This chapter describes an institutional Pedagogical Counseling program-assessment and systematizing initiative in terms of an adapted Community of Inquiry framework. An inquiry through pedagogical-counseling experience-exchange process was set up to analyze, assess and potentiate ongoing support activities by the staff members of the Center for Research and Development in Education (CIFE) in counseling projects of undergraduate and postgraduate programs. Garrison, Anderson, and Archer’s (2000) Community of Inquiry framework has been adapted to the authors’ pedagogical counseling process in order to conceptualize CIFE staff’s review exercise. The process includes ample opportunities to discuss and reflect on key counseling design questions, explore counseling programs from a pedagogical perspective and implement and evaluate new tutoring designs. This chapter describes the inquiry process and the lessons learned from the implementation of the pedagogical counseling inquiry exercise.