User blog comment:B214/Volume 23 discussion blog/@comment-1884090-20170408001538/@comment-10330822-20170410080922

The main difference between Rias and Issei is that Rias is naturally talented at recognizing talent, while Issei has a natural talent for attracting it. Ddraig even said its a common trait for dragons, to attact powerful allies and enemies.

I don't think Issei's a poor leader, he's just inexperienced. Think about it, Rias has been trained as a devil her entire life, and probably has been given plenty of strategy lessons in preparation for her role as a King of a peerage.

On the flip side, Issei has already shown he can develop in one year what takes years for other people. It only took him one year to overpower Rias, when she was trained her entire life. Likewise, I doubt it will take him much longer to surpass her as a leader either.

Besides, when it comes to a match between the two, Ravel is giving Issei that same advantage, so the ultimate question is whose tactics will be better, Ravel or Rias, just like Ravel's tactics are going to be put to the test against Sona upcoming to.

There's also something to be said about the element of chaos Issei adds to anything he is involved it. Nothing goes as planned if he is involved, not even Sona and Rudiger's strategies went off without a hitch because of him. Its just in Rudiger's case, it didn't cost his team the match.