Some workplace problems can be solved with good management, but some problems are just too big for any one person.

So when one overconfident new boss told his employee he simply didn’t know how to handle their most difficult employee, he handed the boss the wheel — and watched him realize his mistake.

Keep reading for the full story!

“I’ll show ya how it’s done”..ok boss, let’s see what ya got

So, circa 2013, there was this woman, around 40 years old or so — we will call her Kay.

Kay was different.

She seemed to have some pretty crazy ideas.

Accused my fellow supervisor of altering the employee handbook while she was reading it (this was an online handbook).

1. Said our company was secretly a company who worked for the NSA or FBI (it changed daily).
2. Found wires loose on her desk and screeched to anyone around that they were listening devices (a fellow employee put the wires there, wanting to see what would happen — I didn’t see him do this, but was told after the fact).
3. Went to HR on me, saying I told her computers weren’t for personal use and that she had to leave if she was clocked out (HR told her yup, and I was right).

Enter a new manager — we’ll call him Dan.

Dan wasn’t the best coworker ever either.

Dan was a fun guy, a solid dude, but not a local guy. He was hired from the west coast, as he had a great pedigree.

Smart man, but a little full of himself — thinking he was the ultimate problem solver.

After around two weeks as my boss, he came to me and my fellow supervisor wanting to know what the problem was with Kay.

We told him she had a little screw loose, and she couldn’t be reasoned with.

Dan thought they just weren’t looking at the problem the right way.

He told us we didn’t know how to talk to her. He would personally show us how to handle someone like her.

At this time, I worked the evening shift 2 to 11pm (this is relevant) and my fellow supervisor worked 8am till 4:30pm. Managers were salary so they didn’t have a set time, and came and went as they pleased.

Around 4pm, Kay had a huge issue. She was demanding paid time off for Columbus Day.

This request made zero sense.

This was not a paid holiday.

She was told she couldn’t have the day off as she had no vacation time left, and it wasn’t a paid holiday.

She kept badgering and barking about how she deserved it and we had zero right to not pay her on a federal holiday.

Time for the petty revenge on Dan — but more of a lesson on knowing these people better than he did.

So this employer decided to let Dan handle the issue since he seemed to know best.

I IM’d Dan and asked if he was busy because Kay would love to talk to him.

He asked what the issue was, and I told him about it all.

“I’ll handle this…send her in,” he typed.

Oh, this was gonna be fun. Good thing I could see him in his office from my desk. I had a fantastic view.

She went into his office around 4:10ish. My fellow supervisor said good night around 4:30 and left.

But Dan severely underestimated just how difficult Kay was to deal with.

Around 9pm, my fellow supervisor called me to ask how Dan handled it.

I told him, “He’s still in there with her.”

I kid you not, dear reader — he was in the office with her until 10pm. I watched the entire time.

He was trying to talk to her in what appeared to be a reasonable manner. I could see her gesturing wildly the entire time, probably about this or that.

This proved to be one of the most challenging meetings of Dan’s career.

His face would go from amusement, to bewilderment, to frustration, and back to amusement. I watched him trying to get out of the whole ordeal.

He knew he had bitten off more than he could chew.

Finally, Dan was forced to admit defeat.

At 10pm his door finally opened and Kay left.

Five minutes later, Dan headed out the door with a look I can only describe as a man who had survived a tornado.

“How’d that go, boss?” I said.

“Jesus…you were right. Next time, send her to HR,” he muttered.

Hmm.. seems like next time Dan should listen to his direct reports!

What did Reddit make of all this?

Dan actually deserves a little credit for how he handled this.

Some coworkers are just laughably ignorant.

This commenter can’t understand how this meeting went on for so excessively long.

Humility really is an underrated leadership quality.

If you liked that story, check out this post about an oblivious CEO who tells a web developer to “act his wage”… and it results in 30% of the workforce being laid off.