Winning Answers to Tough Job Interview Questions

Interview Meeting Handshake

If you’re like most people we know, you’ve gone through different phases in your feelings about the job interview. Early in your career, you dreaded this process. But as you mastered the typical questions and saw that most of the interviewers you met were polite, if not engaging, you started to enjoy it. A little.

But once in a while, you have encountered the tough interviewer. She doesn’t smile, she doesn’t care about your family, or that you noticed something interesting about hers (from her pictures). And of course, her questions are the verbal equivalent of waterboarding. Still, you can survive. You can even advance to a second interview with these winning answers:

How did your college courses prepare you for this role?

Why it’s tough: You can’t remember many courses that had much at all to do with the responsibilities of this role!

How to answer: First, make a general statement about the value of your education in developing the habits and thought processes necessary for the role. Then talk about specific courses that developed specific business fundamentals, and provided practical knowledge that you will use in this role. Then talk about how your approach to academics was geared toward developing the skills you would need in your profession, beginning with leadership. Provide examples, and mark a “W” in the column for this question.

What is your greatest weakness?

Why it’s tough: When this question was first asked, perhaps by the interviewer who hired Betsy Ross, the intent was to elicit some sort of clever way to present a strength as a weakness. Of course, she claimed to be a perfectionist, which wasted fabric and annoyed her colleagues, but made for inspired flags. Now, if you do that, you’re passé.

How to answer: Think about a true weakness and present it candidly, displaying a mild sense of abashment. Then pause… Make eye contact with your interviewer, who thinks you just committed interview suicide.

As she smirks in secret delight, you continue and tell her about the extraordinary lengths you have gone through to overcome this weakness, naming the precise steps you’ve taken. You claim you’re 85% of the way there (not 90%, because rounding to the nearest 5 is more precise), but there’s still one more step, and you name that too! Now you’ve just taken her on the wildest rollercoaster ride of an answer she’s ever experienced. You’re ahead of your time, in control, and deserving of another “W.”

What would your former boss say about you?

Why it’s tough: The question is asking you to tightrope a precarious line between immodesty and being unaware of your own strengths. You need to convey the selling proposition within your true professional reputation, and you need to seem like a likeable team player in doing so. You also need to be consistent with whatever the reference check will ultimately produce.

How to answer: Tell your interviewer that you believe your former boss would mention four or five specific points. Be sure these praises cover your values, your work ethic, your knowledge, and your talent. Then tell him you are confident this is true, and ask if you can show him your letter of recommendation to confirm it. It’s even more impressive if you can pull out a second recommendation to corroborate the first.

While he’s reading the letter, you can write down your third “W” and begin your concealed inner celebration. three big wins like this often means you’re in.