In the sixth episode of Outside the Box, Jermain discusses where he is on his coaching journey as he continues to work with the under-18s at the Tottenham Hotspur Academy. He looks at the work he's done so far, what he's gained from the experience, and compares his current job to his former one - scoring goals - to discover that there's nothing quite like the feeling of being a professional footballer. However, he still loves the feel of the grass under his feet and working with the academy is providing him with a much needed link to the game he loves so much.

In weighing up his future as a manager, Jermain has had some thoughts about who his assistant might be. But before he makes a final decision, he goes to speak to his former manager Harry Redknapp, and to the current Derby County number two, Richie Barker, to discuss the role of a number two and the sorts of things he should be looking for. The pair tell him that above all else, he needs to surround himself with experience.

One of the issues that Jermain is getting to grips with is the confidence to get up and speak in front of a team, to use his voice and his body language to convey the right messages. So, he brings in an unlikely pair of allies: Chris and Lucy Key who have been actors and directors in some of the biggest stage shows in Britain and who currently work with the West End show Les Miserables. Together, they show Jermain what he needs to do to use his voice to command a room, giving him simple tools to work with players and the press.

In the fifth episode of Outside the Box, Jermain travels to Wanstead Flats and his first ever club, Senrab FC, to look back on his career there and to discuss how he was first scouted by Charlton. He spends the evening coaching the youngsters through a number of drills, before discussing how much he learned from last week’s trip to Brighton and Hove Albion to meet Chief Executive Paul Barber and Technical Director David Weir. Defoe also concludes that he needs to begin to prepare a presentation so that should he be called for an interview, he’s able to talk from a position of knowledge about his style of play and management techniques.

He also discusses whether or not he would be interested in the vacant Oxford manager’s job after the incumbent, Karl Robinson, was sacked. And then he hooks up with the former ground commander of the SAS during the London terror attacks, Mark Billingham, to discuss leadership and leadership techniques. Together the pair break down what sort of skills Jermain will need if he’s to fulfil his dream of becoming a manager. And Mark tells him about how how some of his own life experiences in battle can help when it comes to leading a football club.

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.

In Episode 3 of Outside the Box, Jermain travels to Derby County to meet the management team of Paul Warne, Richie Barker and Matt Hamshaw as he seeks to discover more about what it takes to be a manager, especially in the lower leagues. Leaning on Warne's experience as a player in the Football League - and his six seasons in charge of Rotherham United - he seeks an answer to the question about whether he's ready for a top job. He talks to First Team Coach Hamshaw about why he wants the role, how he feels he would like to play tactically should he become a manager, and why ex-pros like Steven Gerrard were always set to become managers. Then Jermain picks Warne's brain about the stresses of the position, about what he will need in a number two, how much an analysis and nutrition team will have to gel with him, and the importance of a coaching staff all being on the same page. Before he departs, Defoe finds out from Warne about the nuanced relationship between managers and chairmen, with Warne telling him that he needs to go and meet some chairmen to ask them what they're looking for. After Jermain heads home, Warne reflects on their afternoon together, concluding that whilst he believes Defoe will get a job, it's his belief that at the moment, he wouldn't be ready.

In the second episode of Outside the Box, Jermain Defoe visits some of his former managers to find out who he was as a player, and whether his experiences in the game and his commitment to being the best, can lend itself to a career in management. He travels to the South Coast to see Harry Redknapp - who signed him on three separate occasions - to discover whether Harry believes he has what it takes to lead a team. Together the pair discuss Jermain's origin story in the game: spotted on the parks of East London and signed first by Charlton and then Redknapp's West Ham, before a loan deal at Bournemouth lit the blue touch paper of his career. Harry tells him cautionary tales of buying and selling players, of dealing with chairmen, and how best to navigate the path of that first job should a team come calling for his services. Back at Tottenham, Defoe tracks down the man who signed him at White Hart Lane, David Pleat, who tells him that he believes he has what it takes to succeed in the cut-throat world of football management. However, both men tell him that if he's to get a job, it will almost certainly be in the Football League. Which gets Jermain thinking.

In the first episode of a new fly-on-the wall series, Jermain Defoe travels back to the estate in East London where he grew up, exploring how his past experiences will affect his future as he begins a journey into the world of football management. From the house he grew up in and memories of his grandparents, to games of football in the street and a trip back to his old school, the former England star is keen to delve into his childhood and the people he shared those years with as he searches for a new career now that no-one’s singing his name. With management the focus, Defoe discusses the end of his playing days, his first coaching job within the Tottenham academy, and the dream of leading a team.

Before he retired, Jermain Defoe scored over three hundred goals for club and country. In a new fly-on-the wall series, Outside the Box details the next step of his journey.