The Best Job Interview Question I’ve Ever Been Asked: A Tribute to a Friend

In 1999, I was sharing a duplex with a friend on the near east side of Indianapolis. I had a grant funded position at the Indiana State Museum and was barely making rent. I was attempting to put my history degree to work but wasn’t digging the museum/government employee way of life. My friend David was working for 328 Performance Hall in his hometown of Nashville, Tenn. His stories about the jackassery that went on at a live music venue/bar had me questioning my chosen career path. Don’t get me wrong, I love history and doing research, but at the time I was twenty-five, single, and bored as hell.

Less than a month before my grant was set to end I saw an ad in the weekly alt wrap about an open position for a promotions assistant at World Mardi Gras, a large nightclub complex in downtown Indianapolis. It didn’t pay as much as my museum job, but considering my grant wasn’t likely to be renewed, it didn’t matter. I was just getting into web design and knew that freelance opportunities would be available in the future. I needed a change and going from a quiet job tucked away in an office in the corner of a museum to being the promotions monkey for a club sounded like a pretty good one.

There was no reason they should hire me considering the only things that I had going for me were the fact that I was in the right age range, and I could more or less speak in complete sentences. My first interview was with the director of marketing who just happened to be Julie. We didn’t know each other at the time. My interview was the first time we ever met. We never dated while we worked together. In fact, we didn’t get along very well for a while. Regardless, I apparently said enough of the right things because I was called back for a second interview with the general manager.

While I came to know Joe as a kind and forgiving boss with a wry sense of humor, he could turn on manager mode when he needed to: a stern look matched with a deep, stern voice. Once you knew him well enough, it became less effective. But I would be lying if I said I wasn’t intimidated by him when I first met him for my interview. He sat across from me in a booth in Brewski’s sports bar. It was in the morning, and we were the only people there aside from the bartender prepping for the day.

The interview started off typically enough with the usual questions. Then he asked me something that I’ve never been asked in an interview before or since: What was your most embarrassing moment?

Joe had a knack for asking questions in such a way to purposely catch you off guard and put you in a quandary as how to exactly respond. He didn’t do it just to be an asshole, but to see how you responded. It was always a test to gauge what kind of a person you were and how you handled yourself. Disconcerting to experience, fucking hilarious to witness. Gaped mouths, blank stares, and dumbfounded looks.

I had plenty of embarrassing moments. Pretty much any of my public interactions up to the point. I could have picked one of the tamer ones. Something dull and non-offensive of something goofy I did in the classroom. Perhaps a story about me tripping and face planting in public. But then I figured, this is a nightclub. All kinds of shit goes down here. If he’s asking, he wants to know. So I told him, and I didn’t spare the detail. It is far too long to share here, but it involves me getting shit ass wasted well before noon at a university homecoming in Wisconsin and puking all over myself in the middle of a house full of strangers. There’s more to it than that, but that’s a story for another day.

He had laughed his laugh at various turns in the story. When I finished, he was smiling and complimented me on my storytelling. I wasn’t sure what was going to come next. I was expecting him to roll right back into the interview and ask me another question. Instead, he shared with me a similarly embarrassing moment. When he was in high school, he was at a party at a friend’s apartment; the bathroom had a line, so he stepped out onto the balcony to relieve himself off said balcony. Whether by accident or by design, he ended up pissing on the police officer who had just arrived responding to a call about a loud party. It gets better. It was in a small town outside Indianapolis where everyone knew everyone else, and his father was on the police force.

I’ve always liked the question because it is a good gauge of both honesty and trust. It can certainly be uncomfortable to answer, but it functions as a two-way street. If someone asked you about your most embarrassing moment and you honestly shared it with them at which point they decided to judge you based on your candor…would you want to work for that person? Would you even want that person in your orbit? If they can’t handle that, they can’t handle you. The fear of saying or doing the wrong thing in front of your boss is thrown out the window because you both have dirt on each other. There is an immediate bond of trust.

They ended up hiring two people for the position instead of one. Unfortunately, I was third on the depth chart. However, one of the girls they offered the job to declined the position and I slid in by default. I hope the list had more than three names on it. I worked there for the next four and a half years until it closed. I didn’t make a lot of money working there, but I had a lot of fun and gained a lot of interesting stories. Many of those stories involving me, Joe, and Julie. Looking back, even with all of the things that didn’t go well, it was one of the best times of my life.

(Edit: People with better memories than mine have pointed out that there weren’t two people in front of me. The original plan was to hire one person, but based on my openness and honesty, Joe suggested hiring two people for the gig. Not sure why I didn’t remember it that way considering it makes for a way better story.)

Joe passed away unexpectedly last week. We were able to get together with him before we left on our trip. He was happy for us and couldn’t stop telling us how awesome he thought it was that we were doing it. We didn’t get a chance to see him after returning, however. Julie, who was much closer to Joe than I was, talked to him on the phone several times, but we were never able to meet.

It’s easy to paint any particular moment in your life as a turning point if you try hard enough, but getting that job was a life changing moment for me. Not to lay it on too thick, but without Joe there is no me and Julie and there certainly wouldn’t have been our trip around the world. I learned a lot from Joe, both from positive and not so positive examples. I have a lot of great memories and stories. I hate that we had to miss the memorial service and wake, rightfully held in a bar, because the stories told by old friends and co-workers would have been fantastic to hear. I’m certainly better for having known him, and I hope I’ll be able to pass on some of the nuggets of wisdom I gained from him. In the meantime, we’ll have a few adult beverages (Joe’s term) in his honor and remember all of the stupid shit we did.

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We quit our jobs at the end of 2013 to backpack around the world. We're sharing our stories, travel advice and hopefully some inspiration. Read more...

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