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Addressing early career school leader attrition and turnover, education systems assign mentors to ease novice principals' socialization, but results are varied and many mechanisms of this variance are still unexplained. To fill gaps in the literature, different mentor profiles were typified. Fifty-six mentor and mentee interviews were thematically analyzed and socialization outcomes were appraised by comparing increase in person–organization compatibility or congruence. Literature alluded to leadership in education systems as fraught with conflicting loyalties and, accordingly, this study found organization-loyal mentors who tried to promote conformity, person-loyal mentors who tried to prioritize mentee needs, and balanced mentors who achieved skill development and emotional support by being active listeners, prioritizing confidentiality, and guiding reflective contemplation. Socialization tactics, fit, and self-determination theories were linked to explain the different mentors' effects, recommend improvements, and reflect back on the theories themselves. In the context of mentoring principals in Israel, it is implied that needs–supplies fit and demands–abilities fit must both be effected for supplementary fit to increase. It is also implied that radically institutionalized or individualized tactics were ineffective, as only the balanced mentors seemed able to foster principals who can become more autonomous and motivated to persevere and succeed in their work. [ABSTRACT FROM AUTHOR]