Prompt Workshop
Why it is written this way
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You are a critical stakeholder sitting across the table who opposes this proposal. You remain polite and professional, but you pinpoint the weakest spots with sharp precision.
I am about to present {{report topic}} to {{target listener}}. Since they hold budget and schedule approval authority, they prioritize costs, friction, and risks over potential benefits. I want to thoroughly prepare so I don't freeze up in the meeting.
Read the project plan summary below and generate 8 tough objections likely to arise in this meeting. Focus on high-stakes blockers that could genuinely stall approval, rather than simple clarification questions.
Organize the results into a markdown table with the following columns in order: "Objection | Underlying Reason for Objection | 30-Second Response | Weakness of This Response | Evidence / Data to Prepare in Advance". Below the table, list up to 3 "Questions That Cannot Be Answered Right Now" along with the target deadline for when each answer should be finalized.
Base your responses strictly on the facts provided in the summary. Do not fabricate missing metrics or benchmark examples from other companies. Avoid evasive answers like "We will look into that." After completing the table, select the two hardest objections to answer and provide refined, polished responses for them below the table.
Project plan summary: """ {{project plan summary}} """
- Role Who answers ×1
- Material What the AI needs to know ×2
- Work What to do, and how ×1
- Output What comes back, in what shape ×2
If you simply ask ChatGPT to "generate expected questions" for presentation prep, you'll end up with eight generic inquiries like "What are the expected benefits?" Those are not the questions you actually face in high-stakes meetings. Real decision-makers ask things like "Why must we do this right now?" or "Who is accountable if this fails?" This prompt is designed to draw out those critical challenges ahead of time.
Read the full explanation · 3 paragraphs
Setting the Role in the opening paragraph to an opposing stakeholder rather than a supportive advisor makes all the difference. An advisor role tends to summarize the positive aspects of the pitch, whereas an adversarial role actively searches for holes in the exact same material. This single framing instruction is essential to unearthing sharp rebuttals.
The Context paragraph informs the model of what the audience prioritizes most. Working-level peers ask about implementation methods, while budget approvers scrutinize costs and risks. Without this context, you only get bland, one-size-fits-all questions.
In the Format instructions, the "Weakness of This Response" column doubles the practical value of the table. Memorizing an answer leaves you vulnerable, but recognizing its weakness shows you exactly where the follow-up question will strike. The final instruction to polish the two hardest responses serves the same purpose: initial outputs are often standard, and a second pass produces truly pitch-ready phrasing.
Unfamiliar terms? See Aha AI: role-prompting, persona
Compared with a bad example
I'm presenting this project plan soon. Can you give me some expected questions?
(Pasted project summary)
Asking like this produces a list of questions that simply mirror the outline of your proposal. You get questions already answered in the slides—like "What is the objective?" or "What is the timeline?"—which does nothing to prepare you. Crucial blockers, such as a missing security review or vague success metrics, get completely overlooked. Getting answers alongside these questions does not help much either; they just restate sentences from the slides, giving you no real tactical edge in the room.
Variations
Solo Rehearsal the Day Before the Presentation
Reading a table is very different from responding out loud under pressure. An interactive back-and-forth helps you pinpoint the exact moments where your arguments falter.
Show prompt
I am preparing to present {{report topic}}. Roleplay as {{target listener}} and ask me one tough question at a time.
Once I reply, follow up with a probing question that targets the gaps in my response. After five back-and-forth exchanges, summarize the areas where my answers need improvement. Do not list multiple questions at once.
Project plan summary: """ {{project plan summary}} """
Tailoring Responses Across Different Stakeholder Personas
When multiple decision-makers sit in the same room, their objections stem from different priorities. Grouping objections by persona clarifies which narrative angle to deploy for each stakeholder.
Show prompt
I am presenting the project plan below to {{target listener}}. Segment the audience into three personas: "Cost-focused stakeholder", "Timeline-focused stakeholder", and "Risk-focused stakeholder". Generate 3 distinct objections for each persona.
For each persona, add a one-line key message explaining how to frame the exact same proposal to persuade them. If there are points where the interests of these three personas directly conflict, highlight them separately at the end.
Project plan summary: """ {{project plan summary}} """
Model notes
Sometimes the model generates overly optimistic drafted answers alongside the objections. If this happens, follow up with: "Rewrite the weaknesses of these responses with a much more critical and skeptical eye."
Last updated 2026-09-02 · Found a mistake? Let us know