How to Answer the 3 Toughest Interview Questions and Sound Like a Pro

For some of you, interviewing is the easiest part of the job search process.  You’re well spoken, out-going and can easily come up with answers on the fly and make it look effortless.  For many others, the interview process is extremely daunting and you spend hours and hours preparing yourself for every question imaginable.  Whether you love interviews or hate them, there’s always a couple of questions that can trip up even the best interviewer.  Here’s the three that you should watch out for and some helpful tips on how to navigate through the answers.

Question 1: Why did you leave your last job/Why are you looking to leave your current job?

This question may sound harmless, but many people fall into this trap.  They say something like “Well, I really don’t like my current boss” or “I’m really tired of working at XYZ company because they are so dysfunctional.”  Here’s a tip: NEVER SAY ANY OF THOSE THINGS.  Talking bad about a previous employer or boss may seem like a good idea at the time, or in the moment you just really want to get out of your current situation that you don’t realize the consequences of an answer like that.  If you’re talking bad about a previous or current employer, the person interviewing you is going to think you’ll do the same thing when it comes to them when you’re ready to leave.  So resist all of your urges to say anything negative about any job on your resume.  Save it for the bar with your friends or family, but certainly keep it far away from an interview.  If the reason you are leaving your current job is because you hate the company or your boss, the safest thing to say is that you’re looking for new opportunities and to grow your career and then say something positive about the company you’re interviewing with.  Positive=GOOD, Negative=BAD.  Remember that simple math equation and you’ll be in good shape.

young ethnic woman working with laptop at table with coffee

Question 2: What is your biggest weakness?

It’s probably safe to say that you’ve heard this question before or heard of someone who had this question and it threw them off for the rest of the interview.  My favorite answer to hear is “Oh, my biggest weakness is that I work too hard.”  The flip side is when you tell them the truth and say “Well, my biggest weakness is I always struggle to get out of bed and can never make it in on time.”  Hopefully, you can see how awful both of those answers are.  One is a lie that both you and the interviewer know is not your biggest weakness and the other is not something you want to be telling someone on an interview, “Oh hey, yeah if you want someone who isn’t gonna be late, you probably shouldn’t pick me because I’m still in bed at 9am.”  I will say though, this is a tough question even if you do prepare.  The best strategy to deal with this question is to give a skill that may not have been your strongest and then turn it into a strength.  Let me explain:

“My biggest weakness early on in my career was my communication skills.  I struggled with speaking up and collaborating with team members, however, throughout the years, I have continually worked at improving my communication skills by finding mentors and taking trainings and have now been able to turn it into one of my strengths by doing xyz.”

By answering this question almost like a politician, you semi mention the weakness part but focus more on how you turned it into a strength.  It’ll make the interviewer see that not only are you a good communicator, but also you are someone who cares about self-improvement.  It’s a win-win for everyone.

people talking to each other

Question 3: Tell me a time in your career where you failed.

This is the evil cousin of the previous question and can trip even the best of us up.  This goes off of how you would answer the question about your biggest weakness.  Don’t tell a lie that everyone knows isn’t true like “Oh, well, I’ve never actually failed at anything,” or even worse, ask them to move on to the next question.  You want to be able to think of a time when you actually failed, tell them what happened and most importantly, how you learned from what happened and how you are better now because of it.  DO NOT throw people you worked with under the bus; DO NOT blame a boss for the failure; and DO NOT turn it into a joke or take it too lightly.  The key here is you want to be truthful but you also don’t want to be too vulnerable.

Being able to answer the tough questions is what can separate someone who gets the job from someone who never hears back from the interviewer.  If you’re prepared for the tough questions and ready with a great answer it will give you the leg up on the competition.  So embrace these questions and be excited when you get them, because now you can answer them like a pro.  

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