June 10, 2026 at 7:55 pm

‘Is This Even Legal?’: New HR Rep Goes Digging After Watching Her Boss Trap Employees With Paid Work Trips

by Benjamin Cottrell

shocked HR Rep

Shutterstock

Using a company trip as leverage to trap employees into staying for a year is not a retention strategy — it is a legal liability waiting to happen.

So when a new HR rep was ordered by her boss to have every employee sign a pact that would fine them for resigning, she had no intention of following through.

And before the meeting was even over, she was already looking up the labor laws.

Keep reading for the full story.

I’m an HR and I just need to get this off my chest

So I’m a fresh grad and I got a job as an HR rep at a small firm.

For context, I’m the only HR here and there are less than 20 employees in my office.

She explains the main drama of the story.

We just had an office outing a couple of weeks ago — basically a paid vacation for 3 days, with 2 days on the road and 1 day with a full itinerary. I have my own opinion about this, but that’s another story.

Back to the problem — today, 2 of our employees submitted their resignation letters.

The boss took this as a huge slap in the face.

This ticked my boss off because “we spent money for the outing and now they’re basically being ungrateful.”

So he decides to act completely unreasonably

So my boss told me to make all of our employees sign a pact tomorrow that states:

If the employee participated in the outing 2 weeks ago, they can’t resign for the next year.

If they want to resign, they need to pay around 60% of their monthly paycheck as a penalty.

If they refuse to sign the pact, my boss won’t give out their reference letter.

The HR lady can hardly believe what she’s seeing.

I was so shocked. That’s beyond cruel.

I’m currently going through the laws about workers’ rights with my friend. I have no intention of making our employees sign that ridiculous pact.

I’m just bewildered and at a loss for words.

The employees will be lucky to have HR on their side.

If you enjoyed this story, check out this post about an IT department who keeps receiving tickets for a company that was previously spun off.

What did Reddit think?

This user affirms just how horrible an idea a contract like this is.

Screenshot 2026 04 09 at 12.30.04 PM Is This Even Legal?: New HR Rep Goes Digging After Watching Her Boss Trap Employees With Paid Work Trips

The boss is being completely manipulative with this stunt.

Screenshot 2026 04 09 at 12.31.04 PM Is This Even Legal?: New HR Rep Goes Digging After Watching Her Boss Trap Employees With Paid Work Trips

HR’s whole job is to step in when things like this happen.

Screenshot 2026 04 09 at 12.31.35 PM Is This Even Legal?: New HR Rep Goes Digging After Watching Her Boss Trap Employees With Paid Work Trips

Maybe it’s possible she could reason with her boss.

Screenshot 2026 04 09 at 12.32.43 PM Is This Even Legal?: New HR Rep Goes Digging After Watching Her Boss Trap Employees With Paid Work Trips

If you have to force your employees to stay at your company, it’s probably a sign you’re not a great boss.

If you enjoyed this story, check out this post about a customer complaint that led to them losing their VIP status.

Benjamin Cottrell | Assistant Editor, Internet Culture

Benjamin Cottrell is an Assistant Editor and contributing writer at TwistedSifter, specializing in internet culture, viral social dynamics, and the moral complexities of online communities. He brings a highly analytical, editorial voice to his reporting on workplace conflicts, malicious compliance, and interpersonal drama, with a specific focus on nuanced stories that lack an obvious villain.

As a published author of rhetorical criticism, Benjamin leverages his academic background in human communication to dissect and elevate viral social media threads. Instead of simply summarizing events, he provides readers with balanced, deep-dive commentary into why the internet reacts the way it does. In addition to his cultural reporting, he is an experienced fine art photography essayist and video game reviewer.

When he isn’t analyzing the latest viral debates, Benjamin is usually chipping away at his extensive video game backlog, hunting down the best new restaurants, or out exploring the city with a camera in hand.

Connect with Benjamin on Instagram and read more of his essays on Substack.