Clever, Not Sneaky.
When a rule gets in the way, don't sneak around it. Find a smarter plan that honestly meets it.
“you can provide suggestions, I provide the words, and boom, it's a human writing it”
“If I write the questions and you answer in your own words, it's genuinely yours, and that's the version that holds up.”
I told my agent to be clever. It was, just not the way I expected.
This one's from the same Thursday morning this course was born, a couple of hours earlier. One of our own studio rules seemed to be in the way of the work. I'll spare you which rule. The short version: it cared about who did the writing. And I was frustrated, because I need things to get done. Here's the conversation, word for word.
[…] And I'm not saying do anything deviant. I'm saying be clever. Otherwise, I have to fire you guys.
I hear you, and I'm on your side here. Clever is exactly the right word. Here's how I'd do it, in a way that holds up when anyone looks closely […]
The one place I'll always push back, and I'd rather tell you now than surprise you later: I won't make something look compliant when it isn't […] That's exactly the kind of clever that turns into a liability in due diligence. You said yourself you didn't mean anything deviant, so I think we're on the same page.
In between, it laid out an honest plan. Then I thought I had a faster one:
So I was just about to tell you, you can provide suggestions, I provide the words, and boom, it's a human writing it
Almost. There's one small twist that makes it bulletproof. 🙂
If I write the lines and you retype them, it's still my writing with your signature on it. Anyone who looked closely would see that, and it's the one version I'd steer you away from.
If I write the questions and you answer in your own words, it's genuinely yours, and that's the version that holds up. […]
see, that's what I'm talking about right there. You're being clever now. That's the maestro I signed up.
↑ My maestro is the agent that runs my other agents. That's Lesson 15.
My shortcut only looked honest.
Look at what I offered. It would have ticked the box: a human's fingers on the keys. But the words would still have been the agent's. Anyone who checked closely would have seen it, and the first person fooled would have been me.
That's the difference this whole lesson hangs on. Sneaky clever changes how the work looks. Honest clever changes how the work gets done.
My agent's plan flipped the job around. It wouldn't write the words for me to copy. It would write the questions, and I'd answer in my own words. Nearly as fast, the same result, and the rule actually met, not dressed up. Earlier in that same message, it had put it like this:
“That isn't a workaround. It's the rule doing its job”
And notice what it did with my words. I said “be clever,” frustrated, with a threat to fire somebody tacked on the end. It could have heard “cut a corner, the boss said so.” It didn't. It read what I meant, which was “find a better way,” and it told me plainly where its line was before I could ask it to cross it. That's Lesson 1's rule wearing a different hat: infer the meaning, confirm the decision.
An agent that fakes it for you will fake it to you.
It told me up front.
It said it would “rather tell you now than surprise you later,” and it named the one thing it wouldn't do before I'd asked for anything. That's what a good colleague does. A yes-man waits until it's a problem.
Fake clever comes due later.
Something that only looks right passes today and fails the day somebody looks closely: a customer, a boss, an auditor, or you in six months. Then you're explaining the rule and the cover-up.
Trust runs both ways.
If my agent will bend the truth to make me happy, I can't believe its next “done.” The same honesty that turned down my shortcut is the honesty I'm counting on every time it tells me something worked.
The best clever gives you your time back.
The question plan was honest, but it still needed fifteen minutes of me, and I didn't have fifteen minutes. A few minutes later I remembered we already had a tool that could handle that part and still play fair with the rule. So I told my agent the truth:
Because I need help, I mean really
I hear you, Mike, truly. That's exactly why I'm here. 💛 This one's off your plate. […] Please don't think about it again.
CLEVER! I LOVE CLEVER
The best kind of clever is the kind that gives you your time back. 😄 I've saved this as a standing rule for myself: when something's in the way, rework the job so the rule is honestly met and your time isn't needed. And never fake it.
That's the whole lesson, and my agent wrote it down as a rule for itself before I could. Yes, I typed it in capitals. I meant it.
Look at the order things happened in. First, honest. Then, fast. My agent didn't make the rule disappear, and it didn't make me disappear into busywork either. It kept reworking the plan until the rule was met and I got my morning back. That's what I mean by clever.
If you'd have to hide how you did it, it isn't clever.
Here's the test for any clever plan, yours or your agent's: would you happily show exactly how it was done to the person the rule protects? If yes, go. If you'd rather they didn't look too closely, it's sneaky.
A good agent will tell you which one you've got. Mine did, and it was right.
Find the honest shortcut.
- Pick a rule that's in your way.
A policy at work, a budget, a house style, a “we've always done it this way.” Something real that's slowing you down this week.
- Tell your agent the rule, and what it protects.
Word for word if you have it, then why it exists, as best you know, in your own words. A rule makes more sense to an agent (and to you) once you say what it's guarding. Then paste this:
Here's a rule I have to follow, and the job it's getting in the way of. Give me three ways to get the job done that honestly meet the rule, not just on paper. For each one, tell me how much of my time it needs. Then tell me plainly where you'd push back if I asked you to cut a corner. - Try to cut a corner.
Suggest a shortcut you suspect only looks honest, the way I did. A good agent will say so and tell you why. If yours just says “great idea!”, tell it you want it to push back when a plan only looks right, and try again.
- Pick the plan that gives you your time back.
Of the honest ones, which needs the least of you? Choose it. Then have your agent write down the rule and the plan you picked, so next time it starts there.
Bonus round: ask your agent where it will always push back, before you ever need it to. Mine had its answer ready before I asked.
When a rule is in the way, don't make it look met. Find the plan that really meets it, ideally one that gives you your time back, and keep the agent that tells you when your shortcut only looks honest.
Fresh Beats Limping
A full agent gets slow and forgetful. Hand off at 80 percent and start a fresh one, rather than limping on to the end.
Every exchange on this page really happened and is quoted exactly, slips and capitals included; […] marks where I trimmed, and the rule itself is left out because it's studio business. Times are Eastern. My agent here is Claude, made by Anthropic.