A Smart Ass’s Guide to Interview Questions

Feel free to skip the intro

My first job out of college: video journalist for CNN. Don’t be impressed. It was factory work. All three responsibilities - teleprompter, studio camera operator and floor manager - no longer exist, replaced by technology that isn’t prone to out-of-body boredom…

By the time I signed-on to pick electronic cotton for Massa Turner, I’d been a writer/reporter/producer for four commercial radio stations (including NPR superstar WGBH), written for car magazines and founded a daily newspaper (Tufts Daily).

OMG was I annoyed by CNN’s endless, mindless routine and blowjob-related promotion process. An opinion I somehow forget to keep to myself. I wrote a letter to management suggesting a better way to organize the factory floor.

A year later, the News Director called me into his office for an interview. I’d completely forgotten about the letter. Bob refreshed my memory and got straight to the point.

“You don’t like the way we do things around here,” he said. This is my poker face Bob. “But if you were me, you’d do the same, wouldn’t you?”

Yes, and I’d be out of the salt mines. No, and I’d be straight back to “the floor.”

I said no (Confessions of an Asshole). Just for fun, I offered more entirely unsolicited, unwelcome suggestions for improvement. And returned to the ninth circle of hell.

In short, I suck at job interviews.

As a Quaker-educated Jew raised on the 1967 version of The Producers, I either make a joke, tell the truth or make a joke that tells the truth (For The Honor of Truth).

So when I encountered the inc.com article 21 Weird but Revealing Job Interview Questions CEOs Love to Ask, I knew I’d found comedy gold.

Here are my five favorite questions, what they advise you to say and what I would say. No, really.

1. "What question did you come in here hoping I would not ask?"

Inc. recommendation: A smart candidate… could use it to get ahead of something they know might be a negative, such as a gap in their employment history.

My reply: That one.

2. "Give me three valid reasons why I should not hire you."

Photo by Javier Allegue Barros on Unsplash

Inc. recommendation: This question [invites interviewees] to candidly own up to their own weaknesses--which everyone has. 

My reply: First, I work hard. Other employees hate me because I show management what lazy fucks they are. Second, I’m always looking for ways to improve things. Even “disruptive” companies don’t like disrupters. Third, I always use contractions when I speak. Clearly your company doesn’t. I mean, does not.

3. "Tell me about someone in your life who is better than you are at something that is important to you."

Inc. recommendation: This is a great question because it invites the candidate to show humility, objectivity, and generosity, as well as tell you what is important to them.

My reply: Other than Jesus? John at Montecristi Custom Hat Works. Another miracle worker. When John makes a hat, it’s perfect! Style, fit, materials, everything.

I can email John a photo of a hat – like the lid Director Peter Bogdanovich wore when he was banging Dorothy Stratten, the Playboy centerfold whose husband blew her face off with a shotgun – and he gets every detail spot-on.

Don’t get me wrong: he wasn’t wearing the hat when he was doing the horizontal mambo with Stratten. As far as I know.

Bogdanovich, I mean. John’s happily married. His wife is no centerfold, but whose is? Other than Tommy Lee Jones, and he divorced Pam when she fell in love with her plastic surgeon.

Not him. His work. Which was nowhere near as good as John’s. Or Peter’s. Paper Moon? Tatum O'Neal starred with her actual father and got an Academy Award, at the age of ten!

Does that answer your question or do you want me to start over?

4. "What do you want to be when you grow up?"

Photo by National Cancer Institute on Unsplash

Inc. recommendation: Questions about the candidate's future goals and aspirations are common interview fodder, of course. But this question invites a more whimsical answer and an acknowledgement that many of us never quite feel grown up, no matter how old we get.

My reply: Vertical.

5. "If I showed up at your front door right now, what would I be surprised to see?"

Inc. recommendation: This… invites the candidate to be honest and revealing, and to tell you what's important to them. The question is likely to surprise them, and how they deal with that should be revealing, too.

My reply: As I’m here now, nothing. If you showed up unannounced and I was home you’d be surprised to find a Benelli M4 Tactical shotgun pointed at your chest. Unless you read my resume; I founded The Truth About Guns website.

Truth is my thing, in case you hadn’t noticed. That and insouciance. When do I start?