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⟩ Tell me what aspect of this position makes you the most uncomfortable?

Most people think this is some sort of filter, but it’s rarely used that way. This is actually an honesty question. No one on earth will like every aspect of every potential job – it’s just not in us. Location? Working hours? People? The company’s too big? The company’s too small? Honesty really works here – I’d prefer to hear a genuine reason for discomfort (particularly one that comes from real observation of the company) than a platitude that isn’t really a discomfort at all. A good way to answer is something like “I’ve never worked in a company this large before” or “I’ve heard some strange things about the corporate culture” or “The idea of working for a startup at such an early stage makes me nervous.”

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