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The hardest interview questions and how to answer them

For most people, the toughest interview questions aren’t quantitative or theoretical. They are those that deal with a candidate’s weaknesses, employment gaps and salary demands, among others potentially difficult personal questions.

If you misstep on these, you’ll hurt you chances of getting an offer, or at least getting the offer that you’re hoping for. But the good news is that you can plan strategies ahead of time to weave honest and meaningful responses.

We talked to a few career coaches – Hallie Crawford, Jane Cranston and Charles Moldenhauer – to get their strategy on how you should formulate answers to some of the tougher questions you’re sure to hear. Their opinions are below.

What are your weaknesses and what should you improve on?

HC: You should never pretend you don’t have any nor come up with a list like “I work too much.” Come up with a real weakness, like prioritization, time management perhaps – something that is real but also wouldn’t jeopardized your ability to do the job and focus on what you do about it. I’m working on improving my time management for example, I use an online calendar and schedule my tasks inside that calendar and plan my week each Monday estimating time needed for each task and project.

What didn’t work in your last position?

HC: Be honest here but you don’t need to lay it all out either, for example if you and your boss didn’t get along. Don’t bash your former employer. It could be the culture, it could be there was little room for career progression, you didn’t agree with the vision of the company say what it is, then move quickly to focusing on what you want instead.

Why is there a gap in your employment record?

CM: While gaps have been more common during the recession you need to show doing something of value. It could include improving your skills, certifications or connections. Building relationships as a volunteer is a usual answer, but you need to show how you were productive. Play down the vacation, reflection time, etc. If you did consulting work build up the value of what you got out of it. Don’t disclose how little you might have been paid.

How much money do you make?

JC: As in any negotiation the person who says the number first is at a disadvantage. You can try and say you are interested in the job and you are sure salary is fair and commensurate with industry levels.  If pushed you say you are looking for a “total compensation package in the range of ___to____”.  In some companies they will insist on a W2 form so don’t lie about current salary.

Why aren’t you looking for a job in your area of expertise?

HC: You’ve done some soul searching, weren’t completely fulfilled or your talents weren’t being utilized enough in the current industry and realized this was the right path for you. I’ve had clients say that to employers and they were impressed they had taken the time to really find their direction and that they had such focus. Another reason could be they want to add to their skill set.

Tell me about a risk you took in a job?

CM: Tell how you used your relationships within the organization to gain support or shift the thinking. It could be a new idea for training, product development or sales. Show how you presented it then how you worked around those that found it negative. Explain how you have used this experience to further improve.

What is it about our company that appeals to you?

CM: Don’t be afraid to talk about their reputation “On the Street” and how you are a good fit. If they are viewed as aggressive for example, talk about how that fits with you, or the interest in where this culture can take the business. Avoid sugar coating your comments as the finance industry is too sophisticated to accept simplistic answers that don’t represent a deeper understanding.

What aspects of your previous jobs have you disliked?

HC: This is similar to the tell us about your weaknesses question. You can't say you have none, and you can't say something fake like I work too hard. You need to be honest here with parameters: Prepare your answer so it comes across in a positive, productive way and not as bashing your former employer. Choose things that are about the job itself preferably, not your terrible boss, so you're focusing on things that don't come across as talking badly about people, which isn't necessary or helpful. Things like the lack of structure or process is an example of something you could say. Or the lack of direction for your department.

Tell me about yourself (ie where do you start, what do you cover personal v. professional)?

JC: Keep in mind they are not asking about you personally but you as a professional or business person.  This is the time to name your strengths in a narrative way. “I am best known for my innovative and strategic approach to complex problems.”  Then tell them how you came to this skillset by talking about your work experience and education. Always start with the present and work backwards.

Two minutes into the answer ask “shall I continue?”  You do not want to eat up all of your interview time and lose the person’s attention with a long-winded answer.  Only at the end can you add something personally by saying “in my off hours I enjoy running and I coach a kids’ track team.”  Makes you human.

Where do you see yourself in five years?

JC: This question is asked less and less because five years is an eternity.  In certain professions it is an easy question.  “I want to be (name your title).  More likely you will say you want to advance to a level to have even greater responsibility, influence and impact.  Always make it sound like you will still be with them for those five years just at a higher level and possibly in a new venture with them.

Tell me about a time when you failed.

HC: Be honest, give something that actually happened and is real. Choose something that is a failure but you were either able to salvage, fix or at the very least you've learned from. Focus on what you do now to prevent that failure in the future. With all of these questions, you need to prepare them in advance so you're not caught off guard, and you have a solid, confident answer for.

What negative things would co-workers say about you?

JC: This is a tricky one.  Always attribute the negatives to a few and not the entire group. “I guess some may think I can be too passionate and a bit defensive when it comes to a project I’m working on”.  And maybe that’s true from their perspective. In general I get along with my co-workers, clients and vendors.  We don’t always agree but we can work together to get the job done.”


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AUTHORBeecher Tuttle US Editor

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