Before you click away, I promise this episode is for you whether you have 20 employees or 40. If you're not at 25 yet, everything we cover today is what you're building towards. You want to get ahead of it now, and you'll think yourself later. If you're already past 25, stick around, because if these three things weren't built when they should have been, you're probably feeling the consequences right now, and we're going to name exactly what that looks like. Ready? You're running a company with 22 employees. And on paper, things look great. Revenue is coming in, you've got a growing team, you're not doing everything yourself anymore, you've got managers or at least people with manager titles, and you've got some processes in place, but something feels off. Your calendar is completely full, and you're still not sure what you're actually doing all day or supposed to be doing. You're answering chat messages from managers who should absolutely know the answer already. Your newest hire that you were so excited about seems disengaged, and you can't figure out why. One team is operating one way, another team is doing things completely different. And you're starting to hear phrases like, "That's not how we do it here," which is really interesting because you didn't know there was a how we usually do it here. You hired more people because you thought it would create stability, but you don't feel stable. Nothing is on fire, no one's quitting, you're not losing customers, but nothing feels right either. And that vagueness, that low-grade friction, it's exhausting in a way that's hard to explain to anyone who hasn't been here. And here's what makes this stage so tricky. Most CEOs don't look at that list of symptoms and think, "I have a people problem." They think, "I have a strategy problem," or a market problem. Maybe we hired the wrong people in the wrong roles, maybe the product needs work, maybe we need a new sales process. So they go fix all of those things. They reshuffle the org chart, they bring in a new tool or a new system, and things improve slightly, or they don't, but that low-grade friction never fully goes away because the real problem was never strategy. It was that the people infrastructure underneath the strategy was never built for that size. That's 25 employees. And I want to be honest with you CEO to CEO, this is one of the most disoriented stages of company building. Because the problems aren't loud, and they certainly aren't obvious to someone who hasn't watched this happen with hundreds of small businesses over the years. They're structural, and they're invisible, but as you push towards 50, they will become painfully obvious if not fixed. At 25, three massive things break, not 10, not 20, just three. But they're big. They're foundational, and they're time-consuming to fix. If you build them now, 50 employees becomes a real scale story. If you ignore them, 50 employees will expose every single crack you're sitting on right now, and your business will feel like a nightmare to work in for everyone involved, no pressure. Today we're going to go deep on onboarding and why yours probably isn't working anymore, employee experience, what most people call culture, and most people are getting wrong. And then finally, leadership capability. I'm okay sounding like a broken record on this one, and I'll explain why. I have a video where I talked about what happens at 15 employees, and in this range between 15 to 25 is where most clients come to us. So I feel these breakpoints not just in my own business, but in almost every new client we onboard. Let's get into it. The first breaking point at 25 employees is onboarding. Let me paint you a picture of what onboarding looks like at 8 employees. Someone starts, somebody gets hired, you sit them down, they're probably near you all day or most of the day, or if you're on if you're remote, you're on a lot of calls with them. They overhear your conversations, they absorb how you think, how you make decisions, how you talk to clients, and within two or three weeks they just get it. Not because you designed an onboarding program, because proximity just did the work for you. That was a gift, but at 25 employees it's gone now. Now your new hire might only interact with four or five people consistently. They're probably not near you, they may not even have reason to interact with you that often at all. They might be on a different floor, a different shift, or if you are like us and fully remote, they only see their team on Zoom and the rest of the company at the very inconsistent all-hands meetings that you have. They won't naturally understand how the whole business works in a few weeks like they did before. They're not going to pick up on your standards through osmosis. And they will not know what good looks like unless someone tells them. Here's what I hear from CEOs around 25 employees constantly. "My employees are just not ramping fast enough." Or, "They don't seem to have ownership." Or, "I don't know if they're really bought in." And here's what I want to challenge you on about those statements. Those are almost never motivation problems. They're almost always onboarding problems. You hired someone capable, then you put them in an environment that didn't give them what they needed to succeed. And now you're frustrated with them. That's really worth sitting with for a minute. So what does onboarding need to look like at 25 employees? It needs to be 90 days minimum. I know that sounds long, it's not. The first 30 days someone is just trying to figure out where the bathroom is and whether they made the right decision in leaving their previous job. Real performance integration doesn't even begin until around day 45 or 60. Onboarding needs to be structured. That means there's a process. A document. I know you didn't start a business to do paperwork, I didn't either, but what I've had to learn is structure over rigidity. That means there is a schedule. There is a clear owner not just, "Oh, their manager will handle it." They need someone who's actually accountable for whether this person is getting what they need. It needs to also be cross-functional. Your new hire should be having intentional conversations with people across the organization. Not just their immediate team. They need to understand how revenue gets made, how problems get solved, and how decisions happen. You cannot expect them to operate like an insider if you've only shown them one corner of the building. And it needs to be outcomes-based. Clear 30, 60, 90-day deliverables. Documented performance standards behavioral expectations that are stated out loud, not just assumed. Because what you don't state explicitly, people will fill in with their own interpretation. And their interpretation is based on every other job they've ever had, not yours. Now, I know what you're thinking. This sounds like a lot of work, and it is. It takes real time to design and refine. It requires a process, it requires managers who actually know how to coach someone through it, and let's be honest, those managers might not even exist yet inside your organization, which is a problem we'll get to in a few minutes. We started working on our onboarding two years ago, and we have refined it with almost every single hire. We have a process that details out almost every minute of their first two weeks and most minutes for their first full month. Then through our skills framework, which I have talked about in previous videos, I've talked about it a lot actually, we know what we are teaching them in months two, three, four, all the way through our onboarding process. It isn't painstaking process to build. But here's the cost of skipping it.  You get inconsistent performers, you get much slower productivity from people who should be contributing already, you get this behavioral drift new people importing habits and norms from their last company because you never clearly defined what behaviors are required to be successful in your company. And then you get higher turnover, because people who don't feel set up to succeed eventually leave. Once you hit 50, fixing onboarding is exponentially harder. Because now you're not just designing a system, you're breaking habits. You're overriding patterns that have been reinforced for potentially years. That's a much heavier lift. One small point of clarification here, onboarding is not orientation. Orientation is a day with a bunch of paperwork and benefits stuff. Onboarding is systemized integration. Into your performance expectations, into your employee experience, into how your business actually operates. At 25 employees this has to exist. And whatever you design here has to scale to the next stage. The second thing that breaks at 25 employees is that culture needs to become more intentional instead of organic. It's always going to have some organic element to it, but I do believe it can be intentionally designed as well. And here's why I believe that. I reframe culture into employee experience. Your culture is what your employees experience while working for you. That words employee experience make it tangible. Something you can feel rather than this nebulous culture word that no one can truly describe. Let me tell you how employee experience works when you're under 10 people. When you're under 10 people, it's you. It's your personality that sets the tone. Your energy in the morning sets the energy for the day. How you respond to a mistake, how you celebrate a win, how you talk about clients when they're not in the room, all of that is you. Your team absorbs all of it constantly because they're always interacting with you. You don't have to define employee experience when you're small because you are it. You just have to show up consistently. Model the behavior that you want to see and then it radiates outward. At 25 or before that stops working. Now you have micro teams. You have different managers with different leadership styles. You have people who hired differently, who think differently, who communicate differently. And you have employees who interact with you maybe twice a week if that at all. Employee experience starts to fragment and it doesn't fragment loudly. You wouldn't even notice it happening. But here are some things that you might notice. One team develops a norm around how they handle conflict. Another team develops a completely different norm. One manager rewards hustle, another rewards process, and suddenly your employees are experiencing three different companies under the same roof. This is where CEOs start feeling like we're losing the thing that made us special. Or it just feels different than it used to and it doesn't feel as relationship-based anymore. And you're right. It doesn't. Because you're no longer the cultural transmission mechanism. You've been replaced by middle management. And if middle management hasn't been given a clear employee experience framework to operate within, they're all making it up as they go. Based on their own experience, which could be minimal. By 25 employees, the employee experience can no longer be vibes. It has to become behaviorally defined. And I want to be really clear about what that means because a lot of CEOs hear define your culture and they go right values on a wall that they downloaded from the internet. That is not what I'm talking about. Values on a wall don't change behavior. Observable, defined behaviors change behavior. So the question here isn't what do we value. The question is what does that value look like in practice? How does that show up? So here are a few questions you can answer to demonstrate what I'm talking about. The first one, what does accountability look like here specifically?  If someone misses a deadline, what happens? Who talks to who? What's the expectation? I could talk for 100 videos about accountability and how a lack of it in small businesses runs rampant and is killing the employee experience. But for this video, I'll say this. The longer you wait to have defined behavioral and performance expectations, with rewards for doing them well, and consequences when they fall short, the harder it gets to actually scale a business. Question two, how do we handle conflict? Do we address it directly? Do we go to a manager? What's the norm? I was in a client's office recently and they had a poster in the break room that said, "If you have a complaint, issue, or conflict that you need support with, start here." And then it laid out who they should call and how to escalate if that person couldn't help them resolve it. That's curated behavior design. Question three, what does good communication look like on our team? How fast do we respond to each other? What belongs in chat versus email versus a meeting? One of my favorite exercises to do with teams is to create SLAs or service level agreements for things around communications so expectations for both sending and receiving are clear. Question number four, what is genuinely unacceptable here? And are you willing to enforce it? And does everyone know what's unacceptable and are they willing to enforce it? Do they know how to enforce it? Seriously, you cannot assume anything. These are the conversations you need to be having right now with employees and leaders. Not because they're fun. They're usually actually not very fun. But because if you don't have them at 25, you're going to be having much harder conversations at 50 when those undefined norms have hardened into entrenched subcultures. Subcultures at 50 require more time than you have to undo. So the time to undo them is before they start. And then—and this is the part most people skip—those defined behaviors have to actually be operationalized. That means you hire for them, you use them in onboarding, you include them in performance reviews, and you address it when someone violates them. If you define your employee experience but don't enforce it, you've actually made things worse. Because now your team knows what you say you value, and what you actually tolerate. And those two things being different absolutely destroys trust. At 25, you still have leverage. The clay is wet. You can still shape this. This is where employee experience becomes engineered, not corporate. Not bureaucratic. Just intentional. Designed on purpose.  The third and final breaking point around 25 employees is leadership capability. And at this number of employees, lack of leadership capability multiplies risk. If this isn't your first time hearing me speak, you know I spend probably an inordinate amount of time talking about leadership in small businesses. Because large organizations can absorb a poorly trained or toxic leader. Your small org cannot. At 15 employees, you might have one or two managers, and honestly, they're probably great individual contributors who got promoted because they were your best people at the time, not because anyone sat down with them and actually taught them how to be a leader. At 15, you're still really involved in their leadership. So if they aren't great, that's okay. You can cover for it. But at 25, you have managers managing managers. You have more layers to your business, and leadership inconsistency really at any size scales faster than anything else inside your organization. Think about whether any of this is actually happening right now across your organization. One manager gives direct, clear feedback. Another manager avoids hard conversations and just hope things self-correct. Is that happening? One manager holds deadlines like they mean something, and another manager extends them to keep the peace. Could that be happening? One manager knows how to develop people. Another one has no idea what that even means in practice. I know that's happening. Oh, and you have at least one manager who doesn't care about people at all and thinks they're title earns them the respect they deserve. You know exactly who I'm talking about. Your employees now have a fundamentally different experience of working at your company depending on who they report to. They are, as I said earlier, working at different companies inside your company. And you are no longer close enough to catch it. When you had eight people, you could feel when something was off. You'd have lunch with someone, and it would come out. You'd overhear a conversation, and you'd know that there was something that needed to be course-corrected. That's gone. Your relying on your managers to be the connective tissue between your vision and your people's daily reality. If those managers aren't equipped, that tissue tears. So what has to happen at 25? Leadership development must formalize. And I want to be really specific about what I mean because again, leadership development can sound like sending someone to a conference for two days or doing a Myers-Briggs workshop and calling that a day. That's not what I mean. That's not development. That's just activity. It's not bad activity. It actually could be fun activity, but it is just activity. Real leadership development at this stage means your managers know specifically how to give feedback. Not just that they should, but how. What to say, how to frame it, how to make it land without becoming a defensive conversation. It means they know how to run a one-on-one that's actually useful. Because most managers run one-on-ones that are just status updates. Those could be texts. That's not management. It means they know how to manage underperformance. Which is probably the skill most first-time managers are least equipped to handle. What do you do when someone isn't delivering? When do you coach versus when do you put someone on a plan? When do you let someone go? These are conversations your managers are going to be having. They're going to have to have these and if they don't know how, they're going to either avoid them entirely or handle them really poorly. Leadership development means they understand what authority they actually have. So what can they decide? What do they escalate? Because ambiguity around authority creates one of the most toxic dynamics in a growing company. And that dynamic is managers who are afraid to make decisions and CEOs who keep getting pulled back into the details. That means there's alignment across your management team. Leadership development creates this alignment around how decisions get made, not everyone is doing things differently. You have shared frameworks. If you skip this, if you just promote good people and hope they figure it out, here's what I know happens based on nearly 15 years of working with small businesses. Everything escalates back to you. Your managers don't trust themselves to make calls, so they ask you. Which means you never actually got out of the weeds, which you should have done way back at 15. You just moved your office. You then get this resentment between teams because one team is being held to a high standard and another isn't. And everyone can see that, so there's this resentment. You got your high performers totally burning out because they're carrying the weight for underperformers and eventually they get sick of that because their manager's not addressing it. High performers always, always leave environments where accountability is inconsistent. At 25, your managers need frameworks. They need consistent expectations. They need to know that your invested in making them better not just holding them accountable for results that they were never trained on. This again takes time, which is exactly why this episode is only three topics. Because they're big. None of these are quick fixes. They are foundational architecture. And they deserve real attention. Here's the thing I want you to understand about 50 employees the next episode: 50 is a completely different animal. You might not believe me, but I see it every single day. I am going to talk about what breaks at 50 in the next video. So if you are not subscribed, now would really be a good time because here is what I see. CEOs hit 50 and all of their problems are 10 times harder because they never fixed the 25-person problems first or even the 15-person problems first or even recognize they were people problems. Weak onboarding at 25 becomes a turnover crisis at 50 because now you've got dozens of people who were poorly integrated, who never really got fully bought in, and they start leaving right around the time you can least afford them to. Undefined employee experience at 25 becomes hardened subcultures at 50, and now you're not shaping employee experience anymore. You're doing surgery, trying to break down those silos. Trying to break norms that have been reinforced for years. It's painful, and it's slow, and it is demoralizing. Untrained managers at 25 become a leadership crisis at 50 because those managers have been making it up as they've gone for years now, and now those bad habits are baked in. And the dysfunction they've created, the teams, that are checked out, the performers who left the conflict that never got resolved, all of that is your inheritance. 25 is leverage. 50 is consequence. And the reason I use that framing, leverage versus consequence, is because at 25 you can still move fast. You can still personally shape these systems. You have enough clarity on your employee experience that you can actually define it. Your management team is small enough that you can invest in each of them individually. At 50, all of that is so much harder; you're far from the work. There are more people to align, to systems are more entrenched. The window is so much smaller. So if you're sitting at 22, 24, 26 employees right now, this is your moment. Most small businesses build reactively. They focus on sales, marketing, product, and seem to ignore or forget that people build the business. A small business where people building is intentional, where leadership is developed, where HR is seen as a growth strategy, that's a business that scales. Let's build that.