Your best people aren't reading your docs

I remember one Monday evening, probably around 7pm. I'd finished most of my work for the day and was wrapping up — checking a few last things before heading home.

On a whim, I opened Confluence. Our HR space. We'd just hired three people recently, and I wanted to see how their onboarding was going.

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What I saw stopped me.

Everything was... done. Properly done.

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Checklists completed. Accounts created. Email signatures formatted correctly. Loom videos uploaded showing they understood the process. A list of questions they'd asked, with answers documented. Even a running list of improvements to make based on their feedback. It was all there. Organized. Clear. Easy to find.

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I sat back in my chair and thought: Holy shit. I didn't have to chase anyone down. I didn't have to remind anyone. I didn't even notice there were problems to fix.

For the first time in years, onboarding had happened without me.

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That wasn't always the case. For a long time, I was a broken record. We'd hire someone. They'd go through onboarding. And then, a week later, I'd see an email to a client with no signature. No footer. No contact details. Just text, like they were messaging a friend on the couch. Or I'd get a message from our accountant: "I still haven't received tax documents from the new hire."

Again.

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And I'd find myself saying the same thing I'd said a hundred times before: "We went over this. It's in the onboarding. There's a whole section. We even have a template."

The person would look confused. Or embarrassed. Sometimes defensive.

"Oh, I didn't see that."

"I thought someone else was handling it."

"I was busy setting up my development environment."

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These weren't bad people. They were smart, capable engineers. But somehow, the things we'd documented — the things we'd spent hours perfecting — just... weren't sticking.

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The moment I realized the problem

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After the crisis in 2012, we started growing again. New partnership, new office — beautiful glass building. We were hiring aggressively.

By then, we had an HR manager handling initial screening. I only did final interviews to check for culture fit.

But every new hire seemed to go through the same cycle:

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Week one: Onboarding.

Week two: Missing email signatures. Tax forms not submitted. Questions about things we'd already explained.

Week twenty: I'm still reminding them about the footer.

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So I decided to do something I should've done much earlier.

I sat with new hires at the end of their first day and asked them to walk me through what they'd done. Show me what they'd opened. What they'd read.

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What I found was eye-opening.

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Case 1: The guy who never got the email.

He'd spent the entire day setting up his machine. Installing his IDE. Configuring his environment. All useful stuff — but none of it was what we'd asked him to do on day one.

Why? Our HR manager forgot to send the onboarding email.

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Case 2: The guy who got the email but ignored it.

He assumed setting up his machine was more important than following the onboarding checklist. After all, no one told him the checklist was mandatory. And he had a bit of an ego — he figured he knew better.

Result? Same problem. A week later, he's asking questions we'd already answered in the docs he never read.

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It hit me then: Writing the process isn't enough.

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People don't automatically read documentation. And even when they do, they don't automatically understand it the way you think they will.

That's the curse of knowledge.

When you know something deeply, it feels obvious. So you assume everyone else will just... get it. But they don't. And it's not because they're stupid or lazy. It's because:

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• They didn't receive the information properly
• They skimmed it and missed key details
• They read it but interpreted it differently
• They forgot it by the time they needed it
• They were hired in a rush and thrown into a project immediately

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And all of that turns into operational debt.

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Questions that should've been answered on day one keep coming back. Processes that should be automatic require constant reminders. Things break because someone didn't know they were supposed to check. And it doesn't just waste your time. It wastes everyone's time — including the HR manager who has to keep answering the same questions.

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What actually fixed it

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We did a few things:

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1. Built in verification.

After onboarding, new hires recorded a short Loom video showing what they'd completed, what they understood, and what was still unclear.

HR reviewed it and followed up on gaps immediately.

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2. Assigned an owner.

Our HR manager became responsible not just for sending onboarding materials, but for making sure people actually absorbed them.

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3. Made it non-negotiable.

We added language to the offer letter: Following all onboarding steps is mandatory. Failure to do so may result in termination during probation.

Sounds harsh. But if someone can't or won't follow company processes from day one, they'll sabotage operations later too.

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4. Created a feedback loop.

Every question a new hire asked went into a log. If the same question came up three times, we knew the documentation was unclear and needed to be rewritten.

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That Monday evening when I opened Confluence and saw everything working smoothly?

That wasn't luck. That was the result of finally understanding: Your best people won't read your docs unless you verify they did.

Not because they're careless. But because reading a document doesn't equal understanding it by default. And if you don't check, you'll never know what they missed until something breaks.

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By the way, there's a useful place for AI here now. Not to write more documentation. But to monitor onboarding completion. Collect questions. Escalate to the responsible person when there are gaps in understanding. Automate the boring, not another content-slop piece.

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One thing to do this week:

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Go through your onboarding process yourself. Or better — sit with the next new hire and watch them go through it. Ask yourself at each step:

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• If they skim this, what will they miss?
• If they misunderstand this, who catches it early?
• If they skip this entirely, when will we notice?

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Then look at your process honestly: Do you assume reading equals understanding by default? Or do you verify? Because one of those approaches scales. The other just creates hidden debt.

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Here's what I'm curious about:

When's the last time you discovered someone on your team didn't actually understand something you thought was documented clearly?

Hit reply and tell me. I bet it's more recent than you think.