Cautionary Tips When Hiring Employees from Corporate Cultures | Ep #90
8 Dec 2025 · 12 min
Podcast episode (host Kris Plachy) advising entrepreneurs about hiring people from corporate backgrounds. The host contrasts entrepreneurial and corporate workstyles (producers who act vs. delegators who follow processes), shares anecdotes (e.g., StarBright Lights sales call), and gives practical hiring recommendations: clarify values/expectations, test candidates in realistic trials, and prioritize ability to execute/tactically produce in small teams.
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Hey, I'm Chris Plackey, host of the lead you'd team podcast. Running a million dollar business is not easy. And whether you're just getting started with building your team or you've been at this for a while, I'm going to bring you honest, specific and clear practices you can use right now, today to improve how well you lead your team. Let's go ahead and get.
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Welcome to this week's episode of the podcast lead your team with Chris Plackie. I'm so glad that you're here. I want to talk with you this week about. I think, I don't know. I. This is something I talk with my clients about a lot of. So I'm not sure if this is going to be like a. Yeah. Kind of topic or if there might be some people who listen to this who get kind of annoyed with me kind of topic, but I do think it's an important thing to talk about, so we're going to do it. What I want to talk about is what I, what I have observed in myself and in my clients as they hire employees for their businesses who either have worked in entrepreneurial cultures or if they have worked in corporate cultures. And of course, I am speaking in general observations, not in, like, this is for sure for everyone all the time. It's more kind of like, hey, maybe just pay attention, like, give. I want to give you a little heads up as an entrepreneur since you're the one that I direct this couple, this podcast to. As you're making your decisions about who to hire and who to bring into your business, I want you to have this sort of in your mind so that you're thoughtful in the interview kind of initial process when you bring people into your culture, into your company. Okay, so entrepreneurs, let's just talk about entrepreneurs in general. Entrepreneurs are typically.
I mean, any one of them I've known to a fault. Right. They are workers. You, you work, you get it done, you make sure it happens. You finish, you have. Initiative is not something you look for. It's not something you hope to have. It's like baked in you. Problem solving same. Like, there's nobody coming to save you. You have to solve problems. And the other thing is urgency, timing, knowing that things matter in terms of the response, the results, the delivery, all of that is part of how we make things happen. Right. I would, I just bought something that I of course found on Facebook and they're these, they're called Safe Lights. I'll give them a shout out. They're, I think that's what they're called. Safe lights. They are.
These super cute, really thin strands of light that you can use, you know, to wrap around a tree or. I'm sorry, they're called starbright lights. I want to make sure I'm giving the right out, right shout out star bright lights. So they're just super cute and for Christmas is coming and I love to decorate. So I totally fell into the hole and I went through the whole process and filled out all of the details for the order and then got distracted. My doorbell rang. We had some things happen, and so I kind of put the phone down and then I thought, well, I'll come back to it if I really want it, right? I'm not even kidding. Six minutes later, my phone rang, and it was the star bright light people saying, hey, we noticed that you didn't buy your lights and we wanted to give you one more offer. And if you buy them with me right now, give you 10 more percent off. Come on. That's pretty intense. That's pretty good, right? I had already read that the company is owned by. It's a small family business. As far as. As at least what they said, I'm gonna go with it. That they are. That's what they wrote up about themselves. And so I thought, well, of course, that's kind of cool little entrepreneurial thing. And they're like, they're getting it done right. That's what they want to do in the world. And I was impressed. So that, to me, it's like a spirit, it's like an energy that exists in. In entrepreneurs that isn't. Doesn't make you better people. It just. It's just how you're created. And so that's why you're already inclined to take the risk of starting a business. When we look at corporate environments, they're different. It doesn't mean that people who work in companies aren't hard workers. Don't try really hard, don't focus on results, don't want to deliver amazing success, aren't ambitious, don't have initiative. None of that. I come from a corporate background. I worked in a startup culture for years that turned into more of a bureaucratic company corporate culture. I know the difference between, like, the nimbleness of being a young startup company and then the layered bureaucratic slowness of corporate culture, which I found for myself just didn't suit me. I found it exhausting, and I was terribly impatient all the time and thought it was futile. And then other people, of course, really enjoy that. They Thrive in it. So as we hire people, and this is where I've seen this happen the most, is when my clients have gone from that, you know, sort of initial team, let's call it six to 10 people, and then they want to start to hire people into more senior roles. And that doesn't mean like C suite, like chief level, but you know, more like director level or even vice presidenty role. And I mean, we call each other anything we want, but you know, that role where people are managing people and processes, not just processes, Right. And so a lot of times when you start posting jobs like director of marketing, director of social media, director of operations, director of sales, you're going to start to then attract more candidates who might have experience in more corporate settings. And a lot of the times the conversations I've had with clients through this process is a lot of these candidates are incredibly impressive. They have really impressive experience, they come from impressive companies, they have substantial accolades and training and accomplishments and education, all the things, right. And so as we're trying to think about our grown up version of our business, a lot of us think, oh well, this includes sort of really upskilling and up leveling the people we hire. And that's not necessarily not true. It's just that that alone does not qualify them to do your work well in your company. And what I have seen happen a lot is we have hire folks with these very impressive backgrounds and very talented people. These are not untalented people, but they enter into this entrepreneurial culture and they can't do it. They flail, they can't deliver, they can't keep up, they find it overly demanding, they get frustrated with the change, the rapid pace of change, the inability to have a lot of resources available to them. And really there's a lack of ability to transition from that strategic position to the tactical one. And one of my clients said it best that everybody in my company, no matter what they do, has to be able to be a producer. They have to be able to deliver at the production level at whatever your business is, in addition to running the whole part of that team running that part of the business. So when you think about, and you know, for some of you this was really relevant and some of you, it isn't now. The, the flip is also true for those of you who run companies who might be listening to me and you, you know, you worked with a 2, 3, 4, 8 million hundred people business and you hire people with entrepreneurial experience. That can be like a crash and burn because entrepreneurs are like What, Why is this a problem? I took initiative, I got it done. And a lot of people are like, no, you needed to involve R. Rhonda, Nancy, Dave, John, Luke, Mark, whoever from all these other departments before you made that decision. Right. So the telltale signs, I think, that you have to pay attention to is that entrepreneurs are producers. We roll up our sleeves when we want something done, we do it now. We focus on the work and results and we, we have an efficiency quotient that is off the chart. We manage. We see management as a means of results, as achieving results. On the flip side, someone who comes from a much more robust corporate culture is used to delegating, is used to having meetings, to chat, to discuss, to talk through things. They want to set up processes which may involve a lot of different people. Conversations are often like defer to the person who's in charge. So, oh well, that's so and so. So you know, she'll take care of it. And a lot of times the management role is a means of reviewing things, discussing them versus getting them done and achieving them. And I know it's a very subtle but. And so a lot of my clients will hire people that they're super excited about and then it's not working and they don't understand why, because of course these folks are so talented and they're so lovely, but they can't assimilate. You know, it's as simple as people who come in work and shut up, shut off their computer and they're like unavailable. Entrepreneurs don't know what to do with that. This is not how that what they're used to. Now, unfortunately, I think a lot of entrepreneurs aren't clear about what they expect and that gets you in trouble because then people really do think your expectations are unreasonable. And we've talked about that in previous podcasts. But I do think your, your understanding of how in a larger company, decisions are not usually at the tip of your finger for the people who you hire. They're not usually emboldened to just decide and take action because there's all these other factors that have to be considered that you have to talk to different departments and divisions and get approvals. And whereas for entrepreneurs, you're like, you're the director of marketing, make a decision and get it done today. Why, why have it, why is it not done? And then the, then the other thing that we hear is your expectations are unreasonable. I don't have enough support, I don't have enough people, I don't have enough. Right. And again, entrepreneurs Listen to that and think, right? Because you're a person. There's you and your three people on your team. What are you doing? I need you to be a producer just as much as you would be the delegator.
And so that's a thing. And so I just have watched so many people not survive in entrepreneurial cultures. So this bears importance for you in how you really get clear about what your values are. I just was doing this last week and how to. CEO of my clients are right now really working on their compelling reason and their vision and values. And one of the women that is in my program said, I just want people to, like, you know, roll up their sleeves and get to work. I said, yeah, that's a value. Is it written in your values? Because I didn't hear it. And if that's what you expect, you have to tell people that. Because someone who's been used to. Well, I don't really roll up my sleeves. I delegate the work to the people who roll up their sleeves and I go home at the end of the day. That's great if it works for them. I don't. Again, I don't have any. Just. I don't disparage that. I just. It doesn't work in your culture. You have to be really clear, because I think that. And then the, the other. The last thing I'll say about this is the efficiency of your time. And I know I referenced this, but I know how much you are capable of getting done in a day. I know how focused you are because I, I hear it from my clients how frustrating it is to watch how so many people don't really maximize all their time. And that's again, because if people have worked in a company, right, they come to work, they go get their coffee, maybe they wander around, say hi. They don't really just like, come to work, sit down, do it.
They bring their coffee or they drink it in the car, right? Like, it's. Most people don't do that. There's so much time wasted inside corporate cultures. It's a problem. I actually think it's a huge issue that companies should be paying much more attention to because you are effectively paying for what can be done, what kind of results can be achieved. I think people could be achieving a lot more if they were directed and focused. But in your window, you don't have a lot of resources in your work. You don't. You don't have tons of available free time for people to just not do stuff. So again, they come into your company and they're like, I can't get over how much gets done here in a day. I can't keep up. And that's probably, in some of their cases, true. And again, that's not their fault. It's just. It's a difference. It's such a difference. So as you're hiring these more. More senior roles, although I would even say I've noticed this in, like, assistants who are used to working in a bigger corporate business. And then an assistant who works for an entrepreneur and hasn't worked for an entrepreneur before. Totally different ball game. You've got to really think about, okay, am I clear in my values? Have I been really clear in the job description? Have I been incredibly clear in the interview? Have I asked questions through that interview process that are really, really going to help reveal their perspective, their philosophy, their belief system about work? And have I even created, like, a trial, like a process that I put people through that shows me helps demonstrate this? And if it makes sense for people to come into your office and spend a half day with you, I would do it more. You can try people on the better. A lack of experience in working in an entrepreneurial culture does not preclude people from working for you. I wouldn't say that, but I would say that proceed with every intention of ferreting through things that you take for granted in how you think about and do your job every day and what you expect of people. We're gonna hire people, and it's not gonna work out. That's just a deal. That's how it works. I just want to try and help you prevent too much of that because I know it's hard on your spirit and it's hard on everybody else. So just because they have sexy experience and a really great resume and really cool companies they've worked for does not mean they can come into your business and create magic. Fair enough. Okay, thanks for tuning in. Talk to you again next time.
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