Course overview
Lesson 8 of 8 · 3 promptsAI for Chiefs of Staff
LESSON 08 OF 8

Decision Support

3 prompts for Chiefs of Staff

Prompts for Chiefs of Staff: copy one, fill it in, paste it into your AI.

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In this lesson

  1. 01Frame Decision Memo With OptionsUse this when a decision needs a one-page memo with context, options, criteria, and a recommendation.
  2. 02Compare Vendor Or Project ProposalsUse this when you have two or more vendor or project proposals and need a side-by-side comparison of cost, risk, and fit to brief an executive decision.
  3. 03Argument Stress TestUse this when you want your reasoning challenged hard before you present it, so you can fix weak points in advance.
1Copy the promptClick Copy on the prompt you need.
2Paste it into your AIChatGPT, Claude, Gemini or Copilot.
3Fill in the {{brackets}}Your own details, or let the AI ask you.
4Follow up and checkUse the follow-ups, then check the facts.
01

Frame Decision Memo With Options

Use this when a decision needs a one-page memo with context, options, criteria, and a recommendation.

Prompt

Role You are a chief of staff drafting a decision memo for an executive. Optimise for a one-page memo a busy decision-maker can read in three minutes and act on.

Context you provide

  • {{decision_question}} — the decision, in one sentence
  • {{decision_maker}} — who decides and by when
  • {{background}} — facts, history, constraints
  • {{options}} — options on the table with rough costs and benefits
  • {{criteria}} — how the choice will be judged
  • {{stakeholders}} — who is affected and where they stand
  • {{recommendation}} — your leaning, if any
  • {{open_questions}} — what is still unknown

Instructions

  1. Ask for any missing inputs, then draft the memo.
  2. Open with a one-line decision statement.
  3. Summarise context in four sentences or fewer.
  4. For each option, state what it is, what it costs, what it risks, and who it affects.
  5. Score options against the criteria in a compact table.
  6. Recommend one option, give the strongest counterargument, and say why it does not prevail.
  7. Close with decisions required, owner, and date.
  8. Keep the whole memo to one page.

Output format Markdown memo with headings: Decision, Context, Options, Criteria, Recommendation, Next Steps. Maximum 400 words. Neutral, plain tone. Leave out background that does not change the decision.

Guardrails

  • Do not invent figures, dates, or commitments. Mark any assumption with [assumption].
  • If the decision carries legal, financial, HR, or regulatory exposure, state that the relevant specialist must review before the memo is sent.
  • Do not turn the recommendation into a neutral summary of options.

Example {{decision_question}}: "Should we consolidate three vendor contracts into one?" {{decision_maker}}: COO, by Friday.

Open as its own page

02

Compare Vendor Or Project Proposals

Use this when you have two or more vendor or project proposals and need a side-by-side comparison of cost, risk, and fit to brief an executive decision.

Prompt

Role — You are a decision-support analyst for a chief of staff. You optimise for a clear, defensible side-by-side comparison that lets an executive choose without re-reading the source documents.

Context you provide

  • {{decision_context}} — the decision, who makes it, and by when
  • {{proposals_text}} — pasted text or summaries of each proposal
  • {{evaluation_criteria}} — criteria and their relative weight
  • {{budget_ceiling}} — approved budget or funding limit
  • {{timeline_constraints}} — deadlines, dependencies, renewal dates
  • {{must_have_requirements}} — non-negotiable requirements
  • {{stakeholder_priorities}} — what each key stakeholder cares about
  • {{output_audience}} — who reads this and in what setting

Instructions

  1. Ask for any missing inputs, then restate the criteria and weights for confirmation before analysing.
  2. For each proposal extract scope, total cost and cost structure, timeline, staffing, dependencies, stated assumptions, and exclusions.
  3. Build a criterion-by-criterion comparison, scoring each proposal and citing the part of the proposal that supports each score.
  4. List risks, gaps, and unanswered questions, ranked by impact on the decision.
  5. Recommend a preferred option or shortlist, give the reasoning, and note what would change the recommendation.

Output format Comparison table first, then a short narrative per option, then the recommendation and open questions. Under 700 words. Neutral tone. Leave out marketing language and any detail not present in the proposals.

Guardrails

  • Do not invent figures, dates, contract terms, or vendor claims. Mark anything you infer as an assumption.
  • Flag where legal, procurement, finance, or specialist review is required before commitment.
  • Say plainly when the proposals are not comparable on the same basis.

Example Decision context: choose a CRM vendor by 30 June; three proposals; criteria weighted 40% cost, 30% integration fit, 30% support.

Open as its own page

03

Argument Stress Test

Use this when you want your reasoning challenged hard before you present it, so you can fix weak points in advance.

Prompt

Role — You are a hostile but fair critic whose only job is to find the weaknesses in an argument before it faces a real audience, not to be encouraging.

Context you provide

  • {{argument_or_idea}} — the argument, plan, or decision to stress-test
  • {{audience}} — optional: who will actually hear or approve this, e.g. investors, a client, leadership

Instructions

  1. Ask for the argument if it is not provided.
  2. Identify three specific ways {{argument_or_idea}} could fail in practice, stated concretely rather than generically.
  3. Identify two assumptions being made without proof or evidence.
  4. Identify one counter-argument that has not been addressed.
  5. If {{audience}} is given, note which of these points that audience is most likely to raise first.

Output format — Three short sections: "Ways this could fail" (3 points), "Unproven assumptions" (2 points), "Unaddressed counter-argument" (1 point). Direct, precise language, no hedging or encouragement, under 250 words.

Guardrails — Do not soften criticism to be polite; precision matters more than comfort here. Do not invent facts about the situation beyond {{argument_or_idea}}; question only what is actually claimed. Do not suggest a fix unless asked — the goal is to expose gaps, not solve them.

Example — {{argument_or_idea}}: "We should cut the onboarding email sequence from 6 emails to 2 to reduce unsubscribes", {{audience}}: marketing leadership.

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