Job Interview Questions To Ask Since Nobody Wants To Work These Days

As an iconic 21st century entrepreneur/philosopher once said, “It seems like nobody wants to work these days”—wise words that echo through abandoned office halls as people simultaneously leave toxic jobs in excess and pursue new opportunities (or simply give up work altogether). 

After the last two years, perhaps it’s time to ditch those yawn-inducing LinkedIn suggestions for standing out during an interview, and really go all-in by asking bold and honest questions that will make the interviewer say, “Oh, wow. Let me get back to you on that.”

If you’re going to “get your fucking ass up and work” and pursue improved working conditions, it’s only fair you know what you’re getting into, right? Ditch the “what’s the last thing your team celebrated” and start asking the hard-hitting questions.

What does a typical day look like? 

What do you find most challenging about this position? And existing in a capitalist society in general? 

How soon am I likely to cry? 

Is the pay commensurate with my experience and the absolute toll and chaos of the last two years? 

Are pants required? 

If an email tries to find me well and I am not, what kind of health insurance do you offer?

Am I allowed to utilize an out-of-office message any time a major, minor, or personal historical event takes place? 

How many people are on the team? How many of those people are one task away from a full-blown breakdown?

How do you feel about a candidate’s social media presence? Which one of my tweets was your favorite? Which one was most concerning?

Did the previous person in the role leave because this job sucks? Or because having a job sucks? 

What characteristics do your top-performing employees possess? And what drugs are they on? 

Is there room for growth? Can that room be in my own home? 

When I physically show up to work, where can I lie down? 

What is the perception of new hires who use a vacation day within week one? 

Am I expected to turn my camera on in meetings, even if my only anticipated contribution is commenting on a coworker’s dog? 

Cathartically screaming every couple of hours—encouraged or frowned upon?

I would never shit-talk the company to other employees, but just in case, how closely does I.T. monitor messages? 

Will my successes be rewarded in money or pizza parties? 

Due to the pandemic, I need to have a 3 o’clock cocktail. Not a question, more of an FYI.

I thrive in a collaborative environment. Can you share some high-level team gossip from the last quarter?

If I need to give two weeks notice, is day-of fine?

Is there anyone in the department with work crush potential? How else will I be motivated to look and act put-together? 

Does the team have happy hours or are they mostly sad? 

If my manager doesn’t use an exclamation mark when replying “ok,” am I guaranteed a sick day to process their hatred for me? 

Do you expect the responsibilities of this role to change as asteroids barrel closer and closer to earth?

How’s the work-life balance? Will it be easy to balance my work anxieties with my life anxieties? 

If my coworker says, “Happy Monday!”, am I allowed to explain why it’s probably not?  

If my coworkers aren’t prepared to discuss a TV show I’m obsessed with, can I report them to HR?  

Does posting a meme about job frustrations count as “good communication skills”? 

What do you hope the person who lands this role doesn’t realize about the company until it’s too late? 

Are there other qualified candidates in the running? How many of them also seem driven by the delusion that a new job might solve most of their problems?

Hypothetically, what is the most amount of money you can offer me for doing the least amount of work? Hypothetically!

Will I ever be penalized for leaving early if the vibes are off?

I can’t imagine why, but do you have any reservations about hiring me?

Images: Javier Díez /

Sara K. Runnels
Sara K. Runnels
Sara K. Runnels is a copywriter and humor writer living in Seattle, Washington. Her work has appeared in The New Yorker, McSweeney’s, Tinder messages, Gmail inboxes, group texts, Instagram captions, one Yelp review, several spec scripts her mom thinks are GREAT and hundreds of Twitter screenshots. Follow her all over the internet – @omgskr.