While many countries are gradually shifting from the master-apprentice model to a more distributed support system, in Russia doctoral students are still highly dependent on their supervisors. This heavy reliance on a single supervisor has triggered numerous investigations into the effectiveness of supervisory functions and styles, yet the initial stage of the supervisor–supervisee relationship remains relatively understudied. Based on survey data of supervisors and their doctoral students (N = 313), we examine how reasons to supervise relate to supervisors’ satisfaction with the doctoral students and doctoral students’ perceived difficulties with their supervisors, as well as to thesis defence outcomes. Our results indicate that supervisors’ decisions to advise based on positive prior interactions significantly reduce the likelihood of doctoral students encountering difficulties, enhance supervisor satisfaction, and increase chances of defending the dissertation within the expected period. We also found that a strong research commitment from the doctoral student does not compensate for a lack of prior collaborative experience with the supervisor. The main conclusion is that prior interactions between supervisors and doctoral students offer significant advantages in dissertation defence. Such early connections are particularly beneficial in the Russian context, where dissertation requirements are especially high. Our research offers valuable implications for doctoral school administrators seeking to bolster doctoral students’ success, particularly in contexts where the ‘master–apprentice’ supervisory model remains prevalent.