We explored the perspectives of career guidance educators from the UK and Pakistan on the training of new career professionals. A qualitative cross-case comparative design, a functional equivalence sampling approach and telephonic unstructured interviews were used. We identified diverse ways in which cultural-contextual variables were linked in the two contexts. Thematic analysis yielded five major themes: role of culture, culture and career guidance, cultural ideation, pedagogy, and empathy. Findings also show how social justice as a lens reveals significant differences in how these aspects were constructed in Pakistan and the UK. The use of Social Justice theory for career guidance training of new practitioners and the formulation of culture-specific theories of career guidance are discussed.