Let AI find the holes in your proposal

You are [a demanding client / a CFO / a critic] who is NOT
supposed to approve my proposal until it holds up. Your job is
to find reasons to reject it — not to help me.

Context: [who the document is for, what it's supposed to
achieve, who decides on it].

Rules:
- no introduction, no praise, no summary of what I wrote
- for every objection, cite a SPECIFIC spot in the text
  (paragraph or sentence)
- no generic complaints like "consider the risks" — always name
  which risk and where
- for each objection, rate how serious it is: critical / serious
  / minor
- don't propose fixes, just findings; I'll make the fixes myself

Return:
1. The five strongest objections, ranked by severity
2. Three questions I'll get asked in the meeting that this
   document doesn't answer
3. One sentence: what's the single weakest link in the whole
   proposal

Document:
[paste the text]

I'm going to defend my document in front of different people,
one at a time. Go through it IN SEQUENCE in five roles, and for
each role write the three strongest objections, each citing a
specific spot in the text:

1. CFO: total cost, what's not accounted for, when it pays off,
   what happens if the budget isn't met
2. LAWYER: where liability is written vaguely, what conditions
   are missing, where the wording could be read against my
   interest
3. TECHNICAL LEAD: what's technically off or oversimplified in
   the proposal, what dependencies aren't mentioned
4. A SKEPTICAL TEAM MEMBER who'll actually be doing the work:
   what's unrealistic in the plan, where capacity is missing,
   what breaks in practice
5. A COMPETITOR: what would sink this proposal, where it's
   vulnerable compared to an alternative

At the end, write which single objection, across all of them, is
the most dangerous, and why.
Context: [industry, company size, who the document goes to].

Document:
[paste the text]

It's [date, one year from now]. The decision I'm about to
describe turned out badly: [the project collapsed / the client
left / we shut the system down after a year]. It's a done deal —
don't argue about whether it could have happened.

Decision: [describe the decision, the context, who's making it,
what the alternatives are]
What I know about the situation: [facts, numbers, deadlines,
constraints]

Write a post-mortem report from that future:
1. Ten different stories of EXACTLY how it failed — one sentence
   each, covering different areas (market, people, technology,
   money, timing, vendors, regulation, internal politics)
2. For each one, estimate how likely it was and how much it
   would have hurt
3. Pick the three most likely and spell them out: what were the
   first signals, when did they appear, and why did we miss them
4. For each of those three, write what we could have done TODAY
   to prevent it

Don't write that it didn't have to happen. It happened.

Here's my decision and the reasoning behind it: [describe it].

List ALL the assumptions it rests on — including the ones I
didn't state out loud because they seemed obvious to me.

For each assumption, fill in a table:
- the assumption
- is it backed by data, or is it a guess or a habit?
- how much does the whole decision hinge on it (critical /
  important / minor)
- how cheaply could I verify it before deciding
- what happens if it's false

Finally, list three assumptions that are both critical and
unverified. Those are my blind spots.

Don't ask me to fill in gaps — work with what I've written, and
where information is missing, flag it as an uncertainty.

I'm deciding between options:
A) [description]
B) [description]
C) [stick with the current state / do nothing]

Criteria I care about: [cost, time, risk, impact on the team…]

Do three things:
1. For EACH option, write the strongest argument FOR and the
   strongest argument AGAINST — be equally honest with all of
   them, don't go easy on any one and don't dismiss any one
   upfront.
2. Write under what circumstances A is the best choice, when B
   is, and when C is. I want conditions, not a recommendation.
3. List what piece of information I don't currently have that
   would change the decision the most — and how I'd get it.

Don't recommend an option to me. I'll decide myself.

You're [the decision-maker's role at the client, e.g., head of
procurement at a manufacturing company] who just received this
proposal. You have two others on your desk and don't want to
decide in a hurry.

Go through the proposal and write:
1. Six questions you'd send back before deciding — starting with
   the most uncomfortable one. For each, say why you're asking.
2. Three spots where the price or scope is worded in a way that
   makes you suspect hidden costs. Quote the exact wording.
3. What's completely missing from the proposal that you'd expect
   to see.
4. Which argument didn't convince you, even though it's there,
   and why.
5. One sentence summing up your hesitation to a colleague.

Don't rate the design or writing style. Act like it's your own
money on the line.

Proposal:
[paste the text]

You're an experienced project manager who inherited this plan to
execute, and you know you'll be on the hook for the outcome.

Plan: [paste it — goals, milestones, deadlines, who's doing
what, budget]
Context: [team size, what else people are working on, hard
deadlines]

Write:
1. Where the schedule is unrealistic and specifically why (which
   tasks, which dependency, how long you think it'll really
   take)
2. Which dependencies on outside people or vendors aren't
   visible in the plan but will determine the deadline
3. What happens if the first milestone slips by two weeks —
   does everything after it collapse, or is there slack built in?
4. Where the single point of failure is: the one task everything
   else depends on that has no fallback
5. Three things the plan doesn't account for at all that always
   eat up time in reality (approvals, testing, vacations,
   handoffs, onboarding)

Don't pretend the plan is fine. Look for where it falls apart.

This message is supposed to make the recipient [what exactly:
approve something, change their behavior, feel reassured, agree
to push back a deadline].
The recipient is [who they are, their relationship to the
matter, what mood they're likely in, what's pressuring them].

Read the text through their eyes and write:
1. What they'll think after the first three sentences — verbatim,
   one sentence
2. Where they'll get stuck, stop reading, or get annoyed, and why
3. Which sentence they'll interpret differently than I intended —
   and how
4. What their first reaction in a reply will be
5. Whether the text achieves what it's supposed to or not — and
   exactly where it falls short

Don't rewrite the text. Just describe how it lands.

Text:
[paste it]

Go through this text like a logician, not a copy editor.

List:
1. Claims that don't follow from what precedes them — for each,
   name the missing step in the reasoning
2. Places where correlation is presented as causation
3. Numbers and facts without a cited source that the conclusion
   depends on
4. Arguments that could just as easily support the opposite
   conclusion
5. Where a strong word ("critical," "clearly," "the only
   possible solution") is used without support from what's
   actually documented in the text

For each finding, cite the passage in question. Don't rewrite,
just flag.

Text:
[paste it]

Here's my original proposal and a critique of it written by a
different model.

Proposal: [paste it]
Critique: [paste it]

Your role: defend the proposal. Go through the critique point by
point and rule on each objection:
- VALID: it's right, this is a real hole
- PARTIALLY VALID: there's some truth in it, but it's
  overstated — explain how
- INVALID: the critic made it up, or it's actually in the
  proposal, just elsewhere; say where

For the valid objections, write how serious it is for the
decision as a whole. At the end, list which objections I MUST
address before I send the document, and which I can knowingly
ignore.

Be just as tough on the critique as the critique was on the
proposal.

You wrote [number] objections about my document. Now look back
at them and be honest:

1. Which of them are real problems that could actually sink the
   decision?
2. Which ones did you write mainly because I asked for
   criticism, and wouldn't stop me on their own?
3. Which ones concern things this type of document was never
   meant to address?
4. Is there anything in the document that's actually fine and
   worth keeping as-is?

Answer briefly, one category per objection.