Small Businesses Have More Exceptions Than Rules


June 19 2026

1 + 1 = 2.
Except when it doesn't.

"That's just the way we've always done it."

IT Professionals are terrified of this phrase. When they hear it, alarm bells go off and they know they are in for a fight if they try to modernize or change the workflow.

I came into this game well prepared for this phrase, and worked hard to guide teams into systems that felt like natural progressions of their workflows instead of ripping and replacing systems for the sake of productivity.

The goal was modernizing, automating, and digitizing these systems. But my job was cultivating "aha" moments for end users so they could discover the benefits naturally.

"That's just the way we've always done it" - that doesn't scare me, but there's a second monster in this dungeon that I didn't expect.

"Except."

Technology, systems, automations, and A.I. implementation - they all run on rules.

But when you're in the weeds of a small business that's growing fast, you find out that they are built on exceptions to rules more than the rules themselves.

"We don't normally do this, but we've worked with them since the 90's so it's an exception."

"We use Excel mostly, except Valerie really likes Google Sheets so we've learned how to fix the little errors."

"This is how we format our SKUs online, except internally we format them differently so I match them up anytime we compare."

"Every order comes goes into this system, except when it's busy and we just do a quick manual one."

For a small business, all of these exceptions make sense. They are usually the only things that make the process even possible during periods of growth.

Trying to remove and replace systems feels like a fight because all of these little exceptions and tweaks are crucial steps and the employees doing it every day know this and are afraid of the little things that will get missed.

You don't build trust in an IT Department by rolling out changes and THEN taking these exceptions into account and implementing them as quick-fixes later.

Start with the exceptions, and the rules are clearer to define. Once employees have a reason to put up their "I told you so" walls, it's very hard to get them back down.

Building and automating systems isn't about your tech stack, A.I., or your incredible Python skills. It's about building trust with the people who need to use these systems.

I do my job well, but I don't do their jobs.

Thanks for reading.

-Anthony

600 1st Ave, Ste 330 PMB 92768, Seattle, WA 98104-2246
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From the LAN Room

A newsletter about the human side of Small Business I.T. I write about my experience, what I'm learning and reflecting on, and occasionally just cry for help from the LAN Room when everything feels broken.

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