…tried unsuccessfully to hide the hole from the boss (6)
I believe the answer is:
editor
'hole from the boss' is the definition.
The definition and answer can be both people as well as being singular nouns.
Maybe they are linked in a way I don't understand?
'tried unsuccessfully to hide the' is the wordplay.
I cannot quite see how this works, but
'to' is within the answer.
This may be the basis of clue (or it may be nonsense).
Can you help me to learn more?
(Other definitions for editor that I've seen before include "Chief journalist" , "Press fellow" , "One who revises another's writing" , "Newspaperman" , "Cudlipp, for one" .)