Time and time again, the young startup promotes their longest-tenured young engineer to become CTO of their 20-something startup. And it makes sense on the surface, because it’s their “best” engineer. And why not? They’ve been there for so long that they know the system they’ve built more than anyone else.
But now they have two problems: they lose their “best” engineer, and on top of that, they gain what’s probably a shit manager.