The awkward stage between solo founder and actual company
We're four people and nothing about our structure makes sense. Too big for one person to do everything but too small for anyone to specialize. Roles overlap. Responsibilities are vague. I'm still doing things a CEO shouldn't do while also not doing things a CEO should. The organizational frameworks designed for twenty-person companies are absurd at our size. Org charts, department structures, formal reporting lines. It's four people in a group chat. But the absence of any structure means work falls through cracks and nobody is clearly responsible for things that matter. What makes this stage particularly uncomfortable is that every process I create feels premature and every process I skip creates confusion. Weekly team meetings feel ceremonial with four people but without them alignment drifts. Role definitions feel corporate but without them people step on each other or assume someone else is handling something. We're figuring it out through a minimalist approach. Clear ownership of specific outcomes rather than job titles. A shared document of who's responsible for what that we update when reality drifts from the plan. Brief weekly sync that's allowed to be two minutes if there's nothing to discuss. Nobody writes about this phase because it's not dramatic enough for a story. Not the exciting early days and not the structured growth phase. Just an awkward middle where you're improvising organizational design for a group too big to wing it and too small for formality.
Posted Mar 5, 2026, 4:51 PM UTC