The Hardest Interview Question I Have Ever Been Asked

This is actually a post I have wanted to write for a really long time. In addition to me personally interviewing people pretty much every day for the last six years or so, I have also been on a lot of interviews. As a recruiter, when someone reaches out to me regarding an opportunity I feel almost obligated to hear them out. I mean how could I not? I have personally called thousands of people out of the blue to tell them about a job they knew nothing about. Many of those people have said they aren’t looking and ended up taking a job. That exact scenario has happened to me twice as well. I’ve been contacted and out of professional courtesy I have listened and ultimately ended up making a move even though I had no desire to do so initially. Anyway, the point I am, getting at is that I am not averse to hearing people out when it comes to a potentially good opportunity. Over the last six or so years I have had many interviews. I also consider myself to be an excellent interviewer. Conducting them every day and hearing the bad answers I should avoid as well as being able to pick up some real gems along the way has really given me a competitive advantage in my opinion. However today I want to tell you about one set of interviews in particular that really gave me a run for my money. Also, if you read through this post I would love to get feedback to see what the toughest interview question you have ever been asked is. Many of my posts get shared on LinkedIn and commented on in the groups they are posted do. In the comments below share the toughest interview question you have ever received. If you happen to share a really hard question, I will send you a copy of my My eBook for free. Anyway let’s get to the questions. Below I will share the questions I was asked during this interview and then I will try and dissect what the hiring manager was trying to find out by asking the questions. The first two are difficult, but I saved the hardest question I have ever been asked until last!


What is your biggest professional regret?


When I was asked this question I was not prepared to answer it at all. If you have read my blog posts in the past then you know that preparation is something I consider to be absolutely paramount to interviewing success. However not only had I never asked this question but I never even heard it before. Typically when I interview every question I am asked is a question I have answered before or I know how I plan on answering it when it comes up. Like two of the three questions on this list, it required me to think on my feet. So let’s dissect the question so we can figure out the best approach to successfully answering the question. This to me is similar to the classic “what is your biggest weakness” question. However everyone knows that question and in all likelihood has a prepared answer that ultimately makes them look good in some way. So while that focuses on a skill or lack thereof, this focuses on something you did in your career that you would do differently knowing what you know now. There are three keys to answering this question. The first thing is you don’t want to voluntarily admit something that makes you look horrible. “Well one time I had a boss who was an idiot so I slashed his tires and I really regret doing that because I got fired.” That would be a terrible way to answer that question. The second is you need it to be something you do that you were able to learn from. If what you reference is something that just happened to you and you moved on with your life, you aren’t taking advantage of the opportunity to showcase growth. The last thing you must do it be positive. If you are able to admit something that isn’t terrible, something you were able to learn from and ultimately appear positive, as if it ended up being a good thing, then you have done a great job answering this. However the caveat here is that it must be significant. If you pick an extremely small example that it’s going to be hard to believe it’s your biggest mistake and likely won’t satisfy the person asking the question.


What task in your current job do you dislike the least?


I hate being asked this question but it’s hard for me to not also love the question. If you really think about it, this is a super hard question to answer. Why is it hard? Well the big reason is that every interview you ever have for the most part will have overlap with your current job. Unless you’re going through a major career change there is a pretty high likelihood that you are going to be doing some of the same things. So, if you point out something you dislike that is a major component of your next role, obviously that is not a good thing. Also, when you talk about something you dislike, it can be pretty easy to get negative quickly. The key here is to make sure it’s something you won’t be responsible for at your next role as well as make sure you are the least negative you can be about the task. For example, what do you think sounds better, “I hate using our current ATS. It is slow, it never works and in most cases I have just given up using it. Our company never replaces anything, they are so cheap. That’s another reason I am looking.” Or “One of the challenges of my current role is the functionality of our ATS. At times it is challenging. In order to make sure this isn’t an obstacle for me I typically print documents out ahead of time so I can be adequately prepared for my meetings.” Do you see what I mean? You can answer this question without being incredibly negative and you can also use it as an opportunity to showcase your problem solving abilities.


If we hire you, in six months, what will I dislike about you?


There it is. The hardest interview question I have ever been asked. I will start of by saying that this wasn’t the friendliest interview I have ever taken part of. This question was pretty emblematic of the overall tone of the interview. Think about it for a minute. This question is so difficult because it’s basically saying to you, in six months when you have learned all the systems and processes and are finally up to speed, what do you do that will make you a less than optimal work in my eyes. Wow. Sometimes I think that questions like this are asked not only for the answers but also so that hiring managers are able to assess how quickly you think on your feet. That’s a question that I was in no way prepared to answer and I would wager that most applicants don’t have a canned answer for that question. This one is difficult because you can’t say something like “well most people don’t like that I occasionally sing show tunes in my cubicle”. If someone is willing to ask the question they will be willing to push back to get an answer that works for them and satisfies their criteria. What’s difficult is that you really can’t put a positive spin on this question. It’s not what will annoy me but ultimately is something you will fix and will be considered a strength. They are literally asking you for a professional flaw that will grate on them. Some of you are probably thinking “well I would just say something very minor and move on”. Maybe, maybe they would hear that and move to the next question but maybe they wouldn’t, The hiring manager answering me brushed off my first answer and probed for something I did that would really annoy him. I don’t remember what my first answer was but I remember that it wasn’t good enough. Ultimately what I ended up saying is that I am loud. As a recruiter you are on the phone frequently and more than a handful times people have stopped by me to kindly let me know they need be to be less loud. I don’t know if that’s a great answer. If I had to do it again I think I would try and find something that isn’t a favorable characteristic but also something that wouldn’t impact the success I would have on the job. That being said, I am not sure what that is and I don’t really have a great answer for you. Maybe not what you were expecting but that’s why it’s the hardest question I have ever been asked during an interview.



Well hopefully my answers for the first two were helpful and at least knowing the third question exists, in its own way is helpful. If you can think of an answer to that question I would love to hear it below. Also, like I mentioned up top, if you have a more difficult question please feel free to share it. I will pick a few of the toughest and send them a copy of my My eBook. If you want to check out some good answers to questions check out 5 Excellent Questions You Should Ask in Your Interview, one of my more popular posts I have written this year. Thanks for reading and have an awesome day!

One thought on “The Hardest Interview Question I Have Ever Been Asked

  1. The most challenging question I have been asked was during 2014 in a voice only telephone interview, which adds it’s own level of difficulty since the non-verbal feedback is missing. I was in the Colonel’s office surrounded by an Army Major, Colonel, retired Colonel, Master Sergeant, and Staff Sergeant who provided their own comical, yet silent, non-verbal feedback. The question was asked by a retired Air Force Major with over 20 years experience in Military Behavioral Health. She asked: “What situation have you experienced where you had conflict with a co-worker or supervisor; what was the conflict; how did you respond; and what was the outcome?”
    To this day, I wish I could’ve captured the others’ non-verbal feedback (which included a collective verbal gasp) on video!
    I have extensive experience being interviewed in civilian, law enforcement, military garrison, and military combat settings. This was the first time I had been asked that question. The question won the title for “most uncomfortable interview question(s),” quickly replacing the dreaded twin questions asking your greatest strength and greatest weakness (which were also asked during this interview). Based on my observation of feedback from the others in the office, that was the first time they had experienced this question as well.
    As 10 pair of laser sharp eyes borred into my brain, in what I perceived as an effort to read my thoughts before I spoke, I replied, using a strengths based perspective. The initial silence that followed was so thick, you could cut it with a knife. The silence lasted only a second before sighs of relief filled the office and a positive verbal response was provided from the 3 person panel on the other side of the telephone.

Leave a Reply

Your email address will not be published. Required fields are marked *