In this chapter, some tensional trends within mentoring, which we call a contradiction between collaboration and assessment, are addressed. The aim is threefold: First, to describe and compare the development of mentoring programmes in Finland and Sweden at the system level; second, to illustrate how the various mentoring systems have been experienced by the persons involved; and third, to discuss the political and ideological circumstances and the possible effects of these solutions. The study is based on empirical data gathered in Finland and Sweden and examines the experiences of mentors and newly qualified teachers (NQTs) as well as the relevant national policies. The findings indicate profound differences between the two national initiatives of mentoring in Finland and Sweden. The mentoring process in Finland, using peer group mentoring, is based on social constructivistic assumptions regarding knowledge and learning. The integration of formal, informal and non-formal learning, as well as the equality and professional autonomy as a person and as a professional, is central. The system of mandatory induction in Sweden is very different, with mentoring, a probation year and the registration of teachers being central components. In such a system, the mentors' role of avoiding direct or indirect involvement in the assessment may become more challenging.