Well, it does matter a little bit. If you define U to be the unitary transformation that transforms kets |a>, then U^-1 will be the unitary transformation that makes the same transformation on the bras <b|. Using this, one should see that the matrix element <b|S|a> under a transformation goes to <b|U^-1SU|a> which means that the matrix S'=U^-1SU is the matrix that represents the operator in this new basis. If I defined U the opposite way, as U is the transformation on bras, then I get the other definition.