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Six tricky job interview questions and answers

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By Bill Wednieski


Been awhile since you interviewed? Or, perhaps you’re not getting the roles you’ve been interviewing for? Maybe you’re a hiring manager looking to ask better interview questions. Debate all you like re: effectiveness, but below are six oldies but goodies – commonly asked candidate questions along with some thoughts on how to (and how not to) answer:


  1. What level of compensation are you targeting?

This question sure fires up a lot of emotion but it is a legitimate question. I’ve had executives that earned over a million dollars annually tell me they would take $275k roles, and I recently had a candidate that had not worked in five years suggest an absurd salary to find her a work-from-home (WFH) role. (And, honestly the candidate was underwhelming.) Sure, this is an emotional question, but recruiters need to find a common ground that works for both the candidate and the employer. I promise I’m not looking to jam you as a candidate, but consider it from the point of view of your future (possible) employer. You’re a flight risk if you take a large pay cut or if you’re seeking a large bump that the employer may opt into to get you onboard, but later resent when the economy turns. It’s my job to make matches that stick and it’s why I ask. Do your own research to determine the salary range for the role you are interviewing for in the geographic area the employer is located. If you want some wiggle room, provide a range within 5-10% when giving your answer, and give yourself the caveat that you need to understand more about the role, benefits offered, and PTO.


  1. Tell me about your biggest weaknesses.

Resist the dusty and lame “I work too hard” or “I am too much of a perfectionist.” Just be straight forward and avoid babbling. True story: A candidate with a speech impediment interviewing at my client once elicited a heartfelt reaction from the interviewer when talking about overcoming speaking with a stutter in team meetings. That’s a pretty extreme example, but it’s a fact that we all have stuff we are great at and stuff we suck at. Personally, I have a tendency to become self-absorbed and focused on what I need to do or my business needs to do and focus (maybe too deeply) on completing tasks. I need to be mindful by checking myself and considering how staff, candidates and clients may feel when I fall into that pattern. That’s pretty deep stuff. If your weakness is technical in nature, like not having Microsoft Excel skills that are up to snuff or being able to find data fast enough in the ERP system, then state that and what you’re doing to get better. It matters way less what the weakness is; the real focus should be in your recognition of the weakness and your plans to improve it.


  1. How would you do this “task” or lead this “effort”?

Just last week a candidate I was screening gave me a horrible answer to this tricky job interview question. The candidate was coming from a very large employer that had an IT team in-house that handled any hardware and software implementations. My client has 500 employees, not 10,000 where this candidate currently worked, and has an outdated system that needs upgrading. I asked, “Would you be comfortable researching some possible system solutions and making a recommendation to your supervisor?” His answer shocked me. He said, “No, IT always handled that where I work.” If he answered this way to the employer there would be a decent chance it would be game over. This was a candidate for a $100k role, and I thought he was otherwise competent. I told the candidate to take a step back and break down what I was asking. I suggested he start with Google to search for a few possible systems. Research those systems – cost, pros, cons, etc. Ask a few colleagues or peers for a recommendation, and put together 1 or 2 slides to summarize for the leadership team. The candidate said, “Oh yeah, I can totally do that.” The point is: If you have not done what the interviewer is asking, then either think of something similar you have done or how you might complete the task they are asking about.


  1. Take a few minutes to tell me about yourself.

Perhaps the oldest question in the book and it’s a true softball. You’ll know you’ve blown this one when you look down at your watch after answering, and realize you’ve been speaking non-stop for 10-15 minutes. Instead, just tell the interviewer why you love doing what you do or what the work personally means to you. Being genuine and showing your personality is how you truly ace this one. If you love a good clean set of books and take pride in it, then say it! My suggestion is to keep it succinct in two or three minutes – this question is more of an appetizer than a meal.


  1. Why do you want to work here?

Another total classic! You can blow it by brown-nosing, or you can blow it by bad-mouthing your current boss or company. Hopefully you’ve done your research on the company (and ideally the interviewers, too). Great answers can simply demonstrate your preparedness by articulating the company’s reputation, the impact their product or service makes, or just generally what makes the company unique and an attractive or exciting opportunity for you. You have a lot of latitude here; just remember to keep it succinct.


  1. How would your co-workers (or supervisors or staff) describe you?

If you are thinking too hard about this question, and don’t like the answer, it could be a bona fide opportunity for you to change and grow professionally. And, for a variety of reasons sometimes candidates just need a fresh start. Are you a delegator or an abdicator of responsibilities? What do you think it was like for the employees reporting to you the past several years? I was speaking to a candidate’s peer leader while performing a reference check on a candidate. The peer manager actually started weeping, took a few seconds to compose herself and emotionally said, “I am not sure how we are going to get by without XX.” Not to get cocky, but I already knew I had an awesome candidate, and this interaction 100% solidified it.


These are the top six tricky job interview questions and answers. Consider preparing with them ahead of your next conversation with a recruiter or employer, or ahead of the next job interview you conduct. Best wishes in your search!