One of my all-time favorite questions for candidates to ask is “What does it take to fail?” It is unexpected, and requires interviewers to stop and think.
It cuts right past the blather about “excellent writing skills, superb communication skills, and the entrepreneurial spirit,” three phrases which communicate no meaningful specific information.
“What does it take to fail?” changes the tone of the interview
If an interview is going well, the interviewer has steered the conversation into “sell” mode, telling the candidate about all of the good things about the culture that can be shoe-horned into 20 minutes. When a candidate asks “What does it take to fail,” the interviewer may reveal the real reason why a job is available or provide valuable insight into an employer’s culture which can never be revealed in a website.