Boss distressed by Conservative's tale of woe (3,5)
I believe the answer is:
sob story
'tale of woe' is the definition.
(I've seen this before)
'boss distressed by conservative's' is the wordplay.
'distressed' indicates an anagram.
'by' is a charade indicator (letters next to each other).
'conservative' becomes 'tory' (informal term for a Conservative Party member).
'boss' anagrammed gives 'sobs'.
'sobs'+'tory'='SOB-STORY'
(Other definitions for sob story that I've seen before include "Sorry tale" , "unhappy tale" , "Tale intended to arouse pity" , "Plea for sympathy from Tory boss" , "Tale of misfortune" .)