How to Answer Difficult Interview Questions

The most difficult interview questions are the ones you aren't prepared to answer. So be prepared! Anticipate that there WILL be difficult questions.

Often, these questions fall into these categories.

1) Questions you wish won't be asked because you haven't come to terms with or become comfortable with the answers. These include "why did you leave your last job?" when you were laid off or fired, "why are you interested in this field?" when you really want to change fields because you hated your last one, "what did you like least about your old job?" when you hated your old boss and are tempted to bash him or her. If you don't exactly match the job description requirements, it can be tricky to explain why you are still the best candidate.

The best preparation for handling these questions is rehearsing the answers with someone else, until you are comfortable - honest and not defensive or attacking. An interview is not the place to criticize a former employer, ever. Figure out how to phrase things in a positive way, as in "this situation was challenging and I realized that I would be able to contribute much more in a role similar to this one."

If you can, return the focus to the job for which you're interviewing. I was fired and had to develop an answer that indicated that I was not to blame, that it was run-of-the-mill organizational politics, and besides, I'd accomplished all I intended there, so it was actually a good time to leave and find something that offered me new challenges, such as this job.

2) Salary questions also can be difficult. A good thing to say is "I'm hoping to make between $X and $Y, and of course am flexible because I really would like to work at this organization." $X is your “live with” number and $Y is your “want to have” number. Your “live with” number is usually lower than your "want to have number" - it is the number you need to live with yourself. With this pay, you can meet your basic needs and then some; you can look yourself in the eye; you will not have a resentment about your pay; and, you will stay at this job for a reasonable period of time (1-4 years) before looking again.

An alternate response is "I'm sure we can come to a mutually agreeable number if this job is the right fit for me and I'm right for you. I don't want money to stand in the way of my getting this job, so perhaps we can continue talking and see whether this is the right fit." If they don't love this answer, use answer number one.

3) "What's your biggest weakness?" is always tricky to answer, as is "what's the most difficult work challenge you've faced and overcome?" It's best to thread in a little self-deprecating humor there - if you say you have no weaknesses, the interview will think you're arrogant or blind to yourself.

On weaknesses, I like to say "weaknesses depend on the job, of course - I'd like to think I have none but of course I have some! I find myself apt to give people more time to prove themselves on the job when it might be better to let them go." To me, that is a real weakness cloaked in kindness. Then I add "so I've learned to establish very clear monthly benchmarks at the beginning of their employment. That way, I can tell very quickly if someone is or is not going to work out." That's the trick - to follow up any discussion of a weakness with a description of how you have learned to compensate for it.

Regarding your biggest work challenge, choose a story where you succeeded when there were odds stacked against you (e.g. tight time frame, few staff or other resources, external partners or circumstances you had no control over). Rehearse telling this story until you can tell it in about 4 or 5 sentences: Here was the goal, here were the circumstances, here's what I did about them, and here was the successful outcome.

4) "Tell me three words that describe you" is another fun one to prepare for, as is "what would one of your employees tell me about your management style?" That last one was one of my favorites, because it asked people to step outside of their own perspective and look a bit more objectively at themselves.

For both, be prepared with responses that fit with your skills and personality in a positive way, and that correspond somewhat with the job. In a vacuum, my three words are "kind," "smart" and "high integrity." Employees would describe me as "fair," "great leader," and "inspiring."

5) Questions clearly related to the specific employer. Perhaps they ask you to respond to an imaginary scenario and tell them what you would do in that situation. The response clearly should involve some knowledge of the company, but you might not have gone through the website in enough depth.

Maintain Your Composure
When an interviewer asks you a question you didn't expect, there's no need to panic - you know the answer. All you need to do is give yourself some time to remember the answer and formulate the beginning of your answer. Here are some tactics that buy you time, giving your brain a chance to quickly come up with an answer. (Plus each of these tactics has some added benefit.)

* Pause before answering if you are unsure of the answer

* Say "that's a great question" (Saying "great question" flatters them and people like that subliminally even if they think they are cynical about it.)

* Repeat the question back to them "so you're wondering if I _____________" and wait for
them to nod or say yes (Repeating the question mirrors them back to themselves, makes them feel smart, AND makes them feel like you were really listening to them.)

* Use the question as the beginning of your answer. For example, if the person asks "tell me about a time you had to organize a project in a short time frame," you say "An example of when I organized a project that had a short time frame is..." (Repeating the question or using it in your answer focuses YOU and your brain on the question and helps you come up with an appropriate answer.)

Take a pause after you have answered the question - in two to five sentences max - to see if the interviewer has a followup question. I call it "the pause that refreshes."

If you're not sure you've adequately answered the question, STOP TALKING. Say "I hope I've answered your question" or "Have I answered your question?" The interviewer will either say yes or no. If s/he says "no," they will then clarify what they wanted you to tell them.

Finally: Remember to breathe.