Actually I couldn't get the interaction to be available every day. I have asked on one day, then the next with the bar still full, best friends with the boss, on friendly status, and talked about work and still no option. She tried every day for a weekend (Friday evening, Saturday, Sunday, and Monday morning before work). The first day she had both promotion and raise available, my fault in a queued up the request and the action before it was negative and dropped from friendly back to social so she was denied. Saturday she worked up and only had the raise option available which was given. Sunday and Monday she got neither option no matter what I tried. So I just gave up, but it would be good to take a sim and test out the timing I think.