In the fourth episode of Outside the Box, Jermain heads to Brighton and Hove Albion to speak to Chief Executive Paul Barber and technical director David Weir to find out how they work with managers and what the expectation is when they bring in a new leader of the football club. After being told by Derby manager Paul Warne that he needs to become more acquainted with the men and women who do the hiring and firing at football clubs, Defoe sits down to find out what they do, how they do it, and what he needs to do to make himself a legitimate contender for a top job in the game. Barber tells him that he needs to begin to prepare a serious presentation for when he has an interview, whilst Weir says that if he ends up working at a club with a director of football or a technical director, that their job is very much more long term, whilst the manager may only be thinking of the next game.

He then hears from Rotherham United owner Tony Stewart on how different life is in the Football League in regards to dealing with chairmen. Stewart tells him that he needs more experience if he’s to be taken seriously, and that being a great player and being a manager don’t necessarily equate. Stewart tells him that he wouldn't employ him at the moment because of that lack of experience, but that could change depending on what he does in the game over the next couple of years.