Two kinds of helper
Imagine you hire someone for a week. You leave them a note: sort out the filing, tidy the shared drive, and get the client folder into shape.
The first helper works through it, and twice a day sends you a short message. Found two versions of the contract, which is the current one. About to delete the old archive folder, confirm. You lose a few minutes answering. You lose nothing else.
The second helper reads the same note and gets on with it. By Friday the drive is beautifully tidy. It is also missing the old archive folder, because that was clearly clutter, and the client folder has been renamed to match a convention they invented on Tuesday and applied to everything.
Both were competent. Both were trying to help. The difference is entirely about what they did when they hit a decision you had not covered. That difference is the whole subject of this lesson.
In plain English
- Stopping rule:
- The condition that tells the loop it is finished, or that it has spent enough.
- Check-in point:
- A moment where the loop pauses and asks you before going further.
- Guardrail:
- A standing restriction on what the loop may do, regardless of what it decides.
- Definition of done:
- A description of the finished state that is specific enough to be answered yes or no.
- Budget:
- A ceiling on passes, time or spend, after which the loop stops whether or not it is finished.
Rule one: say what done looks like
The most common cause of a loop that will not end is a finish line nobody can stand on. Really good, thorough, comprehensive, polished: these describe a direction, not a destination.
A usable definition of done can be answered yes or no by someone who was not involved. Every figure in the table appears in the source document. The summary is under one page. Each of the five questions in my brief has an answer. Notice these are boring. Boring is what makes them checkable.
โ Weak prompt
Prompt
Go through these customer interviews and pull out the key themes. Be really thorough and make it as useful as possible.
Output
Twenty-two minutes of work, a shifting set of themes, several restructures, and a document that is still being reorganised when you come back to look at it.
Thorough and useful have no finishing state. There is always one more angle, so the loop keeps finding one.
โ Good prompt
Prompt
Go through these customer interviews and pull out themes. Done means: no more than six themes, each with two direct quotes from the transcripts, each quote traceable to a named interview. Stop when that is met. If you cannot find two quotes for a theme, drop the theme and tell me.
Output
Six themes, twelve quotes, each labelled with the interview it came from, plus a note that a seventh candidate theme was dropped for lack of support.
Someone who was not involved could check this in two minutes. That is what makes it a finish line rather than a direction.
Rule two: say when to come and ask you
A check-in point is not a sign of a weak tool. It is the single cheapest protection you have against drift, because it puts a human back in the loop at exactly the moment the loop is about to reinterpret your request.
The moments worth reserving are consistent across almost any job. When something is about to be deleted or overwritten. When the AI is about to send anything to another person. When it discovers your brief was based on something untrue. When it wants to widen the scope. When it hits a cost you would want to know about.
That fourth one is the anti-drift clause, and it is worth writing every time. The delivery complaints report drifted to the mobile app because nothing required it to ask before changing the subject.
Before you start, here are your rules.
DONE MEANS
[specific, checkable condition]
[specific, checkable condition]
Stop as soon as both are true. Do not keep improving past that point.
COME AND ASK ME BEFORE YOU
delete or overwrite anything
send, post or share anything with anyone
widen the scope beyond what I asked for
spend more than [limit] or take more than [number] steps
IF YOU GET STUCK
Do not retry the same approach more than twice.
Tell me what blocked you and what you would try instead.
Rule three: say what is off limits
Guardrails are different from check-in points. A check-in point pauses and asks. A guardrail does not ask, because the answer is always no.
These are the things where a mistake cannot be undone by an apology. Do not touch anything outside this folder. Do not contact anyone. Do not make changes to the live version. Do not put customer names into anything you send anywhere. Do not commit to a date, a price or a discount on my behalf.
Write them as never, not as be careful. Be careful is advice. Never is a boundary, and a boundary is the only one of the two that survives a loop deciding it has found a good reason.
NEVER
delete anything, ever. move it to an "old" folder instead
contact anyone outside this conversation
change anything outside [the specific folder or document]
invent a figure, date or quote to fill a gap
agree to a price, discount or deadline on my behalf
WHEN A GAP CANNOT BE FILLED
leave it marked as UNKNOWN and tell me at the end
Write the never list first, before the task. Guardrails added partway through a long job are much less reliable than guardrails set at the start, because the loop has already accumulated its own reasons for what it is doing.
Rule four: give it a budget
Even with a clear finish line, give the loop a ceiling: a number of attempts, a stretch of time, an amount of spend. It is not a substitute for the other three rules. It is the thing that catches you when one of them turns out to have a hole in it.
- DONE MEANS a condition someone else could check, yes or no
- ASK ME the moments where it must pause for you
- NEVER the things it must not do, whatever it decides
- BUDGET a ceiling on passes, time or spend
If you only ever write one of these, write the ask me list. It is what turns the second helper into the first, and it costs you a few minutes a day at most.
Checkpoint
Four rules keep a loop controlled: a checkable definition of done, a list of moments where it must ask you, a never list it cannot argue with, and a budget that stops it regardless.
Quick Quiz
๐ Quiz
Question 1 of 4What makes a definition of done actually usable?