Your Most Difficult Job Interview Questions and Why They Were Asked

You can figure out how to answer interview questions when you consider why they were asked in the first place. Let's run through some examples on this episode of the Work in Sports podcast!

Hi everybody, I’m Brian Clapp director of content for and this is the Work in Sports podcast.

As you hopefully know by now, we have a private Facebook group for this podcast. It has a very inventive name -- we call it - the Work in Sports podcast private group.

I know right? Lots of branding meetings and focus groups went into the creation of the name.

Quick side story -- this is a new record, I've barely even started and I’m already into a side story -- anyway, I was at the NASSM conference a week or two ago and met with many sports management professors. One was Dr. Karen Boleska, from Husson University, I’ve spoken in her class before and it was nice to meet her first hand.

Well, she told me about another podcast she listens to called “How to Be Awesome at Your Job” and she kept discussing what made it great, and all I could think of the whole time was… damn, that’s a much better name for a podcast. I mean outs is brand relevant since we are, and it’s clear we’re going to talk about working in sports… but “how to be awesome at your job” podcast is a pretty good hook.

Ok back on track -- maybe mine should be called the tangent inside a diversion wrapped in an aside podcast -- anyway the reason I brought up the facebook group for the 10,000 time is because I’m going to do something kind of fun and related to it this beautiful Monday morning - I’m going to use it as the launching point for our discussion.

Group member Erin Preuter posted last week:

As I prepare for an interview tomorrow I wanted to ask everyone what was the hardest or most unique question you’ve ever been asked during an interview?

Well, the group responded and I’m going to highlight some of those responses here and then explain a little about why they may be asking them, and how I may answer them.

1: Scott MacDonald --  I was once asked who was my hero and why, and I got kind of emotional talking about my late father, but I feel like it helped humanize me a bit in the interview.

2: Jeff Gillis: I was asked who I was.

3: Ashley Potts: I prepared for a lot of logistical job questions and then got asked which Game of Thrones character I would be and was totally caught off guard haha.

4: William Edward: I was asked what movie or character represented my sales career so far. Caught me off guard!

5: Ramon Sanchez How would you organize weekly tasks?

6: Kevin Wilson:  My question was to describe how you would change the culture, without negatively impacting morale? 

7: Before the last filter at my last hiring process, I set my mind telling myself “this job is mine.” The interviewer was an extravagant guy who asked me what I saw first in his office as I crossed the door, then he made me tell him a real story and a false story, and, finally, he said: “imagine I’m an oracle that will answer any question you may have, what would you ask me?” I said: “how far will I go?” He thought for a second and said: “you’ll break into the top.” They hired me over a year ago and now he says he “relies on me blindly.


Today's Sponsors!

Hey everyone it’s Brian, we’ve got a really fun podcast episode coming up today, but first let’s talk about the Masters in Global Sport from NYU -- the associate dean of the program is an  industry leader, Vince Gennaro, he’s consulted with major league baseball teams, been one of the originals in the world of analytics, and is totally dedicated to the globalization of sport and all that goes into it. I just conducted an interview with Vince for the podcast, and I’ll be honest i was ready to run through a wall… well, metaphorically speaking. He got me fired up, his passion and his intellect for the business was inspiring. I can only imagine what class is like!

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And the Work in Sports podcast is brought to you by the Sports Career Game Plan presented by -- this is my baby. We are releasing this online course really really soon -- actually, it’s four courses you can bundle into one low price, or just buy individual modules.

All of the courses are designed to make you an expert in getting a job in sports. That’s it, we’re not teaching sales techniques or how to make a marketing strategy, we’re going to teach you the tactics and strategies to get hired in sports.

If you like the content we share on the podcast, trust me this goes even deeper into building and maintaining your network, gaining the right experience, your resume cover letter and personal band, and how to interview for jobs and internships.

I’ve had so much fun building it, and I can’t wait for you all to jump in and become masters at getting hired in sports.

Look for release information coming from me soon -- keep an eye on our social media and your inbox… it’s coming.

By Brian Clapp | June 17, 2019
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