The Norwegian government wishes to implement, on a large scale, e-learning in all schools, and at the same time modernize e-learning in accordance with 21st century skills [1] [2] [3] [4]. This is a challenge, as it will require radical changes to Norwegian teachers' teaching methods, because they will have to shift from the physical environment and classroom teaching to an online learning environment. The complexity of the challenge may cause unease and insecurity among teachers. The Principal at the Vestfold Vocational School in Vestfold County, Norway wanted to engage his group of teachers, who did not see the potential of the technology, in co-developing e-learning strategies, and at the same time integrate the 21st Century skills. This paper tells the story of how this task was initiated, focusing on teachers' everyday practice, and how the teachers themselves took the first step in the process of change. Our approach was based on action research, and initially a preliminary study was conducted, focusing on the institutional setting and the work culture of the school. Based on the preliminary study a workshop was conducted with the teacher group. The workshop was framed within the Collective Memory Work (CMW) approach [5] [6] and enhanced through dialogue-oriented intervention by an informed facilitator. It is an explorative, group-based method, which brings forth the individual experiences of a given phenomenon in the first step. In the second step, it supports the participants in identifying common patterns of experiences, and on this basis articulate common ground. The analysis of field observations and the written material produced by the participants, alone as well as in collaboration with the facilitator, especially showed that a) the teachers were willing to change their teaching methods when being supported in doing so, and b) were willing to conduct e-learning, if they received technical support. During the CMW-workshop, for the first time, the teachers shared knowledge of their individual teaching practices and problems, and came to reflect upon their (rather) negative experiences with e-learning. This in turn resulted in becoming aware of their frustration and feelings of incompetence as teachers, and enabled them to distinguish between didactic problems and technological problems. As a result, the teachers spontaneously suggested solutions to the common problems around e-learning, being very concrete and practical e.g. close collaboration with technical staff, and one could argue that the teachers took the first steps in establishing a Community of Practice [7] [8]. Thus, the CWM-workshop helped the teachers feel competent and resourceful, and participation motivated them to meet the challenges of e-learning.