Mostly, it is certain people that I have to deal with that make me cringe.  You know the type - everyone in  the world (except them, of course) is stupid - everyone is out to get them - policies were enacted just to make THEIR life difficult, blah, blah, blah.

And inevitably those are the people who have the most complicated transactions and something always goes wrong somehow.

So, I guess the most times I cringe is when I know I have to contact these people.