Dumb Bosses

2PM Call Technician

Copier Technician: Sir, your software isn’t compatible with this machine. It’s outdated.
Offie Manager: Well, the sales guy promised it would work.
Copier Technician: Did you try it out before you bought it?
Office Manager: No, I trusted the sales guy that it would do what he said it would do.
Copier Technician: Well, this isn’t the first time you’ve dealt with a sales person, is it? When I make a significant purchase, I try it before I sign the contract.
Office Manager: How you ever going to get married, son?
Copier Technician: Sorry?
Office Manager: I said how you ever going to get married?
Copier Technician: I am married, sir.
Office Manager: Well, did you try out your wife before you got married?
Copier Technician: What?

310 Dorla Court
Zephyr Cove, Nevada

Sure, She Meets Lots of New People, but She Doesn’t Get Their Names

Development manager: … So then I told my wife that even if we raised our granddaughter she could still end up like her mother. I mean, she doesn’t have tattoos, but she does drugs and she’s a tramp.
IT analyst: Don’t call your daughter a tramp, that’s not nice!
Development manager: Why not? She sleeps with every Tom, Dick and Harry!
IT analyst: At least she has a social life.

1600 South 900 West
Salt Lake City, Utah

Overheard by: Jealous

10AM Staff Meeting

Manager: Don’t send information; it just confuses me.

8787 Orion Place
Columbus, Ohio

But He Is Dating Both Allen and Julia

Boss: I don’t know why he’s so moody.
Employee: I know! I think he’s bipolar.
Boss: No, I don’t think he even likes the cold.

Imperial, Pennsylvania

Trained Boll Weevils

Boss: How do I get a binder for this stuff?
Assistant: There’s one in the cabinet.
Boss: Um, how do I get the holes?
Assistant: What?
Boss: How do the holes get in the paper?

3080 Broadway
New York, New York

I Always Say Friendly Fire Is Better Than No Fire

Boss on phone: I’m the entrepreneur type — I shoot from the hip. I figure I’ll fix it when I’m finished messing it up.

Hayward Avenue
Carteret, New Jersey

Overheard by: Jay-B

Welcome to the Club

Front office girl at medical spa, hanging up phone: The client says we are not taking her concerns seriously, and she is going to report us to the Surgeon General.
Ditzy manager: The Surgeon General? But we don't have anything to do with smoking!
Front office girl, under her breath: I can't believe I have to report to you.

Charlotte, North Carolina

Overheard by: OMG The IQ level here is amazing

4PM Technical Meltdown

Boss on phone: I just want a human beeeeeeing! Bahhh! Why can’t I just have a human being?…Oh thank god!Finally! A human being! Wait, you are a human being, right?…You haven’t gotten this before?

2810 Blaine Drive
Chevy Chase, Maryland

5PM That’s a Wrap

CSR: This is my senior picture in high school.
Manager: You were a cheerleader?
CSR: Yeah.
Manager: What happened?

730 International Parkway
Richardson, Texas

Overheard by: El Gee

Woulda Been a Lot Easier Just to Say, “Sure, No Prob”

Boss: Hey, can you make a calendar that looks like this? [Hands a paper to her.]Underling: Yeah. You know this is from [the other agency], right?
Boss: Yeah, the client likes it. We have to go with that.
Underling: But their calendar is a copy of the one I did for the client. The client just handed it to them, and they made all these little changes.
Boss: Yeah, just do it like that.
Underling: But I already did it. They only took my calendar and messed with it.
Boss: Just make it look like this one!
Underling: But it’s my calendar!
Boss: Just make it look like this one! [Boss stalks off.]Underling, to entire office: Am I in a Dilbert cartoon?

3rd Avenue
New York, New York

© 2026 OverheardinTheOffice.com
Hat Tip 🎩 to The Marketing Scientist