So you are throwing a bitchfit here because Jack is going to stand there, listen, and not do anything to change the outcome of this meeting.
...Seriously Lantz, this is mindboggling to me that you're doing this. Again. He's just standing there. Not. Doing. Anything. He's just listening in. So your complaint is pretty much invalid because holy shit he's not doing anything but listening in on a private conversation (Which is what his freaking job is, he's a private investigator) and thinking about how to use the information he gets.