Some Tough Questions to Ask

Professor John Sullivan argues that sizing up a company means asking “bone-chilling” questions—and seeing whether people are willing to answer. “Be skeptical,” he says. “You need an accurate job preview, and that means posing tough questions.” Here are a few of his favorites:

  • What are the worst aspects of your company’s culture?
  • What does the company plan to do over the next year to make things better?
  • Who is your best customer? Your worst? What would those customers say about your company and its products?
  • When top performers leave, why do they leave and where do they go?
  •  What are the biggest problems facing this department over the next two years?
  •  If you were my best friend, what would you tell me about this job that you haven’t already said?

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