LearnAI home

Catching Problems ยท Lesson 6

Your Reliable AI Working Session

A repeatable way to run a long piece of work.

From five techniques to one routine

You now have the parts. Restate rules at decision points. Ground answers in your own material. Watch for vanished hedging. Start fresh rather than argue.

Techniques you remember in the moment are worth something. A routine you run every time is worth much more, because reliability is not about being sharp on the day. It is about the checks happening whether or not you thought to be suspicious.

Here is the routine. Four phases, and none of them are long.

Phase one: set up, once, properly

Two minutes at the start buys you the whole session. Before any real work, paste a brief into ChatGPT, Claude, Gemini or whichever assistant you use, and get it read back.

Prompt you can copy: session opener

We are starting a long piece of work. Before anything else, here is the brief for the whole session.

Goal: [the decision or output this session must produce] Audience: [who reads the final result] Source: work only from material I paste. Do not add general knowledge and do not use your own earlier answers as a source. Always:

  • [rule]
  • [rule] Never:
  • [rule]
  • [rule] Uncertainty: if my material does not settle a point, write UNCLEAR and stop there. Do not estimate and do not fill the gap.

Now read this brief back to me as numbered rules in my wording, state the task in one line, and list anything ambiguous. Do not start work yet.

Read the read-back. Rules that came back wrong were never as clear as you thought, and fixing that at minute two is free.

Phase two: checkpoint every few exchanges

A checkpoint is one short message roughly every five to ten exchanges, or before any output that could be sent to someone. It refreshes the rules into recent context and gives you a place to notice slippage.

Prompt you can copy: the checkpoint

Checkpoint before you continue.

  1. List the rules from my brief that apply to what you are about to do.
  2. State in one line where we are and what we have settled so far.
  3. Name anything you are currently uncertain about.

Then wait. Do not continue until I confirm.

Phase three: verify before anything leaves

Run this on the actual output, not on your feeling about the output. It is the difference between believing the work is fine and knowing which sentences are checkable.

Prompt you can copy: the verification pass

Verification pass on the draft above. Do not defend it and do not rewrite it yet.

  1. Sentence by sentence, mark the source: MY MATERIAL with an exact quote, GENERAL KNOWLEDGE, or YOUR EARLIER ANSWER in this conversation.
  2. List every number, name, date and citation that you cannot attach to a quote from my material.
  3. List every rule in my brief this draft breaks.
  4. List anything here that contradicts something you told me earlier.
  5. List any claim you stated flatly that my material only hedges.

Then give me a revised version with every unsupported sentence deleted rather than softened.

Deleted rather than softened, every time. A softened fabrication is a fabrication wearing a cardigan.

Phase four: know when to abandon the thread

Not every session is salvageable, and the skill is calling it early rather than heroically.

Abandon when the same error returns after two clear corrections. Abandon when a verification pass finds unsupported claims in work you had already verified. Abandon when you are spending more effort managing the assistant than doing the work. Abandon when you no longer trust the earlier parts of the conversation and cannot face auditing them.

Abandoning is cheap if you carry the right things across: your brief, your source material, and a decisions list that you wrote or personally confirmed. Never let the old thread write its own handover, because it will pack the error neatly into a paragraph that sounds like a conclusion.

The sunk cost is not real. Two hours of conversation has no value in itself. Only the decisions you can personally stand behind have value, and those move to a new thread in about ninety seconds.

In plain English

Checkpoint:
A short message every few exchanges that refreshes your rules and surfaces uncertainty before work continues.
Verification pass:
A structured audit of a draft against its source, run before the work goes to anyone else.
Handover:
The brief, sources and confirmed decisions you carry into a fresh conversation when you abandon a thread.
Session brief:
The short block of goal, audience, sources and rules that governs an entire piece of work.

Your reliable session checklist

This site keeps no accounts and stores nothing, so this artifact lives with you. Copy the block below into a note, a document, or wherever you keep things you actually reopen. It is the whole course on one page.

Copy this into your own notes

RELIABLE SESSION CHECKLIST

SET UP [ ] Wrote a brief: goal, audience, source limit, always, never, uncertainty [ ] Pasted only the material that bears on the goal, not everything I have [ ] Had the brief read back to me and fixed what came back wrong

DURING [ ] Checkpoint every five to ten exchanges [ ] Restated the relevant rules before every sendable output [ ] Asked what it is missing rather than guessing how much context to give [ ] Watched for hedging quietly turning into flat fact

BEFORE SENDING [ ] Ran a verification pass on the actual draft [ ] Traced every number, name, date and citation to a quote [ ] Deleted unsupported sentences rather than softening them [ ] Checked the draft against my original rules, not my memory of them

ABANDON THE THREAD IF [ ] The same error returned after two clear corrections [ ] Verified work turned out to contain unsupported claims [ ] Managing the assistant now costs more than doing the work [ ] I no longer trust the earlier half of the conversation

CARRY ACROSS, NOT THE THREAD [ ] The brief [ ] The source material [ ] A decisions list I wrote or personally confirmed

Print it, pin it, keep it in the note you paste from. A checklist that lives in a folder you never open is a checklist you do not have.

The prompt pack

Six prompts, and you have all of them now. The session opener and the checkpoint are above. The constraint audit and the two-minute drift test came from lesson one. The grounding instruction is in lesson four. The provenance question is in lesson five. Collect them into one note today, while you still remember which is which, and paste rather than retype. A prompt you retype from memory arrives shorter and weaker every time.

If you adopt exactly one habit from this course, adopt the verification pass. It is the only one that stands between a fabricated figure and a colleague who assumes you checked.

Finish the quiz below and the Context Keeper badge is yours. Fitting, really, for a course about not losing track of things.

Checkpoint

Set up with a brief and a read-back, checkpoint every few exchanges, run a verification pass before anything leaves, and abandon a thread that keeps reproducing the same error. Carry the brief, the sources and confirmed decisions, never the conversation.

๐Ÿ“ Quiz

Question 1 of 4

What is the point of having the assistant read your brief back before any work starts?

Found this useful? Pass it on.