Anderson, 57, who started his coaching career with Stow in the Border Amateur League over 30 years ago, has developed a friendship with current Roma manager Mourinho since they first met 17 years ago.
"It was back in the days when I was a football development officer and I was doing my UEFA A Licence,” Anderson told The Southern Reporter.
"Mourinho was at Chelsea at the time and had just come across and won the league.
"I was keen to see some good practice to help me with my A Licence so I thought I would write to the top manager at the time.
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"I had the view that 99 times out of 100 I would never hear back from somebody like that.
"But a couple of weeks later I got a letter through the post from him saying it was OK for me to come down to Chelsea to view one of his sessions.
"I think the connection was when Jose was at Barcelona he had done his B Licence in Scotland, so the fact that I was working with the Scottish FA probably had an influence on him letting me in.
"It was absolutely fantastic. I was totally delighted and surprised that I was going to go down there.”
On what happened when he viewed Chelsea training under Mourinho one Friday, Anderson said: “Jose’s attention to detail was second to none, I always remember him moving markers just six inches on the pitch because it wasn’t quite right, stopping the play when somebody was just a couple of feet out of position in terms of the shape that he wanted.
"He was working with top players, John Terry, Frank Lampard, Didier Drogba, all these guys.
"Jose invited me to come down again because I hadn’t really seen him work properly because it was the day before the game.
"I went down again, watched a full week with him at Chelsea and kept in touch, visiting him again when he was at Inter Milan and Re al Madrid.”
And Anderson – who is currently doing his UEFA Pro Licence as a candidate alongside former Scotland internationals James McFadden, Kenny Miller and Shaun Maloney who all hope to graduate in October – crossed paths with Mourinho again last year after getting in touch with him via email.
"He had just lost his job at Spurs,” Anderson said. “I asked if he would deliver a session on the Pro Licence for us and he did an hour-and-a-half session for our group over Zoom about a year ago.
"Years ago when you saw him on the TV you maybe thought it was all about him and he was a bit arrogant.
"But behind the scenes when you meet him away from that he’s a very quiet, humble, generous guy who is very family orientated and very good with people.
"He has a small group of people that he knows and trusts and if they work with him he knows how to get the best out of them.”
Anderson feels privileged to be doing his UEFA Pro Licence course.
He added: “It was a lifetime ambition of mine to get on the Pro Licence course.
"I never really thought I would. There are only 20 people every two years that get accepted for it, with hundreds of applications from all over Europe.
"It’s been a lot of work over the last two years so after I get it done I will take stock.
"I like trying to help some of the young, up and coming coaches. Scott Brown has been in my group and he’s gone on to get his first job at Fleetwood.”
Anderson has no ambitions to become a manager in his own right.
"What I enjoy as a coach is being on the grass working with the players and trying to improve them,” he said.
"You find out on the Pro Licence course that there is a massive difference between being a manager and being a coach.
"A manager needs to deal with the boardroom, deal with players, recruit players, deal with fans and staff, select the team, deal with players that are upset etcetara.
"When you are the assistant or a coach you are mainly focused on delivering sessions on the grass and that’s probably what I’ve enjoyed most and where my best qualities are.”
An eventful coaching career has seen Anderson work in various jobs alongside a quartet of ex-Hearts stars – Colin Cameron, Lee Makel, Gary Naysmith and Robbie Neilson.
After his humble beginnings when he served as Stow Amateurs player/manager in the Border Amateur League for several years, Anderson then moved onto Gala Fairydean Rovers as assistant manager and co-manager with David Smith.
Anderson followed this by doing scouting work for Sunderland, before becoming first team coach to manager Cameron and his assistant Makel at Cowdenbeath.
In their first season in 2011/2012, the Blue Brazil won the Scottish second division.
After helping Cowdenbeath avoid the drop the following season, Anderson bossed Hibernian under-15s for three months before returning to senior football as East Fife first team coach, at a time when manager Willie Aitchison was assisted by Naysmith and Neilson.
Anderson then became East Fife assistant boss to Naysmith and they won the second division in season 2015-2016.
When Naysmith took over as Queen of the South manager in December 2016, Anderson spent two-and-a-half seasons as assistant boss there before becoming Scottish FA coach education and development manager and Scotland under-19 assistant coach to Billy Stark.