It’s great at the beginning. We started with a team of mostly self-motivated people and the lack of upward review made technical decision-making easy.
Eventually, you hire someone who is not self motivated. Also, some existing people get wise to the fact that no one will check up on them, and read Reddit for half the day.
About 4 months in, every team had 1 person like that. They had to work around them - one team can’t ever get designs cause the designer is checked out, one team’s backend work takes 1.5x as long as everyone else.
People say things to the underperformers, but there’s no teeth to anything, no one is anyone’s manager, so it’s just suggestions. They get ignored. Resentment builds into each individual team’s culture. Deadlines start slipping.
1 year in, non technical leadership is fed up. They don’t see benefits from the flat structure, and hire a new CTO and new middle management layer.
The new managers come in briefed with “the team is lazy.” The underperformers get pushed out, and have trouble finding work because their skills have absolutely atrophied. Any remaining high performers are permanently tarred with the reputation of the org from the flat structure days, and get micromanaged. To the new managers, they are kids who will misbehave the second they aren’t watched (which, in fairness, is kinda what happened at the organizational level when they weren’t watched.)
Sone good middle management providing timely oversight and feedback could’ve avoided the whole situation.