I think it depends on the type of character I'm playing really. A character more invested in diplomacy or manipulation will be more likely to hear Josephine out while a more tyrannical character would mix between Cullen and Leliana (take out enemies in any way possible).
I do know my first (blind) playthrough will be more sensible, focusing more on what solution sounds like the best idea. If I need forces taken down or some extra manpower, Cullen will be my guy. If I feel someone can be reasonable or there's a nonviolent way to deal with the situation, Josephine's the one to call. If someone just needs to be taken from the shadows, Leliana will be chosen. I'm not going to favor one over the other based on who I like more or dislike, at least not in my first run. Probably not in my subsequent runs either considering I'm not the biggest Leliana/Cullen fan (or hater for that matter. Could actually care less about either one really. Glad to have their service and aid for what it is and leave it at that).