Jemain is back where it all began for him when Harry Redknapp signed him as a sixteen year-old from Charlton Athletic as he heads to West Ham's training ground to talk to his former teammate and now the current Hammers Women's team manager Paul Konchesky. They talk about Paul's journey from finishing playing, his 8-month break where he could do all the things he couldn't as a professional - including skiing. Paul explains how he was taken on by West Ham as a defensive coach for the academy, moved to being a Loan Manager - looking after the players that are on loan at other clubs and then to assistant to the WSL team and now the manager of West Ham Ham women in the Women's Super League. Paul and Jermain speak about the differences in coaching and managing female players compared to boys in academies and senior male teams. They also discuss the importance of having different characters needed for a manager's coaching staff and in particular, for the women's game, to have a female coach in West Ham's Danielle Bowman who can relate and demonstrate to the players things that Paul and his male coaches might not be able to do. Jermain also praises Paul and his coaching team on the quality of the training session that Jermain watched and Paul asks him, again to come back and do a finishing clinic with the squad, he just needs to bring his boots next time.

Jermain and former SAS soldier Mark 'Billy' Billingham discuss leadership and team building in this bonus episode of Outside The Box. Billy advises Jermain on what good leadership is, what it takes to build a team, when to delegate and how to spot and deal with individuals that have professional or personal problems or issues within his squad. Billy also talks about his time in the military on missions, recalling a near miss in the field and how he coped with pressure situations including when he was leading a squadron that was outnumbered, surrounded and under heavy fire. Billy also talks about being the head of the counter terrorism unit during the London 7/7 attacks and how he used his training and experience to cope with a high stakes and high pressure situation with his team and the government looking at him for answers, action and strong leadership. The two talk about Jermain's time with England doing exercises with the Royal Marines and what Jermain took away from that experience, and, Billy recalls a tricky situation in Rome whilst working as a bodyguard for two bonafide A-list celebrities and the paparazzi.

Jermain speaks to former England international and ex teammate Sol Campbell about his journey from calling time on his playing career to becoming a football manager in the lower leagues. Sol talks about know he wanted to go into management in the latter stages of his career as he was an on-field coach for Arsenal and his centre-back partner of Kolo Toure. He also revealed the managers that he took the most from, Ossie Ardielles at Tottenham in how to deal with players, Gerry Francis also at Spurs with the focus on fitness, strength and conditioning and Arsene Wenger at Arsenal and the sports science and practices he introduced from Japan. Sol also talks about his two forays into management as the boss of Macclesfield, who he helped keep in the Football League and Southend during the pandemic. The pair also discuss the lack of opportunities for black managers in the game and Sol reveals that from thirty jobs he's applied for he's only had four interviews. Sol talks about his interview with England Under 21s and says that there needs to be more visibility and time on the grass for black coaches to gain experience and get more jobs at clubs.

Jermain heads to the south coast and to Harry Redknapp's house to catch up with his 3-time former manager. The pair discuss when Harry first heard of a young 16-year old Jermain and how he signed him from Charlton to West Ham, sending him on loan to Bournemouth, scoring in his first 10 consecutive games. Harry talks about his time in the USA with Bobby Moore and also the importance of managers having a keen eye on the youth teams of their clubs and getting to know each player not just in and around the club but also on a personal level too. Harry also gives Jermain advice on how to deal with big stars - recalling when he signed Javier Margas after a had good World Cup, only for the Chilean international and his family to get extremely homesick a few month into the season, culminating with Margas fleeing through a bathroom window and on the first plane back to Santiago. Harry also talks about giving Nigerian star Kanu and England's Paul Merson leeway to train when they liked whilst at Portsmouth and Jermain and Harry reminisce about the mercurial talent that was Paolo Di Canio and the Italian infamously sitting crossed-legged in the penalty box whilst the game was going on around him. Harry also reveals how low he got when he was given the sac and the amazing circumstances around his leaving of Portsmouth, signing for their most bitter of rivals Southampton and then rejoining them after a few bottles of red with the the owner chairman Milan Mandarić.

In the final episode of Outside the Box, Jermain reflects on his journey to this point, looking back on what he's learned through the series and what he hopes to achieve in the next weeks and months.

He's been informed that he has an interview to attend - his first - with the Chief Executive of Brighton and Hove Albion, Paul Barber who will put him through his paces in a simulated interview that will give Jermain the sort of experience he will need when he comes face to face with a chairman.

The two meet in London and Barber grills Jermain on his plans: why he wants to manage, what his philosophy will be, what style of football will he play, who will be on his coaching team and what culture he'd like to set. Across a couple of hours they talk back and forth before Barber calls time and the pair review the process.

After looking at some of the highs and lows, they depart, only for Jermain to find out that there are rumours linking him to a position with the Spurs first team, and for him to receive an important phone call.

The penultimate episode of Outside the Box begins on the day job for Jermain and another session with the under-18's. But after eight months at Spurs, how's he getting on? His manager Stuart Lewis gives us a status update on his progress so far.

A week on from visiting the north east and the family of Bradley Lowery, Jermain reflects on some much needed perspective that the trip offered him. Coaching helps, but so does the opportunity to reflect on other aspects of his career that he regrets, notably the way his time in the MLS ended. He discusses what went wrong in Toronto in 2014, how he feels for the fans and the club, and how much he'd like to go back and coach the team. All that gets him thinking about managing abroad and so he reaches out to the former Scotland manager Alex McLeish to discuss his time with Genk in Belgium and Zamalek in Egypt.

From there, he heads back to one of his old clubs - West Ham United - to speak to an old friend. Paul Konchesky played with Jermain at England and after retiring form the game in 2016, began working at the Hammers academy. In 2022 he took over as first team manager of West Ham's women's team who are currently 7th in the WSL table. It gives Jermain the opportunity to find out more about the women's game and whether that could garner him the experience he needs to pad his coaching resume.

Before he heads home, he gets an important phone call which may help shape his future in the game.

This episode discussed child bereavement and you can find details of organisations offering information and support at bbc.co.uk/actionline

In episode ten of Outside the Box, Jermain takes an emotional trip to the North East to see the family of Bradley Lowery, the young boy who he befriended after being diagnosed with neuroblastoma at just 18-months of age.

This episode discussed child bereavement and you can find details of organisations offering information and support are available at bbc.co.uk/actionline

He travels from his home outside London to the small colliery village south of Sunderland to see Gemma and Carl Lowery so that he can sit down and discuss Bradley's life. As Carl looks after the new baby, Gemma and Jermain begin by talking about what sort of boy Bradley was, how his cheeky smile won so many people over, and how football was so important to him. They discuss how the family discovered he had cancer, and the moment when Bradley and Jermain met for the first time - in the Sunderland dressing room ahead of a fixture against Everton in 2016.

Bradley, who was there as a mascot, immediately became attached to Jermain and from that day forward, until the day he passed away some ten months later, the pair became great friends.

They talk about the day Jermain led England out against Lithuania with Bradley as mascot, before things started to get worse with the cancer becoming more aggressive and the family preparing for the worst. Jermain discusses how his faith was the thing that got him through and how his relationship with the Lowery's has made him stronger as a person, despite tragedy in his own life.

The episode ends with Gemma discussing how she talks to Bradley even now and had recently asked him for a sign that he was still there. She tells Jermain that she received a message from someone who wanted to send a poem they'd found which had been written from the perspective of a dead child to their mother. Gemma then reads the poem to an emotional Jermain.

In the ninth episode of Outside the Box, Jermain talks to current and former managers about the stress of the job, finding out about the pressures of running a football club, and discovering what it means to be sacked.

His journey begins closer to home as his club, Tottenham, announce the departure of their manager, Antonio Conte. That leads to questions about his possible replacements which are taken up by 5 live's Monday Night Club show, including one listener who believes Jermain should be given an opportunity.

One of the recurring themes of the series has been the undercurrent of pressure that the managers he's speaking to are facing up to. He wants to dig deeper into the stress of the job, so travels back to the south coast to speak to his former manager, Harry Redknapp, who tells him how difficult it can be, talking about the strain he felt and the knock-on effect for his family, especially his wife Sandra.

For Jermain to really understand the problems he might face, he needs to talk to someone for whom the game became too much. So he joins the former Reading and Leeds manager Brian McDermott at a talk he's giving to the Brentford Academy players about the pitfalls of the modern game.

As more footballers and their managers open up about their mental health struggles, Jermain finds out about the number of players who've talked about suicide, and hears from one manager who was having suicidal thoughts.

Part of the pressure on managers is the fear of the sack, and so he talks to current and former managers Paul Warne, Brian McDermott, Harry Redknapp, Chris Hughton, Richie Barker and David Weir about what happens when you're sacked, before finding out from a chairman and a chief executive what it's like to actually do the firing.

In episode eight of Outside the Box, Jermain heads to Media City in Salford to work as a pundit on Match of the Day 2. It's a post-playing world that has always interested him, and for a football obsessive like Jermain the idea of watching and talking about games is extremely appealing.

He speaks to the show's editor Steve Houghton about what's required, and then reminisces about growing up watching a programme he's about to appear on. Smoothing his path on this night will be his fellow pundit and former Tottenham and England teammate, Jermain Jenas who discusses how difficult he found life after hanging up his boots, how he got into punditry, and how he's developed his skills to try and best convey his opinions to the watching public.

Before long the show is underway and Jermain is offering opinions on the Sunday fixture list including Fulham against Manchester United, and digging into a well-rounded performance from a fellow striker: Aston Villa's Danny Ings. At the end of the show, Jermain heads back to London and readies himself for a day with the U-18's at the Spurs Academy.

Although management remains at the forefront of Jermain’s mind, his trip to Manchester has made him wonder how the media could work with him - and against him - if and when he takes over at a football club. So he brings together two of the most prominent journalists in the business to get their thoughts on the relationship between the press and managers: the Chief Football Writer of The Times, Henry Winter, and his counterpart at The Daily and Sunday Telegraph, Jason Burt.

The pair discuss many of the issues Jermain will come face to face with when he makes the jump from academy coach to first team manager.

In episode seven of Outside the Box, Jermain confronts the game’s ugly past to discover if management is really something he wants to get into by asking why there are so few jobs available for black managers. He tackles the problems in society pertaining to race and wonders whether he really has what it takes to fight racism in football and beyond.

His journey starts with his mother Sandra, as the pair get together to discuss what it was like for her to watch him play throughout his career, often in environments which were hostile towards black players. She discusses the worst time: a 2004 game in Madrid when England played Spain in which the visitors' black players were relentlessly abused from the crowd, often with monkey chants whenever they touched the ball. They talk about what that was like from a playing perspective and how it felt to be in the stands watching, with Jermain saying that it was the only time in his career when he wished he wasn't on the pitch.

Defoe is keen to find out more about the history of black managers in football and so he tracks down Sarita Collins, daughter of the late Tony Collins who was the first black manager in the English game. After a successful playing career which began at the end of World War II, Collins became manager of Rochdale in 1959, leading them to the League Cup Final.

From there he goes to see one of his heroes, John Barnes, to talk about how racism affected him during both his playing and managerial careers. Barnes talks about what it was like to have bananas thrown at him during games, how he reacted to the National Front sitting near him on a flight to Brazil in which he scored his famous goal for England, how racism has never left the game, and how it affected his career as a manager with a lack of opportunities because of the colour of his skin.

And finally he talks to Troy Townsend. The father of Jermain’s former Tottenham and England teammate Andros, he’s also Head of Player Engagement at football's equality and inclusion organisation, Kick it Out. The pair discuss how far the game has to go, what needs to be done in society, and look back on how the England trio of Marcus Rashford, Jadon Sancho and Bukayo Saka were treated in the aftermath of the Euro 2020 penalty shootout defeat to Italy.