Ah, the classic boss and secretary dynamic—always ripe for some good-natured jokes! Whether it’s the overconfident boss trying to flex his power or the secretary who’s had enough and knows exactly how to put him in his place, there’s no shortage of funny stories.

These workplace relationships often lead to hilarious moments, especially when bosses try to be the smartest one in the room. But as we all know, sometimes the best laughs come when the secretary gets the last word.

Ready for a joke that shows exactly that? Here’s a funny little story that shows just how quickly things can backfire when you try to show off in front of your new employees…

A female secretary was assisting her new boss set up his PC and asked him what word he might want to use as a secret key to sign in with.

Needing to humiliate his new secretary a piece and let her know where they stood, he pompously advised her to enter ‘pen!s.’

Without squinting or saying a word, she entered the secret phrase.
She then nearly passed on chuckling at the PC’s reaction:

Secret key Dismissed.
NOT LONG ENOUGH!

BONUS: ANOTHER FUNNY JOKE

This funny (and fictional) story is about a shy and young salesman from North Dakota. At first, I felt really sorry for the guy, but after reading the end I couldn’t stop laughing! So damn good – the best laugh I’ve had in a while!

Looking for a job in the big city

Matthew, a young guy from a small town in North Dakota, moves to Miami. He enters a large department store trying to find a job.

He finally gets an interview with the boss, who asks him:

“Do you have any sales experience?”

“Yeah. I was a vacuum salesman back in North Dakota”, answered the youngster.

The boss was unsure, but he liked Matthew — so he gave him a chance.

“You start tomorrow at 8.00. I’ll come down after we close and see how you did.”

Matthew’s first day on the job was rough, but he got through it. After the store finished closing, the boss came down to the sales floor and gathered all the employees.

“How many customers did you have today Matthew?”, asked the chief.

Felt bad for chewing him out

Matthew, being shy, frowned and looking at the floor muttered:

“One.”

The boss, after hearing that, shouted:

“Just one?! Each sales staff in this store averages 20 to 30 customers a day. This has to improve! And soon! If you want to continue working here. Our sales standards are very strict over here. One sale a day might have been acceptable in North Dakota, but you’re not in the countryside anymore, son. Get it together, or get out!”

The young man listened to the manager’s complaint but continued to stare straight into the floor. The boss felt bad for chewing him out on his first day, so he asked:

“Okay, how much was your one sale for?”

Matthew looked up and answered:

“$150,000”

Sold him some fish hooks

The boss, astonished, yelled:

“$150,000?! What in god’s name did you sell?!

The young man explained:

“Well, first, I sold him a few new fish hooks. After that, I got him a new fishing rod to go with his new hooks. While talking to him about the rod, I asked where he was planning to go fishing, and he said down the coast, so I told him he would need a boat, so we went down to see the boat section and I sold him the new twin-engine model we have on display. The man said he didn’t think his car could actually pull the new boat, so I took him to our car department and sold him the latest 4×4 Dodge truck model.”

The boss’ jaw hit the floor, and after a minute of silence he asked:

“So this guy came to buy fish hooks — and you sold him a boat and a new truck?!

Matthew replied:

“Actually, the guy came in looking for tampons for his girlfriend. But then I told him, ‘Dude, your weekend’s busted, might as well go fishing’.

The following day, the boss gave Matthew a promotion…

What a comeback! I was laughing so hard I couldn’t keep my coffee inside.

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