15 Funny Questions to Ask Your Boss

Your boss is only human (we hope) and they have a life outside of work as-well.

While we always encourage a “professional environment“, sometimes it’s nice to relax a bit and ask some funny and personal questions to build rapport.

That’s why we’re going to go over funny questions to ask your boss.

We have a small disclaimer below, but hope that these questions will help you build a better relationship with your manager.

Based on some personal experience, most managers aren’t averse to easing a bit on the formalities once you’ve built up a good working relationship.

You’ll still want to be careful to not cross any lines, but these questions should be able to help you get started.


You should really understand the relationship your manager and you have.

If your manager is a bit more buttoned-up and business only, then it may not be prudent to ask some of these questions.

While you and your friends may be sure to get a laugh, you don’t want to offend your manager or have them not take you seriously.

If money was no issue, what career would you choose?

This is a good question because it still has some work connotations.  

Make sure you have your answer ready if your manager asks you the same question back!

If you could be on any sitcom as a reoccurring character, what sitcom would it be?

Definitely a question that takes some thinking, I still don’t know which sitcom I would choose (definitely not Black Mirror though)

Would you rather go 200 years into the future or the past for a day?

The future, duh!

What was the best thing before sliced bread?

Honestly, there is nothing better than sliced bread, so they probably won’t have an answer here.

If you could only eat one type of dessert for the rest of your life, what would you choose?

 Gotta go with the cookies here

What’s your favorite fast food restaurant?

 Chick-fil-A by a wide margin

Aisle or window seat of a plane?

This one always throws me off, some people actually prefer the aisle seat to the window and that just baffles me

If you could write an article to be featured on The New York Times, what would the subject be about?

I have nothing – I’m blanking on my own question

Would you rather have a personal chef or a personal butler?

Chef, I live to eat!

If you could meet one person, living or dead, who would that person be?

This question should really get a good response on what type of people your manager cares about

If you could have any one on speed dial, who would it be?

Again, another question that lets you see who your manager values

If you could fly anywhere in the world for lunch, where would you go?

Good to know what kind of food your manager likes for the next time you plan the company party!

Would you rather live in a world with Pokémon or dinosaurs?

Pokémon all the way here, I mean, they’re practically dinosaurs anyway

Would you rather have no phone access for a year or no car access?

No phone access, I need my car way too much

If you could master any sport overnight, what would the sport be?

Golf, it’s a lot more difficult than it appears

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