Toughest Interview Questions

Walking into an interview is already stressful but those tough questions bring your stress to the next level.

Here are some of the toughest interview questions and how to approach them.

1. Are you willing to fail?

The employer want to understand how you analyze failure. Unfortunately, everyday will not be a win but it is all about how you deal with these issues.

Ideal Answer:
“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!'”1

2. Are you lucky?

This is an open ended question to see if you are an optimistic person. Uses this question to show off your strengths. 

Ideal answer:
“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.”1

3. What have you learned from your mistakes?

The employer knows everyone makes mistakes. This question is to understand your flexibility and your willingness to own your errors and to learn from them.
Ideal Answer:
“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.” 1

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