Back on topic, if I understood it right the sim doesn't need any particular trait, must have 3/4 of the job performance bar filled, be a good friend with The Boss and can only ask for it once every 3 days, correct?
Two things I didn't get: do ask for raise and ask for promotions exclude one another, or you can ask for both? If the sim fails in its request, do the 3 days stand off apply?
The brave trait gives you an independent option ( it has nothing to do with bosses) clicking on work place, every 5 days ( if you fail, your performance goes down)
Now, for asking your boss, you need a high relationship with him and a high performance bar, you must ask for a raise first, then for a promotion, otherwise it excludes the raise, and yes, you can try later if you fail. (i think its 2 days, and you must be on a different career level)
Again: sorry for bad English.