The first answer is a draft: the complete guide to iterating with AI

Here was my original request: [paste original prompt]
Here's the answer I got: [paste answer]

Don't rewrite the text. Answer me in three blocks:
1. How you interpreted my request — what you treated as
   mandatory and what you filled in yourself because I
   didn't say it.
2. Which specific pieces of information were missing from
   my request badly enough that you had to fall back on a
   generic phrasing instead. List them as questions.
3. If you had to nail it on the first try, what three
   sentences should I add to my request? Write them exactly
   as I should paste them in.

Be specific — I don't want general advice about writing
prompts.

Take your last version and revise it according to these
shifts. Don't write the text again from scratch — build on
what you already have.

- Significantly more concrete: every general claim should
  either get a number, date, or name attached, or be cut.
- Less salesy: no superlatives, no “unique” and no “critical.”
- Shorter: [250] words maximum total.
- Leave the paragraph about [topic] exactly as it is — that
  one's right.
- Delete the first two sentences and start right at
  [specific point].

At the end, outside the text, tell me what you cut for
length, so I can decide whether any of it should come back.

The tone of this version isn't right, and I don't want to
describe it in the abstract. Here's the anchor instead:

- The reader is [recipient's role, e.g. the client's CFO],
  who has thirty seconds for this email and doesn't know
  the project details.
- The relationship is [long-term vendor, formal but not
  stiff].
- It must not sound like [an apology / a sales pitch / a
  complaint].
- The closest thing to what I want is this older text of
  mine: [paste 5-10 lines of your own writing that captures
  the tone]

Rewrite the last version in this tone. Leave the content and
facts unchanged, change only the phrasing. Where you'd have
to drop information because of the tone, keep it instead and
flag it separately below the text.

Go through your last version and turn it into a version
where every sentence asserts something. Specifically:

- Replace every generic statement (like “the process was
  made more efficient”) with a concrete detail from my
  source material, or cut it entirely.
- Don't add any numbers, dates, or names that I didn't give
  you. Where a specific detail should go but you don't have
  it, write FILL IN: [what's missing] in its place.
- Cut sentences that only introduce other sentences (“In the
  following section, we'll look at...”).
- Keep the facts and the order, only change the level of
  concreteness.

At the end, attach a list of every FILL IN.

I want you to write [what should come out of this, e.g. an
email to a client about a delayed delivery]. I'm not going
to tell you anything else yet.

Before you start writing, ask me 5 questions whose answers
would change the result the most. Rules:
- ask about things you can't guess (context, relationship,
  what happened, what I want, what I want the other party
  to do),
- don't ask about things you can reasonably infer from
  common practice,
- order the questions from the one that changes the result
  most,
- for each question, write one sentence on why it matters.

Once I answer, write the text. If something from my answers
is still missing, say so instead of guessing.

Here's a request I want to send you. Don't act on it yet.

[paste request]

Evaluate it as a request:
1. What's ambiguous in it — where I could picture two
   different ways of fulfilling it, both matching the text.
2. What's missing from it, and what you'd therefore have to
   guess. For each item, write what you'd assume by default.
3. What's unnecessary in it, or contradicts itself.
4. Rewrite the request into a version that doesn't have these
   problems. Don't add anything from your own head — where
   information from me is missing, leave a bracket to fill in
   in the rewritten request.

Points 1-3 first, then the rewrite.

Write three versions of [what, e.g. a message to the team
channel about the deadline slipping]. The source material is
the same for all three:

[paste facts, numbers, context]

Version A: businesslike and as short as possible, bare facts,
no explaining.
Version B: explanatory — why it happened and what it means
for everyone else, longer, calmer tone.
Version C: takes ownership and gives a clear next step, who
does what by when.

Rules:
- the versions must differ in approach, not just reshuffled
  words,
- the facts must be identical across all three, don't add
  anything,
- no intro or closing commentary, go straight into the three
  blocks,
- one sentence under each version: what situation it suits
  and what risk it carries.

I'm taking version B as the base. Adjust it like this:
- take the first paragraph from version A, it's better,
- add the last sentence from version C (that concrete next
  step) at the end,
- cut the middle section from B in half,
- keep the tone as in B.

Send just the final version, don't comment on what you did.

I'm ending this conversation and starting a new one. Write me
a handoff brief for a new chat that won't know anything from
this conversation.

Include:
1. What the task is, in one sentence.
2. The facts and numbers I gave you in this conversation
   (only the ones from me, nothing you filled in yourself).
3. Decisions we agreed on — format, tone, length, structure.
4. What I explicitly rejected and shouldn't come back.
5. The current best version of the text, unchanged.

Write it as a brief for the model, not as a narrative about
our conversation. Points 2 and 5 verbatim, don't rephrase
anything.

Here are the last [8] corrections I've repeatedly given you
across different conversations:

[list the corrections, however roughly you remember them]

Turn them into a permanent instruction I can save in my
settings that will apply to all my conversations.
Requirements:
- phrase them as rules, not requests,
- group them into 3-5 thematic blocks (style, format, what
  to avoid, how to behave when you're missing source
  material),
- drop duplicates and contradictions, and flag any
  contradictions for me,
- [200] words maximum total, it has to fit in a field with a
  length limit,
- don't add rules I didn't give you.

Below the instruction, separately list any rules I gave you
that contradict each other, so I can decide.

We've gone through [5] rounds of edits together and the last
version is right. Reconstruct the request that would have
produced this final version on the first try.

- Include everything I refined during the iterations
  (length, tone, structure, what to leave out).
- Replace anything that changes every time this task comes up
  with brackets like [this].
- Don't write an explanation, just the prompt itself, ready
  to copy.
- Below it, briefly list which brackets I need to fill in
  when I use it and what goes in each.

This is the final version of [type of text] that I want to
send to [who, in what situation]:

[paste text]

Don't rewrite it. Check it and list:
1. Claims the text makes that aren't backed by anything I
   gave you — especially numbers, dates, and promises.
2. Sentences the reader could interpret differently than I
   intend, and how they might read them.
3. What's missing from the text for the reader to be able to
   do what I want from them.
4. The three weakest spots, and why.

For every finding, quote the passage in question.