How will the Blues bring through their best academy players? When will they decide they're finally ready for the first team?
Yesterday the loan departure of promising defender Tomas Kalas to Cologne was confirmed by Chelsea, leaving many to wonder, will outstanding young players ever be given a chance at Stamford Bridge again?
Kalas put in a phenomenal performance at the end of last season, when the Blues went to Anfield, a place where Liverpool had annihilated most other Premier League teams, and defended heroically to ensure a clean sheet as part of a 2-0 win.
He isn't the first youngster to be shipped out of Chelsea just as he began to display the sort of ability that would normally see him integrated as a permanent member of the first team squad.
For Kalas, David Luiz has just been sold, yet instead of being promoted into one of the four centre back positions, he is sent away from the club, while another young defender, Kurt Zouma, is brought in in a multi-million pound deal.
No player has come through the academy into the first team since John Terry in 2000, and with Frank Lampard and Ashley Cole departing, Mourinho surely knows that his side could benefit from some homegrown talent when it comes to meeting FA and UEFA quotas.
Chelsea have seemed to regularly snub their own promising young players in favour of bringing in expensive youths from other clubs, even when some of their own youngsters were cherry picked from other academies for their own significant fees. Is their any proof that Mohamed Salah is better than Lucas Piazon or Gael Kakuta, who were both signed amidst fanfare and showed promise in the Chelsea first team at one time or another? Is their any proof that Marco van Ginkel is better than Nathaniel Chalobah or Josh McEachran, two players long championed as the future of the club?
You can have all the promise in the world, but if you don't get a chance to integrate into a group of senior players, to stake a genuine claim at playing 10-12 games a year at your club, it will always be difficult to make the grade there.
How will the likes of Islam Feruz, Lewis Baker and Ruben Loftus-Cheek, all talented players, gatecrash Jose Mourinho's squad? It is likely the trio of teenagers will not be seen for three or four years if at all.
There is of course a lot of sense in one club signing as many as of the best young players as they can, maximising the possibility of one turning into a world class player.
But when it is damaging the path from the academy to the first team, is it still the right thing for a club to do?