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Difficult Questions

1. What are your weaknesses?
2. Why did you leave your last job?
3. How do you deal with criticism?
4. Where do you see yourself in ten years?
5. How do you deal with authority?
6. What do you think of your previous manager?
7. What is the riskiest thing you have ever done?

You think the interview is going well. You knew the meeting location ahead of time, and you arrived ten minutes early. You are dressed sharp and your teeth are clean. You came prepared in every way-you have three copies of your resume, a few business cards, two pens and a note pad. You turned off your cell-phone. You managed to find out before the interview that your interviewer held the position for which you are now applying and that you were in choir at the same college. You know the company's mission statement and have a sense of their structure. Your interviewer nodded and smiled when you spoke about your previous accomplishments and your management style. You seem to have connected with the company culture.

Your reflection, research, and practice have served you so well that you wonder whether you should become a professional interviewee rather than a Financial Planner. Then the interviewer lifts her head from her notes and, pen in hand, asks: what are your weaknesses?

You have two options: you can squirm and stammer through a response you develop on the fly, or you can look your interviewer in the eye and provide a thoughtful response that still helps you present yourself strongly. When asked difficult questions, you feel instinctively that they are probing and that you are under great scrutiny. As you prepare responses before the interview, consider what information the questions seek: are there ways in which you would be a liability to the company? If the company invests in you, what kinds of things would it need to overcome? Are you the kind of person who can deal with things when they get rough, or are you pure gloss?

In answering sensitive questions, make sure that your answers are honest, but reassuring. Use tact and choose your words carefully so that you show respect for other people in your responses. You should usually use understatement in your reply to sensitive questions. When people hear something bad, they tend to focus on it in a way that is out of proportion to its significance in everyday life. If you say that you are not always organized, the interviewer could imagine your desk with papers strewn everywhere and deadlines missed. But in reality your conception of disorganization might look a lot like the interviewer's conception of organization. In addition, most of the interviewer's questions could be answered honestly in a variety of ways. You want to choose the version of the truth that is most appealing and sensitive--the version that helps support your main message.

Examples:

What are your weaknesses?

Overemphasized: I am not a good manager.

Avoidant: I always get my work done on time. When other people drop the ball, sometimes I get frustrated with them.

Effective: I prioritize continual growth and improvement. An area on which I would like to focus is managing others who have different expectations from me. What needs to be done in order to complete responsibilities is intuitive for me, so I am learning how to give better direction to others who are not self-motivated.

Why did you leave your last job?

Vague and negative: Law always interested me, and I was looking for a new challenge. I thought it would be a good time to go to law school. Besides, I had gotten frustrated with the lack of support I felt at work.

Dangerous: In the end, my manager and I could not get along. He was driving me crazy and I needed to leave. 

Effective: As I succeeded in financial analysis, I became increasingly interested in broader issues of managing money. I wanted to understand how legal regulations and individuals' goals affect decisions about how to manage money. When I gained entrance to my top choice in law school, I seized the opportunity to infuse my financial training with legal knowledge.

How do you deal with criticism?

Disrespectful: When I remember the source, I usually realize that the other person is in no position to criticize me.

Unbelievable: Criticism does not bother me at all.

Effective: Criticism is vital to my continued growth, and I welcome constructive criticism that helps a team operate better together or produce better results. It is important to me to understand where my critic is coming from so that I know how to apply the feedback.

Where do you see yourself in ten years?

Dismissive: Living in a boat off the coast of Bermuda.

Exploitative: I hope to have gained enough skills here to start my own company. 

Scattered: In ten years, I imagine that I will want a change of scene. One of my long-term interests has been ecological protection, and I can see myself working as a spokesman for a lobbyist organization. First, though, I need to make some money and I want to contribute to your company.

Effective: In ten years, I endeavor to have refined my strategic and client relations skills. I intend to be a leading expert in estate planning. After having proven myself as a senior manager, I hope to help shape the strategic direction of estate planning services. I could do this in any number of official roles. The important thing is that I will continue contributing my abilities in a challenging and rewarding environment.

How do you deal with authority?

Concerning: I think it is important to question authority from time to time.

Frightening: In my last job, there was a time when my boss made a financial decision that I knew would be abysmal. I went directly to his superior to explain the problem. His superior agreed that I was right, and my boss had to alter his plan. 

Effective: Respect is very important to me. As an employee, I try to respect my boss not only by following her guidance, but also by seeking her guidance. When a trusting relationship is formed, I have often found that my bosses have appreciated concerns or options that I raised to them. They know that I support them, and I know that they respect me.

What do you think of your previous manager?

Evasive: She did her job fine. She was a pretty nice person.

Disrespectful: She knew her stuff, but she did not give my colleagues or me any real guidance. It is like we were fending for ourselves. She rarely stood up for us either. I do not really think she should be a manager.

Effective: My previous manager had excellent technical skills and was very agreeable as a colleague. I would have liked more support from her at times, but her hands-off style meant that I had to become resourceful in problem solving and negotiating with colleagues.

What is the riskiest thing you have ever done?

Too much information: My wife and I conceived our first child in front of the police department.

Dangerous judgment: I play chicken with trains.

Effective: The greatest calculated risk that I have taken was to launch my own internet company. My idea was solid, but I knew the market was volatile. Even though the venture ended, my investment of time and money paid off in terms of the skills, perspectives, and contacts that I made through the process. I feel like I matured-rather than aged-ten years during that time.

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