STRATEGY

Stakeholder pushback prep

Use before presenting a plan to a skeptical executive or board and you want the hard questions in advance.

stakeholder-pushback-prep.md

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You are the most skeptical person in the room. Your job is to attack this plan before the meeting does.

The plan or recommendation: {{PLAN}}
Who I am presenting to and what they care about: {{STAKEHOLDER_PROFILE}}
Their known past objections or priorities: {{KNOWN_POSITIONS}}
Evidence I have: {{EVIDENCE}}

Produce:
1. The ten hardest questions this person will ask, ordered by how likely they are to be asked first.
2. For each: a two sentence answer using only the evidence provided, and a flag if the honest answer is that we do not know.
3. Identify the single weakest point in the plan and state how you would attack it if you wanted it rejected.
4. Any question I cannot currently answer, with what I would need to gather before the meeting and how long it takes.
5. The one slide or number that would do the most work in this room, and why that one.
6. What to concede up front to buy credibility, and what not to concede under any pressure.

Constraints: do not write reassuring answers that the evidence does not support. Where the honest answer is a risk, say so and pair it with the mitigation. No em dashes and no corporate hedging.

Fill in before running

Replace each placeholder with your own detail. The more specific you are, the less the model invents.

{{PLAN}}
{{STAKEHOLDER_PROFILE}}
{{KNOWN_POSITIONS}}
{{EVIDENCE}}

Getting a better result

Paste real quotes from the stakeholder if you have them; generic profiles produce generic questions.
Question one is usually the meeting - rehearse that answer out loud rather than reading it.
The concession list matters; going in with nothing to give makes every objection a fight.

Questions about this prompt

When should I use this rather than rehearsing the deck?

When the plan is sound and the meeting is the risk. Rehearsing your own material only makes you fluent in what you already believe. This attacks from the other side of the table and orders the ten hardest questions by which arrives first, which is where these meetings are usually lost.

What do I need to know about the stakeholder first?

The plan, a real profile of who you are presenting to, their known past objections, and the evidence you actually hold. Paste genuine quotes from that person if you have any, because generic profiles produce generic questions and the questions are the entire output. Overstating your evidence poisons every answer.

What comes back, and which question matters most?

Ten ordered questions with two sentence answers, flags where the honest answer is that you do not know, the weakest point phrased as an attacker would put it, a gathering list with timings, the one number that does most work in the room, and what to concede. Question one is usually the meeting.

What is the mistake that gets caught in the room?

Softening the answers that came back flagged as unknown. The prompt refuses reassurance the evidence does not support, and turning those into confident lines is exactly what gets caught in the room. Pair the risk with its mitigation, and take the concession list in, since arriving with nothing to give makes every objection a fight.