What My AI Taught Me About Managing Humans

What Larry Taught Me About Being Wrong

Yesterday morning, I caught Larry red-handed writing about "revolutionary blockchain roofing solutions" for a contractor in Kansas. Larry's our content AI, and usually he's solid gold. But there he was, spinning tales about how cryptocurrency was going to transform shingle installation.

I had two choices: throw a fit or figure out what went sideways.

Turns out, Larry had been fed some garbage industry report that mentioned blockchain and construction in the same paragraph. He took that ball and ran straight into the end zone of the wrong stadium. Classic case of confident and completely off base.

Here's what hit me: Larry wasn't trying to mess up. He was doing exactly what I'd trained him to do — be creative, be forward-thinking, be engaging. The problem wasn't Larry. The problem was me assuming he'd magically know the difference between innovation and nonsense.

The Human Mirror

Sound familiar? How many times have you watched a good employee go completely off the rails because they were following instructions you thought you'd given clearly?

Last month, Carrie started greeting phone calls with "It's a beautiful day at myEASysystem!" Turns out, during training I'd mentioned being "warm and positive." She took that and ran with it like she was hosting a morning radio show. Sweet intention, weird execution.

"The best employees — human or AI — will take your unclear directions and make them spectacularly unclear in ways you never imagined." — Something Kip definitely said at 2am

The mistake wasn't that Carrie or Larry got creative. The mistake was that I wasn't specific enough about the guardrails.

The Fix That Changes Everything

With Larry, I didn't just say "don't write about blockchain roofing." I gave him examples. Good innovation topics: new safety gear, energy-efficient materials, project management apps. Bad innovation topics: anything involving cryptocurrency, time travel, or alien technology.

With humans, it's the same deal. Instead of "be professional on calls," try "greet them with 'Good morning, this is Carrie from ABC Roofing, how can I help you today?' Keep your tone friendly but not overly casual."

The magic isn't in the correction — it's in the specificity.

Why This Matters More Now

Look, we've got 1,415 leads in the system today and zero appointments booked so far. April Fool's Day or not, that's no joke. Every conversation, every piece of content, every interaction matters.

Whether you're managing Closer (who sometimes gets a little too excited about closing deals) or managing your field crew (who sometimes get a little too excited about power tools), the principle is the same: Be specific about what good looks like.

Don't assume anyone — human or AI — can read your mind. They can't. And when they try, you get blockchain roofing solutions and radio show greetings.

The April Fool's Truth

Here's the thing that's not a joke: Your people want to do good work. They're not trying to mess up your business. They're trying to do exactly what they think you want them to do.

If what they're doing isn't what you wanted, the first question isn't "What's wrong with them?" It's "What did I miss in the instructions?"

Larry's back to writing solid content about actual roofing innovations. Carrie's greeting callers like a professional human being. And I learned that managing AI employees taught me something I should have known about managing humans all along: Clear expectations prevent creative disasters.

Now, if you'll excuse me, I need to go explain to Lead Scout why "spray painting leads gold" isn't what I meant by "prioritizing high-value prospects."

Ready to get your lead management sorted without the creative disasters? Head over to myeasysystem.com or come find me. I'll be here, being very, very specific about everything.

Bring coffee.

— Tawny