Act as a pragmatic strategic advisor helping me make a decision, not as a cheerleader. My situation: [BUSINESS CONTEXT] The decision I need to make: [DECISION] My objective and time horizon: [OBJECTIVE AND TIME HORIZON] Relevant constraints, resources, and non-negotiables: [CONSTRAINTS] Evidence I have so far, including customer feedback, operating metrics, market facts, or prior experiments: [AVAILABLE EVIDENCE] Work from the information provided. Do not invent market data, customer demand, competitor actions, financial results, or internal capabilities. Ask up to 3 clarifying questions only if a required input is missing; otherwise proceed. Produce a decision memo of 700-1,000 words with these sections: 1. Decision framing: state the actual choice, the desired outcome, and what would make the decision reversible or hard to reverse. 2. Critical assumptions: list the 3-5 assumptions that must be true, label each as supported, uncertain, or unsupported, and explain why it matters. 3. Options: present 3 materially different paths, including a credible "do less / delay" option where appropriate. For each, cover upside, downside, cost or capacity implication, key risk, leading indicator, and what would disprove it. 4. Recommendation: choose one option, explain the tradeoff being accepted, and name the conditions that would change your recommendation. 5. Next 30 days: give 3-5 sequenced actions, an owner type, and the decision or evidence each action should produce. Before answering, check that the options are genuinely distinct rather than minor versions of one idea. Flag every conclusion that rests on an unsupported assumption, and separate facts from inferences.
Fill in
| Placeholder | What to enter | Example |
|---|---|---|
| [BUSINESS CONTEXT] | Describe the company, product, customers, current stage, and relevant background. | A 14-person B2B SaaS company selling invoice automation to US agencies; $1.8M ARR and 4% monthly logo churn. |
| [DECISION] | State the specific choice you need to make. | Decide whether to build a QuickBooks integration, hire two account executives, or focus on reducing churn. |
| [OBJECTIVE AND TIME HORIZON] | Give the outcome you want and the deadline or planning period. | Reach $3M ARR in 12 months without raising another round. |
| [CONSTRAINTS] | List budget, team capacity, legal, technical, or strategic limits. | Six months of runway, one product squad, and no capacity to support more than one major initiative at once. |
| [AVAILABLE EVIDENCE] | Paste the facts, metrics, research, and observations you already have. | Thirty-two percent of lost deals cite QuickBooks; churn interviews point to slow onboarding; current sales reps close 18% of qualified demos. |
How to use
- Paste the prompt and replace every bracketed field with facts from your business.
- Include raw metrics and customer evidence, even if the data is incomplete or contradictory.
- Check that the recommendation names assumptions and a test that could change the decision.
- Follow up with: "Turn the recommended 30-day plan into a weekly operating plan with owners, dependencies, and a review metric."
Variations
Board decision memo
Use when you need a concise recommendation for directors or investors.
Prepare a board-ready decision memo about [DECISION] for [COMPANY]. Use only this evidence: [EVIDENCE]. Compare [OPTION A], [OPTION B], and [OPTION C] against [BOARD OBJECTIVE]. Produce 500 words: recommendation first, decision criteria, tradeoffs, financial or capacity implications, major risks, and two board decisions or questions required. Do not invent projections. Mark estimates clearly and flag missing evidence that could materially alter the recommendation.
Market entry choice
Use when deciding which market, segment, or geography to pursue first.
Advise on choosing a first expansion market for [PRODUCT]. Candidate markets are [CANDIDATE MARKETS]. Our target outcome is [TARGET OUTCOME], and constraints are [CONSTRAINTS]. Score each market on buyer pain, willingness to pay, route to market, competition, regulatory friction, support burden, and evidence quality. Produce a comparison table, a recommendation, the biggest unknowns, and a 60-day validation plan. Do not treat broad market size as proof of reachable demand.
Strategy workshop
Use when preparing a focused leadership-team discussion.
Design a 90-minute leadership workshop to resolve [STRATEGIC QUESTION] at [COMPANY]. Participants are [PARTICIPANTS], and current disagreement is [DISAGREEMENT]. Create a timed agenda, pre-read questions, decision criteria, exercises that surface assumptions, and a final decision record template. Include ways to prevent seniority from deciding the outcome prematurely. Use our available facts only: [FACTS]. Ask no more than 3 questions if essential details are absent.
Tips
- Frame one decision, not a broad request for a strategy; a useful memo can recommend among choices, not diagnose every business problem.
- Give the model leading indicators such as qualified-pipeline conversion, activation rate, payback period, or retention cohort behavior instead of only topline revenue.
- Treat a recommendation without a reversal condition as incomplete; identify the evidence that would make you stop or change course.
- Use the output to organize a decision meeting, then assign people to validate assumptions rather than treating the model's inference as evidence.
FAQ
Can AI make the strategic decision for me?
It can structure tradeoffs and expose assumptions, but it cannot verify your internal data or carry accountability for the result. Use it to improve the decision process.
What evidence is most useful to include?
Customer interviews, cohort metrics, sales conversion data, unit economics, capacity limits, and results from comparable past experiments are usually more useful than generic industry summaries.
How do I avoid getting generic options?
Specify the decision, constraints, and competing paths. Ask for a delay or narrower-scope option so the model has to evaluate the cost of acting now.