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.

To get this one solved, I had to engage Claire-en mode. I demanded to speak to a manager. When the first person wouldn’t call a manager, I hung up and called again.

You know why their checks are cut by ADP? Because most of them work at big, old companies and switching payroll providers is really, really hard at that size. And because people don’t know any better.

The PEO issues the paycheck, but you pay the wages, taxes, and employer portion of benefits. Since the PEO is the employer on paper, they handle registering for state agencies and tracking compliance laws. And because PEOs can pool all of their client-employees, you get access the more affordable and flexible large-group benefits.

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.

COBRA isn’t real, like Santa Claus and the Tooth Fairy. I’m not saying that companies don’t have to follow the law. I’m just saying that there isn’t a basket of COBRA snakes in Washington, DC administering your health insurance like the IRS administers taxes.

White collar work is also more likely to lead to burn-out and mental health disability, which leads to longer and more expensive claims than many physical injuries.

I’m launching a Substack where I’ll anthologize my more informational content into practical, educational posts that tell you how I actually GSD. You can expect thrilling topics like state labor regulations, insurance regulations, payroll tax insights, deep dives into obscure payroll settings, workflow design, free practical resources, calls to action, and buttons to click.

One does not simply fire someone in a position of leadership. Loose lips sink ships.

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.

If you’ve been trapped in your workplace unable to leave, eating Doritos from the vending machine for dinner and sleeping under your desk, should you be paid for that time?

And speaking of equal opportunity, pirates welcomed escaped sailors from marginalized identities, giving them opportunities for advancement that they never would have had in the navy or merchant marines. Lady-pirates could even become captains, like Ching Shih, who led a fleet of 1,200 ships and a workforce the size of Morgan Stanley. You could call it D-E-Aye-aye-matey.

If you build a workflow that requires more than half of their brain, they’re going to mess up. The best workflows can be done while driving in the 2-minute gaps between chat support responses from the corner of the couch with Dora the Explorer playing at top volume in the background.

Spybots... I mean, 'AI notetakers' freak me out. Not because I’m paranoid. Because I sit in on a lot of meetings that people wouldn’t want recorded. Luckily, I live in California, which is a two-party consent state. Meaning those nosey little spybots need to announce themselves.

But hang on, what’s the point of making someone find a printer, and a scanner, and a pen, and those little “sign here” stickies anyway? Why, crime, of course!

The most common reason to hold on to employment records is because at some point, someone is going to need them. You may get a zombie tax letter with a five-figure fine from a state where no one’s worked for years. An employee may go through a nasty divorce and need payroll records from several years ago. Someone could file a complaint of systemic bias, and you’ll need complete records going back years to defend yourself. You may want to run a report on long-term trends and n

When someone is paid for a day they didn't work, it MUST be entered into payroll as some kind of Paid Time Off type. Otherwise, there's no way to pay it. Most of the uncommon leave types don't allow negative balances in payroll systems. So if your time off isn't allocated to another bucket, it can't get paid. The discrepancy could even block payroll and prevent everyone from getting paid.

Your handbook should help people make decisions. Not just disciplinary decisions. The handbook should draw bright lines where possible, and give guidance for situations that are unclear. Your handbook should give guidance on the unspoken habits your organization runs on.

Hiring the right people is only one ingredient to elite operations. Excellence is also about preventing the circumstances that leave room for mistakes. The procedures for putting down the CAUTION WET FLOOR signs that prevent the slip-and-falls of history.