4 Unusual Interview Questions That Reveal A Lot

Not too long ago, I received a LinkedIn message from somebody that I know on Twitter but haven’t met face-to-face.  It was short and to the point, and asked me simply, “if you were interviewing an account executive, what’s the most important question you’d ask?” This person was planning on relocating, and was doing some research about what to expect in interviews by asking different sources. I was honored that I was asked, and I took some time to reflect on the many, many interviews I have done over the years.

There are plenty of questions that should be asked of an interviewee regarding work history and capabilities, but some of my favorite topics have helped me to understand their personality and character nuances better than boilerplate questions.  Below are the four questions I shared with him, and a short explanation of why I ask them. I hope you find this useful in your next interview, no matter which side of the desk you are sitting on.

  1. “What kind of music do you listen to?” –  Seems like a strange question, right? I’m less concerned with the type they reply with, and more interested that that can nail down an answer. I find wishy-washy people to get uncomfortable with this question. I think they get in their own head too much and wonder what I’ll say if they reply with a type that I don’t like. If this is the case, they try to tell me that they like all kinds, but will never nail down a genre or artist. In my experience, people who answer this way will never give me honest feedback when we are brainstorming idea or creative…they are too concerned with having an unpopular opinion. Although I don’t want to work with contrarians, I do want to work with people that can thoughtfully express honest opinions, even if they aren’t the most popular. I think we all know that everybody loves music, and they usually have pretty strong opinions about it. Those that can quickly tell me a genre or artist they like are usually good in group meetings and strategic plannings.
  2. “What do you do for fun on the weekends?” – If they tell me something work related, this is a big red flag for me. Really, you like to work on the weekends for fun? I don’t, and I don’t want you blowing up my phone all weekend long while I’m trying to decompress a little.
  3. “How do you deal with unresponsive clients?” – This is a big one. There isn’t really a right or wrong answer, but it helps me to understand their temperament. Are they hot heads? Are they too relaxed? Do they get frustrated easily? I want to have them ask me questions in return like “how long have they been unresponsive?” “does the client prefer email, text or phone conversations?” This shows that they are thinking about how to communicate in a way the client prefers, not trying to force the client to communicate in a way they prefer. One of our best clients actually communicates with me via Twitter DM, so that’s how I reach out to them as well.
  4. “What is your biggest pet peeve in the workplace?” – Another one with no right or wrong answer, but it helps me to understand their temperament for coworkers. If it’s something small like “people chewing gum too loudly” then I’m guessing this person is going to be a real pain in the ass to work with. This questions stumps a lot of people. I think they think I’m asking more than I really am. They don’t want to appear neurotic, but also when you ask people about their annoyances, they cannot help but talk about them. It’s a good reflection of character and maturity.

When interviewing potential candidates, I prefer an even mix of questions that help reveal work ability as well as personality.  Working with somebody that is good at their job is very important, but working with somebody that is a good cultural and personality fit is even more important.  You shouldn’t have to compromise one for the other, but in my experience, a person can be trained to make up for skills they lack, but a bad personality cannot be changed…at least not by their employer or coworkers.

* Image Credit: I’m not sure who owns this photo, but it can be found at various download sites.  Although it doesn’t directly have anything to do with interviewing, it gives the sense of adventure and taking a risk, something that you should feel when applying for a new job. I love this picture.

By Matt Singley

Personal: husband to Alison, father to four amazing kids. I used to live a fast but enjoyable life in Los Angeles, now I have chickens on acreage in Charlotte, North Carolina. Just a bit different. I'm an advocate for cycling as much as you can and eating as cleanly as you can afford. Professional: I'm the CEO of Singley + Mackie, a creative digital agency that serves well-known lifestyle and entertainment companies around the world. Clients include Microsoft, Samsung, Hulu, YP and others. If you want to find the more-professional me, go to