Want Your Team to Actually Use AI? Start By Doing This One Thing

When I stood up at our all-staff meeting to announce that B:Side Capital was adopting AI, I came armed with a deck about efficiency and the future of work. The first hand up ignored all of it. “Is this how the layoffs start?”

I don’t remember exactly what I said back. I remember the silence before I said it.

Here’s my situation, so you know where I’m coming from. I run a nonprofit lender that specializes in Small Business Administration (SBA) loans, and I started a another company, Main & Machine, that builds AI systems for small businesses. I sit on both sides of this: the owner buying the technology and the builder shipping it.

From both chairs, I can tell you the software is never what decides whether this works. Most owners spend months comparing tools and pricing tiers while their team quietly decides whether to trust the whole project. The team decides first, every time.

The fear isn’t some quirk of your shop, either; 52% of U.S. workers worry about how AI will be used in the workplace, according to Pew Research Center.

I assumed the answer was better training, maybe a slicker tool. Wrong on both. What worked was doing the whole project in reverse: Before AI touched a single workflow, we decided what it would never touch.

Decide what AI will never touch before it touches anything

Before we looked at a single vendor, we sorted our work by judgment instead of by task. At B:Side, the machine never acts alone on a credit decision. It never talks to a borrower about hardship, and it never commits the company to anything.

The reasoning fits in one line: A machine can hold knowledge, but it can’t hold responsibility. When borrowers call because a business is failing, they aren’t looking for information. They’re looking for a person who can own an answer.

Try the same sort on your own operation, using three buckets: automate, assist and human-owned. Automate is anything where a mistake is cheap and fixable. Assist means the machine drafts and a person decides.

Human-owned is where your business earns its trust. Nothing in that bucket ever moves, and everyone on your team should know what’s in it by heart.

The buckets travel well. A restaurant owner might automate inventory counts, let the machine draft the weekly schedule and never let it anywhere near an unhappy customer. Your list will look different from mine, but the sorting question is the same everywhere.

Lead with what will not change

My original announcement was built around efficiency, and it died in the room. Tell people a tool will make everyone more productive, and what they hear is that the company will soon need fewer of them. I watched it happen on their faces while I was still talking.

So we threw out the pitch and led with a plain list of what would not change. A person makes every credit decision. No customer ever discusses hardship with a machine, and nobody gets punished for leaning into the new tools; the people who learn them get rewarded.

Those commitments cost me nothing to say. What bothers me now is how close I came to never saying them. Once they were on the table, people stopped scanning the announcement for threats and started asking how the tools actually worked.

I see the same fear now in every business Main & Machine works with, whatever the industry. The teams that adopt fastest never have the best software. They have an owner who said out loud, before anything launched, exactly what would stay human.

Give the machine the work nobody will miss

Our first instinct was to build something impressive, a flagship we could show off. We killed it and pointed the machine at document intake instead, the sorting and checking and transcribing that everyone dreaded. The least glamorous option on the list turned out to be the right one.

The machine has a name, by the way. Main & Machine built MARCUS for us in-house, and it does a lot more than read documents: it works through an entire loan file, checks the documents against each other and flags the discrepancies a junior analyst would catch. Every conclusion it reaches can be traced, questioned and overruled by a person, because nobody at B:Side should ever have to work under a black box.

We named it for Marcus Aurelius. The emperor’s test of character was quiet, repeated work rather than grand gestures, and I wanted the machine held to the same standard. It’s also how you win over a skeptical team: one boring, reliable proof at a time.

The results settled the argument. A loan file that used to eat three to four hours of manual review now takes less than one, and those hours went back into judgment calls and conversations with borrowers. Nobody mourned the transcription work.

Adoption mostly took care of itself after that. Within a quarter, nearly the whole team was using MARCUS without being asked. The first thing AI did in our building was take away work nobody wanted, and people noticed.

Here’s where I’d start this week: Write down the three things in your business that only a human should ever do, and say them to your team before you spend a dollar on software. Then hand the machine the tedium.

The question from that all-staff meeting deserved a straight answer, and the honest answer was no. Done right, AI isn’t how the layoffs start; it’s how the judgment work finally gets room to breathe. The best AI companies will not be the least human.

When I stood up at our all-staff meeting to announce that B:Side Capital was adopting AI, I came armed with a deck about efficiency and the future of work. The first hand up ignored all of it. “Is this how the layoffs start?”

I don’t remember exactly what I said back. I remember the silence before I said it.

Here’s my situation, so you know where I’m coming from. I run a nonprofit lender that specializes in Small Business Administration (SBA) loans, and I started a another company, Main & Machine, that builds AI systems for small businesses. I sit on both sides of this: the owner buying the technology and the builder shipping it.