Why Strategy Needs Structure
Most strategic planning sessions end the same way: a whiteboard full of sticky notes, a shared document with bullet points nobody revisits, and a vague sense that “we aligned.” Three months later, the team is executing on assumptions that were never tested and priorities that were never properly ranked.
The problem is not a lack of strategic thinking. It is a lack of structured thinking. When leaders sit down to plan, they tend to anchor on the first scenario that feels plausible, skip over uncomfortable risks, and default to consensus instead of rigorous analysis.
AI does not fix this by being smarter than you. It fixes this by forcing you to be specific. A well-structured prompt requires you to articulate your assumptions, define your constraints, and state what “good” looks like before you get an answer. That discipline alone improves decision quality, regardless of what the AI returns.
Insight
How AI Fits Into Strategic Planning
AI is not a strategy consultant. It will not tell you whether to expand into Europe or double down on your core market. What it will do is help you think through those decisions more thoroughly than you would on your own.
AI helps strategic planning in three specific ways:
1. Forcing specificity
To get useful AI output, you must define your market, your constraints, your timeline, and your success criteria. This alone eliminates the fuzzy thinking that derails most planning sessions.
2. Generating scenarios you’d miss
Teams have blind spots. AI can rapidly generate alternative scenarios, competitive responses, and second-order effects that your team might not consider because of anchoring bias or groupthink.
3. Stress-testing assumptions
Every strategy rests on assumptions. AI can systematically challenge those assumptions by asking “what if this is wrong?” across every key variable in your plan.
Warning
Scenario Analysis Prompts
Scenario analysis is where AI adds the most value in strategic planning. Instead of debating one plan, you can rapidly explore multiple futures and prepare for each.
You are a strategic planning advisor. I need a scenario analysis for a market entry decision. CONTEXT: We are a B2B SaaS company ($12M ARR, 85 employees) that sells inventory management software to mid-market retailers in the US. We have 340 customers, 92% retention rate, and $35K average contract value. Our platform supports English only. DECISION: We are evaluating expansion into the UK and Western Europe market within the next 18 months. TASK: Generate 4 distinct scenarios for this expansion, ranging from highly favorable to unfavorable. For each scenario: 1. Define the key conditions that would make this scenario happen 2. Estimate the revenue impact over 24 months (use ranges, not point estimates) 3. Identify the 3 biggest risks specific to this scenario 4. Recommend the strategic response if this scenario materializes CONSTRAINTS: - We can allocate $1.5M to expansion without additional funding - We have no existing European customers or partnerships - GDPR compliance work has not started - Our sales team has no international experience FORMAT: Present each scenario as a named section with the four elements above. End with a comparison table showing investment required, expected ROI range, and risk level for each scenario.
You are a competitive strategy analyst. I need you to model competitor responses to a pricing change. CONTEXT: We are a project management SaaS ($8M ARR) competing in a market with three main rivals: - Competitor A: Market leader, $200M ARR, enterprise-focused, prices at $45/user/month - Competitor B: Mid-market, $30M ARR, similar feature set to ours, prices at $25/user/month - Competitor C: Startup, $3M ARR, AI-focused features, prices at $15/user/month We currently price at $20/user/month. Our CEO wants to raise prices to $28/user/month for new customers. TASK: For each competitor, analyze: 1. Their most likely response to our price increase (and why) 2. The timeline for their response (immediate, 1-3 months, 6+ months) 3. How their response would affect our customer acquisition 4. What we could do to mitigate negative effects Also model one scenario where a new entrant uses our price increase as an opportunity to enter the market at $12/user/month. FORMAT: Structured analysis per competitor, then a summary of the net impact on our business. Include a decision recommendation with conditions (e.g., "proceed with the increase IF...").
You are a strategic advisor to a retail business. I need a scenario plan for a major operational shift. CONTEXT: We operate 12 physical retail stores in the Midwest selling outdoor gear and apparel. Annual revenue is $18M, with 65% of revenue from in-store sales and 35% from our e-commerce site. Foot traffic has declined 15% year-over-year for two consecutive years. E-commerce is growing at 22% annually but margins are 8 points lower due to shipping and returns. DECISION: Should we close 4 underperforming stores and redirect that capital ($2.4M annually) into e-commerce infrastructure, fulfillment, and digital marketing? TASK: Build three scenarios: 1. Close 4 stores and invest heavily in e-commerce 2. Keep all stores but reduce inventory and staff, invest moderately in e-commerce 3. Close 2 stores, use savings for a hybrid model (stores as showrooms + fulfillment hubs) For each scenario, provide: - Year 1 and Year 2 projected revenue (with assumptions stated) - Impact on existing customer base (store loyalists vs. online shoppers) - Staffing implications (layoffs, retraining, new hires) - Key risk that could make this scenario fail - One leading indicator to watch in the first 90 days FORMAT: Present as a structured comparison. End with your assessment of which scenario best balances risk and growth potential, and what additional data you would want before making this decision.
Risk Assessment Prompts
Good risk assessment is not about listing everything that could go wrong. It is about identifying the risks that are both likely and consequential, then building specific mitigations before problems occur.
You are a risk analyst conducting a pre-mortem exercise. CONTEXT: Our company (B2B SaaS, 120 employees, $15M ARR) is about to launch a new AI-powered analytics feature. The project has taken 8 months, cost $1.2M in development, and is our biggest product bet of the year. We plan to launch in 6 weeks. EXERCISE: Imagine it is 6 months after launch. The feature has failed. Customer adoption is below 5%, three enterprise clients have churned citing the feature as a factor, and the board is questioning the investment. TASK: Working backwards from this failure, identify: 1. **Technical failures** (3-4 scenarios): What went wrong with the product itself? 2. **Go-to-market failures** (3-4 scenarios): What went wrong with how we launched and sold it? 3. **Customer failures** (2-3 scenarios): What did we misunderstand about what customers actually needed? 4. **Organizational failures** (2-3 scenarios): What internal dynamics contributed to the failure? For each failure scenario: - Describe specifically what happened (not vague risks, but concrete events) - Rate likelihood (high/medium/low) and impact (high/medium/low) - Identify one early warning sign we should watch for starting now - Recommend one specific mitigation we can implement before launch FORMAT: Group by category. Use a table at the end summarizing all risks with their likelihood, impact, early warning signs, and mitigations.
You are a strategic risk advisor. Build a risk matrix for a major business initiative. CONTEXT: We are a healthcare technology company (200 employees, $25M ARR) planning to expand from our current EHR integration product into patient engagement software. This requires: - Building a new product line ($3M investment over 12 months) - Hiring 15 new employees (product, engineering, sales) - Navigating HIPAA compliance for a new product category - Competing with 4 established players in patient engagement - Maintaining our core EHR product during the transition TASK: Create a comprehensive risk matrix covering: 1. **Strategic risks**: Market timing, competitive response, product-market fit 2. **Financial risks**: Cash flow, ROI timeline, opportunity cost 3. **Operational risks**: Talent acquisition, team bandwidth, quality of core product 4. **Regulatory risks**: HIPAA, state regulations, data privacy 5. **Customer risks**: Existing customer satisfaction, new customer acquisition For each risk: - Describe the specific risk in one sentence - Probability: 1-5 scale with justification - Impact: 1-5 scale with justification - Risk score (probability x impact) - Mitigation strategy (specific, actionable) - Risk owner (which role should own this) FORMAT: Present as a table sorted by risk score (highest first). Follow with a narrative summary of the top 5 risks and a recommended risk review cadence.
- Be specific about your context: Generic risk assessments are useless. Include your company size, industry, financial position, and competitive landscape.
- Ask for concrete scenarios, not categories: “A key engineer leaves during migration” is better than “talent risk.”
- Request early warning signs: The most valuable part of risk assessment is knowing what to watch for, not just what could go wrong.
- Include organizational risks: Most teams skip internal dynamics like burnout, misaligned incentives, and communication breakdowns.
- Iterate: Run the prompt once, then ask AI to challenge its own assessment and identify risks it may have underweighted.
Resource Allocation Prompts
Resource allocation decisions are where strategy meets reality. These prompts help you evaluate trade-offs with explicit criteria instead of defaulting to whoever argues loudest in the planning meeting.
You are a product strategy advisor helping prioritize investment across initiatives. CONTEXT: We are a SaaS company ($20M ARR, 150 employees) with $4M in discretionary product investment budget for the next fiscal year. We have 5 product initiatives competing for funding: 1. **AI Assistant** - Natural language interface for our analytics product. Estimated cost: $2.2M. Expected impact: 15% increase in user engagement, competitive differentiation. 2. **Enterprise SSO & Compliance** - SOC 2, SSO, audit logs. Estimated cost: $800K. Expected impact: Unblocks $3M pipeline of enterprise deals currently stalled on security requirements. 3. **Mobile App** - Native iOS/Android app. Estimated cost: $1.5M. Expected impact: Addresses top customer request (asked by 35% of users), unclear revenue impact. 4. **API Platform** - Public API for third-party integrations. Estimated cost: $1.1M. Expected impact: Enables partner ecosystem, long-term platform play. 5. **Performance Overhaul** - Rebuild core data pipeline for 10x speed. Estimated cost: $1.8M. Expected impact: Reduces churn from performance complaints (currently 12% of churn reasons). TASK: Evaluate these initiatives against these criteria (weighted): - Revenue impact (30%): Direct or attributable revenue in next 12 months - Strategic positioning (25%): Long-term competitive advantage - Customer retention (20%): Impact on reducing churn - Feasibility (15%): Risk of delays, technical complexity - Opportunity cost (10%): What we lose by NOT doing this Provide: 1. A scored comparison table (1-10 per criterion, weighted total) 2. Your recommended portfolio allocation (which initiatives to fund, in what order) 3. What you would cut and why 4. Two alternative allocation strategies with trade-off analysis FORMAT: Comparison table first, then narrative analysis, then alternatives.
You are an operations advisor helping with headcount planning. CONTEXT: We are a growing B2B SaaS company ($10M ARR, growing 40% YoY) with 80 employees. We have budget to hire 12 new people in the next year. Current team distribution: - Engineering: 30 people (including 4 managers) - Product: 5 people - Sales: 15 people (8 AEs, 4 SDRs, 3 managers) - Marketing: 8 people - Customer Success: 10 people - G&A (HR, Finance, Legal): 12 people Current pain points: - Engineering velocity has slowed; teams are stretched across too many projects - Sales pipeline is strong but AEs are at 130% capacity - Customer Success is reactive; no proactive outreach, contributing to 8% monthly logo churn - Marketing has no dedicated content or SEO person - No dedicated data analyst; decisions are made on gut feel TASK: Recommend how to allocate 12 hires across departments. For each recommendation: 1. Role title and department 2. Why this hire matters more than alternatives 3. Expected impact within 6 months 4. Dependency on other hires (e.g., "hire this person before that one") Also identify: - Which department gets zero new hires and why that is acceptable - The single most important hire (if we could only make one) - A phased hiring plan (Q1, Q2, Q3, Q4) that accounts for onboarding time FORMAT: Prioritized list with the analysis above, then a quarterly hiring timeline.
Decision Framework Prompts
Established frameworks like SWOT, Porter’s Five Forces, and decision matrices exist because they work. AI can apply these frameworks faster and more consistently than a team brainstorming on a whiteboard. The key is providing enough context for the framework to produce specific, actionable insights rather than generic observations.
You are a strategy consultant conducting a SWOT analysis. CONTEXT: We are an online education platform ($5M ARR, 40 employees) focused on professional development for mid-career professionals. We offer 120 self-paced courses in business, technology, and leadership. Our courses are priced at $49-$199 each or $29/month for all-access. Key facts: - 18,000 active subscribers, 6% monthly churn - Course completion rate: 23% (industry average is 15%) - NPS: 62 - 80% of revenue from individual buyers, 20% from corporate - No mobile app; 40% of users access via mobile browser - 3 direct competitors, largest has $50M ARR and 300 courses TASK: Conduct a thorough SWOT analysis. Go beyond surface-level observations: **Strengths**: What specific advantages do we have? Use the data above to support each point. Do not list generic strengths. **Weaknesses**: What is holding us back? Be candid. Identify weaknesses that are fixable vs. structural. **Opportunities**: What specific market trends, gaps, or moves could we exploit in the next 12-18 months? **Threats**: What could seriously damage the business? Include competitive, market, and operational threats. For each item in the SWOT: - State it in one specific sentence - Provide evidence or reasoning - Rate its significance (high/medium/low) End with 3 strategic priorities that emerge from this analysis, each tied to specific SWOT findings. FORMAT: Four-quadrant structure with rated items. Strategic priorities section at the end.
You are a competitive strategy analyst applying Porter's Five Forces. CONTEXT: We are evaluating whether to enter the corporate wellness software market. Here is what we know: Market size: $7B globally, growing 12% annually Current players: Virgin Pulse (largest), Wellable, Limeade, plus dozens of smaller tools Buyers: HR departments at companies with 500+ employees Our position: We currently sell HR analytics software to 200 enterprise clients. We have existing relationships and distribution but no wellness product. TASK: Apply Porter's Five Forces to the corporate wellness software market: 1. **Threat of New Entrants**: How easy is it to enter this market? What are the barriers? 2. **Bargaining Power of Buyers**: How much leverage do HR departments have? What drives their purchasing decisions? 3. **Bargaining Power of Suppliers**: Who are the key suppliers (data providers, content creators, health APIs)? How dependent would we be? 4. **Threat of Substitutes**: What alternatives exist outside of dedicated wellness software? 5. **Competitive Rivalry**: How intense is competition? Is the market consolidating or fragmenting? For each force: - Rate it (strong/moderate/weak) with specific justification - Identify the key factor driving this force - Explain what it means for our entry decision specifically Conclude with: - Overall market attractiveness rating (1-10) with explanation - The single biggest factor that should influence our go/no-go decision - What we would need to believe to justify entering this market FORMAT: Five forces as separate sections, then conclusion. Use specific examples and data points, not generic framework descriptions.
You are a decision analysis advisor. Build a weighted decision matrix. CONTEXT: Our leadership team is evaluating 3 options for our next major company initiative: Option A: Build a partner/reseller channel program Option B: Launch a self-serve product tier (currently sales-led only) Option C: Expand into an adjacent vertical (currently serve only fintech; considering healthtech) Company context: B2B SaaS, $18M ARR, 130 employees, Series B ($20M raised). We need to reach $30M ARR in 18 months to position for Series C. TASK: Create a decision matrix evaluating these three options against these criteria: 1. Revenue impact in 18 months (weight: 30%) 2. Resource requirements - people, capital, time (weight: 20%) 3. Risk level (weight: 15%) 4. Strategic optionality - does this open future opportunities? (weight: 15%) 5. Execution confidence - can our team actually pull this off? (weight: 10%) 6. Customer impact - benefit to existing customers (weight: 10%) For each option and criterion: - Score 1-10 with a one-sentence justification - Calculate weighted scores Then provide: - A clear recommendation with reasoning - The key assumption behind the recommendation, and what would change if that assumption is wrong - A "combination play" if any two options could be pursued together FORMAT: Decision matrix table, then narrative analysis.
Pro Tip
Before & After
The difference between a vague strategy prompt and a structured one is the difference between getting a Wikipedia summary and getting an actual strategic recommendation you can act on.
What are the risks of expanding internationally? Give me a risk assessment.
You are a strategic risk advisor for a mid-market SaaS company. CONTEXT: We are a US-based B2B SaaS company ($12M ARR, 85 employees) selling inventory management software to mid-market retailers. We have 340 US customers, 92% retention, and $35K ACV. We are considering expansion into the UK and Western Europe within 18 months. Budget: $1.5M. No existing European customers, no GDPR compliance work started, no international sales experience on the team. TASK: Conduct a risk assessment for this international expansion. Identify risks across five categories: 1. Market risks (demand uncertainty, competitive landscape, pricing) 2. Operational risks (hiring, timezone management, support coverage) 3. Regulatory risks (GDPR, local data residency, tax implications) 4. Financial risks (currency exposure, higher CAC, longer sales cycles) 5. Strategic risks (distraction from US growth, brand dilution) For each risk: describe it specifically, rate probability (1-5) and impact (1-5), calculate risk score, provide one mitigation action, and identify an early warning sign. FORMAT: Risks grouped by category in a table sorted by risk score. Include a narrative summary of the top 5 risks and a recommended go/no-go checklist with 8-10 conditions that should be true before we proceed.
Success
Common Mistakes
These are the patterns that consistently produce poor strategic analysis from AI. Avoid them and your outputs will be significantly more useful.
1. Asking AI for “the answer”
AI does not know your business well enough to tell you what to do. Prompts like “Should we expand to Europe?” will get a generic pro/con list. Instead, ask AI to analyze specific scenarios with your actual constraints and data. You make the decision; AI helps you think.
2. Not providing enough business context
A prompt that says “analyze this market” without mentioning your company size, revenue, competitive position, or constraints will produce generic output. Include specific numbers: ARR, team size, budget, customer count, retention rate. The more specific your context, the more actionable the analysis.
3. Accepting the first output
The first response is a starting point, not a finished analysis. Follow up by asking AI to challenge its own assumptions, identify what it might have missed, or explore the scenario it rated as least likely. Strategic planning is iterative; your AI prompts should be too.
4. Using AI to avoid hard conversations
Some teams use AI analysis as a shield: “The AI said we should do X.” AI output should inform debate, not replace it. If your team has fundamental disagreements about strategy, those need to be resolved through honest discussion, not outsourced to a language model.
5. Treating AI output as confidential analysis
Do not paste proprietary financials, customer lists, or trade secrets into AI prompts without understanding your organization’s data policies. Use aggregated data, ranges, and anonymized examples. The prompts in this guide use realistic but fictional company data for this reason.
Quick Reference
Use this table to find the right prompt approach for your strategic planning need.
| Scenario Type | Recommended Approach | Key Elements to Include |
|---|---|---|
| Market entry | Multi-scenario analysis | Market size, current position, budget, timeline, competitive landscape |
| Competitive response | Per-competitor modeling | Competitor profiles, pricing data, market share, your planned action |
| Risk assessment | Pre-mortem or risk matrix | Initiative details, investment size, team capacity, known constraints |
| Resource allocation | Weighted scoring with criteria | Budget, initiative details, evaluation criteria with weights, constraints |
| Strategic decision | Decision matrix or framework analysis | Options, criteria, company context, success metrics, timeline |
| Operational pivot | Side-by-side scenario comparison | Current state, options with costs, revenue projections, staff impact |
| Headcount planning | Prioritized allocation with sequencing | Current team structure, growth rate, pain points, budget for hires |
Next Steps
You now have a library of strategic planning prompts you can use immediately. But writing these prompts from scratch every time is tedious, especially when you are under pressure to make a decision.
AskSmarter.ai automates the hard part. Our prompt builder asks you targeted questions about your strategic context, then constructs prompts that include the right level of detail, the right framework, and the right output format. You focus on the decision; we handle the prompt engineering.
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Answer a few questions about your strategic decision. AskSmarter applies proven frameworks and structures to create prompts that produce analysis your leadership team can act on. No prompt engineering required.
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