On-the-job social support, especially from a manager, is viewed as an effective antidote to work-related stress. That said, our knowledge of what induces employees to turn to supervisors for such help remains incomplete. Revolving around in-depth interviews with 24 teachers and 12 principals and a focus group consisting of 12 school counselors, this qualitative study endeavors to fill this void. Our findings indicate that structural-cum-organizational and dyadic factors influence whether teachers will turn to their principal for socio-emotional backing. The structural-organizational determinants include a low formalization structure, a supportive and open work atmosphere, common goals, and a principal with solid professional expertise, while the dyadic indices are quality of relationship and demographic affinity between executives and their subordinates. What is more, we aver that various types of psychological distance play a major role in whether employees view their boss as an accessible resource for affective support.