Career Doctor: Handling Those Tricky Interview Questions

Even a minor gaffe can derail an interview. It’s always a good idea to practice your responses to potential questions and assess your interviewing style.

By Dave Willmer


“Unlike others I know, I’ve been called in for several interviews for promising IT positions. But I never seem to get an offer. I know my resume is strong, and I think I’m reasonably articulate and well-mannered. What am I doing wrong?”

Dave Willmer responds:

While there’s no way to answer your question definitively, you may be mishandling some common but tricky interview questions. Since the questions call for highly subjective answers, you might not recognize that your responses are working against you. And because most firms are being extremely cautious about their personnel investments, even a minor gaffe can derail an otherwise strong application.

Before you address how you should answer the questions you’re asked, assess your interviewing style. It’s wise to practice your responses to ensure they’re clear and concise. If your answers are too brief, the interviewer might wonder if you’re omitting information; if they’re too long, he or she might miss your point. Practice your responses with a friend who is willing to give you candid feedback so you can refine your approach if necessary.

Here are several tricky questions interviewers commonly employ, along with tips for handling them.

Can you tell me about yourself?

All job candidates should be ready to answer this one, since it’s very likely to come up.The question isn’t an invitation to share your life story. Instead, keep your response brief and focused on professional goals and interests. Follow up with a short overview of what you enjoy most about your career and how you could contribute in the specific role for which you’re interviewing.

Where do you see yourself in five years?

You should seem ambitious, but not to the point that you come across as threatening to the hiring manager (e.g., “I plan to have your job in five years.”).You also shouldn’t present your plans as if they’re set in stone. The best response is one that involves a logical future step in your career. For example, you might express interest in a goal that will challenge you to manage entire IT projects, including creating support teams and overseeing implementation.

What’s the biggest mistake you’ve made in your career?

Saying you’ve never made a big mistake will immediately raise questions about your honesty.Think of a situation in which something didn’t go as well as planned  — perhaps you recommended a product to your boss that didn’t perform as expected, for instance.Be sure to explain what you learned from the error and how you corrected it.

Why should we choose you over other candidates?

Highlight your proven strengths and how they can benefit the employer. A strong response might be, “It sounds like you need a database developer who can hit the ground running and meet tight deadlines. I have extensive experience in this type of role and have worked at firms with high expectations. I’m a great problem-solver who has the SQL Server skills needed to make an immediate positive impact.”

What are your biggest strengths/weaknesses?

Instead of soul-searching, keep your responses concrete and rooted in your work history. Before your interview, review several projects you’ve handled that demonstrate your skills in areas related to the position you’re seeking. The wisest way to talk about a weakness may be to address a skill that you’ve begun to develop but would like to continue to improve.

What’s your favorite color of M&M and why?

Interviewers sometimes ask off-the-wall questions like this one to test your critical thinking skills and to see how you handle surprises. They may seem silly, but it’s important to answer them thoughtfully. It’s best not to overthink these types of queries, though. Instead give a short, honest response.

Other Considerations

Beyond tricky interview questions, consider other impressions you may be giving, both inside and outside the interview room. Most managers will solicit feedback from others in the company before making a final hiring decision.Everyone you meet — from the receptionist to top executives —  may play a role in whether you receive a job offer, so be sure to treat them all with courtesy.

If you interview with multiple employees, try to tailor the points you make to the experience level of each individual. For instance, supervisors will be interested in how well you interact with senior management; potential colleagues might like to know about your ability to work as part of a team. Lastly, make sure you’ve done your research on the employer. Firms need to know that you’re interested in working for them specifically — and that you’ve invested some time to learn what that experience might entail. Whenever possible, frame your qualifications in the context of what you can offer the company in the specific role being discussed.

Ultimately, you may not uncover a clear explanation for your lack of offers. It’s entirely possible that you’ve performed quite well during your interviews, and that you’re simply experiencing the effects of a very competitive job market. But by re-examining your approach, learning to avoid common stumbling blocks and maintaining an optimistic attitude, you’ll increase your chances of receiving a job offer.

Dave Willmer is executive director of Robert Half Technology, a leading provider of IT professionals on a project and full-time basis. Robert Half Technology has more than 100 locations worldwide and offers online job search services at

3 Responses to “Career Doctor: Handling Those Tricky Interview Questions”

  1. Sanjay

    Your only option to migrate to the US to work is to find an employer who will sponsor you. Alternately, you may consider coming to the US to study (MS/MBA etc) and ‘may’ find employer sponsorship a bit easier since you are already in the US and have a US degree.

    All the best

  2. Jinendra Wijeratne

    I`m a mechanical engineer(B.Sc.Mechanical Engineering) & my wife is a software engineer(B.Sc.Computer Science).We both are Srilankans and having 5 years of industrial experience.
    We want to migrate to U.S.A and work there.So we have been applying to U.S.A jobs through internet for more than 6 months.Most of the time we got the reply from employers as ¿can you get the VISA to work in U.S.A without our sponsorship so we¿ll be able to offer the job for you.¿
    As we both don`t have working VISA for U.S.A what are we supposed to do?

  3. Ruthe Foy

    The tricky situation I frequently face is “and when did you get your degrees”?

    If you provide this information, you are providing your age.

    Any way to gracefully get around this?