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The six trickiest interview questions and how to answer them

While banking and finance interviews are typically littered with technical industry questions, it’s the more generic inquiries that tend to trip people up. “What didn’t you like about your previous job?” “How much do you currently make?” Bungle these and you’ll hurt you chances of getting an offer, or at least getting the offer that you’re hoping for.

We talked to two career coaches – Atlanta-based Hallie Crawford and New York’s Jane Cranston – 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. You can also check out our post from last year on how best to respond to other challenging questions, including the dreaded “biggest weakness” query.

What aspects of your previous jobs have you disliked?

Jane Cranston: Stress that in general you like your jobs very much.  You can say that the organization hit a few rough patches (if that is true) and it was hard to see some good people lose their job.   Or, say that you believe every position has an amount of necessary tedium and of course you would have rather work on something new and exciting all the time but realize the importance of things such as expense reports and monthly overviews. You can also say you always work best in busy times so late August is not your favorite time in the office but you manage to find something to address.

Hallie Crawford: 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.

HC: Start with professional, give a quick summary of your experience and history professionally. My background and degree is in X. Expertise and passion lies in XXX. At XX company handled XX projects, at current position manage XXX. Give them the highlights of your professional history. Let them know at this time why you're excited to be interviewing with them and how it relates to your career goals and passion. You can mention something personal here that's appropriate to mention in a professional setting and not too personal, but keep it to one thing only.

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.

HC: You need to have an answer for this and it needs to be professional not personal. The catch is, if you don't see yourself at their organization in 5 years what do you say? First, if that's the case you need to consider if applying for this job is the right thing to do in the first place, is it the right fit? And if the answer is still yes it's the right fit but you want to move on to another organization in 5 years, focus your goal instead on the role you want to be in within 5 years. You don't have to say I will be here for the next 10 years, instead focus on your career goals, the type of role you want to be in, and what you want to have accomplished along the way.

Tell me about a time when you failed.

JC: You always answer this with something you did not do well and then show how you fixed it and don’t do it now.  “In the past one could say I was too eager.  I’d jump to conclusions without doing a thorough analysis. I was young and inexperienced.  I learned a tough lesson on a project early in my career and with the guidance of my supervisor and self-monitoring I can assure you I now drill down on all aspects of a problem.

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.”

HC: Again be honest, you can't make something up and it can't be something that is actually a strength - like they would say I'm too driven. This is similar to tell us about a weakness you have, let them know a co-worker may say you could improve your communication for example. Be more clear when you are making a request. Keep them in the loop more. Come up with something that is accurate but that you are aware of and working on. Ideally you want to choose something that is accurate, but would not be a make or break for the job you are applying for. So for example, if you are terrible at writing marketing copy, and that's the job you are applying for - don't choose that one. And question why you're applying for that job in the first place if you can't perform the duties!

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.

HC: This is tough and can be awkward. And you need to answer truthfully. I would suggest finding out the salary range from them first if possible, and at the very least you must do your homework re salary range for your industry, location and role so that when you answer this question, you know where it lies within the range and you're prepared to say I make X because of these qualifications and experience I have. So tell them what you make and you can say not including benefits it is X, and you can tell them you are willing to be flexible within the range of X and y salary if needed. If the salary you make now is higher than they can offer you, you have a decision to make. But either way you must be prepared to make a case for why you are worth X salary.

AUTHORBeecher Tuttle US Editor
  • Ma
    Martin Waters
    28 January 2020

    What are your salary expectations? Perhaps one could give a very broad range. "Well, my research tells me that the range for the base salary for this job range from $150,000-$300,000 so I would be within that range in terms of expectations - but to be honest the numbers aren't what are the most important for me in the role; it's how much I can contribute to the [fill in the blank - growth of the company, etc.]"

  • JP
    29 January 2014

    I'm in agreement with MM here... the only reason you might be at a disadvantage when putting out the first number is if it is low/below their range, or so far above that they feel you're bluffing or unobtainable. The research bears this out, but on a personal note, I've had this strategy succedd many times: I put out a number intentionally right at the top of their range or slightly above, justified why I was worth it, and got a counteroffer very close to my ideal (or with other concessions such as flextime if it was above their range).

  • RA
    29 January 2014

    The most asked and failing question in any interview- Would you like to ask me something ? - from the interviewer... How to answer this question?

  • MM
    28 January 2014

    "JC: As in any negotiation the person who says the number first is at a disadvantage."
    *Sigh* Despite years of conclusive research to the contrary, this tired advice still propagates. (Don't take my word for it. Check HBR: ) The first number mentioned in a negotiation anchors the discussion, and the final number almost always ends up closer to it. So if you let the employer give out the first number, you will almost assuredly get less.
    While recognizing that giving too high a number risks losing the job completely, if you've done your homework on appropriate compensation and can support your position with facts, make the first bid at the high end of the reasonable range. You probably won't get it, but you'll likely end up on the high side of the middle.

  • Wi
    27 January 2014

    How should I respond to a question on compensation where my current package is likely significantly higher than that for the job I am interviewing for?

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