For those who aren't old enough to remember the outstanding AC Milan side of the late '80s and early '90s, current Bayern Munich manager Carlo Ancelotti was an integral part of their midfield.

Industrious, hard-working and an excellent passer of the ball, the now 58 year old most famous moment in the red and black jersey came in the 1988-89 European Cup semi finals when he fired in a cannon of a shot from long range during a 5-0 thrashing of Real Madrid, a club - like AC Milan itself - that he would go on to lead to Champions League glory as a manager.

The 2014 triumph with Real was the third time he won European club football's highest honour as a coach, following two previous wins with Milan.

And yet, to an extent Ancelotti still flies somewhat under the radar. Recognised as an elite manager capable of taking charge at any major club side, he does so in such an understated manner in often ego-driven locales that one isn't quite sure what his main qualities as a coach are. 

You can listen to our full chat with Richard on the podcast player or stream/download on iTunes along with our recent interviews with Darius Vassell, Johan Neeskens, Tomasz Radzinski and India manager Stephen Constantine: 

So to get a handle on Ancelotti's qualities that have kept him in the elite managers bracket for at least two decades, we were joined by our regular Italian football guest Richard Hall, founder of the excellent Guardian Sports-network member The Gentleman Ultra to run the rule over his career, including how he was inspired to transform Andrea Pirlo from an attacking midfielder to a world class deep-lying playmaker and how Ancelotti's love for AS Roma could see him take on the manager's job there before he decides to retire from management.