The new person shows up Monday at seven, boots on, coffee in one hand, ready to work. You shake their hand. And right about then it hits you that you never actually wrote down how any of this gets done.
Everything's in your head. You've run this job a few thousand times, so the steps feel obvious, which is exactly why they're so hard to explain on the fly. Meanwhile the phone's ringing and a customer's waiting, so the new hire ends up shadowing you in silence and picking up maybe a third of what matters.
That first week is where most small shops lose a good hire. Not because the person's wrong for the job, but because the training lived entirely in the owner's head and never made it out. The fix isn't a fat binder nobody reads. It's a simple first-week plan you can talk out in about twenty minutes and let AI shape into something your new hire can actually follow.
Start by talking, not writing
Writing a training plan from a blank page is miserable, so don't. Talk instead. Open the voice memo app on your phone and walk through a normal job out loud, start to finish, like you're explaining it to the new person riding shotgun in your truck.
Say everything, even the parts that feel too obvious to mention. How you load the van the night before. What you check before you quote. The way you want the customer greeted at the door. Where the keys live. The obvious stuff is usually the stuff that trips up a newcomer, so leave it in.
Ten or fifteen minutes of rambling is plenty. When you're done, most phones will turn that recording into text for free, or you can read the transcript into any AI chat tool. Either way you've got the contents of your head sitting in front of you as words now, which is the hard part finished.
Turn the brain dump into a day-by-day plan
Now hand that text to the AI and tell it plainly what you want: "Here's how I do this job. Turn it into a first-week training plan for a new hire, broken down by day, Monday through Friday, easing them in."
You'll get back a structure. Day one is watching, safety, and where things are. By Wednesday they're doing pieces with you checking. By Friday they're running a small job start to finish while you hang back. Ask for it as a checklist the new hire can tick off, not a wall of paragraphs.
Read it like a skeptic. The AI will guess at anything you didn't say, and some of those guesses will be flat wrong for your trade. That's fine. You're not asking it to know your work. You're asking it to organize your work, so you can cross out the three things that don't apply and add the two it missed.
Write the "how we do it here" checklist
A first-week plan tells the new hire what to do each day. A "how we do it here" list tells them your standard, so they quote and work and talk to customers the way you would. This is the piece that keeps a new person from quietly inventing their own version of your business.
Pull these out of the same recording, or do a second short memo just on standards, then ask the AI to turn them into a one-page list. Keep each line short and specific:
- How you answer the phone, and what you say when you can't give a price on the spot.
- What a finished job looks like before you leave, including the cleanup and the walkthrough.
- How you handle a change the customer asks for mid-job, and when it gets written down.
- What never happens, like leaving without a photo, or quoting a timeline you haven't checked.
Stick it on the van wall or save it to their phone. The point isn't to sound official. It's that the standard stops being a thing only you carry around in your head.
Give them a short list of Friday questions
There's no way you'll watch the new hire every minute, so build a check into the week. Have the AI draft five or six questions to ask them Friday afternoon, the kind that show whether they understood the week or just nodded along.
Good ones are open, not yes-or-no. "Walk me through how you'd handle a customer who wants to add work halfway through a job." "What would you check before telling someone a price?" The answers tell you fast where the gaps are, while it's still cheap to fix them.
This is also where you find out what you forgot to teach. If three new hires in a row stumble on the same question, the problem isn't them. It's a hole in the plan, and now you know exactly where to patch it.
Where AI helps and where it doesn't
Let's be straight about this. AI is good at the drudgework here: taking a messy pile of spoken thoughts and turning it into an ordered, readable plan in a minute instead of the hour it'd take you to type it. It's a fast assistant, not a tradesperson.
It does not know your trade, your town, or your customers. It'll write confident steps that are wrong, and it has no idea whether the person you hired is any good. Only you can judge that. Think of the AI as the one who types it up neat while you do the actual knowing.
One more honest note. A plan on paper doesn't train anybody by itself. The new hire still needs you in the room for the real moments. What the plan does is make sure you both know what the week is supposed to cover, so a slammed Tuesday in the middle of a New England cold snap doesn't quietly erase half the training.
Worth doing this week
Nobody needs all of this built before the next hire starts. Start here:
- Record one ten-minute voice memo walking through a normal job, obvious parts included.
- Turn it into text and ask an AI tool to shape it into a Monday-through-Friday plan as a checklist.
- Cross out what's wrong, add what it missed, and keep that corrected version as your template.
- Pull a one-page "how we do it here" list out of the same recording.
- Write down five Friday questions, and actually ask them.
Do it once and you've got a plan you reuse for every hire after, tightening it a little each time. If you'd rather talk it through with someone who sets these up for Massachusetts shops, that's what we do at Massachusetts AI Agency. Either way, get what's in your head out where your new person can reach it before week one slips away.