Tries to get a lift with company, which makes a painful squash (10)
I believe the answer is:
thumbscrew
'lift with company which makes a painful squash' is the definition.
The definition and answer can be both man-made objects as well as being singular nouns.
Perhaps you can see a link between them that I don't see?
I can't explain the rest of the clue.
Can you help me to learn more?
(Other definitions for thumbscrew that I've seen before include "Instrument of torture (crushing the pollex)" , "agonised by it?" , "excruciating instrument" , "It puts the squeeze on" , "That could be unpleasant!" .)