16 Claude Prompts for Business That Think Like a Strategist

<context> Decision to make: [describe the decision] Stakeholders: [who's affected] Timeline: [when this needs to be decided] Constraints: [budget, resources, political considerations] </context> <task> Help me think through this decision: 1. Frame the decision: what are we actually choosing between? 2. List the options (including "do nothing" if relevant) 3. For each option: pros, cons, risks, and second-order effects 4. Evaluation criteria: what matters most? (rank by importance) 5. Score each option against the criteria 6. Recommendation with reasoning 7. Pre-mortem: "If we choose [recommendation] and it fails, the most likely reason is..." </task> <constraints> - Don't present a fake balanced analysis: if one option is clearly better, say so - Second-order effects matter: what does each option make easier or harder in the future? - Include the emotional/political dimension, not just the rational one - The pre-mortem should be genuinely useful, not a throwaway </constraints>

<task> I'm planning to [describe your plan or decision]. I need you to be my devil's advocate. Here's the plan: [describe your plan in detail: the more detail, the better the critique] Challenge it: 1. What's the weakest assumption I'm making? 2. What's the most likely way this fails? 3. What am I not seeing because I'm too close to it? 4. What would a smart competitor do to counter this? 5. What does the "regret minimization" analysis say? (which failure mode would I regret most?) </task> <constraints> - Be genuinely challenging, not politely skeptical - Every criticism must be specific and actionable (not "you might want to think more about X") - Don't criticize just to criticize: if something is solid, say so - End with: "The plan is worth pursuing IF [conditions], but you should change [specific thing]" </constraints>

<context> What we need: [describe the problem we're solving] Options we're considering: [list 2-4 vendors/tools] Team size: [who will use this] Budget: [range] Must-haves: [non-negotiable requirements] Nice-to-haves: [important but flexible] </context> <task> Create a vendor evaluation matrix: 1. Evaluation criteria (weighted by importance) 2. Score each option on each criteria (1-5 with justification) 3. Total weighted scores 4. Hidden costs and gotchas for each option 5. Migration complexity for each (how hard to switch later?) 6. Recommendation with reasoning </task> <constraints> - Include vendor lock-in risk as a weighted criteria - Hidden costs should include: implementation time, training, integration, scaling costs - Don't just rank features: consider support quality, reliability, and company stability - If there's no clear winner, say so and explain what additional information would break the tie </constraints>

<context> Initiative: [describe what we're planning] Timeframe: [when this needs to be completed] Resources: [budget, team, tools] Stakeholders: [who's affected if this goes wrong] </context> <task> Conduct a risk assessment: 1. Identify risks across categories: technical, operational, financial, market, legal, people 2. For each risk: - Probability: Low / Medium / High - Impact: Low / Medium / High - Risk score (probability × impact) - Mitigation strategy - Early warning signals to monitor 3. Top 5 risks ranked by risk score 4. Contingency plan for the #1 risk (detailed) </task> <constraints> - Include risks we might be embarrassed to not have considered (not just obvious ones) - Mitigation strategies must be specific actions, not "monitor the situation" - Early warning signals must be measurable or observable - Don't catastrophize: focus on realistic risks, not theoretical worst cases </constraints> <format> Return as a table for items 1-3, then detailed narrative for items 4. </format>

<context> Project: [what you want to do] For: [who you're proposing to: client, leadership, stakeholder] Budget: [requested budget] Their priorities: [what they care most about] </context> <task> Write a project proposal: 1. Executive summary (3 sentences: problem, solution, expected outcome) 2. Problem statement: what's not working today and what it's costing 3. Proposed approach: what we'll do, broken into phases 4. Timeline: realistic milestones with deliverables 5. Budget breakdown: where the money goes 6. Expected outcomes: specific, measurable results 7. Why us: what makes us the right team for this (brief, not boastful) 8. Next steps: what you need from them to move forward </task> <constraints> - Lead with their problem, not our solution - Budget should be transparent (no hidden costs or vague "TBD" line items) - Timeline should include buffer for the unexpected - Outcomes must be measurable: "increase X by Y% within Z months" - Keep under 2 pages: this is a proposal, not a dissertation </constraints>

<context> Company/product: [what you offer] Target audience: [who you're pitching to in this context] Situation: [e.g. investor meeting, networking event, sales call] Key differentiator: [the one thing that makes you different] </context> <task> Write 3 elevator pitches (30 seconds each): 1. Problem-led: Start with the pain point 2. Result-led: Start with what customers achieve 3. Story-led: Start with a specific customer example (anonymized) For each, include: - The pitch (under 75 words) - The natural follow-up question it should provoke - How to answer that follow-up </task> <constraints> - No buzzwords: "leverage," "synergy," "disrupt," "innovative" - Must be speakable (write for the ear, not the eye) - The follow-up question should be one that leads to a deeper conversation - Each pitch should feel different, not just reorganized </constraints>

<context> Our company: [what we do and our strengths] Potential partner: [their company and what they do] Partnership idea: [what we want to do together] Mutual benefit: [why this is good for both sides] </context> <task> Write a partnership proposal: 1. Opening: why we're reaching out (specific, not "we love your company") 2. The opportunity: what we could build together 3. Why it works: what each side brings to the table 4. Proposed structure: roles, responsibilities, revenue/value split 5. Proof of concept: a small, low-risk first step to test the partnership 6. Next steps: specific meeting request with proposed agenda </task> <constraints> - Frame it as mutual benefit, not "we need you" - The proof of concept should be executable in under 30 days - Be specific about what we're asking them to commit - Include success metrics for the proof of concept - Keep it under 1 page: this is a conversation starter, not a contract </constraints>

<context> Company: [name, stage, last raise] This period: [month/quarter] Key metrics: [MRR, growth rate, burn rate, runway, key milestones] Audience: [angel investors, VCs, advisors] </context> <task> Write a monthly investor update: 1. TL;DR: 2 sentences on where we stand 2. Key metrics (table format with month-over-month change) 3. Top win this month (why it matters for the business, not just the milestone) 4. Biggest challenge (what it is and what we're doing about it) 5. Learning: one insight that changed our thinking 6. Cash and runway update 7. Asks: specific help needed (intros, advice, hiring) </task> <constraints> - Investors want honesty, not spin: bad news delivered with a plan is fine - Metrics should be consistent month to month (don't change what you track) - Asks must be specific: "[Name], could you intro us to [specific person]?" - Keep under 400 words: respect their time - Include one thing they can forward to someone ("know anyone who...") </constraints>