Years ago, during COVID, I made it a company goal to stop relying on paper. I wanted us to be able to run the whole company without a printer. What I didn’t know then was how much that decision would help me when it came to AI. Everything was in one spot instead of two. No more filing cabinets.
But one spot isn’t the same as organized. I had hundreds of old quotes sitting on our server. Every time a new bid came in, I’d dig through them looking for one close enough to copy. Folder by folder, builder by builder, hoping I’d done something like it before. Earlier this year, I knew there had to be a more efficient way. That’s where my journey with AI began.
First I copied them into a folder of my own, so nothing on the server got touched, and pointed it there. That was it. I didn’t label them or sort them first. It read through every one. Then I asked it how I could be more organized. It didn’t sugarcoat it. My file names were all over the place. Some had the builder. Some had the job. Some just said a month and a year. No builder, no job. You’d never know what was in it without opening it.
So I set one rule. Every file gets named the same way: builder first, then the job, then the date. Then it went through and renamed every one of them for me. Builder first, so when you sort a folder, every job for one builder lines up together. Date last, so the newest one jumps out.
The folders mostly stayed how I had them. One folder per builder, a folder for each job inside. Turns out I’d gotten that part right on my own.
Then it built me a brand new spreadsheet of all my bids, sorted by type of job and size of job. That folder became my own folder, set up my way, and it’s still the one my AI is pointed at today.
If you’ve never touched AI, that’s how I’d start. Don’t worry about learning the tech. Pick one thing that eats up your time, like those quotes did for me. Make a folder just for it, and put copies in there, not your originals. Then decide how you’ll name things before you hand it anything.
Then treat it like a new guy in the office. He’s read just about everything ever written, he works fast, and he never calls out sick. But he’s never been on a job site. He doesn’t know your builders or how you do things. So you have to tell him. Exactly. Leave a blank and he’ll fill it with his best guess, and he’ll say it with a straight face even when he’s wrong.
Before you sign up for anything, find out what your company already has. Ask your boss, or whoever set up your email, or the computer guy you call when the printer dies. Two questions: do we already have this, and is there anything we shouldn’t put in it?
I did this one backwards. I handed it the quotes before I checked what our account does with them. Check first. Until you hear back, keep the private stuff out. Passwords, bank numbers, anything about your guys, your pricing. Take the names and numbers out and it still works fine.
Start smaller than I did. Have it clean up an email. Have it explain a spec section in plain English. Have it turn a messy list into a checklist.
You don’t need special words for any of it. Type to it the way you’d talk to the new guy. I type to mine the way I text, typos and all, and it figures it out.
What matters is being exact. “Clean up this email” gets you something that sounds like a bank wrote it. Try this instead: “Clean up this email to a builder. Keep it short, keep my words, and don’t add anything I didn’t say.” Now it sounds like you.
Then read what comes back. Every time. It almost never gets it right on the first try. When it misses, don’t just say try again. Tell it why. “Too long.” “That’s not what I did.” “What does this even mean?” Then go again. Tell it why, and the next one gets closer.
And those old quotes? I used to dig for one every time a bid came in. Now I search one place and it’s right there. That’s the time I got back.
Steal this
Open whatever your company already has, or a free one for practice, and paste this in. Fill in the bracket first.
I work in the office of a [what your company does]. In plain English, tell me five things you could help me with this week, and one thing I should never ask you to do. Keep it short.
Then ask it one thing you’d normally Google, and see how it does.
Next Tuesday: why my AI nailed something once and never did it the same way again.


