Jim isn't planning to stay at Dunder Mifflin forever so doesn't really believe he should be acting the part of a manager.
Michael tries to give the assignment to Jim who prefers he focus on his own job. Jan tells him that part of being a manager involves giving unpleasant news.
Michael, wanting to be liked, isn't enthusiastic about cutting their benefits. With downsizing possible, it's important that Michael chose an inexpensive plan for his employees. He wants to choose the Gold Plan which Jan explains that even she doesn't have. Because he is in charge of choosing a health plan for his employees, Michael decides that makes him the equivalent of their doctor.
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