Implies the boss of a job once did exceptionally, but their ability to lead/direct a team of employees has deteriorated overtime and refuses to quit or accept that changes need to be made, or are afraid to do so.
They may still be effective at their own work, but they cannot realize that their business/team is underperforming and are no longer able to shift the situation in their favor.
"How's work been?"
"My broken boss won't bring more staff on, he keeps filling reservations but there's no one to help."