Research seems to be explicit on children’s benefit from parents’-school partnership and enhanced relationship. The ways in which parents can be better involved, however, are not yet apparent even though a variety of educational approaches and programs are studied worldwide. Through Action Research (AR), the effect of an initiative parental – school engagement has been explored in a kindergarten school in Greece during 2014-16. The successful engagement of philosophical practices for the students in previous years exposed the need for adopting the specific tool of Philosophy for Children (Lipman, 1991) for the parents. Carefully selected stories have been used as a stimulus for raising philosophical questions that were discussed in depth by parents and teachers. The aim was to strengthen the relations of teachers with the parents of the students at each school with a dialogical model whose positive results can have an auspicious and even transformational effect on the comprehensive development of the individual's personality on a cognitive, moral, and emotional level. More specifically, this study incorporated and studied the potential transformative effect of thoughtful dialogue and critical thinking on adult participants, parents and educators through their active participation and collaboration in the philosophical educational community.