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Boss Thinks He’s Outsmarting An Employee, But The Employee Plays A Better Game

by Annie Nguyen
November 29, 2025
in Social Issues

Workplaces have a funny way of becoming mini soap operas, especially when a clueless manager and a frustrated employee get thrown into the same storyline. And nothing fuels chaos quite like a boss who thinks “more tickets = more productivity” without understanding what any of the tickets actually mean.

Anyone who has worked under someone like that knows the unique mix of annoyance, confusion, and quiet plotting that starts bubbling underneath the surface.

In this story, a tech-savvy employee finds himself dealing with a boss who can’t tell a complex system issue from a sticky note request. When the boss notices that a coworker is closing more tickets, he jumps to conclusions and sets off a chain of events that becomes… well, far more entertaining than he intended.

Especially when he asks the employee to do something that, on paper, sounds innocent until it absolutely isn’t. Want the full behind-the-scenes drama? Scroll down for the original post.

An employee gets asked to train a new hire, only to sense his boss has a hidden agenda

Boss Thinks He’s Outsmarting An Employee, But The Employee Plays A Better Game
Not the actual photo.

'Will you train your own replacement and make yourself obsolete? Of course I will!?'

On mobile, English is not my first language, throwaway, bla bla the usual.

Let me first say I have been a lurker here for quite some time and always enjoy your stories. Especially when you stick it to stupid bosses!.

This happened some time ago, but as I think it would fit here.. Actors (names changed obv.):

Bob: Boss at the time, old, can't keep up with technology but had been with the company for a long time and so got to be my boss.

Hans: Hero of this story, friend from school who works in the same company but in management but in a different Department.

Helped me get this job 4 years prior.

Caroline: Coworker who is not the smartest tool in the shed but makes up for it in work ethic.

Carl: Normal coworker who has worked at company for 6 years and handles mostly the old clients accounts.

Has a family, very busy.. Me - Well, me. Guy in his late 20's, a little geeky, likes computers.

This was a small company and our team of 3 were best described as tech support for our clients but it went a bit further than that.

I usually helped with setting up databases and also advised clients from time to time if they would benefit from upgrading their plan etc.

As normal with tech support, we got tickets from the clients and would work away at them one by one.

I liked the challenging problems and usually tried to work hard at them, and it just so happened

that Caroline liked the more standard problems and enjoy doing something she already knew over something new every day.

Nothing wrong with that. As you might imagine, we to made a good team and had this kind of unwritten rules who took which tickets.

Win-win-win-win. (Me, Caroline, company and client) Until we got a new boss, Bob. He immediately noticed that I was working far fewer tickets than Caroline.

I tried to explain to him how not every ticket is the same workload, but because he wasn't very tech-savvy and didn't understand half

the stuff I was doing, he did not understand.

Also, around one month later, we got a huge new client and I spend a week on site and setting up all the databases and stuff they needed.

This drew down my month-average ticket numbers even further, duhhh.

If Bob would have only had half a brain cell he could have figured out why.

Now came something I did not expect from Bob: He said we need more help on the team and he was approved to hire a forth member for our team.

I was exited, we all were. We had this new huge client and things were not yet running smoothly and anyway our company was expanding fast so this actually made...

And he specifically asked me to basically do the recruiting process and to work the new guy in

(he might have figured out that he did not have a clue what we were doing I thought), which I was happy to do.

That same night Hans calls me which is weird because Hans is not a caller, he is a texter.

He basically said: "You should come over to my house tomorrow, I have some beers that need drinking."

So the next day I get to Hans' house and we are just talking about normal stuff,

we see each other maybe once per month and have a big overlapping friend pool. But this time it was just me and him drinking beers, no other friends around.

After some beers he mentioned that he had just updated his resume the day before and that everyone should always have an updated resume on hand.

"Do you have an up to date resume" he asked.

I felt this was a weird question and had an idea where this was going so I said no, but should I?

Is there something you know about that you want to tell me?

Well I am just saying that everyone should have a resume ready but I of course couldn't tell you

if Bob thinks about letting you go but I also couldn't tell you if Bob is not thinking about letting you go.

I thanked him very much for the beers and left shortly after that.

So I know I am getting fired and I have the suspicion that Bob has just asked me to hire my own replacement and train him to do my job...

This is finally where the sweet MC comes in, I fully comply with hiring a "forth" member of the team and also pick one best suited for what Bob wants:...

So I am thinking not so smart person with a sloppy attitude that does not care if the customer is happy.

After all customer satisfaction was not important to Bob when he talked about my ticket numbers.

I get right on it. Many people apply, some good ones, but I weed those out very quickly.

Resumes with lots of spelling mistakes and little experience in the sector are the ones I invite for an interview.

The interview stage is trickier because now Bob and someone from HR is sitting in with me,

but I am still asking most of the questions and giving my opinions on the candidates.

But because I weeded out the good ones when Bob makes a decision he just chose the best of the worst

(in my opinion not even the best because one applicant was actually quite good but I asked him stupid questions

that did not even make sense and when he could not answer them I made him look really bad, sorry John).

I advise one candidate he ends up picking because he will work very fast and will get a lot of tickets done.

At this point I have another job lined up in 4 months time, but I wanted to get fired by Bob to get some sweet severance pay.

After 2 months of training Mr.. New guy, I have just shown him how to do basic tickets

(which he can do quite well and fast but makes a lot of mistakes with) and have let the hard ones slowly build up.

Carl notices and as he would be the only one after my firing to be able to handle them I let him in on what I was doing.

As chance will have it he had just gotten an offer from another company and since he also did not like

Bob he already decided that he will take the offer but said he could sit on it a few weeks and time it with my firing for maximum destruction.

Then I tell Bob I am done working in the new guy and a week later he tells me he sadly needs to let me go

because my numbers had not gotten better (he actually used against me that I had not been doing that many tickets

while I was training the new guy, how dumb can you even be, Bob?).

He also wished me a lot of luck finding a new place to word at with my work ethic.

This had been the day I was waiting for and I just thanked Bob and reminded him of the 4 months worth of severance

I was owed now and also 2 month worth of vacation I had not taken and carried over and was now entitled to get paid out.

As I am heading out I tell Carl what had just happened and he opens his drawer with the signed two weeks notice and walks into Bob's office.

My girlfriend had vacation time left and we decided to leave for a 4 week holiday to New Zealand the next week.

I proposed to her there (as the saying goes: spend 1/4 of your severance on the engagement ring)

I started my new job one month after returning from NZ and even got a nice pay bump and a good boss!

I made sure to thank Hans again and he kept me in the loop on how my old department went down the drain very quick and Bob was let go...

When that happened they actually approached me for taking his job and I declined, but that would have been the ultimate f__k you to him...

About 5 years later (last year) I started a company together with Hans doing much of the same thing

but in a different city and so far it is going really well!

TL;DR: who reads tldrs in this kind of subreddit?Boss does not understand what I do,

gets me to hire my own replacement which is of course not a good fit and I get a fiance and better job out of it.. ​

Edit: Spelling and formatting. You pointed out the irony of my spelling mistakes but please see my first sentence.

I am sure there are still plenty of mistakes in the text. If you find them, keep them. Also, TIL that a lot of people in fact to read TL;DR's

There’s a familiar kind of emotional sting that comes when someone’s hard work is misunderstood or undervalued. Many people can relate to the frustration of being judged by the wrong metrics, especially when a supervisor lacks the knowledge to appreciate the complexity behind a job well done.

In this story, both the employee and the boss move from two very different emotional spaces one rooted in competence and pride, the other shaped by insecurity and a fear of being left behind as the workplace evolves. When these perspectives clash, feelings of resentment, doubt, and the instinct for self-protection begin to accumulate.

For the employee, the moment he realized he might be training his own replacement wasn’t just a professional blow; it was an emotional trigger. Psychological research shows that feelings of betrayal or unfair treatment often awaken a strong desire to restore balance.

According to studies published by McCullough and colleagues, humans may possess evolved cognitive systems for revenge and deterrence, mechanisms that historically helped individuals signal when they would not tolerate exploitation.

Seen through this lens, his decision to engage in meticulous, subtle, malicious compliance was not fueled by cruelty. It was an attempt to reclaim his autonomy in an environment where he felt increasingly sidelined.

Instead of confronting the boss aggressively, he let the situation reveal its own flaws, allowing the company to experience the natural consequences of its misjudgment.

However, research also warns about the emotional aftermath of revenge. The Association for Psychological Science highlights that while retaliation can provide brief satisfaction, it often prolongs negative emotions like anger or stress, making revenge a complex and emotionally risky coping mechanism.

Interpreting this in the context of the story reveals something meaningful: the employee’s “victory” wasn’t simply about watching his boss fail. It was about regaining a sense of dignity after being treated as replaceable.

His actions allowed him to walk away with confidence, but they also reflect a deeper truth that revenge may soothe in the moment, yet it rarely resolves the hurt that caused it.

Here’s what people had to say to OP:

These Redditors roasted Bob’s incompetence and laughed at how perfectly his downfall unfolded

ex0trix − Ah, the stupid boss who only looks at the number syndrome.

[Reddit User] − How dumb do you have to be to not understand "some jobs are more complicated than others"?

It doesn't even take any tech knowledge to understand that.

If you were all house painters, and Caroline was painting cottages and you were painting mansions, she'd do more jobs than you also. Bob got what he deserved.

squishles − I'm surprised bob's job survived longer than that afternoon.

That's the tell for you dun fucked up in the manager hiring process.

If it's one guy every now and then yea you can back a manager on that it's probably the employee, but when the employees start leaving in groups that's a...

Especially for what sounds like technical rolls; the mcdonalds school of management doesn't work when you're talking about skilled technicians, they're expensive to replace.

wKbdthXSn5hMc7Ht0 − Damn, the resignation right after the firing was exquisite.

Surprised Bob didn't come running to try and hire you back.

BelgianAle − I am a fan of these things.

These commenters highlighted the importance of office politics and backed the idea that OP’s choices protected better candidates from a toxic workplace

jazzb54 − There is a LPT in this story - make sure to make friends - not enemies, at work. Office politics are very important.

This story almost qualifies as /r/ProRevenge

saichampa − You did all the good candidates a solid by rejecting them and not wasting their time in the interview

and even John by helping him avoid the job. To bad you couldn't let him know later what was going on.

[Reddit User] − Love it! If you have to make decisions that involve a department which does not fall under your area of expertise,

listen to the damn experts. Question: What happened to poor Caroline?

Also, I kind of feel guilty for liking this story on account of all those poor candidates who were screwed over,

especially the ones who actually scored an interview and had their hopes up,

These folks chimed in with humor, enjoying the TL;DR joke and the “one-quarter severance ring” moment

fjzappa − TL;DR: who reads tldrs in this kind of subreddit? LOL! !

MaslowsHireAchy − The ring is supposed to cost 1/4 of your severance I die!

This user admired OP’s long vacation and reacted with envy and amazement

JBaker2010 − A 4wk vacation? ? Wow. ..one can only dream and drool for a week vacation as it is.

These commenters felt sympathy for John and pointed out how unfortunate it was that he got dragged into the hiring chaos

DisGruntledDraftsman − You did John a favor.

Crowbarmagic − not even the best because one applicant was actually quite good but I asked him stupid questions that did not even make sense

and when he could not answer them I made him look really bad, sorry John Ahw:(. I really feel bad for that guy now.

Thinking you can do it, but then the recruiter starts to asks b__lshit questions and he doesn't know what to say

These Redditors raised concerns about collateral damage, especially toward Caroline and the job applicants affected by OP’s compliance

Iplaymeinreallife − I get that this is malicious compliance, but you didn't only f__k over Bob, you also fucked over Caroline and the people applying for the job.

Not saying you were wrong, per se, but it's a bit sloppy to leave so much collateral damage to innocent people in your wake.

etds3 − I feel bad for Caroline.

This story shows how quickly a department can unravel when leadership focuses on metrics instead of meaning.

The OP walked away with a new career, a proposal, and a clean escape, while the boss who misjudged everything watched his team disappear like dominos. But was the malicious compliance justified or did it create too much collateral damage along the way?

Would you have done the same in his shoes, or taken a different route? Share your thoughts below!

Annie Nguyen

Annie Nguyen

Hi, I'm Annie Nguyen. I'm a freelance writer and editor for Daily Highlight with experience across lifestyle, wellness, and personal growth publications. Living in San Francisco gives me endless inspiration, from cozy coffee shop corners to weekend hikes along the coast. Thanks for reading!

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