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.

But what passes for “security” in these agencies is a cruel joke. It is no more realistic for you to expect me to tap Mr. or Ms. Business Owner on the shoulder and hand them the phone than it is for me to demand that you tap the governor on the shoulder and get him/her on the phone. 

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. 

But why would someone take a 40+% pay cut by choice? That time must be more valuable than money. There are plenty of reasons besides laziness why this might be true. 

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?

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. 

Let's get one thing straight: It's perfectly fine for your company to reimburse people for having a life. But if there's no business purpose or tax-preferred program for it (like an HRA, commuter benefit, or 401k), it has to be taxed as income. 

A PEO is an insurance broker, a guardrail, and a payroll provider. But it’s not a brain. Some people need a PEO. Some need a person. Most don’t know which they are.

I saw a founder on LinkedIn bragging about “solving” six-state compliance. His brilliant solution was... ...wait for it...

Did you know: Payroll doesn’t update tax settings automatically when someone moves. If you live somewhere where it’s common to commute across state lines, having different settings for where someone lives and works seems natural.

As someone who’s familiar with the tools and regulations/processes they manage, it’s painfully obvious that most of these complaints are user error. Not because the user is incompetent. Because people underestimate the difficulty of driving an HRIS. 

Most teams frame it like a software switch. In reality, you’re rebuilding your company’s approach to employee data, payroll, benefits, and compliance from scratch.