You’re in the pub with two friends. There’s one conversation happening. Everyone gets a turn to talk, everyone’s listening to the same stories and jokes.
Add two more friends, and now there are usually two conversations. Three people in one corner, two in another. Different stories, different jokes. Keeping everyone in one conversation becomes possible but hard.
Now imagine you’re in that same pub with 250 friends…
This is exactly what happens to your company between 50 and 250 employees. It’s not just growth. It’s the moment informal communication dies, and most founders don’t see it coming.
The Invisible Breaking Point
At 50 people, information still flows naturally. The engineering team knows what sales is working on. Marketing hears about customer complaints. The CEO can walk around and sense the energy, catch problems before they explode, share vision through casual conversations.
But somewhere between 50 and 250 employees, something breaks. Not dramatically. Not all at once. It’s more like a slow leak in a tire that you don’t notice until you’re stranded on the side of the road.
The breakdown isn’t about headcount. It’s about communication pathways. At 50 people, you have manageable connection points. At 250, you have an exponential web of potential miscommunication, misalignment, and missed opportunities.
When “Just Tell Everyone” Stops Working
Remember when you could fix a problem by walking over to someone’s desk? When you could align the entire company in a single all-hands meeting? When everyone knew what everyone else was working on because Janet from accounting sat next to Mike from product development?
Those days are gone, but most CEOs keep operating like they’re still there.
The informal networks that carried your culture, your strategy, and your urgency simply can’t handle the load anymore. Information gets filtered, diluted, or lost entirely. Decisions that used to take minutes now require meetings to schedule meetings.
What used to be one company starts feeling like multiple companies sharing an office lease.
The Multiplication Problem
Here’s what’s really happening: you’re not just adding people, you’re multiplying complexity. Each new hire doesn’t just need to connect with you, they need to potentially connect with everyone already there.
At 50 people, new hires can reasonably understand how the whole company works. They can see the connections, understand the priorities, feel the culture through daily interactions.
At 150 people, new hires are lucky if they understand their own department. By 250, they might not even know what other departments do, let alone how their work connects to the bigger picture.
The company that once felt like a tight crew working toward a shared goal starts feeling like separate departments with separate agendas.
The Leadership Bottleneck
As the founder, you become the bottleneck without realizing it. Information flows up to you and back down, but it doesn’t flow across. Teams wait for your input on decisions they could make themselves, if they only knew what you knew.
You find yourself repeating the same explanations in different meetings. Answering the same questions from different people. Feeling like you’re the only one who truly understands what the company is trying to achieve.
The entrepreneurial energy that drove your growth starts getting consumed by the communication overhead that growth creates.
What Really Needs to Change
The solution isn’t trying to maintain the same informal communication patterns with five times more people. It’s recognizing that you need different systems for different scales.
At 50 people, your culture spreads through presence and proximity. At 250 people, it needs to spread through systems and structure.
The companies that navigate this transition successfully don’t try to preserve what they had. They evolve it. They build communication systems that can handle complexity. They create development processes that embed culture and alignment into how people grow within the company.
They stop relying on informal networks to carry critical information, and start building formal systems that ensure nothing important gets lost in the noise.
Building the Bridge
The growth crisis between 50 and 250 isn’t about having too many people. It’s about having the wrong communication infrastructure for the people you have.
Companies that thrive through this transition invest in alignment systems before they need them. They build platforms and processes that help information flow horizontally, not just vertically. They create development programs that help people understand not just their role, but how their role connects to everything else.
The pub analogy breaks down here, because unlike a social gathering, your company can have one conversation at scale. But only if you build the systems to make it possible.
The informal communication that got you to 50 won’t get you to 250. But the intentional communication systems you build for 250 will get you everywhere you want to go.