Like you can just tap them on the shoulder and hand them the phone. “Excuse me, Mr. Zuckerberg. Can you please talk to this guy Doug in Minnesota?”

This year, as you wallow in anxiety waiting for the tax team to get back to you, I have a fun project for you. Make sure your state payroll tax settings are correct. This is the only time when it DOESN’T feel irrelevant and boring. So Take advantage of it.

Because some of a company's most sensitive and highly-regulated data flows through the HRIS, very few people get full insight into everything that’s happening in the platform. HR software is a pretty blind item. You don’t get to try before you buy. Even with the providers who give you a sandbox, it’s hard to get a true sense of performance until you have live data.

How does this even slip through? For THREE YEARS? Part of it had to do with a quirk of how taxes work in reciprocity states like Wisconsin. Part of it was because state agencies don’t talk to each other. And implementation teams aren’t tax experts. And some payroll providers don’t have enough error flags for situations like this. And humans are flawed. They make mistakes.

Here’s why your paycheck takes so long: Many companies pay in arrears. Which is a fancy way of saying that there’s a gap between the end of the pay period and when you actually get paid. If you’re paid hourly, there’s literally no way to get you paid without a gap. Here’s what’s happening in that time:

I just really, really love Rippling. Because I’ve used it. And I’ve used its competitors. And, in my opinion, Rippling is better. At (just about) everything.

Hey, Tyler. I noticed you have seven dependents on your tax form. Usually those would be people in your immediate family who share your living expenses and rely on your income, like a spouse and kids. Are you sure that all of these people would actually be considered dependents for tax purposes?

For my small business clients (who aren’t considering a PEO), the decision often comes down to Bamboo or Gusto. Both Bamboo and Gusto have clean, easy-to-understand user interfaces with cute graphics that really do make dry and stressful processes less intimidating and occasionally “delightful.”

I’ve worked on the payroll of more than 100 different companies. There’s one question I get all the time. What’s the difference between gross and net pay?

When you work overtime, you’re paid time and a half. The OBBBA only applies to the “and a half” portion of your pay. The OBBBA only applies to federal overtime, or hours worked beyond 40 hours in a week.

Many companies with fewer than 200 people will literally sign away legal control of their employees and pay multiple times more for payroll services. Just so they don’t have to think about state tax settings.

So your company’s In-N-Out reimbursement policy is a taxable benefit. But how do you tax a burger that's already in your belly? In payroll, this problem is solved with what’s called an “in-and-out.”

“I was disappointed to learn that I was paid the same as the guy checking receipts at Walmart.” He said in his annual self-review after getting a big, fat check.

Imputed pay is a type of non-cash benefit whose value is still taxable by the IRS. It could be life insurance, a domestic partner’s benefits, bills your employer paid for you, gifts. Answer: Your payroll person adds an “imaginary” dollar to your paycheck. That’s imputed pay.

I’m talking about the small business where an employee is on their spouse’s insurance or a Marketplace plan and the company just reimburses them for all or part of the premium like a regular business expense. You're not supposed to do that.

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: