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. 

What started as a step back became a growth hack. When it came time to brand my service, I knew exactly what I was good at, where there was a gap, and what people would pay for. 

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.

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.

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.

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.

Just like us, dogs align themselves with power. Oscar intuitively knows who the pack follows. Once he knows who’s the boss, he tries to win them over just like everyone else does. 

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.

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.

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.

Don't put up with a broken back office just because you don't want to deal with HR. A fast-growing startup needs someone with the operational range AND depth to think on their feet.

If your team is always reacting, you’re not scaling—you’re surviving. The embassy had her visa application for 10 months, but they only...