"Il faut que tu remplisses la tasse de la chef."
Translation:You must fill the boss's cup.
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In 2019, the Académie française said they would begin to recognize the feminine equivalent of job titles in France.
It is just plurals that end in "s" where you add only an apostrophe for possession. For singular nouns that end in "s" you add the extra "s" after the apostrophe. If there were more than one boss with a cup (what does this phrase even mean?) then it would be "bosses' cups"
Le Petit Robert 2021 says that chef can be masculine or feminine. The language is evolving, and profession names that were once masculine-only are getting feminine forms (la sculptrice) or allowing for feminine articles (la prof et la chef).
Translating from English, both de la chef and du chef should be accepted. Of course, only de la should be accepted if transcribing the spoken French.