I need a practical strategy prompt pack tailored to my situation. Context Business or team: [BUSINESS CONTEXT] Decision to make: [STRATEGY QUESTION] Goal and time horizon: [GOAL AND HORIZON] Known evidence: [EVIDENCE AND CONSTRAINTS] Create five separate, copy-paste prompts for ChatGPT, Claude, or Gemini. They must cover: 1) choosing a market or customer segment, 2) diagnosing a positioning problem, 3) comparing strategic options, 4) responding to a competitor or market change, and 5) turning the chosen strategy into a 90-day execution plan. For each prompt, write 140-190 words in my voice. Include the relevant context, a specific role for the AI, the decision it must help me make, and an exact output format. Ask for a decision memo rather than a generic brainstorm: assumptions, 2-4 options, evaluation criteria, trade-offs, recommendation, risks, and next actions where relevant. For the execution prompt, require an owner, leading metric, milestone, dependency, and stop condition for each workstream. Do not invent market facts, customer research, competitor behavior, budget, or internal capabilities. State where evidence is thin and specify the fastest test or data needed to reduce uncertainty. Before giving each prompt, check that it distinguishes strategy (where to play and how to win) from tactics. Also check that its recommendation criteria connect directly to my stated goal. Ask up to 3 clarifying questions only if a required input is missing.
Fill in
| Placeholder | What to enter | Example |
|---|---|---|
| [BUSINESS CONTEXT] | Describe the company, offer, customers, business model, and current stage in a few sentences. | A 12-person B2B SaaS company selling onboarding software to HR teams at 200-1,000 employee firms. |
| [STRATEGY QUESTION] | State the decision you need to make, such as entering a segment or changing positioning. | Should we focus next year on healthcare HR teams or expand within our current technology customer base? |
| [GOAL AND HORIZON] | Give the measurable outcome you want and the period in which it matters. | Reach $1.8M ARR by December 2027 while keeping net revenue retention above 105%. |
| [EVIDENCE AND CONSTRAINTS] | List useful facts, research, resources, budget limits, risks, and non-negotiables. | Healthcare has longer security reviews; technology customers close in 45 days; sales budget is $180,000; no enterprise implementation team. |
How to use
- Choose the strategy task closest to your immediate decision and paste that prompt into your AI tool.
- Replace every bracket with current evidence, including constraints that could rule out an option.
- Check that the answer names a clear choice, its trade-offs, and evidence gaps rather than only listing ideas.
- Follow up with: “Turn the recommended option into a one-page decision memo for [AUDIENCE], and separate facts from assumptions.”
Variations
Strategy decision memo
Use when leaders need a recommendation on one defined choice.
Act as a strategy analyst. Based only on [DECISION CONTEXT] and [AVAILABLE EVIDENCE], write a 700-word decision memo for [AUDIENCE]. Define the decision, objective, and constraints; compare 3 feasible options against [EVALUATION CRITERIA]; recommend one option; list its trade-offs, key assumptions, and the next 30-day validation steps. Do not add facts not in my inputs. Flag claims that require research. Ask up to 3 questions only if a required input is missing.
Positioning diagnosis
Use when your message is not converting or customers do not understand the difference.
Help me diagnose our positioning. Our offer is [OFFER], intended for [TARGET CUSTOMER], and our current message is [CURRENT MESSAGE]. Evidence from customers and sales is [CUSTOMER EVIDENCE]. Produce a positioning brief with the customer problem, alternatives buyers use, our credible differentiated value, proof required, messages to stop using, and a homepage headline/subhead test. Do not claim differentiation without evidence. Flag any proof gap. Ask up to 3 questions only if needed.
Ninety-day strategy plan
Use after a strategic choice has been made and work needs sequencing.
Convert this strategic choice into a 90-day plan: [STRATEGIC CHOICE]. Team capacity and constraints: [TEAM AND CONSTRAINTS]. Success measures: [SUCCESS METRICS]. Produce three workstreams with a weekly sequence, accountable role, leading metric, milestone, dependency, and stop-or-adjust trigger. Identify the smallest test that can invalidate the plan early. Do not assign named people or assume resources I did not provide. Ask up to 3 questions only if a required input is missing.
Tips
- Start with one decision, not a request to “make a strategy”; strategy work becomes useful when the choice is explicit.
- Give the AI the constraints that eliminate attractive but impossible options, such as sales-cycle limits, compliance requirements, or team capacity.
- Ask it to label assumptions separately from evidence so your team does not mistake polished language for validation.
- Use a pre-mortem after choosing: require the model to name the three most likely ways the plan fails and early warning signals.
FAQ
Can AI decide our strategy for us?
It can structure options and expose assumptions, but leaders still need to judge evidence, risk appetite, and organizational capability.
What evidence should I include?
Include customer interviews, win/loss notes, conversion data, retention patterns, competitor facts you can verify, and resource constraints.
Why ask for tests instead of a final answer?
Many strategic uncertainties can be reduced cheaply with interviews, message tests, or sales experiments before a large commitment.