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.

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. 

Putting words to those operating principles won’t just help someone ramp faster. It gives your whole team a shared language to spot and fix misalignments.

Ops drag isn’t obvious at first, but it compounds quickly. Fortunately, small systems create big leverage. And a few smart fixes now can save you from spending your days scrambling as you grow.

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. 

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

The company had built an "inclusive" culture that didn’t distinguish between employees and contractors. The systems were set up to put a fig leaf over the fact that there were two classes of team members.