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Difficult Interview Question Samples

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Samples of difficult interview questions, along with examples of good and not-so-good ways of answering, are continued below.

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 scenery. 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 hope 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 the concerns or options that I raised. 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 was 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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Difficult Interview Question Samples
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