1. ‘How long are you willing to fail at this job before you succeed?’
This is one of the favorite tough questions of Jon Sterling, co-founder of Interview Circuit. It’s tricky because “I don’t have an answer in mind when I ask it,” he says, “and I use it to see how the candidate reacts.”
A variety of answers would be acceptable in this scenario. “A good answer would be, ‘I’m willing to stick with this job for as long as it takes to succeed,'” Sterling says. This shows endurance and that you’re in it for the long-haul.
Alternatively, you could say that you plan to fail as quickly as possible so that you can learn from your mistakes and move on. “That answer would indicate that they’re impatient, aggressive, and not afraid to fail (which are things I like),” Sterling says.
Bad answer: “A few months, or I don’t know … what do you think?”
2. ‘What are you most proud of in your career?’
Kimberly Bishop, a retained executive recruiter, often gets blank stares when she asks candidates this question. “‘I don’t know … that’s a good question!’ is often the answer,” she says. Rookie mistake.
There should be no pause or confusion — whatsoever.
The best way to answer this question is to tell them one significant accomplishment and explain why you are proud of it. In other words, how did your proud moment impact the bottom line, overcome a hurdle or knock out a personal goal?
3. ‘What skills are you lacking?’
How you explain your biggest weakness is one of the most telling interview questions of all. “Interviewees show up thinking they should just be talking about what they’re great at, but I’m more interested in where the gaps are and if they are self-critical,” says Mel Carson of Delightful Communications, a social media consultancy company.
To answer this, LinkedIn’s Career Expert Nicole Williams recommends that you should never draw negative attention to yourself by stating a weakness that would lead an employer to think you’re not the best person for the job. An honest but positive answer would be something like “I have a tendency to say yes and get over-committed,” Williams suggests. “Then follow that with an example of how you are working on prioritizing and setting personal limits.”
4. ‘Which past manager has liked you the least, and what would this person tell me about you?’
Here’s a doozy of a question that tests not only your self-awareness but also demands that you talk about your weaknesses from the perspective of others. “A good way to approach this one is to be positive about your past relationships at work, be honest about your shortcomings, and be candid about what you have learned,” says Allison VanNest, head of communications at Grammarly, a software suite service for perfecting written English.
Be careful not to cross the line into self-deprecation — or worse — pointing fingers at how annoying your old boss was. Positivity is golden here.
5. ‘Tell me what you felt was unfair to you in your last job.’
“If they say nothing, they are lying,” says Don Phin, president of HR That Works, a human resources management and consulting agency. “And you don’t hire liars.” According to Phin, the fact is that things are guaranteed to feel unfair at some point — it’s all too common — and he wants to know how you deal with it before he hires you.
This is another question that aims to uncover some of your weaknesses. Where will you shift the blame? Once again, the best way to approach this is honestly, but positively. (See a pattern here?) Tell your interviewer about an unfair circumstance (without dwelling). Shift the conversation toward the proactive steps you took to rectify the situation, like speaking up and confronting someone, reporting it to HR, or forgiving, letting go and moving on for something minor.