User blog comment:Piyush Banerjee/Shin DxD 2 discussion/@comment-2600:1702:3600:12F0:1DB7:CCBE:4F4:B192-20190207160114/@comment-24552694-20190207223006

I didn't mean to under sell Issei but i may have been over estimating the support given to Rias (I'm am generally assuming that Rias, Sona and Seekvaria are getting all the support they can from the families as possible) but i do think my point still stands. Rias has experience and training in leadership. Issei does not have any training at all. As a noble house I’m sure that the Gremories have someone who could give him some basic stuff at least  but a major issue seems to be that despite knowing his dream was to advance no one thought to actually teach him anything at all. Azazel I think realised he had screwed up with Issei in general as well when he was in the hospital and his parent’s where there but

Remember that a major point of Sona's dream is improving the training non noble’s receive in the underworld and Issei is a prime example of what can happen. I think Issei has been lucky with has charisma bringing him a lot of allies but he still struggled a lot in the begging due to the sheer bad luck of only just starting out.

Rias on the other hand had years of training to lead and they reason she lost was because she tried to beat Issei in a one on one fight. Whilst Issei’s team is good he is without a doubt the strongest member of his team and none else could really compete at his full strength any more, except Grayfia but even then with the black armour not really. That is a huge weakness since if he went down they lose but Rias still had Strada and Crom Crouch and if she had them fight Issei first then she would have won. Issei’s team played the delay game to get Issei to rias first and then they won from their as whilst Issei is weak as a leader he is crafty since he did take down a super terrorist with a toy.