HR Horror Stories

By Julia Wengrovitz

Working in any business with coworkers can lead to some cringeworthy moments. We’ve gathered up three HR nightmares to make you laugh this Halloween, and some ideas on how you can avoid these awkward moments yourself. Enjoy!

Employer pays $250,000 in paychecks to terminated employee

A New York subway cleaner was paid a quarter of a million dollars in bi-weekly paychecks after allegedly not being informed of his termination. The employee was laid off in 2013, and claimed to be on sick leave since 2015.  But due to an error in payroll, he’s been collecting his paycheck every 2 weeks for the past four years.  

When the error was finally discovered by an employee at the Metropolitan Transportation Authority, the MTA employed a very non-traditional method to let him know he no longer worked there.  When the employee tried picking up his paycheck in early October 2019, he was arrested for criminal trespassing and informed that he’d been fired six years ago.

“If I’m terminated, how am I still collecting checks?” the employee said he asked a boss after his arrest.  

“That’s not my problem, that’s payroll’s problem,” the boss allegedly responded.

The employee continued to receive other correspondence from his employer, including a letter telling him to go to training that was sent the month before his arrest.  A spokesman said the MTA is investigating after a Transit manager raised internal questions. It’s unclear how the employee ended up back on payroll in 2015, two years after the alleged termination.  The paychecks noted the number of hours worked, and didn’t mention a disability.  


The scene is straight out of the movie Office Space, where a similar payroll error affected terminated employee Milton Waddams. Per consultant Bob #1, “Apparently what happened is that he was laid off five years ago and no one ever told him, but through some kind of glitch in the payroll department, he still gets a paycheck.”

In the fictional movie scene they just chose to fix the glitch and not tell the employee of his termination. As the other consultant Bob #2 described, “So he won’t be receiving a paycheck anymore – so it will work itself out naturally.”

In real life, there are several important lessons that your business can learn from this incident.

  • First, using comprehensive HR software that integrates Payroll and Talent Management ensures that employee data and payroll is tracked accurately.
  • Second, it’s important that your company has a formal employee offboarding process in place to deal with terminated employees.
  • Finally, if you’re the affected employee and looking to avoid a pair of handcuffs, you should know that you’re legally liable for payments you may receive in error.

Interested in learning how your business can reduce payroll errors by outsourcing HR?

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Termination Gone Wrong

A decision was made by the CEO, myself, and the Department Manager to terminate an employee. The Department Manager seemed to be completely onboard with the decision. The two of us went to carry it out together. I advised the employee that today would be her last day and the employee became combative. I was fully prepared to explain that there would be no negotiation and escort the employee from the building.

But instead, the Department Manager started to cry!

She cried and blurted out apologies and sympathies. The Department Manager insisted on going back to speak to the CEO to rescind the termination. I attempted damage control by trying to carry out our original decision to terminate, but it was impossible with the employee’s manager begging me not to.

We had to go back to the CEO and re-strategize. We ended up downgrading the termination to a suspension and the Manager was demoted.

This huge fail still haunts me!


Having difficult conversations is certainly part of any manager’s role, but being properly trained for having those difficult conversations might not  be a top priority, and maybe it should be. Working with an HR Outsourcing partner like a Professional Employer Organization (PEO) could have helped avoid this situation. PEOs often assist small businesses with training and providing a clear process and workflow for addressing terminations.

Want to learn more about how outsourcing HR can streamline your process to hire (and fire) employees?

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An Applicant Tracking Mistake of Their Own Making

My company has about 30 employees at its Montreal headquarters and a total of approximately 100 worldwide. In a spring 2015 hiring blitz tied to the company’s expanding business, we were looking to fill seven open positions. The jobs were posted on Indeed, LinkedIn, and Monster, and we used a combination of Gmail and our CRM software to manage applications, schedule interviews, and handle follow ups. The hiring team used a shared email address to receive applications and reply to job candidates. We created a master folder in Gmail for the hiring spree, and within it, unique folders for each candidate.

On the fateful day, one of my HR colleagues meant to send a rejection letter to an applicant named Tricia. Instead, he hit “Reply All” and sent it to every name in the master hiring folder. The staffer immediately knew that he’d made a mistake but it was too late. What was done was done. We needed to figure out how to fix it.

He alerted the company’s top brass and, together with the HR team, that evening they called or emailed everyone who’d received a “Dear Tricia” letter. The HR staff already had ruled out 90 of the 110 applicants as prospects, but everyone agreed we owed them all a personalized explanation of what had happened, along with reasons why they weren’t being considered for a job.

Dealing with the other 20 candidates was harder. Most understood that it was a clerical error. But half a dozen were upset. One woman who’d interviewed for the same job as Tricia assumed the rejection letter meant she was getting the offer instead. In the end, six of seven candidates we made job offers to accepted and the seventh declined for a better opportunity.


Tracking applicants is often a manual, time-consuming process for small and mid-size businesses. Using your email platform to track candidates may work if you’re occasionally posting a single job with just a few applicants. But for most companies trying to fill multiple roles across potentially hundreds candidates, such a manual process invites disaster.

All of this could have been avoided if a solid Applicant Tracking System (ATS) was in place. Using a properly automated system can save a lot headache, making it easier and streamlined to post jobs, manage applicants, run background checks and ultimately send out offer letters.

Managing HR can be a nightmare. While there’s no silver bullet for squashing your HR nightmares, having a strong human resources outsourcing partner can help you avoid many of them by managing payroll, employee benefits, and compliance functions so you can rest easy.

Want an easy way for your business to find an outsourcing partner to simplify how you manage HR?

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