Managing all of this takes time and brain power. You’re contacting the employee, looking up policy details, doing unconfident math, and trying to figure out payroll work-arounds. The lost productivity cancels out the amount you’re saving by relying on these outside subsidies. Meanwhile, the new parent thinks it’s all your fault and blames you for the terrible experience you’re putting them through.

Here's a rule of thumb: The best states to work in are some of the worst states to work with.

Before you start planning how you’ll spend that “free” paycheck before your finance department re-balances the budget for 2026 you need to know that your payroll provider is probably smart enough to anticipate this. There are two methods that payroll providers use to solve the 27-paycheck problem: Pro rata and pay as usual.

These days, it seems obvious that workers should be able to demand an accurate accounting for their time. But it wasn’t always that way. 

Here are five examples of mundane breakdowns that I’ve seen lead to payroll errors:

Except that something didn’t add up. They didn’t even have employees for half that time, and one of the people they were assessing violations on wasn’t even in the state. 

People and companies who never admit fault or ignorance don’t inspire confidence. In this situation, the right support response would have been, “I don’t know, but let’s figure it out together.”

Letters from government agencies can be real scary sometimes. Especially when they contain words like "Warrant" and penalties with commas in them. By all means, take these letters seriously. But don't let them scare you.

If more people could see the data, maybe they’d want to renegotiate. But they might also have a better understanding of how their value is measured, and therefore find ways to bring more value to the company.

The many layers of humans and technology that go into insurance deductions can make it hard to track down where the problem is. And because of the old school systems insurance companies still use, it can be like traveling back in time. 

Nearly everything that happens in the company goes through payroll. And the person managing it needs to have the skills of an accountant, IT, lawyer, insurance agent, and operations manager, all rolled into one.

You run a draft payroll the regular way to get the numbers, enter the gross pay into an off-cycle payroll, and it spits out a number that’s off by 17¢ from what regular payroll said.  Why? Whyyyyy?

It drives me crazy when people treat a company’s FEIN (Federal Employer Identification Number) like it’s a big secret. FEINs are public information. 

If a California-based employee leaves, check that your provider calculates the accrual on a calendar day basis. If the employee has used some of their balance, this can get tricky. 

One month your paycheck covers 9 workdays. The next month, it covers 12. You get paid the same each time. If you leave in the middle of your next pay period, how is your pay prorated?

She couldn’t control the mayhem upstream, but somehow she was the one apologizing.  “Have you ever heard of a ‘blameless post-mortem’?” I asked. It’s a concept that I learned from software companies. When a bug causes a major incident, the review isn’t about a bad line of code but the whole causal chain.

He was quite confident that people always know when their paycheck is wrong. I wish that were always true. Payroll is complex, and you don’t know what you don’t know. I see a ton of these kinds of silent errors with 401(k)s. 

There is something that payroll administrators can do to mitigate the Big Check Suckerpunch. It’s not shady and doesn’t expose the departing employee to risk.

Riddle me this: What responsibility is sometimes handled by senior finance and other times by entry-level HR? What function manages a budget of millions but often gets assigned to the person with the lowest hourly rate? 

Choosing payroll software is like tasting wine with the label on the inside: all polish up front and, too often, regret on the back end. By the time you know what’s inside, you’re already seeing double. Picking the best tool is about knowing in advance what “best” means for your working style. The settings you skip during setup are the ones that bite.