This paper investigates the pedagogic issues of information systems (IS) education through the constructivist approach of problem-based learning (PBL). In particular, the paper presents the perspective of how a group of students could be empowered in practicing the process of IS development through the nurturing of self-directed learning and group collaboration. The discussion puts forth the ideas of how to develop PBL groups of students as collaborative learners, as collaborative problem solvers, and as collaborative supporters of individual development within the group. There are also the concerns over what methods to teach in the development of IS for knowledge work. In particular, the discussion deliberates on the essence of PBL as a model of collaboration applicable to group-based project work in IS development, which is followed by a deeper investigation of the PBL model as a pragmatic means of problem solving in the context of elaborating suitable IS support for peculiar organizational scenarios. The paper describes some initiatives in the systems thinking of group-work design to substantiate IS education in terms of creating a rich framework of pedagogic activities to help students acquire the important learning demanded of IS professionals in their future careers. The paper concludes by discussing some of the important observations in the areas of organization transformation, and knowledge management, which render tremendous implications in the education of IS practitioners if we want our students to succeed in their future endeavors of IS design, construction and management, amidst the challenge of the 21st Century knowledge society.