Do bosses over time gradually lose the ability to rightly estimate how other perceive them? Yes, according to a recent article in The Economist:
So not only do bosses set too much store by their strengths, as our Schumpeter column notes, they also habitually overestimate their ability to win respect and support from their underlings. Somehow, on reaching the corner office, they lose the knack of reading subtle cues in others’ behaviour: in a further experiment Mr Brion found that when a boss tells a joke to a subordinate, he loses his innate ability to distinguish between a real and fake smile.
Read the whole article (“Deluded Bosses: Who’s Behind Me?”) here.
I wonder if this is more an issue in the corporate world than in the church, although I suppose it’s true that any leader could be prone to this phenomenon.
It reinforces the importance of regular evaluation in organizations (especially large ones)–as well as making sure that there are accessible systems and processes in place for folks to meaningfully offer input.
Words on the Word 
The Army has started to do “multi-source assessment and feedback (MSAF)” to avoid this phenomenon. It’s an anonymous survey with ratings and comments from superiors, peers, and subordinates. It’s required, but only for personal use, promotions still rely on our evaluation reports written by our superiors.
That’s a great idea.