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.

Once upon a time, I was fired from a high-profile job and had to develop an answer to this question. The one I came up with was honest from my perspective (and that’s the only one I have!).  I said that it appeared to be due to organizational politics, and as I’d accomplished all I intended there, 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. “How much are you looking for?” and “What was your last salary?” are the two most often asked. 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?” can be tricky to answer.

It’s best to answer with a real aspect of your work self that you find challenging. If you say you have no weaknesses, the interview will think you’re arrogant or blind to yourself.Because everyone has weaknesses. Immediately follow this answer with a description of how you’ve learned how to address it, compensate for it, overcome it. This is you showing yourself capable of learning a new skill. Finally, link this learned skill to the job for which you are interviewing, to show how you will apply it in this new situation.

Here’s an answer I’ve given:  “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 even though it’s dressed up as kindness. I then say “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.” I end with something like this: “in this position, I would start by looking at everyone’s job descriptions, then talking to them about what they do and how they measure their accomplishments. This would both tell me about the person’s attitude toward their job, and give me a sense of how the organization sets and reaches goals as a whole and for each employee.”

4.  Another favorite of interviewers seeking to get inside your head to see how you think and solve problems is “what’s the most difficult work challenge you’ve faced and overcome?”

Answering this definitely requires preparation and rehearsal, because if you try to answer it off the top of your head in an interview, you will probably go on too long, pepper your answer with a lot of “ums” and “you knows,” and not really get to the point.

My suggestion is to choose a story where you succeeded when the odds were 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.

5. “Tell me three words that describe you” is a question that used to be favored more. It asks you to show some self-awareness, and is used to get a sense of your values. The purpose is to see if your values are congruent with the organization’s.

I strongly urge you to answer honestly. If your values are NOT congruent with the employer’s, you will not be happy working there for very long – even if the money is great.  So think about those three words.  Ask your loved ones and friends what they would say about you. If you are applying for jobs that seem to be your “right fit” work, you can then tie these words back to the employer.  For example, my three words are “kind,” “smart” and “high integrity.” I would look for a position in a company that valued those things. Through my research, I might have noticed that the employer stresses integrity. I can say that I was delighted to see that we shared some values, using this question as an opportunity to stress that I am a “right fit” for this position.

6. “What would one of your employees tell me about your management style?” This is one of my favorites to ask because it tells me so much about a candidate’s management style and organizational culture preferences – and I always look for a culture ‘right fit.’  It asks people to step outside of their own perspective and look a bit more objectively at themselves.

Be prepared with responses that fit with your skills and personality in a positive way, and that correspond somewhat with the job.  Employees would describe me as “fair,” “great leader,” and “inspiring.”Since I would be applying for jobs that required leadership and vision, I could easily link my response to the requirements of the job.

7. 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.

8. The Unexpected Question!

There is usually one question you did not anticipate. Don’t 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 ways to buy time and give 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.