Get Ready for These Challenging Interview Questions

Challenging interview questions can hit a nerve for most of us. The idea of a rapid fire inquisition, whether in a confined room or in front of a panel of C-level executives, is unsettling at best.

Interview questions can be especially jarring if they tap into personal insecurities or fears. Specific topics may make you uncomfortable because of a past professional experience, such as a firing. Creative employers may even throw out wacky questions, like asking you what’s your spirit animal or your favorite body of water, that cause you to stumble.

I know this because I’ve been there. I’ve been in interviews where I had difficulty finding my words – sometimes even with the least challenging interview questions – struggling to put together a coherent answer. 

To get over my interview fears, I researched top interview questions and prepared as much as possible. I made a list of the most challenging interview questions that caused anxiety and practiced the answers over and over. I reminded myself that interviewers are human, too, and they often have the same insecurities.

Designed to have you think on your feet, challenging interview questions can range from formal to informal, off-the-wall to right on target. What makes certain ones easier than others – and how can you prepare for either option?

To get you started, here are eight frequently asked challenging interview questions that may come your way:

Tell me about yourself.

A common opening inquiry in most interviews, it’s tough to even know where to begin and how to know if you’re oversharing or not giving enough detail about your background. Says Alison Doyle of The Balance:

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“Be prepared to talk about yourself, and why you’re an excellent fit for the job. Try to answer questions about yourself without giving out too much, or too little, personal information.”

She explains that a ‘present-past-future’ model is the best way to address this question, starting your answer with your current situation, leading to how you arrived at the position, and where you see yourself heading in the future.

Why are you leaving your last job?

Generally asked on the heels of the first question, every employer wants to know  why you are leaving your current or previous ) position.. Answers vary drastically, and certainly include family emergencies, continued education, or a need for greater professional growth. What do you say when the answer isn’t so nice, like a management disagreement or an unpleasant dismissal? According to Alison Green of “Ask A Manager”:

“It’s hard to tell you how you yourself should answer this question without knowing more specifics, but one option might be talking about how you ended up in that situation, what you learned from it, and what you do differently now as a result.”

So plan ahead, practice your response, and don’t let your nerves derail you.

How would your boss or coworkers describe you?

Fun-loving? Helpful? Willing to go above and beyond with every assignment? There are no wrong answers to this somewhat challenging interview question. The Muse suggests three possible avenues for attacking this question, including offering short bits of positive traits.

“Try to think of three positive traits you bring to your work or workplace. Then, have a short example after each.”

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What is your biggest weakness?

One of the top interview questions, talking about your weaknesses is easier said than done, whether it’s a missing skill or a gap in your employment history. Honesty is always the best policy, and in this case, it’s critical to be honest with both yourself and a potential employer. Address the obvious, but be sure to emphasize how you’re working to improve on your weaknesses.

Why do you want this job?

Companies want to hire people who are enthusiastic about the role, so you should have an answer ready to go.

It only gets awkward if you realize during the interview that you don’t want the job. The best approach is being honest so you don’t take up anymore of the employer’s time. Thank the interviewer for their consideration, explain that the job isn’t the right  fit, and include your reasoning for walking away.

Tell me about a conflict at work and how you resolved it.

This frequently asked question offers the employer insight into how you handle conflict resolution, particularly in an office environment. Start with a clear example of a real situation. Give details to explain your role in the conflict and who was involved in the argument or debate. Finally, describe what you did to resolve the conflict. This is an excellent opportunity to show your human side.

What’s your salary history?

With recent legislation, asking a candidate for their salary history is now illegal in many states – including Oregon. Pivot the discussion to focus on your salary expectations from a concrete perspective, based on your experience, industry, and local job market standards.

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How many light bulbs are there in Portland?

A favorite question of a top CEO here in Portland, this is a curious one. So why does it make you nervous? Because there is no right answer.

Why does she ask it? Because it’s not about the answer. She wants to know how you think.

The key is to recognize these kind of challenging interview questions for what they are – creative insight into your critical thinking. Don’t let these kinds of questions shake your confidence. Go with your gut and remember that there’s no right or wrong answer.