Good Job

Photo illustration by Slate. Photos by Deagreez/Getty Images Plus and AaronAmat/iStock/Getty Images Plus.

Good Job is Slate’s advice column on work. Have a workplace problem big or small? Send it to Laura Helmuth and Doree Shafrir here . (It’s anonymous!)

Dear Good Job,

I work in a small office (fewer than 15 people) in a fairly niche industry. We’re a pretty close-knit group, and the vast majority of us have been here for a decade or more—we all love the work we do and get along really well. It’s in so many ways a unicorn of a company, especially compared to the stories I hear about other workplaces! This unfortunately makes staff difficulties that much harder to navigate. We’re struggling with one staff member currently—let’s call her “Amy”—and it’s turning into a potentially complicated situation.

Amy has been at the company for 15 years and is approaching (if not already reached) retirement age.…