Decisions, Team Work and Vision I believe. You need a combination of that from both players, one to pass, and the other to regulary 'see' the option to run for the short pass.
Happends a lot in my Barca side, but then again the players are all ridiculously good, the funny thing is that a lot of the time you pass square it and the receiving player buries it into the keeper despite him being an awesome finisher and 80% of the goal beind open or they only pass with diagonal balls to the far post
To be fair though, an 'easy square' like that never seems to actually happen in FM for me, it's an obvious choice for most top teams but it's just too rare.