Very fun concept. It's a bit hard to choose the wrong topic because they repeat themselves to often, though. A timer that gives you a limited amount of time to choose each round could add a good bit of tension. Also, it would be fun if the boss had items in his office that alluded to the things he liked.
I encountered a bug on the main menu. I opened the how to play page and somehow also opened the credits page on top of it. I was eventually able to close both of them, but I could neither start the game or exit out after.