Difficult Interview Questions

Take a look at career articles and the topic of “questions everyone hates” comes up regularly. So, of course, you can learn a lot about how to answer many difficult questions with a fast search.

Here are some which I get asked about regularly at job fairs and seminars.

Question 1: What are your weaknesses?

Now the cliche answer is some variant on bragging. “People tell me I work too hard.” That will disqualify you as dumb in many hiring managers’ eyes. But what do you really say?

The best answers are those where you can talk about a weakness you are working on. Maybe you hate to give presentations but work in an area where they are necessary. An answer which talks to the fact that you are nervous doing presentations so you have taken the following three steps to improve, or gotten a coach/a mentor, or taken a speaking seminar, or joined Toastmasters, all would be good ways to approach this question.

The formula is: You know you need to do X better and you have been working to improve via specific actions.

Question 2: Have you talked to your current boss about other job options, rather than looking externally? And if not, why not?

As companies become more concerned about turnover, hiring managers tend to ask questions like this to see if you look like someone who will jump ship at the first opportunity.

Yet many bosses do not want to talk about career options with you, especially in this economy. And some companies mark you as a problem if you even bring up dissatisfaction. What are you to do?

Be honest but positive. No comments about your boss being a jerk or your company not recognizing your value. If you have talked about your career with your boss, say so. And then say that there is not the career growth you seek or your company is not growing. If you have not talked to anyone about your career, say so. But have some explanation – that your boss is known to hate to lose people from his team, or you like the company but it is not a good cultural fit for you. And if you are looking at internal opportunities, say that too.

And whenever possible, do talk about the positives. You have been at your current job for X years and have grown your skills. You have been promoted within your company. You seek a place to continue to grow and contribute!

Question 3: Where do you expect to be in five years?

This is a golden oldie and you might think in the current economy that no one would ask it. But some hiring managers still do.

So despite a desire to say “in your boss’s job,” don’t. Talk about what is important to you. For example: to be in a job where you are still working on the leading edge of technology; to have grown your product skills and contributions; to be developing into a program manager. The critical issue is to demonstrate that you have actually thought about your career and have ideas about the aspects which matter to you. This video may also help:

Titles, job levels, and other status related issues are not going to help you here. Interest in growth and development or further education, plus some basic planning and the ability to contribute to the organization, are.

Good hunting!

Leave a Comment


Leave a Reply

Paul Homan

I am so terrible at interviews! I think this is so helpful – I never have good answers to these questions. I always have to practice and write down what I think interviewers might say.

The best response I have ever heard to #3, was “I want to be a parent”

Kathleen Smith


Thanks for the feedback! Yes, interview questions do get harder and harder. Add on top of this that we are all so nervous when we are in interviews we tend to go back home and ask ourselves “what was I thinking!”

As to your best response, honesty is the best policy!

Bob Ragsdale

I love the question about whether the applicant has spoken to their current boss about other job options, I will be adding that to my interview script.

A question I ask that often trips applicants up is “What do you know about our organization and where did you go for information in your research.” It is amazing how many people I interview that haven’t really taken the time to look into what we do. It’s a worry to me if a person isn’t willing to take the time to get a complete picture of the organization they want to work for.

Kathleen Smith


That is a good question! We frequently remind job seekers in multiple forums to do their research – what the company does, or what contracts they have been awarded. There are many tools out there to help job seekers find this information.

Allison Primack

The following response was posted on GovLoop’s LinkedIn group by Stuart Lesley:

“One question I like to end with when I do interviews is “Is there any question that I haven’t asked that I should have?” I’m looking for two things when I ask that question. First, the initial reaction — it’s usually an unexpected question so I get a chance to see how the person handles that situation, e.g. are they comfortable with silence enough to give themselves a chance to think, etc. The actual answers tell me a lot too. BTW: In my opinion there is no “right” answer to this question however I have heard a few wrong ones.”