If you're somewhere between 20 and 75 employees, there's a good chance the leadership habits that got you here are now holding you back, and the tricky part is that they used to work really well. Most founders assume leadership problems show up because people stop caring, stop performing, or stop being accountable, but that’s usually not what’s happening. What’s actually going on is this: you’re still leading the way you had to when you had 10 employees, except now you have 50. In this video, I walk through four leadership habits that are perfect early on but start to break down as your company grows. First is direct access to you—when you’ve got 10 employees, it works because everyone knows what’s happening, decisions move fast, and you’re the hub, which is efficient, but at 50 employees that same habit starts undermining your leadership team as people go around their managers, decisions become inconsistent, and leaders can’t actually lead because you’re still the easiest path forward, turning what felt supportive into confusion. Next is “I’ll just do it” leadership—early on it’s survival mode because you’re faster, you know it’ll get done right, and you’re filling gaps everywhere, but at 50 it teaches your team that ownership only lives with you, so people start waiting, escalating, and hesitating, leaving you feeling indispensable while actually building a team that depends on you for everything, which leads to founder burnout and stalled growth. This is why it’s so important to look at what breaks when, not just what feels wrong right now, because as headcount grows there’s often a gap between how leadership is operating and what the business actually needs, which is why I built a headcount diagnostic based on nearly 15 years of work inside small businesses to show what typically starts breaking as companies grow. If this already feels uncomfortably familiar, that’s because the next two habits are where friction really shows up. The third habit is informal accountability—at 10 people, accountability is mostly understood, expectations are shared, and course correction happens naturally, but at 50 almost nothing is truly shared anymore, different managers enforce different standards, high performers notice, low performers hide, and resentment builds, which leaders often label as culture issues when the real problem is expectations that never scaled and a lack of structured accountability. Finally, there’s decision by proximity—early on, decisions are made by whoever is in the room, which works when everyone is basically in the same room, but as you grow it creates chaos through different answers to the same questions, constant rework, second guessing, and leadership fatigue, not because anyone is doing something wrong, but because the system never evolved. The takeaway is this: most leadership problems aren’t caused by bad leaders, they’re caused by good leaders using habits that no longer fit the size of their business, and if any of this felt familiar, that’s a signal to pause, reflect, and start leading differently on purpose instead of reacting—let’s build that.