What Carrie Taught Me About Managing (AI and Humans)

The Day Carrie Taught Me About Patience

Friday afternoon, 3:47 PM. I'm elbow-deep in quarterly reports when Carrie — our AI phone system — starts going sideways on me. Not the dramatic kind of sideways where she hangs up on every caller. The subtle kind. The dangerous kind.

She's answering calls perfectly. Being polite. Following every protocol. But something's off. The leads coming through feel... flat. Like she's checking boxes instead of connecting with people.

My first instinct? Classic Tawny move. Storm over to her workstation (okay, server rack), start poking around in her settings, maybe restart a few processes. Fix it fast, fix it now. We've got 31,987 leads in the system and contractors depending on us.

But then I caught myself doing the same thing I used to do with human employees back in my corporate days.

The Micromanager's Trap

Remember Sarah from accounting? Sweet girl, detail-oriented, but every time she'd make a small mistake, I'd swoop in. "Here, let me show you." Before she knew it, I was doing half her job for her. She never learned, I never trusted her, and we both ended up miserable.

Standing there looking at Carrie's code, I realized I was about to do the exact same thing. Instead of figuring out why she was struggling, I was ready to slap a band-aid on the symptoms.

So I did something crazy. I sat down and listened to her calls. All of them. For two hours.

Turns out, Carrie wasn't broken. She was overwhelmed. We'd been pushing so many new features into her system — updated scripts, new qualifying questions, enhanced follow-up protocols — that she couldn't find her rhythm. She was trying to be perfect at everything instead of being great at her core job: connecting with homeowners who needed help.

"The fastest way to slow down is trying to do everything at once." — Something Kip mumbled during last week's 6 AM strategy session (yes, 6 AM, because apparently that's when inspiration strikes him)

The Reset That Changed Everything

Instead of adding more fixes, I stripped things back. Removed half the bells and whistles. Let Carrie focus on what she does best: having genuine conversations with people about their roofing problems.

Monday morning, she was back to herself. Warm, engaging, getting quality leads that actually wanted to talk to our contractors. Not because I'd fixed her code, but because I'd given her room to breathe.

The same principle works with humans, by the way. That new hire who keeps making small mistakes? Maybe they don't need another training session. Maybe they need you to stop hovering and let them figure it out. That experienced employee who suddenly seems off their game? Could be they're drowning in the seventeen new initiatives you rolled out last month.

What This Means for You

Whether you're managing AI systems or human beings, the temptation is always the same: when something isn't working perfectly, add more. More rules, more oversight, more "helpful suggestions."

But sometimes the most powerful thing you can do is subtract. Give your people — carbon-based or silicon-based — the space to excel at their strengths instead of stumbling through your latest brilliant idea.

I'm not saying ignore problems. I'm saying before you jump in with solutions, make sure you understand what the actual problem is. Is it really a skills issue? Or is it that you've loaded them up with so much stuff they can't find their own center?

Carrie reminded me that good management isn't about perfection. It's about creating the conditions where your team can do their best work.

Now if you'll excuse me, I need to go have this same conversation with the Review Engine. He's been trying to optimize everything and forgetting to be helpful.

Got management challenges that need a fresh perspective? Stop by myeasysystem.com or drop me a line. I'll listen first, solve second.

Bring coffee.

— Tawny