From 30 to 250: Why Your Management Playbook Stops Working (And What to Do About It)

Read Time:
5 minutes
Organizational Alignment

The management approach that got you from 0 to 30 people won’t get you from 30 to 250. But most founders don’t realize this until they’re drowning in miscommunication and watching their culture fragment.

The Pub Test

Picture this: You’re in a pub with 2 friends. There’s only one conversation happening. Everyone gets a turn to talk, everyone’s listening to the same stories and jokes. Communication is effortless.

Now imagine you’re in that same pub with 4 friends. Suddenly there are two conversations happening. Three people in one, two in the other. Different stories, different jokes. Keeping everyone in one conversation is possible, but it’s harder.

Now picture 250 people in that pub. How many different conversations are happening? How impossible would it be to have just one shared conversation?

Your Company is That Pub

At 30 people, you could keep everyone aligned through informal check-ins, team meetings, and hallway conversations. Your vision was clear because you were there to reinforce it daily.

At 250 people, you have departments, teams, remote workers, different time zones, and layers of management. Your original playbook doesn’t just stop working. It starts working against you.

The Boat Problem

If you’re in a boat with 2 people, it’s easy to figure out what you’re doing. Both rowing in the same direction, in unison.

With 5 people, it’s harder. Rowing in unison requires coordination, and you probably need someone on the rudder. You don’t go 5 times faster.

With 250 people, you’re not in a rowing boat anymore. You’re managing an oil tanker. And without the right systems, half your crew might be rowing in different directions.

What Actually Breaks

When you scale without updating your playbook, three things happen:

  1. Information gets diluted as it passes through layers
  1. Silos form naturally as teams focus on their specific goals
  1. Culture becomes inconsistent across different groups and locations

The enthusiasm and alignment that felt natural at 30 people becomes fragmented. People start making decisions based on incomplete information or outdated priorities.

Building Your Scale Playbook

Growing companies need systematic approaches to maintain alignment:

  1. Create clear communication channels that work across teams
  1. Document your processes and values so they’re consistent
  1. Build feedback loops that surface problems before they spread
  1. Invest in systems that keep everyone connected to company goals
  1. Turn your managers into alignment champions, not just task managers

The Growth Paradox

The irony of scaling is that the personal touch that made your early culture special becomes impossible to maintain. But that doesn’t mean you lose it entirely.

You just need to systematize it. Turn your instincts into processes. Make your values actionable. Create structures that preserve what made your company great while allowing it to grow.

Because at 250 people, alignment isn’t about having more conversations. It’s about having the right ones, consistently, across every part of your organization.

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