This article investigates and exemplifies the personal side of our supervising skills. This is inspired from psychotherapeutic research specialized in investigating openminded contact and authentic meetings. The article is based on our experiences supervising project groups at Roskilde University. Supervision is sometimes a challenging task that may manifest and confront personally-related issues. We advocate combining an academic and personal approach to supervising project groups. We provide a range of empirical examples from the supervising project groups, illustrating the type of personal challenges we meet. These challenges are characterized and conceptualized, and some concrete ways to deal with them are proposed.