Short term disability insurance (STD) isn’t sexy. It doesn't attract top talent, but it can keep a company from the kind of tough decisions that can end with lawyers. Many employers don’t even know that the situations that are draining their budget are insurable. 

She couldn’t control the mayhem upstream, but somehow she was the one apologizing.  “Have you ever heard of a ‘blameless post-mortem’?” I asked. It’s a concept that I learned from software companies. When a bug causes a major incident, the review isn’t about a bad line of code but the whole causal chain.

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. 

Companies don’t reward you for masking dysfunction. They rely on it. They reward the person patching it up with even more responsibilities. Not the kind that come with a promotion, but responsibilities that come with with more fire drills and more late nights. 

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. 

“Everything is broken and I hate it here.” Have you ever worked at one of those places where the work-arounds become the job? Onboarding someone new isn’t about learning your product or roadmap. It’s about learning where the landmines are, how to use The Beast and navigate the playbook.

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.

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

Let me give you a “hypothetical” example that has definitely never happened in real life. It’ll make your blood run cold.

When teams don’t plan for leave, the work gets spread across people already maxed out. That’s not “lean,” it’s a recipe for burnout.

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. 

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.

It feels “leaderful” to manage policies, approve exceptions, or update payroll. That’s how power shows up for managers at big companies. But when founders take on those tasks, they lose sight of the strategic decisions that compound long-term.

I forgot. I’d asked the new office manager to grab “breakfast” for the VIP meeting. I forgot “breakfast” was code for something different around here.

Even the fancy ben admin tools. Somewhere behind the curtain, someone is downloading a form and forwarding it to a carrier. Often using unsecured email.

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.

People Ops doesn’t have to be in-house. It doesn’t have to be full time. It doesn’t even have to “feel” like HR. But it does have to be done right.

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