Most of the time yes, unless they 2 are polar opposite to each. But some times you just can't get a retinue member away from a guy. In on of m y Brutii campagins I can't get a sword bearer away from one of my old family members into a younger guy I want to groom for field command but the sword bearer just won't go. The young guy has almost no traits and no retinue yet and it won't go.