ObjectiveTo assess the effectiveness of politeness strategies used by pharmacy students to avoid embarrassing or imposing on others during objective structured clinical examinations. MethodsA total of 19 objective structured clinical examinations video recordings of 10 students (participants) interacting with mock patients were examined using the framework of Politeness Theory (PT). All relevant participant acts (speech activities) were coded using PT into (1) type of face threatening acts (ie, potentially sensitive situations—as regarded by PT) and (2) politeness strategies used to mitigate them. Conversation Analysis was then used to examine the effectiveness of conversational strategies by judging the ‘patient’ responses to these strategies. ResultsMost acts had the potential to impact patients’ negative face needs (ie, desire to act autonomously, eg, upon the practitioner making a request), positive face needs (ie, desire to be liked, eg, upon the practitioner making a diagnosis), or both. Despite applying a variety of positive politeness strategies (eg, avoiding disagreement, or expressing understanding) to prevent embarrassment to the patient, and negative politeness strategies (eg, being indirect, using hedging, or minimizing the imposition) to avoid directly imposing on them, “dispreferred responses” showed participants mostly focused on avoiding impositions, corresponding to what they have been taught, rather embarrassments. ConclusionParticipants were less aware that discussing sensitive topics could cause embarrassment to patients, with the potential to upset them. Developing teaching and evaluation methods to consider patients’ face needs could help in assessing and improving pharmacy students’ communication skills.