
Episode 10: Founder vs. CEO: Why Your HR Pitch Needs to Change
Season 1

Sabrina Baker
July 14th 2025
14 mins 59s
When you're in a small company, the CEO is usually your go-to person—but let’s be real, not all CEOs lead the same way. In this episode, we're breaking down the difference between a Founder CEO and a Hired CEO, and why your HR strategy must shift depending on who’s in charge.
Whether you’re pushing for a new HR system, a culture initiative, or a budget for benefits, how you ask matters.
We’ll show you how to tweak your message so it lands, gets support, and turns into real action.
Jump ahead
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0:00–2:05 | How Sabrina realized this difference is a BIG deal
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2:15–5:14 | How Founder CEOs think about the business
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5:15–6:52 | How Hired (non-founder) CEOs think about the business
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6:53–9:00 | HR Tech example: how to pitch it differently
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9:01–11:17 | Cultural initiative example: framing it to fit your CEO
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11:18–14:00 | The big takeaway—and how you can apply this right now
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14 years ago, I started a business offering fractional HR support to small employers. This is any employer with less than 500 employees. And with my first two clients, I learned a very valuable lesson. One that has stuck with me over the last 14 years, one that I train every person who comes into my team about one thing that we talk about quite often, and even as my team is asking for feedback or advice on how to deal with somebody we talk about this fact. These two CEOs could not be more different. One of them was resistant to every kind of change, even the ones that were obvious, or that he had hired me to do. This is what he'd hired me to do, and yet he was really, really resistant to wanting to do these things. The other CEO was onboard. He was ready to blow up his entire HR playbook and let me build everything from scratch, if that's what we needed to do. And I would just bang my head against the wall around what is the difference between these two? It's more than personality. It's more than just how they want to be talked to or the words that I need to use. And it finally finally struck me. That the difference is that one of them was a CEO who was a founder. He had started the business in his basement. This was his baby. And the other one was hired after the fact, after the founder had exited. And he saw this business more as a business. There was less emotional attachment for him. And from that moment, a realizing that I changed the way that I approached the founder, CEO, and our relationship changed forever. If you are managing human resources in a small employer and you want to understand or need to understand how you can talk differently, whether your CEO is a founder or not, then this episode is for you. Let's start with founders. As a founder, I can tell you that everything I'm about to say is absolutely true. Founders have an emotional connection with their business. They may have started it at their kitchen table, in their garage, in their basement, like me, in a moment of being pushed off a cliff, being laid off, uh, not choosing of my own doing, but but having this time where I had to figure out what I was going to do next quickly, with a baby. The business feels like an extension of who they are. This is something that they built from the ground up. And in some cases, with literal blood, sweat, and tears, they have lost sleep. They have leveraged mortgages. They have maybe almost gone bankrupt. They have had so many highs and lows in a single day. You can't even imagine. So there is this very emotional connection to every aspect of the business. So when you go and you suggest change or you try to give them feedback about something that you think is not working well, it's like you're talking to them about one of their children. It's a very different feeling from somebody who doesn't have that emotional connection to the organization. When I would go to CEO founders before I realized what a big deal this was, and I would suggest change that seemed so very obvious to me, or even when we've had employees who were maybe a little toxic and they really needed to be moved out of the business, but they were somebody that was with the founder in the beginning, the founder is often really, really they really struggle to make those changes. We could be doing everything and spreadsheets, everything could feel so archaic. We could have these toxic employees, and yet the founder is resistant to making those changes because all of those things that we're talking about got them through some really hard times in the beginning. And removing those or changing them feels like erasing history. When you are coming at a founder who you need to get buy-in, you need to affect change, you're trying to build some HR infrastructure or HR strategy that they might be a little resistant to, you want to make sure that you are remembering this emotional connection and aligning with their values and not challenging their identity, which is tied into the business. So let me give you an example. Rather than saying, "Hey, we need to revamp our onboarding process because it's really inefficient," when that inefficient onboarding process probably onboarded most of the people that are currently in the business and seemed to work fine then, what you want to say is you have built a culture around valuing people as they come into the organization, making them feel engaged and empowered. And if we can make some changes to this onboarding program, that is going to help us continue to do that as we grow. You must align whatever it is you're suggesting with the values that they want to keep, that they envision for the business in the beginning, and that they are trying to perpetuate. And when you do that and not challenge the identity of the business, you will go much further. Now let's talk about CEOs who come in either after the founder has exited the business or the founder is taking more of an advisory role, a high-level board-type position, and they're allowing this CEO to manage the business. Typically, they are being brought in to help scale the business, help grow the business, make it more efficient, make it more profitable. They are going to be very uh much more metrics-driven than maybe your original CEO founder. They weren't there in the beginning. They weren't there in the early days when products were being shipped out of a garage. So they don't have those emotional ties that a CEO founder is going to have. They truly care about performance. They are going to want to understand the ROI. They are going to want to know metrics over feelings. This is a facts over feelings situation for sure. And they're going to want to understand how HR contributes to the growth that they're trying to achieve. So the difference when you are talking to a CEO who came in after the fact is that everything must be metrics-driven. Rather than saying, "We need to change our onboarding because the managers are struggling to manage it," you would say, "We need to change our onboarding because in our last engagement survey, 30% of respondents said that they really struggled through the onboarding process, leading to a longer ramp time, a longer time for them to be uh productive." And so we need to change our onboarding experience to shrink that ramp time. They are going to respond so much more to metrics than they are to the emotion. Let me give you two quick examples of how this can play out uh to show you the difference and how I would approach a CEO founder or a CEO who was hired after the founder. And in the first example, let's say that you are trying to get the funding, the budget for a new HR tech system, a new HRIS system. Maybe you don't have one, uh maybe you've been doing things manually, and you are trying to get your CEO to give you a budget to implement a new HR tech system. The way that I would go about the initial conversation with either of these individuals changes whether they are the CEO founder or whether they were hired after the fact. So first, if I were going to approach the CEO who is the founder, here is what I would say. I know we've been using spreadsheets and email for a long time. That's worked well up to now. But as we grow, I want to make sure our new hires feel the same level of care and clarity that you worked so hard to build. This new system helps us keep that consistency without losing our personal touch. This again aligns with the values of this owner. It does not challenge the identity. It doesn't say spreadsheets are boring or wrong or old school. It just says, "Hey, those worked for a while." And all founders know, all entrepreneurs know, we have to do what we have to do for a while until we can do better. But once we can do better, then when you align your question, your whatever it is you're trying to get buy-in for, when you align that with the values, the core values that they built the business on and that they are trying to perpetuate as they grow, then you are much more likely to get that buy-in. Now let's see how the approach changes if I am dealing with a CEO who is not the founder. They came in later. They don't have that emotional attachment. Remember, they are very, very metrics-driven. Here is what I would say to them. We are spending over 20 hours a week on manual onboarding tasks. This system would cut that by 60%, reduce errors, and improve the employee experience. I estimate we'd save about $2,500 a month. Same outcome, same ask. In both scenarios, you are trying to get a budget for an HR tech system. But I would absolutely change the way I approach it based on which one of those two individuals I'm talking to. Let me give you one more example. Let's say you have a culture initiative that you want to implement. Maybe it is a monthly all-hands meeting. And you think that the CEO should be a part of that. And enhance the communication that is going on in the organization. Again, I would change how I bring this up based on whether that CEO is a founder, or whether they are hired after the fact. So let's start with the founder. Here is exactly what I would say to them. You built something really special here. As we scale, I want to make sure that the culture you created doesn't get diluted. Right there, you are leading into what you've built, your values, is something that I'm trying to protect here. The minute that they feel as though you are trying to protect the values with which they gave their blood, sweat, and tears for, the more likely they are to actually hear out the rest of whatever it is you're trying to get them to do. Now let's talk about how I would change that if I were talking to a CEO who was hired after the fact. Here's what I'd say to them. Our turnover is trending up. A more intentional focus on culture and communication could reduce that churn and protect our investment in talent. Again, the difference is that with the CEO founder, I am going to go on values alignment. I am going to go on an emotional connection to the business. And on a CEO who's hired after the fact, I'm going metrics. I want to reduce turnover and I want to reduce that that churn. I want to, we're seeing it trending up and I want to do something about that. And their ears are going to perk up differently based on who they are and the approach that you take. So I'm sure you you get the point here. When you are dealing with a founder, and especially if you know you are asking for something that's going to be represent a really big change for them, then you are going to want to come from a values place. And if you are, if you are talking to a CEO who is hired after the fact, you are definitely going to want to come from a metrics place. So here's your takeaway. Knowing who your CEO is helps you understand how to approach them. Is it foolproof? Am I trying to say that CEOs who are founders never think about metrics? Of course not, because they do. I'm just saying that if you are looking for major change, if you are questioning something that maybe has been a deeply held belief, something we call a sacred cow, whether that's a process, a system, or a person, then you are going to have to come at the two a little bit differently. The CEO founder versus the hired CEO a little bit differently to get the outcome that you want. Our job as human resources is to adapt. It's to adapt to the individual that is in front of us. And there is no more important person to adapt to, especially when you're trying to get buy-in, than your CEO. I always like to give you one thing you can do, one thing that you can do today to move in this direction. If this is something that resonated with you, then what is what now? What do you do now? This one's an easy one because you just have to sit and think for a few minutes. You just have to sit and think about who is my CEO? Are they the founder? Are they not? And can I think about situations where I tried to come at them from a metrics approach, but maybe should have come at them from a values? Or I came at them from a values and should have maybe looked at metrics. Maybe think about how the next time you're trying to get buy-in or you're trying to get them to change their mind about something, that you approach it a little bit differently and see if it works. I can't say it works 100% of the time, but I can tell you without fail, even as people are trying to give me feedback about my business or trying to get me to change something, when they come at me with, "Here's what you built and we're trying to protect that," I'm so much more willing to listen um than I am if they just come at me and say, "Something is very broken in this business that I have a really emotional tie to." So the the one thing you can do is just really kind of sit and think about your CEO and think about how have you approached things, especially if you've gotten a no in the past, and do you think the outcome could have been a little bit different if you had approached it differently? If you do this, if you have a story about this, we are always looking for people to feature in later seasons of this podcast. Those managing HR in small employers. So if this is you and you have a story about how you have changed your approach based on founder or hired CEO, and it worked for you, then I would love to hear from you. You can always send me a message on LinkedIn. um And connect and maybe we could feature you in a future episode. The next episode of the HR Connection talks all things AI, can AI manage human resources for small employers? um This is such a hot topic. I know, and it's something that I get asked all the time. So if you're not already subscribed, please do so that you uh get the notifications for that. It's going to be a really good one. Thanks so much for being here on the HR Connection, and we'll see you next time.

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