Tell Me Your Biggest Weakness

Tell me your biggest weakness: it’s that awful, cringe-worthy question anyone inside or outside of corporate America will immediately recognize as the most overused, clichéd line in the job interview script. “I work so hard I tire myself out,” you’ve probably once said. Or, even better: “I’m too much of a perfectionist.” You groan—we all groan—because the very premise of the question is absurd. Why would anyone give away their worst quality at the moment when they’re supposed to be at their best?

Take a step outside of the interview room, and the question evokes a sense of dread. Its real absurdity is its sheer difficulty. How are you supposed to articulate a legitimate vulnerability in the space of a two-minute ...

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