Here are two scenarios:
Scenario One
Jester: 'I am going to try to bluff the monarch that the task presented to us is much too difficult for the amount of gold he is offering us. I want him to give us more!'
DM: 'OK, roll your bluff check.'
Jester: I got a total of 29. THAT SHOULD GET ME SOMETHING.
DM: (rolling insight of 30). The monarch sees what you are doing and does not appreciate you trying to take advantage of his generosity.
Jester: C'mon man! I rolled a 19 plus my bonus. The DC cannot be that high. You just want me to fail.
DM: I just told you you failed.
Jester: That sucks! What a waste of a good roll!
Scenario Two
Jester: 'I am going to try to bluff the monarch that the task presented to us is much too difficult for the amount of gold he is offering us. I want him to give us more!'
DM: Ok! One sec..(rolls Jester's bluff check 20 vs monarch insight 21). Unfortunately, the monarch sees what you are doing and does not appreciate you trying to take advantage of his generosity.
Jester: Shucks! Allright, I apologize to the monarch and we will take his mission.