What if the skills that made you successful are now holding your company back?
Rand Fishkin built Moz to 150 employees before admitting he'd become the company's biggest bottleneck. His mistake wasn't incompetence. He kept doing the job that worked at fifteen people.
This is the transition nobody prepares you for. Not once, but repeatedly. At ten employees, at fifty, at a hundred. Each stage demands a different CEO, and that CEO has to come from inside you, even when everything you've mastered becomes obsolete.
The Ten-Person Cliff
At five employees, you can take the whole company to lunch. Everyone knows what everyone else is working on. Information flows through hallway conversations and shared context. You don't need systems because the company fits in your head.
Somewhere between ten and twenty, that breaks. You can't hold every commitment, every project status, every interpersonal dynamic in working memory anymore. The tribal knowledge that made you fast becomes the bottleneck that makes you slow.
The Operator Trap
When things get uncomfortable, founders retreat to what they know. The CEO who should be thinking about market positioning is debugging code because debugging feels productive. The leader who should be developing strategy is closing deals because closing deals is what worked at fifteen people.
This isn't laziness. It's the opposite. You're working harder than ever, just on the wrong things. Every hour you spend doing work someone else could do is an hour stolen from work only you can do.
The Self-Awareness Paradox
Everyone thinks they're self-aware. But the founder who rates themselves a six out of ten on self-knowledge is probably more self-aware than the one who claims a nine. The challenge is structural. Employees won't tell you the truth because their careers depend on pleasing you. Advisors often won't tell you the truth because they want your business.
The only reliable source of honest feedback is other founders with nothing to gain from your success or failure. Finding people who will confront you with hard truths isn't optional. It's the only way to see what you can't see about yourself.
What Each Stage Requires
At zero to ten, you need to listen and sell. At ten to fifty, you need self-awareness and the ability to let go. At fifty to a hundred, you become a leader of leaders. At enterprise scale, you need presence and communication skills that work at distance.
The skills that made you successful are not the skills that will make your company successful at the next stage. The founders who make these transitions share one thing: they're willing to fire themselves from jobs they're good at to take jobs they've never done before.
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