Nussbaum (1998) proposed that Socratic activity is a worthwhile pursuit with regard to academic advising relationships. While it offers the promise of certain benefits, such as the development of critical thinking skills, Socratic activity arguably cannot be universally applied to all advising relationships. In presenting and analyzing issues related to the Socratic method, I offer support for a model of quasi-Socratic activity in advising as first identified by Hagen (1994). Referred to as "beneficial dialectic," it can function from a more contextual standpoint than the traditional Socratic questioning method because through it advisors can consider factors such as level of student development, learning environments, and individual proclivities.