Never Guess.
Your agent should work out what you meant. It should never guess what you decided.
- What I said“number one, the 1st one we ever saw”
- What a helper agent guessedAn earlier Santa
- What I meantNumber one in the gallery
The wrong Santa Claus. Twice.
One Tuesday morning in November I was fixing a document before it went out. One page had a picture of Santa Claus on it, and it was the wrong Santa. We'd made a dozen of them for a project, and they sat in a numbered gallery. So I told my agent which one I wanted. I thought I was being perfectly clear.
This is not the right Santa. We wanted to go back to number one, the 1st one we ever saw. […]
My agent handed the fix to a helper agent. The helper had to decide what “number one” meant. It didn't ask. It picked an earlier Santa, the first realistic one anybody had made for the project, and my agent told me the job was ready to send, once I confirmed the picture. Before I could answer, I opened the file.
You say they're correct, report is ready to send, but I just opened the report and it still has the old Santa in it, so help me understand
That one was a different problem: the fixed copy was sitting in another folder. (That's Lesson 4, “Done” Where?) A few minutes and one blank page later, I finally saw the Santa the helper had picked.
I'm getting a little concerned here, Maestro. This is not my Santa Claus.
↑ “Maestro” is what I call the agent that runs all my other agents. More on that in Lesson 15.
You're right, he's the wrong man, and I'll stop guessing. I'm pulling every Santa the studio has made onto one numbered page, oldest first, so you can point to yours.
Yeah, never guess
You're right, and I'm sorry. […] I passed its guess to you as ready, and that's how two wrong Santas reached you. I've saved “never guess” as a standing rule for myself and every session: when a pick could mean more than one image, you see the candidates and choose.
[…] Which one is your Santa: a letter from the sheet, a number from the gallery, or something else you've seen?
“Its guess” is the helper's. In the trimmed part: a contact sheet of every Santa we'd ever made, lettered A to G, plus the numbered gallery.
From the stills gallery, number one […] plump gold spectacles […]
Number one in the gallery. Gold spectacles. Twelve minutes, two wrong Santas and one blank page after I first asked, a single question settled it.
Both readings made sense. That's the trouble.
Read my words again: “number one, the 1st one we ever saw.” In my head that was one picture, the top of the gallery. But we'd made Santas before that gallery existed, and you could fairly call the first realistic one of those “the first one we ever saw.” Read cold, my sentence pointed two ways. The helper picked the other way.
That's what makes a guess dangerous. A silly guess gets caught right away. A reasonable one sails through, because it sounds right to everyone who handles it. The helper guessed. My agent passed the guess along as “ready.” By the time it reached me, the guess looked exactly like a fact.
Infer the meaning. Confirm the decision.
When I typed “Dab's workd is fantastic,” my agent read “workd” as “world,” told me so, and kept going. That's inference, and it's exactly what I want. If it had read me wrong, I'd have lost a few seconds.
The Santa sentence was no sloppier than that one. What was different was what rode on it. Which picture goes in a document I'm about to send isn't a meaning, it's a decision, and decisions are mine. Here's how I tell the two apart now.
Two good readings, two different results.
If both readings land in the same place, it doesn't matter which one the agent picks. If they lead somewhere different, it's a decision. Ask.
It's about to leave your hands.
Sent, published, printed, spent, deleted. A wrong guess you catch on your own screen costs a minute. A wrong guess in somebody's inbox costs a lot more.
Someone else is about to build on it.
A guess handed from one agent to another, or from your agent to you, loses its “maybe” on the way. Ask before anyone builds on it, not after.
Whose fault was it? Nobody's. Here's the fix.
Two hours later, while we were setting a new rule about failed fixes, my agent counted the Santa mess against itself. I wasn't having it.
that you failed in anyway? If anything, I have
↑ Yes, that's the whole message, starting mid-sentence. You can still tell what I meant, and so could my agent.
That's generous, Mike, but I'll split it fairly. “Number one” really could mean several images, so the Santa mix-up was nobody's fault, and asking you to choose fixed it. The blank page was mine alone, and the new check means it won't happen again. […]
Okay, so let's do a better job communicating. I'll happily answer any follow up questions from the overly generalized language I tend to use.
Deal, and thank you. That makes my job easier. From now on, whenever your words could mean two things, I'll ask one short follow-up right away, with the choices laid out, before anyone builds on a guess. I've saved that as a standing rule for me and every session.
Believe me, Claude, if you could read my mind and just go do it all, that would be ideal. But I don't think we're there just yet. […]
[…] Until then, I'll take a good follow-up question over a confident wrong guess.
That's the deal, and it's the fourth idea running through this whole course. I get to talk the way I talk, overly generalized language and all. My agent works out what I meant. And when what I meant could go two ways and it matters, it asks me one short question, and my job is to answer it.
That's not a chore. Answering a good question takes five seconds. Unpicking a wrong guess took us twelve minutes and a blank page.
One question, the same afternoon.
The new rule got its first real test about seven hours later. My Mac needed a system update, and a couple of my external drives were due to be wiped and rebuilt. I asked my agent to schedule “the update.” It could have guessed what I meant by that. It asked instead, in one line, with its own pick right there:
“Well, go ahead and schedule the update for us too. I guess maybe around 10pm or something like that.”
“[…] does that mean just the macOS update tonight, or the drive rebuilds too? I'd keep tonight to the update only. Rebuilding the Games drive means copying it off, which takes 8 to 12 hours, and WoW lives on that drive, so it would collide with your 2 AM launch.”
A minute earlier I'd mentioned that I was getting up at 2 AM to play a new game on launch night. My agent remembered, and its question came with the catch already spotted. I answered “drive rebuilds too” anyway, the opposite of its pick. So it didn't argue and it didn't guess. Its next message began: “Happy to, but two things collide tonight, so here's the safe order:”
A guess either way would have cost me something: skip the drives I wanted done, or sit down at 2 AM to a game drive in pieces. One question, and we had a safe order for both before anything was touched.
If a guess could turn into a decision, ask.
When two readings lead to different results and the result is hard to take back, your agent stops and asks one short question, with the choices laid out and its own pick first, so you can answer in a word. Everything else, it works out and gets on with.
And a guess never gets passed along as “ready.”
Make the same deal with your agent.
One paste, then a little noticing. You keep talking loose. Your agent learns when to stop and ask.
- Give your agent the rule.
Paste it into a new chat, or into your AI's custom instructions or project settings so it reads it every time.
When my words could mean two different things, work out what I most likely meant and keep going, as long as being wrong is cheap and easy to undo. Tell me in one line how you read me. But when the two readings lead to different results and it's something I can't easily take back (sending, publishing, spending, deleting, or choosing which version goes out), stop and ask me one short question first. Lay out the choices, lettered or numbered, with your recommendation first, so I can answer in a word. Never pass a guess along to me as finished, and if a helper made a guess, tell me it was a guess. - Listen for your own loose words.
“The first one.” “The latest.” “The usual.” “The one we talked about.” Those are the phrases that point two ways. When you use one on something that matters, watch whether your agent asks. If it just picks, ask it: “Did you guess just now?”
- Answer the follow-up.
When it asks, answer in a word or a letter and let it get on with it. That's your half of the deal, and it's the cheapest five seconds of your day.
- Watch the hand-offs.
If your agent hands work to other agents, or brings you something it didn't make itself, ask: “Is any of this a guess?” A guess that's been passed along is the one most likely to look like a fact.
Let your agent work out what you meant, never what you decided: when your words could go two ways and it matters, it asks one short question, and you answer it.
Put It Right in Front of Me
When an agent needs your OK, the thing you're approving belongs right beside the question, or better, in a simple form. Never “see above.”
Every exchange on this page really happened and is quoted exactly, slips included; […] marks where I trimmed. Times are Eastern. My agent here is Claude, made by Anthropic.