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. 

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

This wasn’t payroll. It was a cold case. Policies contradicted payroll data. Contracts were locked behind sharing permissions from people who’d left the company. Folder names were gibberish. People paid hourly were getting flat rates with no timecards to confirm overtime. A million Scribe docs with no annotations. Hours of 20-minute videos with no transcripts.

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

As an HR department of one, she’d created an environment where people loved to work. I was called in because they were having trouble with a few vendors. And as usual, the problem wasn’t the vendors, but how the company was using the tools.

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. 

These problems don’t show up right away. They lie in wait until someone balances the books and notices thousands of dollars missing. 

Meanwhile, mistrust over the final paycheck was just one in a list of disagreements leading to a quickly deteriorating relationship

A man claiming to represent the New York Workers' Comp Board had shown up at my client's home in upstate New York, demanding proof of coverage. It would have been laughable, except that it was real.

The leasing office closed in 15 minutes, so he needed the pay stub NOW.  But when he hit “download” in the payroll app… nothing happened. 

Just like how airlines impose inconveniences to keep air travel safe and sustainable at scale, PEOs impose restrictions and rigid workflows

Running the People side of your business takes a lot of work, but hiring a PEO comes with trade-offs that you may regret later.