The Silicon Valley Voice

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When Good Questions Go Bad

Believe it or not, some people do not enjoy job interviews.

To thee and me, a job interview is a wonderful opportunity to meet fascinating people, many who are A-list celebrities from a company’s glamour division, the HR department.

At its best, a job interview is like free therapy, where you can receive valuable feedback on your career and your life from a person who is better than you because they have a job and you don’t. Even at its worse, a job interview represents an opportunity to demonstrate that you are in touch with your deepest emotions by putting you in a situation where you can feel free to whimper and beg as security leads you out of the building and deposits you by the side of the road.


In other words, to enjoy a job interview, you have to be a masochist, or you have to be prepared. That’s where Chad Brooks can help. In an article he wrote on, Brooks reported on the top five questions favored by five top hiring experts. Unfortunately, the experts did not provide the top five answers to the top five questions, but that’s where I’m something of an expert myself. When you’ve had as many red-faced bosses pointing fingers in your direction while they sputter with outrage, you learn to come up with answers, quick.

Question No. 1 is from author Michael Murphy. “When you finish your work, what do you like to do?” This question is “artfully vague,” according to Murphy, since it allows the applicant to prove himself or sink himself, without any help from the interviewer. As you would expect, a good answer is “When I finish my work, I ask my boss for more work, because I have no life outside of work, and I’m always working to get more work.”

A bad answer is when the candidate talks “about personal, nonwork activities they would do, such as eating, going out or other entertainment, or playing with their kids, family or pet.”

Clearly, people who want to have a personal life and indulge in non-productive activities, like eating or playing with their children, are anathema to the hiring manager. And rightly so. That’s why I suggest your answer goes further than the tired “work is my life” approach. Instead, explain that the minute you learned you had this interview, you divorced your spouse and gave your children up for adoption. You boarded up the kitchen, took your puppy to the pound and put your aging parents in a nursing home.

Hey, anyone can say they’re going to focus on work; you’ve proved it.

Question No. 2 is “what’s the nicest thing you’ve done for someone.” Again, skip the obvious answer about your charity work in the third world or the 12 rescue cats you’ve adopted. Show your sense of self-worth by humbly saying, “Well, I was born.”

Question No. 3 is an old chestnut, “Tell me about yourself.” Many people hate this question, but career counselor Arlene S. Hirsch believes job seekers should “embrace it.” That way they can take advantage of the opportunity to getting “the time and space to really talk about themselves in a meaningful and convincing way.” I agree, but why limit your answer to talk? What better time to commandeer the interviewer’s computer and take him or her very slowly through your entire timeline on Facebook? Bring that wonderful delivery room video your father made when you were born, too. And speaking of video, those sex tapes you made somewhat later in life will definitely add dimension to your self-portrait.

Question No. 4 is sneaky. “What type of reference do you think your former boss will give you when I call?” The idea here is to get you to reveal information that your boss would never provide for fear of a lawsuit. So play it safe. “My former boss will say that I’m a lazy, psychotic employee, but she was really sorry she had to fire me for embezzling money from the Christmas party fund.” Trust me, compared with the real reason, it’s a much better story.

Question No. 5 is also tricky. Tell me “about a time when you were at your best” may seem a simple question, but when your best times are so few and far between, you could be stumped. That’s why I recommend that you answer this question with a question of your own — “Would you like to take another look at my sex tape?

Bob Goldman was an advertising executive at a Fortune 500 company, but he finally wised up and opened Bob Goldman Financial Planning in Sausalito, California. He offers a virtual shoulder to cry on at


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