“Wait. You use it for permits?”
Pool contractor
“Permits were what got me interested. I'm checking the same permit records over and over. Most of the time, nothing's changed.”
Other student
“So you asked it to check for you?”
Pool contractor
“I did. Before we could set that up, Josh and I tested whether it could navigate the county's permitting site.”
Communications specialist
“Which tool were you using? When you say ‘it,’ I'm not sure what you're referring to.”
Pool contractor
“I started in ChatGPT. I asked whether it could help me keep track of a permit and explained what I wanted to know. That conversation led me to Codex.”
Other student
“What changed when you moved to Codex?”
Joshua
“For this project, we used the chat to work through the idea and prepare the instructions. Then we used Codex to put those instructions to work with the tools and access available in the app.”
Pool contractor
“We started with the county's public permitting website. I asked Codex to find the project information. We tested which parts it could access and where it ran into problems.”
Classmate
“Did you do that before asking it to send you updates?”
Pool contractor
“Yes, because being able to open the website didn't necessarily mean it could reach the information I needed. I wanted to check that first.”
Other student
“So you were figuring out what you could actually ask it to monitor?”
Pool contractor
“Yes, I wanted the updates to be based on information it could actually reach.”
Regulatory attorney
“So the source was the county record itself?”
Joshua
“Yes. That's what we asked it to read. If it couldn't reach part of the record, we needed to know that.”
Classmate
“What happened once you knew it could read the record?”
Pool contractor
“We started with Josh's project and asked for automated updates twice a day, at 8 a.m. and 4:30 p.m. That was the test.”
Communications specialist
“Why did you start with just one project?”
Pool contractor
“I wanted to see what updates came back and whether they were useful on one job before trying it on the others.”
Classmate
“How did you decide to start with two updates a day?”
Pool contractor
“I wanted one update at the start of the business day and another near the end. That gave me regular updates without having to open the same page throughout the day.”
Other student
“So you didn't start by trying to automate your whole business?”
Pool contractor
“I'd need robots for that, not just AI. For now, I started with one thing I needed: a way to keep track of a permit. The information was on a public website. I wanted help keeping the paperwork moving while we kept the jobs moving.”
Classmate
“Did you keep using it after that first project?”
Pool contractor
“Yes. We followed Josh's permit through to issuance, so we had a successful test to build on. Since then, I've used it on three other projects. I've got two running with it now.”
Communications specialist
“Okay, that's the part I wanted to hear. You kept using it after you tried it. Being able to repeat something useful is a big part of the appeal.”
Pool contractor
“Exactly. And using it on those projects has given me more ideas about what I'd like it to do.”
Other student
“I'm still trying to separate the parts. Is checking the website actually AI?”
Joshua
“The schedule is automation: it tells the process when to run. The agent is what works through the task using the tools it has available. For this job, that means finding the permit record, reading what it can access, comparing the information with the previous check, and preparing the update.”
Other student
“So asking for an update twice a day sets the timing. It doesn't explain all the work that happens during the check?”
Joshua
“Right. We still had to work out what it could reach and what the update should contain. An agent can take several steps and use the results of one step to decide what to do next. Whether those steps work depends on the website, the tools, and the access we've given it.”8
Pool contractor
“That's why we tested it on Josh's permit first. I wanted to see what the updates looked like and whether they were useful. Let me show you one of the updates we received.”
Regulatory attorney
“I'd like to see that, especially which information it could actually access and read.”
Classmate
“What are you looking for in the updates? I was picturing a message saying the permit's ready.”
Pool contractor
“That would be a nice message, but a lot happens before the permit is ready. I'm looking for requests we need to respond to, comments I need to pass to the person handling the plans, or progress on a review. I don't want us waiting for the county when the county is waiting for something from us.”
Regulatory attorney
“I'd also want to know what ‘approved’ means in that update. What was approved, who approved it, and what can you do next?”
Pool contractor
“Exactly. The record shows plan-review approval and permit issuance as separate steps. I need to know which step moved. When I went back to ChatGPT, those were the details I asked it to help me put into the instructions for Codex. It also suggested tracking the time between steps.”
Regulatory attorney
“That could help you compare how long a step actually took with how long you expected it to take.”
Pool contractor
“Exactly. I'd still have to look at what happened on the job, but I'd have the dates in front of me.”
Communications specialist
“Would you let it send the update straight to the customer?”
Pool contractor
“I'd want to read it first.”
Communications specialist
“Is that because the update might contain an error?”
Pool contractor
“That's one reason. But even an accurate update could leave the customer thinking we're coming Monday.”
Joshua
“As the customer, I can see how I might make that assumption.”
Pool contractor
“And before I could promise a start date, I'd still need to check the crew's availability, the equipment, the materials, the weather, and our other jobs. The update helps me plan, but I still have to put the schedule together - for now.”
Communications specialist
“So the update needs to give you enough information to decide what to tell them.”
Pool contractor
“Yes. I want the job identified, what changed, when it checked, and a link to the record. If there's a comment, I want to read the actual comment. I shouldn't have to dig through three paragraphs to find the job's address.”
Communications specialist
“You already know how you want it written.”
Pool contractor
“I know what I need when I'm checking my phone between jobs or calls.”
Regulatory attorney
“That's a pretty good place to start.”
I spent about forty minutes with him one Thursday afternoon, helping him get set up and walking him through the process. We tested the site, worked out what it could access, and requested updates twice a day on one project. He tried it on additional projects after that initial test.
We could follow the sequence together and stop at any step that needed another explanation.
“Can you show me what you actually type?”
Classmate
“I mostly use it when I'm stuck on a reading. I'll ask it to explain something another way.”
Other student
“Does that help?”
Classmate
“It usually helps. Sometimes, though, an explanation seems so clear that I think I understand it immediately. Then I try to explain the concept in my own words and realize I'm still stuck.”
Joshua
“We've had that conversation.”
Other student
“Do you give it the reading?”
Classmate
“I sometimes provide the reading, depending on the class rules. I check whether they prohibit that use. Most of the time, I just ask about the concept.”
Joshua
“We'd need to check the school's rules and the professor's instructions for any assignment. For a conversation like this, we could use a publicly available court opinion to show each other how we approach it.”
Communications specialist
“You could do the same with an email.”
Other student
“Actually, could you show me how you'd approach an email if a project is delayed and you need to tell the person waiting for it?”
Communications specialist
“What do we know about the delay?”
Other student
“Let's say we only know that the project is delayed.”
Pool contractor
“That's about how much you know some days.”
Communications specialist
“Then I'd start with that fact: the project is delayed, and we don't yet have a new date. I'd explain who the email is for and ask, ‘Help me explain this delay clearly. Don't add a date we haven't agreed on.’”
Pool contractor
“I'd definitely include that instruction about the date.”
Other student
“Would you start a new chat each time?”
Communications specialist
“I keep a project thread and a separate Word document. In the document, I save what I've asked it to help draft and the changes I've made to get the wording how I want it. When I come back to the project, I have those examples to refer to.”
Other student
“Would it be enough to ask, ‘Make this more professional’?”
Communications specialist
“I've tried that. Sometimes I get an email I would never send.”
Joshua
“Why? Does it sound too formal?”
Communications specialist
“Sometimes, but it can also add reassurance or promises I didn't intend. For example, I might write, ‘We expect to hear back Friday.’ A rewrite might turn that into, ‘We'll have an answer for you Friday.’”
Pool contractor
“Oh no. Friday comes, you still don't have an answer, and now you have to explain why the email promised one.”
Regulatory attorney
“That's interesting. A small change in wording can change what the person reading it reasonably expects.”
Communications specialist
“Yes, a sentence can become easier to read while becoming less accurate.”
Pool contractor
“I'd also want it to sound like me. If a customer calls after reading it, I should be able to carry on the same conversation.”
Communications specialist
“Then tell it that. A few suitable texts or emails can give it a sense of how you normally talk to customers. I'd remove private details before using them and still read the result to see whether it sounds like something I'd actually say.”
For work we share with each other, public or sample material gives us a way to learn without pulling private client or customer information into the conversation.1
“But did it save you any time?”
Regulatory attorney
“That's what I keep coming back to. If I spend twenty minutes checking something it wrote in thirty seconds, what have I saved?”
Joshua
“You might not have saved any time. I have a paper saved that raises that concern: the time spent checking can take away much of the benefit.2 I'd like to come back to that in another conversation, because ‘useful’ can mean a few different things. Are we talking about time saved, a better result, or something else?”
Communications specialist
“I don't always save time.”
Regulatory attorney
“Yes, that's what I'm trying to understand. What makes it worthwhile for you when it doesn't save time?”
Communications specialist
“Sometimes it helps me try an approach I wouldn't have thought of. I might spend the same hour and come away with something better.”
Classmate
“How do you tell whether the result is better or simply different?”
Communications specialist
“I compare it with the first version. Sometimes I prefer what I had before.”
Pool contractor
“For me, part of the value is reducing interruptions. If I'm wondering whether a permit has moved forward, I check again. If a customer calls for an update, I stop what I'm doing and look.”
Classmate
“So you still read the update, but you don't have to keep looking to see whether there's one to read?”
Pool contractor
“That's the idea. And if I can give a customer a clear update before they have to ask, that helps.”
Communications specialist
“What would you say when nothing's happened?”
Pool contractor
“I'd tell them the permit is still pending, when we last checked, and what we're waiting for. I might be keeping track of several jobs, but they're thinking about their pool. If they haven't heard from me, they may wonder whether anything is happening.”
Other student
“What if the system stops checking?”
Pool contractor
“Then I need to know that, too.”
Other student
“Would the system tell you if a check failed?”
Pool contractor
“That's still something I want to understand better. I do check all the permits myself at the end of each day. The updates have reduced the checking I do during the day, and the anxiety that comes with wondering whether something changed.”
Joshua
“Let's look at what it reports when it can't reach the record. We need to be able to spot that.”
Regulatory attorney
“I'd ask the same thing of a regulatory monitor. Did nothing change, or did the check fail?”
Other student
“This is a bit more than ‘send me an alert.’”
Pool contractor
“Exactly. The updates are useful, but I still want to understand what happens when something goes wrong.”
Other student
“What would you do if it stopped working and Josh wasn't available?”
Pool contractor
“I'd check the records myself if it stopped. I'm still responsible for keeping the job moving.”
Those questions help me understand what someone means when they say a tool is useful. The answer includes the time spent maintaining it, checking it, and recovering when it fails. Research on AI agents raises similar questions about cost and whether a result can be reliably reproduced.3
“I thought you already knew how to do this”
Classmate
“I think that's why I hesitate to ask. Someone shows me something impressive, and I assume they understand the whole thing.”
Joshua
“I can show you something I've figured out and still get stuck on the next step. We all need help.”
Regulatory attorney
“I run into that, too. I know the questions I need to ask about a requirement, but I don't necessarily know how the software arrived at its answer.”
Other student
“What would you ask?”
Regulatory attorney
“I'd want to know where the information came from, whether it's current, and who it applies to. Am I looking at an actual requirement or a proposal that someone discussed in an article?”
Pool contractor
“I run into something similar with advice about permits. Someone tells me what they did on another job, but that job was in a different county or city.”
Regulatory attorney
“And that experience may be helpful. I'd still want to check what applies to this one.”
Classmate
“Would you still check all of that if the answer included a link?”
Regulatory attorney
“I'd open it. The source could be real and still not support the answer.”4
Communications specialist
“That's familiar. I can check every date in a message and still miss the impression the whole thing gives.”
Pool contractor
“You can also understand a reviewer's comment without knowing what it will take to address it. We might need revised plans, an answer from someone else, or another piece of work completed first.”
Joshua
“I can help get the reviewer's comment into the update. What I'd like you to show me is how you decide who needs to deal with it.”
Pool contractor
“Yes, I can walk you through that. And I still need your help when I get stuck in the software.”
Other student
“What would you want to use it for next?”
Pool contractor
“I'd like help with scheduling. But then I start wondering what information I'd have to give it.”
Joshua
“Those are questions I'd want answered before connecting more information. I wouldn't assume a tool is suitable just because it did the first job well.”
Communications specialist
“I have that feeling when it writes something good. I want to give it the next thing straight away.”
Joshua
“I get that same urge to try it on the next task.”
Having a person involved does not, by itself, settle whether the combined process works well.5 This is where the questions become useful: What am I able to check? What would I miss? Whose experience would help me see it?
Pool contractor
“I'd rather ask than overlook a problem with something I'm relying on.”
“Do you have fifteen minutes?”
Other student
“How do you ask without making it somebody else's whole afternoon?”
Communications specialist
“Ask for one thing.”
Other student
“Could I ask you to show me how you wrote the email?”
Communications specialist
“Yes, you could say, ‘You mentioned using it for that task. Could you show me how you start?’ That lets me know what you're asking, and I can tell you when I have time.”
Pool contractor
“What helped me was sitting down with the laptop and trying the steps while Josh talked me through them. I talk about this freely with customers and other people now because he was so willing to share it with me.”
Joshua
“Thanks for that. How has it been when you've gone back to it on your own?”
Pool contractor
“That's when I find out what I understood. It's easy to follow when you're doing the clicking. On my own, I might get stuck on a screen we went past quickly.”
Classmate
“The person showing you might move quickly through a step because it seems obvious to them.”
Pool contractor
“Exactly, and that's where I'd need them to slow down and explain it.”
Joshua
“That helps me, too. I may need to slow down at a step that seems obvious to me.”
Pool contractor
“And let me show you what happens after the alert. You might set it up differently once you've seen how I've used it.”
Regulatory attorney
“I would find that helpful. Hearing how it affects the work tells me what else to ask.”
Communications specialist
“That's true of the customer message, too. I'd want to know what they usually call back about.”
Pool contractor
“We'd probably have a few questions for each other.”
Other student
“Yes, but what if I try it later and it doesn't work?”
Joshua
“Reach out. Show us what happened.”
Communications specialist
“Yes, showing us where you got stuck helps us work through it together.”
That is the invitation I want these conversations to leave open.
Someone takes a little time to show you something. You try it, find a question they did not anticipate, and bring it back. Now you have something to show them.
The reading and the material I have collected in my student capacity give me questions to bring along: about accuracy, privacy, ownership, responsibility, and what these tools can actually do.6 Conversations like these help me understand what those questions look like in somebody else's day.
A permit update becomes a question about a crew's schedule. A smoother email becomes a promise somebody has to keep. A clear explanation becomes a chance to find out whether I can explain it myself.
There is a lot to learn from someone who does different work. There is also a lot to learn from the person beside you in class, or the student you meet during an internship who asks why you do something that way.
You do not have to arrive with an impressive example. “I'm still trying to understand what you mean” is enough. So is, “I've been doing this by hand. Is there another way?”
If you have found something useful, choose one task or example you can share in a short conversation. Leave enough time for the other person to try a step and ask why you approached it that way.
Fifteen or twenty minutes will leave plenty unanswered. It might also leave both people a little less hesitant to ask next time.
“Could you show me?”
“Yes. Let's take a look.”
“The process is mutual; for men learn while they teach.”
— Seneca, Moral Letters to Lucilius, Letter 7.8, translated by Richard Mott Gummere.7