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Before you send the plan, ask AI for the objections

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Before you send the plan, ask AI for the objections
What most of us ask. We paste the plan and ask: “What do you think of this proposal?” The fictional sample replaces a Monday meeting with written updates and a Thursday call “only for items marked Need a decision.”

What most of us ask

We paste the plan and ask: “What do you think of this proposal?” The fictional sample replaces a Monday meeting with written updates and a Thursday call “only for items marked Need a decision.”

The vague question led with praise. In this run, the vague question led with praise and called the plan likely approvable. Its six suggestions did flag time cost and success criteria, but none raised decisions waiting until Thursday.

The vague question led with praise

Real output · GPT-5.5 (OpenAI API) · Oct 2026

Overall, it’s a strong proposal: clear problem, simple replacement, low-risk trial, measurable evaluation, and a specific ask. … My verdict: **good proposal, likely approvable.**

In this run, the vague question led with praise and called the plan likely approvable. Its six suggestions did flag time cost and success criteria, but none raised decisions waiting until Thursday.

Give it a job with stakes. Put the model in a skeptical manager's seat and give it a ranked job. Claude's prompting guide describes a similar loop: draft, review against criteria, then fix. Here you write the draft and the model does the review.

Give it a job with stakes

Put the model in a skeptical manager's seat and give it a ranked job. Claude's prompting guide describes a similar loop: draft, review against criteria, then fix. Here you write the draft and the model does the review.

Source: Claude Platform Docs, Prompting best practices, Oct 2026

The objection prompt. Name the reader, ask for three ranked objections, tie each one to a quoted line, and rule out the praise.

The objection prompt

Before I send this proposal to my manager, act as a skeptical manager reading it. List the three strongest objections they would raise, ranked from most to least likely to block approval. For each objection, quote the line of the proposal it targets and name the evidence or change that would answer it. Skip general praise and minor wording issues.

Tested in GPT-5.5 (OpenAI API), Oct 2026

Name the reader, ask for three ranked objections, tie each one to a quoted line, and rule out the praise.

It found the real risk. Its top objection: a decision raised Monday could sit until Thursday. The proposal promised same-day replies to blockers, but not to “Need a decision” items.

It found the real risk

Real output · GPT-5.5 (OpenAI API) · Oct 2026

**Decision-making may slow down.** If items marked “Need a decision” wait until Thursday, Monday issues could sit for several days, which is risky for Customer Support Ops. … “We keep a 15-minute call on Thursdays, only for items marked Need a decision.” … Add an escalation rule: urgent blockers or customer-impacting decisions get same-day handling, not Thursday.

Its top objection: a decision raised Monday could sit until Thursday. The proposal promised same-day replies to blockers, but not to “Need a decision” items.

Check the numbers it invents. Its math works for its own inputs, but the minutes are guesses. Its 90% and 4/5 thresholds are made-up examples too, and it assumed Slack. The vague run also flagged time cost.

Check the numbers it invents

Real output · GPT-5.5 (OpenAI API) · Oct 2026

**The time savings may be overstated.** The proposal counts the current meeting cost but not the replacement cost: writing updates, reading them, replying to blockers, and holding Thursday calls. … Total expected cost: ~4.5 hours vs. 9 hours.

Its math works for its own inputs, but the minutes are guesses. Its 90% and 4/5 thresholds are made-up examples too, and it assumed Slack. The vague run also flagged time cost.

Fix it, then send it. Fix the top objection in the document itself. Before pasting a real plan, remove names and figures you can't share, and check your tool's data policy or your employer's approved tools.

Fix it, then send it

Fix the top objection in the document itself. Before pasting a real plan, remove names and figures you can't share, and check your tool's data policy or your employer's approved tools.

Try it: Paste your next proposal with this prompt and fix only objection one.

Sources and assumptions

Assumptions:

The short version

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