25 Tricky Interview Questions and How to Answer Them

Questions in Interview

What were you making in your last job?

If at all possible, do not volunteer information about your past salary. A diplomatic way to put the salary question aside is to reply, “I was well compensated in my previous company, but really do not wish to prejudice myself here by being too high or low. Can we delay this until after we’ve looked at all the aspects of your current needs? What is your range for this job?”

If the answer is yes, have a good explanation worked out and tested with friends. For instance: “We had a change in general managers, and although I had been doing a great job as you can see from my accomplishments, I was let go for one of his former associates.” Or: “The company decided to close down its California operation and offered me a job in Chicago. We would like to stay in this area, so that’s why I’m looking around.”

What has been your biggest failure?

Discuss this question with friends, mentors, and possibly your references before the interview. If at all possible, think of something you were later able to correct. Then the story isn’t just about a failure, but also about a learning experience.

Rather than discuss your feelings, per se, stress your accomplishments. For instance: “When I started with the Blake Company, I was given responsibility for their operations in Mexico and Costa Rica. After I turned them around, they made me general manager for Mexico and Central America. How are your international operations performing?” An answer like this communicates great information about your value as an employee while still conveying positive feelings about your progress.

Why Are Tough Interview Questions Important?

Preparing for an interview is a good chance to reexamine yourself. The interviewer wants to see what type of personality you have. These questions get to that core and dig into who you are on a personal level. Your response will help the interviewer determine whether you are a good match for what the organization is seeking in the employees they hire.

1. Are you willing to fail?

While I don’t enjoy failure, sometimes it happens – particularly when you’re not sure which approach would be best for a project and you choose the wrong one. Not everything you try is going to work, and you just have to accept this and know when to change course. I learned this for the first time when, as a new project manager at Building Designers, I was tasked with coordinating the installation of a green HVAC system in a historic hotel. It became clear, after construction started, that the materials we were using would lead to a substantial cost overrun – so I had to resort to my “Plan B” in order to provide the deliverables we’d promised. One should always have a “Plan B!”

2. If you could relive the last 10 years of your life, what would you do?

What They Want to Know: This is a “trick question” that employers will sometimes use to see if they can trip you up and make you reveal character flaws. So, be careful not to provide too much information. It’s also fine to say that there’s nothing about the last 10 years that you regret.

The last 10 years have been the most exciting of my life, and I wouldn’t change a thing. I’ve been blessed in that I’ve had so many opportunities to learn and to grow both as a professional and as a person, first in college and then in my first job at ABC Corporation.

3. Are you lucky?

What They Want to Know: This open-ended question is asked to determine whether you are an optimistic or a pessimistic individual. Is your glass half-full or half-empty? Tailor your response in such a way that you can highlight the unique strengths you offer.

I consider myself to be extremely fortunate in that I’ve been offered some great opportunities by some wonderful people and have been able to take full advantage of them. My manager at Hughes Hotel saw my potential back when I was a front desk agent, and she encouraged me to develop my skillset and to become an event planner. Since I love to cook, I also earned my chef certification so that I could offer private catering to clients to complement my event planning services.

The “Weakness” Questions

It’s also a bad idea to offer canned answers such as, “I’m a perfectionist.” (The interviewer will rightfully suspect that you don’t consider that to be a weakness, and will chalk the question up as a loss — or worse, judge you for being cagey.)

The best way to answer questions about weaknesses is to be honest, positive, and focused on solutions. Choose a weakness that wouldn’t be a deal-breaker, and then describe how you overcame it. For example, describe a time when you realized your skills needed brushing up and then talk about what you’ve done to improve yourself.

4. What have you learned from your mistakes?

What They Want to Know: No employee is perfect 100% of the time – everyone makes mistakes occasionally. Employers ask this question to gauge your flexibility and your willingness to own your errors and to learn from them.

Mistakes are great learning experiences. While I try very hard not to make them, I’ve come to recognize that sometimes you just make a bad call. Years ago, our department was sorely understaffed, and the pressure was on to hire a new paralegal. So our selection team basically hired the first candidate who walked in the door, without really vetting him or extending our job search. He lasted all of two weeks. We learned that it pays to take the time to find good talent, even if you yourself have to work overtime until the position is filled.

5. What do people most often criticize about you?

What They Want to Know: This question assesses your self-awareness and your ability to accept criticism. A good strategy is to talk about a “weakness” that has actually proven to be a strength.

People often tell me that I’m too hard on myself – I invest a fair amount of my ego into my work, and always worry that the copy I produce might not be “good enough.” I think that’s a fairly common mindset among writers, though, and I’d rather try to raise the bar than to complacently dash off a lot of ill-conceived text.

6. Why have you been out of work?

What They Want to Know: When they review their job candidates, a major red flag for employers is when someone has been unemployed for more than a few months. It’s in their best interest to learn whether this was a result of the candidate’s personal weaknesses (lack of ambition, laziness, or a poor work ethic) or whether there were extenuating circumstances beyond the individual’s control.

After the company I worked for was sold and I was laid off, I decided to take the time to really assess my career trajectory. Although working at the call center paid the bills and it allowed me to capitalize upon my “people skills,” the work itself had become monotonous for me. So I decided to go back to school to finally become a physical therapist – a dream I had put on hold.



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