Construct: The globalization of healthcare has been accentuated by the export of health professional curricula overseas. Yet intact translation of pedagogies and practices devised in one cultural setting may not be possible or necessarily appropriate for alternate environments. Purposeful examination of workplace learning is necessary to understand how the source or “home” program may need adapting in the distributed or “host” setting. Background: Strategies to optimize cross-border medical education partnerships have been largely focused on elements of campus-based learning. Determining how host clinical supervisors approach assessment in experiential settings within a different culture and uphold the standards of home programs is relevant given the influence of context on trainees’ demonstrated competencies. In this mixed-methods study, we sought to explore assessor judgments of student workplace-based performance made by preceptors sharing a pharmacy curriculum in Canada and Qatar. Approach: Using modified Delphi consensus technique, we asked clinical supervisors in Canada (n = 18) and in Qatar (n = 14) to categorize trainee performance as described in 16 student vignettes. The proportion of ratings for three levels of expectation (exceeds, meets, or below) was calculated and within-country group consensus achieved if the level of agreement reached 80%. Between-country group comparisons were measured using a chi-square statistic. We then conducted follow-up semi-structured interviews to gain further perspectives and clarify assessor rationale. Transcripts were analyzed using thematic content analysis. Results: The threshold for between-country group differences in assessor impressions was met for only two of the 16 student vignettes. Compared to Canadian clinical supervisors, relatively more preceptors in Qatar judged one described student as meets rather than exceeds expectations and one as meets rather than falls below expectations. Analysis of follow-up interviews exploring how culture may inform variations in assessor judgments identified themes associated with the profession, organization, learner, and supervisor performance theories but not their particular geographic context. Clinical supervisors in both countries were largely aligned in expectations of student knowledge, skills, and behaviors demonstrated in patient care and multidisciplinary team interactions. Conclusions: Our study demonstrated that variation in student assessment was more frequent among clinical supervisors within the same national context than any differences identified between the two countries. In these program settings, national sociocultural norms did not predict global assessor impressions or competency-specific judgments; instead, professional and organizational cultures were more likely to inform student characterizations of performance in workplace-based settings. Further study situated within the specific experiential learning contexts of cross-border health professional curricula is assuredly warranted.