25+ Best Boss Jokes


Lighten up your workplace by reading the funniest boss jokes that’ll make everyone at the office laugh, including your boss.

Big boss and small employees.
Photo courtesy of Canva.

Hilarious boss jokes

1. My boss told me to have a good day.

So, I went home.

2. What are the best ways to be a good boss?

If you’re in charge, ponder. If you’re in doubt, mumble. If you’re in trouble, delegate.

3. Boss: Are you good at using PowerPoint?

Me: I Excel at it.

Boss: Was that a Microsoft Office pun?

Me: Word.

4. How are Christmas and work similar?

You do all of the work, and the fat guy in the suit gets the credit.

Related: 15+ best bar jokes

5. My boss threatened to fire the employee with the worst posture.

I have a hunch that it might be me.

6. Me: Boss, can I have a week off around the holidays?

Boss: It’s May.

Me: Sorry. May I have a week off around the holidays?

7. What’s the definition of a power struggle?

Your boss has the power, and you have the struggle.

8. My boss calls me the computer.

It wasn’t a compliment. It’s because I go to sleep after 15 minutes if left unattended.

9. Boss: This is the fourth time you’ve been late this week. Do you know what that means?

Me: Yes. It means it’s only Thursday.

Related: 100 best comebacks ever

10. What did the can crusher tell their boss?

I quit. This is soda-pressing.

11. My boss says I have a preoccupation with vengeance.

We’ll see about that.

12. What’s the best way to criticize your boss?

Do it quietly so they can’t hear you.

13. How many executives does it take to change a light bulb?

None. They like to keep their employees in the dark.

14. My manager told me not to worry about a raise because money won’t make me happy.

I just want a chance to prove that it’s true.

Related: 25+ hilarious computer jokes

15. Why don’t managers get breaks?

It would take too long to retrain them.

16. What do you do if your boss keeps emailing you about your work?

Reply with “unsubscribe.”

17. How do you make people think you’re the boss?

Stand around and do nothing.

18. I heard my boss say I was worth paying attention to.

He was telling a security guard.

19. My boss said that my math skills are average.

That’s just mean.

20. What did the doughnut maker say to their boss?

I quit because I’m tired of the hole business.

21. My boss asked me to start my presentation with humor.

So, I put my paycheck on the first slide.

22. I told my boss that I wanted an increase in my paycheck.

My next one had a larger font.

23. My boss asked me why I’m always sick on weekdays.

I said I have a weekend immune system.

24. What do you tell your boss when they say they’ve been looking for you?

Good employees are hard to find.

25. What do you say when your boss cracks a joke?


26. I complimented my boss for driving a Ferrari.

My boss said, “If you work hard, put all of your hours in, and strive for excellence, I’ll get another one next year.”

Related posts:

Featured image courtesy of Canva.