Job interviews can be high-pressure situations, even when keeping in mind that most interviewers want you to do well in your interview. Even interviewers who want you to do well, though, are likely to ask you some challenging questions. Usually there are two main reasons for this: 1. They want to know the answer to the question and/or 2. They want to see how you handle stressful situations.
In a previous article, we looked at four common job interview questions and how to answer them, and in this article we’re going to look at four of the most difficult questions interviewers commonly ask.
While you’ll occasionally get a difficult question that comes out of left field, you can anticipate and prepare for some of the more common difficult questions. As we’ve said elsewhere, the goal is not to have totally pre-memorized answers to the interview questions, but instead to not be surprised by questions and to have a general idea of how you’ll answer.
So, here are four of the most difficult questions job interviewers are likely to ask and suggestions for how to respond to them:
- “Why are you leaving your current position?”
You’ll need to tread carefully here. On the one hand, you don’t want to come off as dishonest or evasive, so you’ll need to give an honest and convincing reason. On the other hand, there are some reasons for leaving that you probably shouldn’t mention. Generally, you don’t want to say you’re leaving for more money, due to poor evaluations at your current job, or due to interpersonal conflict with your boss or coworkers. Even if some or all of those things are going on, hopefully there are some other reasons you’re moving on that you can focus more on discussing in your interview.
In general, you want to avoid bad-mouthing your previous or current employer in any way.
Instead, try to put a positive spin on your response to this question. Try to focus on new opportunities for growth and new experiences that changing jobs might open up for you. The specifics will vary by industry and position, but the advice to keep it positive always applies.
- “Tell me about a conflict you had with your previous boss.”
Here, again, you need to walk the fine line between not appearing evasive and not bad-mouthing your previous employer.
In responding to this question, it’s best to focus on a professional difficulty you had that you resolved on your own initiative. So, for example, you might describe a situation where your boss wasn’t clear on how you were spending your work time, so you created and shared a Google Calendar with them, so they could have a clearer idea of how your time at work was spent.
In general, you’ll want to stay away from thornier issues, issues that are/were unresolved, or issues that are mainly interpersonal.
Even if you had a terrible previous boss, who really was the source of all the conflict, it’s probably best to not mention that. Remember, from your interviewer’s perspective, if you had difficult problems with your previous boss, they’re going to consider that you may be a difficult person or that you may have or create a lot of conflict in general. Hopefully that’s not the case :), but you don’t want to give your interviewer any reason to hesitate about you or worry that you might be difficult to work with.
- “Impossible calculation”-type questions
You might get asked to make an incredibly difficult calculation on the spot in an interview. Something like, “How many pencils are there in Philadelphia?”. The interviewer is not expecting you to know the answer to this off the bat. The purpose of these questions are multifold. They allow your interviewer to see how you react when faced with an unexpected and difficult situation. They also allow the interviewer to see your reasoning and communication skills.
So, for example, if you’re asked how many pencils there are in Philadelphia, the interviewer might be looking to see if you ask for a pencil and paper to make your calculations, or if you ask if it’s OK if you use your phone to look up the population of Philadelphia, or they might be looking to see if you ask for clarification on whether the question is about Philadelphia within the city limits or the greater Philadelphia area including suburbs.
After you have the resources and information you need, you will probably want to walk the interviewer through the process of making your estimation. You might say something like, “Well, let’s see. Philadelphia has about 1.6 million people in it, and let’s say there are ten pencils per person between work, school, and home. My estimate would be about 16 million pencils in Philadelphia.”
The interviewer isn’t really that concerned if you got the answer exactly correct (They, themselves, probably don’t know exactly how many pencils are in Philadelphia). Instead, they’re looking to see how you approach the problem, how you organize and communicate your process, and how you report your results (Do you seem overly confident in your estimated results? Or do you make it clear that this is an estimate?).
These questions can come in a variety of forms, but if you’re asked a question like this that seems impossible, this is probably what’s going on and how you should respond.
- “Tell me about a time you failed at work.”
Here, again, you need to thread the needle between being honest without making yourself look bad. Even if you’ve had some really horrible mess-ups at work (most people have), this isn’t the time to focus on them. You want to give an answer that is honest but moves in a positive direction. So, focus on something you once did wrong, but have fixed in a way that ensures it will never happen again, especially not at your new job at your new employer.
These are among the most difficult questions you’re likely to be asked, and they are commonly asked, so you’ll want to prepare for them. Having good answers to these questions that you feel confident in will show your interviewer that you are experienced, prepared, positive, and good at handling difficult situations, both in a job interview and at work in general. Good luck!