Raymond's advice is very, very sound. It's worth reading that EXTREMELY LONG
post two or three times, to let it really sink in. I know from a work experience of forty-plus years that what he says is gospel truth.
The question to ask in difficult situations is: what can I do to benefit everybody that's suffering from this problem? This is the positive approach that Raymond advocates.
I've engaged in my share of confrontations in the workplace, and there hasn't been
one of them that hasn't left a bitter taste, even if I seemed to win at the time. Far better to think of some constructive way to improve things that will not result in any loss of face or hard feelings.
Sometimes, of course, this may even mean just quitting the job.
One other note: there are people (I've known a few) who are so stingy by nature that it hurts them--I'm talking about emotional pain--terrifically to do something like cutting a paycheck. Ideally, these people should not be in a position to have to make expenditures. I believe it's a form of mental illness that needs professional help. Such people's families are often made to suffer needlessly because of this ingrained tight-fistedness. It's possible your boss is one of these unfortunate souls. But he still might respond to creative, helpful ideas.