As the use of ICT in education and training continues to take shape, a variety of challenges are raised that pose new questions for pedagogy and the relationship between teachers and students. The original classroom models of teacher as lecturer are called in to question, and most research today argues the need for more collaborative relationships between students, altering the role of teacher (Palloff and Pratt, 1999; Salmon, 2000). One of these important places is in the field of mentoring, where teachers are often considered the mentor for students, and also where teachers mentor other teachers. Most forms of mentoring offline have followed a tradition in which a two people work together, one serving as the wise knower and the other serving as the learner. This is often referred to as the apprentice model (Funk and Kochan, 1999). While this model has served well many, and continues to serve well many, the model is not so befitting an online culture that is based on collaborative and collective learning. Mullen and Lick (1999) argue that it is time to rethink the role of mentoring, and what is mentoring. They suggest that the traditional form of mentoring does not serve well the contemporary needs of professional development and learning. They call for a new dimension, to which they refer as a "cultures of synergy". Such synergy cultures are based on a bi-directional relationship between two or more people, from which co- mentoring takes shape. No longer is the knowledgeable one the mentor, but rather all parties are knowledgeable about different things and have something to share with one another. This notion is in keeping with the theories of collective knowledge development (Sorenson and Takle, 2002) and social learning online (Lave and Wenger, 1991). This presentation will present findings from a two-year research study on an online international program for educational leaders in seven countries. The program model was based on traditional pedagogical models of teaching and more contemporary models of mentoring. Using ethnographic and case study methods adopted for online research, the findings indicate that traditional models of pedagogy have the possibility to kill effective mentoring online, while a culture of synergy opens the possibilities for meaningful collaboration and co- mentoring to take place online, and cross culturally. The findings also highlight the role of technology and culture in shaping different kinds of co-mentoring and collective learning. Four models of co-mentoring will be presented. It is hoped that this presentation will stimulate dialogue among audience members about how to develop effective cultures of co-learning and mentoring for educators through the use of ICT.