The Northern Irishman was brought to Chelsea as a youth and reserve coach during the Portuguese boss' Stamford Bridge reign, before going on to launch his career with WatfordLiverpool boss Brendan Rodgers has told of how Jose Mourinho gave him the confidence to go into football management.
The Portuguese looks set to leave Real Madrid to rejoin Chelsea this summer following three turbulent years in the Spanish capital and it was under Mourinho at Stamford Bridge where the Reds manager got his first real coaching experience, having been appointed head youth coach and then reserve team manager before leaving to take over Watford in 2008.
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"He encouraged me and gave me that belief that I could go on and become a manager but until you actually step out there ... it's a different ball game altogether.
"One of my strengths is I learn and I like to learn from all sorts of people in all walks of life. I try to implement my own ways of making teams successful."
Looking ahead to next season, Rodgers played down hopes of Champions League qualification, citing a lack of competitive financial resources and therefore the ability to attract big-name players.
"It's a difficult ask," he observed. "Look at Tottenham - they finished in the top four last year and spent a lot of money to try and retain their place in there.
"Chelsea, who were the Champions League winners, finished sixth last season so for us it's a huge ask but it's our goal and it's where we want to go. We want to keep growing and we want to look to win trophies.
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"We know that at the top end you have to spend money but we won't have the resources that other clubs have. So we're trying to build our way there. A lot of our work is going to be in terms of our coaching and making the players better. We know that we need to have some experience in there as well and that hopefully can help project us forward again."
Part of that strategy will involve blooding young players, something that Rodgers has been keen on doing during his time at Anfield.
"Youth will be a very important part in our growth as a club and I'll always look for young players," he added. "But you have to have the balance and that's important.
"This season, Raheem Sterling played against Manchester City when he was just 17 years of age. He could even play for our youth team next year - that's how young he is.
"But to go from being a youth player to making his full international debut for England is a great credit to him. He knows he's got a lot of hard work ahead.
"Andre Wisdom has played a number of games this season; Jonjo Shelvey is still only very young. Boys like Suso have played as well."