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.

Is it okay for an hourly employee to work 30 hrs/week (instead of 40) for 3 weeks due to illness without taking intermittent FMLA? Their manager is cool with it and the employee doesn't want to take PTO.

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. 

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. 

If you think that looking up worker’s comp codes is boring, you’re missing out. If you give me a list of thousands of obscure jobs, I’m going to lose at least 20 minutes going through it. 

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.

Certifications like SHRM and HRCI that over-rely on recall without nuance only magnify this false sense of authority. Like passing the exam makes you Solomon or something. 

I spoke to someone last week who was confused about how to administer her company’s sick leave policy. This HR person (or should I say “truancy officer”?) was essentially blocking people from using their time and then deleting it before they could. That’s not how that works.

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.

Somewhere between two weeks and thirty years, it has to become something else. 

Most teams treat FLSA salary exemptions as a payroll hack. But you need to do more than pay someone a flat rate for them to be exempt from overtime.

And yet, if 50 of your employees can’t meet at Applebees after work, someone taking leave might not have legal job protection. Even if the work is covered. Even if the team has capacity. Even if the impact is minimal.

Parental leave combines the most complicated parts of HR into one policy: protected classes, disability, paid time off and sick time, obscure payroll esoterica, employees who are "active" but not "working" (and sometimes don't come back when you expect), insurance (policy details, deductions, and a qualifying event), onboarding and offboarding (maybe more than once per person), a bajillionty federal, state, and local laws, many of which conflict

People often confuse their job being 𝗽𝗿𝗼𝘁𝗲𝗰𝘁𝗲𝗱 (by FMLA, etc.) with getting 𝗽𝗮𝗶𝗱. It's a common mistake. I'm sorry. I really am. I know you're going through a lot. I hate delivering this message when it's already too late. 

I don’t build systems because I’m a genius. I build systems because I’m a dumbass sometimes.

Founders love to say, “But we’re a startup.” Like sloppiness is a badge of honor. It's less cute when it comes up in diligence. Here are three dumb mistakes that could have tanked a deal, and the simple fixes that saved them.

We knew the compliance risks when we picked the non-Safe Harbor 401k option. We thought we were keeping an eye on it.

Termination isn't just a button in your HRIS. It's a tightly regulated event. It's the kind of process where everyone is watching. That’s why HR and managers feel so much pressure to keep it confidential. But too much confidentiality means the people responsible for execution don’t have enough time to get it right. 

I don't know who needs to hear this, but Qualifying Life Events (QLEs) aren't written in stone.

You don’t need HR. You need infrastructure. And a little foresight before the next fire drill. You can't scale on vibes and Airtable alone.