You fail by not being able to go any further.
Think about it... you need access to the offices, but if no-one is left to grant you access then you can't go on...
I like this, love that you can plan it to be massively convoluted.
It's a great game.
Plus anything pirate-based is great for us Pastafarians...
RAmen.
I find this waaay to slow when you select an attack; seems to take ages to get onto the next move. Also, once you've moved then attacked you don't need to see the options screen, it should just move on to the next character.