When speaking up to your boss, as an intern you ultimately risk your job. That of course is the most extreme response, but lesser versions of that might be not getting a return offer, or your boss going around telling people you are hard to work with. Interns thrive as helpful proactive go-getters and second-guessing the boss’s instructions goes against that. Taking up the dubious task on the other hand may also land you in trouble. The boss’s boss may not have been on board and you could get in trouble simply for not speaking up; it presents a bit of an impossible situation.
To speak up, the intern should
1) Realize that speaking up to Mr. Moon is difficult. They have barely met, and probably work in different “context” (high vs. low) workplaces. It is a tricky conversation to have, but going through with the task might leave the intern even more uncomfortable. Communicating that to Mr. Moon is crucial.
2) Lessen the social and status threat to Mr. Moon. The intern should email him and assume complete best intent, using language that disarms the situation and opens the floor to honest dialogue without threat. The intern could first schedule a short call and on it explain that she knows Mr. Moon only wants the best for her and the company, but this particular instruction causes her some discomfort. She could also offer a similar but less dubious alternative, or better yet, brainstorm one together.
3) Finally the intern should have a plan for each scenario that could arise after confronting Mr. Moon with her discomfort. The paths are threefold: 1) they reach a mutual agreement 2) she is still forced to use an MBA email and 3) she loses her internship.
