The six hardest interview questions and how to answer them

Beecher Tuttle | E-Financial Careers

In interviews, the hardest questions are often those without “correct” answers. Sure, prospective investment bankers hear plenty  of mathematical and theoretical questions that would make a layman’s eyes cross, but in those situations you either know the answer or you don’t.

The questions that truly challenge candidates are those that deal with their baggage: weaknesses, employment gaps and career failures. These questions are particularly vexing because, depending on the resume, candidates are often greeted with them in nearly every interview.

We talked to two career coaches: Atlanta-based Hallie Crawford and Charles Moldenhauer, founder of Executive Transitioning, a coach focusing on C-level executives and senior managers, to get the skinny on what questions candidates hate to hear and how best to answer them.

What are your weaknesses and what should you improve?

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. (This is a basic answer but gives an example).

CM: Give a clear example of taking a suggestion or direction, and how you worked to improve. Then give the financial results. How you turned around a client relationship would be a good example. You want to show your “self view,” interest in taking direction and actually producing results. Then say what you are doing now to keep improving.

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.

CM: Measured performance is crucial in the financial industry so explain how you converted what was not working to better results. Describe the reasons behind what didn’t work, how you adapted and the actual financial return. Everyone has blind spots so you may describe yours and how you are now a better potential employee. The industry is close knit so make sure your story can be collaborated.

Why is there a gap in your employment record?

HC: Have to be honest here as well. Laid off, whatever it is. Employers these days understand this more because of the tough economy.

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.

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.

CM: Demonstrate the transferability of your financial skills, organizational ability or market understanding. What about your success with like  teams, passion for this company’s expertise and future potential? And how about explaining the energy you get from taking on new challenges?

Tell me about a risk you took in a job?

HC: Again something you can answer but don’t want it to be an example that would jeopardize the job you’re applying for. Nothing unethical of course for example. It could be simple like you called a client directly to solve a problem, made a needed decision without asking your boss first and it worked out well. Come up with a risk that worked out well. And maybe even one that didn’t, just in case they ask. And be honest, and say what you would do differently next time – similar to weaknesses question.

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?

HC: Be honest here too and do your homework. Look on glassdoor.com to find out about their culture. It could be the reputation, the work they do, their mission or values, the opportunity for growth. Just have a well thought out answer and not something that sounds canned – like if it’s partly for reputation that’s great, but is a typical answer. Explain why that’s important 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.

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