work on week, you know, most weekends, like we honor rest and renewal and if you have, things, you know, to do, like, I will do everything in my power to like honor the things that you're committed to, but, or, and, you know, if you come with the expectation that you're never going to work on weekends, you're probably going to be frustrated. And so like just creating clarity around that and then, you know, actually created less frustration than the kind of being more amorphous. So I guess that's more an example of clarity. Like clear agreement that like, you mean, so I guess the way that if someone really wanted to change that, then they would talk to the, you know, talk to him and say, hey, can we change this policy? I think we shouldn't have it, right? Instead of it being kind of amorphous. Loyalty is a funny thing too, because it's like, how loyal are you to your team? Like, is that even a real thing? Like, if, you Most leaders I know, if times are tough or they're running out of money or revenue falls, like they will lay people off. And so is it reasonable to expect your team to be loyal if you're not loyal to them? And I just think it's worth acknowledging that, that like also that if someone actually would be better off in another role, I, I think we get a little overly attached to our teams. Their team members and assume like team member leaving is bad, team member staying is good. Like, I think what's optimal for everybody is for people to be at a company in a role where they're thriving. And so if someone's not thriving in the role, it's, it ends up being a lose-lose. Like, wouldn't you rather have someone who's thriving in the role? If they are thriving in the role, they're not that likely to leave. So I think it actually works out pretty well generally. I mean, the other thing to think about is like zone of genius and like really being thoughtful that people are working in their zone of genius, which is that intersection between what they're awesome at and they love to do. And again, if people are getting to spend most of their time doing things that they love to do, they're much less likely to leave and they're much more likely to thrive, which is a win-win as well. Joe Ed said this thing in one of his podcasts that like Basically, he'll ask people like, what's their dream job? And if their dream job is the job, then he'll hire them, you know? And if not, he won't. And I think he's like come off that a little bit because not everyone knows what their dream job is. But in essence, it's part of like the enjoy over manage. Like, ideally people are in a job that is exactly what they want to be doing, in which case you know, they're less likely to leave. And so, you know, and they require less management, right? A lot of, a lot of leaders are like, how do I motivate my people? Ideally, you solve that upfront by having people who are in a role that they're really excited about and in a company where they're really inspired by what the company's doing. They don't require motivation or even much, all that much management. And So I think a lot of it is won or lost by like, do you have the right people on the bus and in the right seats? And then, you know, do you actively work to get the wrong people? I don't say wrong like they're bad people, but like the people that aren't a fit, you know, off the bus or at least, you know, out of the wrong seats. Because that also creates a lot of frustration and tension is when you have— when you tolerate people who aren't, you know, a good fit, you know, it, it is a drag on the people who are because they'll likely complain and sometimes out of defensiveness they'll start trying to like, you know, say that the leader's bad because they're anticipating they're going to get fired because they know they're not doing that great a job. So I think one of the things you can do that is the best Like one of the best things you can do for your, you know, top performers is not tolerate low performers or people who are not a culture fit because they'll be just like a drag and that doesn't feel good. And I've seen this, you know, yeah, I have a client I can think of where they hired a bunch of really extraordinary, you know, leaders and those leaders hired some extraordinary team members. In one division, but then in the other it wasn't happening. And it like they got really frustrated. It's like, wait, we're, you know, like we hold ourselves to a certain standard, but that's not, you know, true across the company. And that's the kind of thing that really can create dissatisfaction. So not, you know, not tolerating low performers or bad culture fit, I think, is one of the things that makes the biggest difference for the people who are high performers and good culture fit to feel excited and want to stay. And that's usually just fear, you know, fear of those tough conversations. Right. I think I may have shared this before. I had a coach who said like our most fulfilling lives and relationships are one 5-minute sweaty palm conversation away. We could say like same for like culture, right? Like maybe it's a series of those, but like most leaders tolerate, you know, I don't wanna say mediocrity, but like the wrong people for way, way, way too long. Cuz they just are scared to have that conversation or scared. They convince themselves that maybe I'm wrong or maybe I don't deserve, you know, that's too high a standard, or I can't get the people I really want. So like at least I have someone in the role who's doing the work. And those are the kind of trade-offs that tend to erode. Culture and morale over time.
I see you covered a lot of surface.
Yeah, it's almost like a tolerance tax. We could call it like, like conscious leadership calls it like a drama tax. Like there's a tolerance tax. The more you tolerate, you know, lower performers and non-culture fit, like it's like a tax that builds on the company. There might be a better word for it anyway.
What are some, I guess, key indicators of those top performers, A+ team members, all that?
They, they tend to require, they're the ones you don't really have to think about, right? Like they're just consistently, reliably, you know, kind of make great decisions, have good judgment. Do great work and they're sort of like, it's a, it's like in the bank. It's like, you know, you just, you sort of know if you give it to them, like it's gonna happen as well or better than you would've done it. And they don't require much management. And generally, like the team members require a lot of management where you find yourself thinking a lot about, kind of drain your energy. Those tend to be less so. So like, yeah, when you think about them, that you probably get energy rather than drain energy because you realize how much they contribute and they see they're like motivated on their own because they actually are excited about what they're doing and they, you know, consistently, reliably deliver great results. It's not that you don't have to like create clarity around like what's the vision and, you know, what are the goals and occasionally give feedback, but they generally don't require the level of management and energy and thought that people who aren't quite as a good fit










