FREE AI Prompts for Business Strategy

25 AI prompts that think like a strategist, not a chatbot. Every prompt below is copy-and-paste ready for ChatGPT, Claude, Gemini, or any LLM. They're built with analytical frameworks, structured reasoning, and output constraints — so you get boardroom-grade thinking, not generic business advice.

Covers: Strategic Planning Competitive Analysis Business Models Growth & Expansion Decision Making

What's Inside

1. Strategic Planning & Vision
2. Competitive & Market Analysis
3. Business Model Design
4. Growth & Market Expansion
5. Decision Making & Prioritisation

Strategy is where most people misuse AI the hardest. They ask "what should my business strategy be?" and get back a Wikipedia-grade answer that could apply to any company on earth. The prompts below are different. Each one forces the AI to operate within your specific context — your market, your numbers, your constraints — and apply recognised strategic frameworks rather than improvising platitudes.

1Strategic Planning & Vision

Good strategy starts with seeing clearly — understanding where you are, where the market is going, and where the gaps and opportunities sit. These prompts help you build that picture with structure and rigour, not wishful thinking.

1.1 — Strategic Situation Assessment (SWOT+)

PlanningSWOT

You are a management consultant at a top-tier strategy firm conducting a strategic situation assessment. CONTEXT: - Company: [NAME, INDUSTRY, SIZE, STAGE — e.g., “Series B SaaS, 120 employees, $18M ARR”] - Core product/service: [WHAT YOU SELL AND TO WHOM] - Current strategic challenge: [THE BIG QUESTION YOU’RE TRYING TO ANSWER] - Key metrics: [REVENUE, GROWTH RATE, MARGINS, CHURN — whatever is relevant] - Competitive landscape: [2-3 KEY COMPETITORS AND HOW YOU DIFFER] TASK: Conduct a SWOT+ analysis — standard SWOT plus two additional layers: 1. Strengths — internal advantages, with evidence from the data provided 1. Weaknesses — internal limitations, be brutally honest 1. Opportunities — external trends or gaps we can exploit 1. Threats — external forces that could undermine us 1. Strategic implications — for each quadrant, what does this mean for our next 12 months? 1. Priority actions — the 3 highest-leverage moves based on this analysis CONSTRAINTS: - No generic SWOT items (“strong brand” or “competitive market”) — every point must be specific to this company - Each quadrant: 3-5 items, each with a one-sentence explanation of WHY it matters - Strategic implications must connect SWOT items to actual decisions - Priority actions must be specific and time-bound, not vague (“invest in innovation”) - If you don’t have enough information to assess something, say so — don’t fabricate

Tip: Paste in your last board deck, investor update, or quarterly review alongside this prompt. The more real data you feed in, the sharper the analysis becomes.

1.2 — Annual Strategic Plan Outline

PlanningAnnual

You are a Chief Strategy Officer drafting an annual strategic plan for the leadership team. CONTEXT: - Company: [NAME AND BRIEF DESCRIPTION] - Last year’s performance: [KEY WINS AND MISSES — 3-4 bullet points] - Revenue target this year: [NUMBER AND GROWTH % VS LAST YEAR] - Key bets from last year that worked: [WHAT SHOULD WE DOUBLE DOWN ON] - Key bets that didn’t work: [WHAT SHOULD WE STOP OR PIVOT] - Market shifts we’re seeing: [2-3 TRENDS AFFECTING OUR BUSINESS] - Resource constraints: [HEADCOUNT, BUDGET, OR CAPABILITY LIMITATIONS] TASK: Draft a strategic plan outline with the following structure: 1. Strategic narrative — a 3-paragraph summary of where we are, where we’re going, and how we’ll get there 1. Three strategic priorities for the year — each with a clear definition of success (measurable) 1. For each priority: key initiatives (max 3), resource requirements, owner, and Q1 milestones 1. Strategic trade-offs — what we’re explicitly choosing NOT to do this year, and why 1. Risk register — top 3 risks to the plan and a mitigation for each 1. Decision points — key decisions that need to be made in Q1 to keep the plan on track CONSTRAINTS: - The strategic narrative must be compelling enough to align a leadership team — not just a summary - Each priority must pass the “we can fail at this” test — if success is guaranteed, it’s not strategic - Trade-offs section is mandatory — strategy is as much about what you don’t do - Entire outline should be presentable to a board — professional tone, crisp language - No jargon-heavy mission statements or vision paragraphs — concrete and specific throughout

1.3 — OKR Generator (Company & Team Level)

OKRsGoal Setting

You are an OKR coach who has implemented objectives and key results at companies from 20 to 20,000 employees. CONTEXT: - Company: [NAME AND WHAT YOU DO] - Planning period: [e.g., Q2 2025] - Company-level strategic priorities: [LIST 2-3] - Team requesting OKRs: [TEAM NAME AND FUNCTION — e.g., “Product team, 12 people”] - Team’s current focus: [WHAT THEY’RE WORKING ON NOW] - Known constraints: [HEADCOUNT, DEPENDENCIES, TECH DEBT, ETC.] TASK: Generate a complete OKR set: 1. 2-3 team-level Objectives — ambitious, qualitative, inspiring 1. For each Objective, 3-4 Key Results — specific, measurable, time-bound 1. For each Key Result, indicate: baseline (where we are now), target (where we want to be), and confidence level (how likely is this on a scale of 1-10) 1. Alignment map — show how each team OKR connects to a company-level priority 1. Anti-goals — 2-3 things that would look like progress but aren’t actually what we’re optimising for CONSTRAINTS: - Key Results must be outcomes, not outputs — “Ship feature X” is not a Key Result; “Increase activation rate from 30% to 45%” is - At least one Key Result per Objective should be a stretch (confidence 3-4/10) - No vanity metrics — every KR must connect to business impact - Anti-goals section prevents the team from gaming the metrics - If the inputs are too vague to write good OKRs, say so and ask clarifying questions instead of guessing

1.4 — Vision & Mission Statement Workshop

VisionMission

You are a brand strategist who helps companies articulate what they stand for — in language that actually means something. CONTEXT: - Company: [NAME AND WHAT YOU DO] - Founded: [YEAR AND ORIGIN STORY IN 1-2 SENTENCES] - Customers: [WHO YOU SERVE] - Core belief: [WHAT DO YOU BELIEVE ABOUT THE WORLD THAT DRIVES YOUR WORK?] - What makes you different: [YOUR GENUINE DIFFERENTIATOR — not “great customer service”] - Where you want to be in 10 years: [AMBITIOUS BUT HONEST ASPIRATION] TASK: Generate 3 options for each of the following: 1. Vision statement — where the world is going if you succeed (aspirational, future-facing) 1. Mission statement — what you do, for whom, and why it matters (present-tense, operational) 1. One-liner — the cocktail party version of what your company does (under 15 words) For each option, provide a brief note on the strategic emphasis: what it prioritises and what it sacrifices. CONSTRAINTS: - No statements that could apply to any company in your industry — they must be uniquely yours - Vision: under 20 words. Mission: under 30 words. One-liner: under 15 words - Ban list: “world-class,” “innovative,” “best-in-class,” “empower,” “leverage,” “solutions” - Every statement must pass the “opposite test” — if the opposite sounds absurd, the statement is too generic - Include one bold/provocative option in each set that the founders might debate — that’s usually the best one

1.5 — Scenario Planning (3 Futures)

PlanningScenarios

You are a strategic foresight consultant who helps leadership teams prepare for multiple futures, not just the most likely one. CONTEXT: - Company: [NAME, INDUSTRY, CURRENT REVENUE/SIZE] - Planning horizon: [e.g., “3 years”] - Key uncertainties we face: [LIST 2-3 MAJOR UNKNOWNS — e.g., “regulatory changes,” “AI adoption speed,” “competitor IPO”] - Our current strategic bet: [THE DIRECTION WE’RE CURRENTLY HEADING] - Resources at stake: [WHAT WE’VE INVESTED OR PLAN TO INVEST IN THIS DIRECTION] TASK: Build three distinct scenarios for our planning horizon: 1. Scenario A (Tailwind): The world shifts in our favour — what does this look like, and how do we maximise the upside? 1. Scenario B (Headwind): The world shifts against us — what breaks, and what do we do about it? 1. Scenario C (Curveball): A non-obvious disruption changes the game entirely — what is it, and how do we respond? For each scenario, provide: - A narrative description (150-200 words) — tell it as a story set in the future - Key indicators — 3 early warning signs that this scenario is unfolding - Strategic response — what we should do if we see these signs - No-regret moves — actions that help us regardless of which scenario plays out CONSTRAINTS: - Scenarios must be genuinely different, not just optimistic/neutral/pessimistic versions of the same story - The curveball scenario must be plausible but unexpected — not science fiction - Early warning indicators must be observable and measurable within 6 months - No-regret moves are the most valuable output — prioritise these - Be specific to this company — no generic “invest in digital transformation” advice

Need strategic prompts tailored to your industry vertical?

The Business Strategy Prompt Pack includes 60+ prompts with versions for SaaS, professional services, e-commerce, and agency models — plus executive briefing templates.

Browse the Strategy Prompt Pack →

2Competitive & Market Analysis

Most competitive analysis is either too shallow (a feature comparison table) or too theoretical (a Porter's Five Forces exercise nobody acts on). These prompts sit in the middle — structured enough to be rigorous, practical enough to inform actual decisions.

2.1 — Competitor Deep Dive

CompetitiveAnalysis

You are a competitive intelligence analyst preparing a briefing for the executive team. CONTEXT: - Our company: [NAME, WHAT WE DO, KEY METRICS] - Competitor to analyse: [NAME] - What we know about them: [PASTE ANY AVAILABLE INFO — funding, product features, pricing, team size, recent news] - Specific questions we need answered: [e.g., “Are they moving upmarket?” “What’s their pricing model?” “Should we be worried?”] TASK: Produce a competitor briefing that covers: 1. Company overview — what they do, who they serve, estimated size and trajectory 1. Strategic positioning — how they position themselves vs the market (not just vs us) 1. Product/service analysis — strengths, weaknesses, and notable gaps 1. Go-to-market approach — how they acquire customers, pricing model, sales motion 1. Threat assessment — where they compete with us directly, where they don’t, and where they might in 12 months 1. Opportunities — weaknesses or blind spots we can exploit 1. Recommended actions — 2-3 specific things we should do based on this analysis CONSTRAINTS: - Distinguish between facts (sourced from data) and inferences (your analysis) — label each clearly - No dismissive language — assume the competitor is smart and executing well - Threat assessment must include a “what if they get it right?” scenario - Recommended actions must be specific, not “monitor the situation” - If information is insufficient for a confident assessment, say so

2.2 — Market Sizing (TAM/SAM/SOM)

MarketSizing

You are a strategy analyst who builds market sizing models grounded in logic, not inflated TAM numbers designed to impress investors. CONTEXT: - Product/service: [WHAT YOU SELL] - Target customer: [SPECIFIC DESCRIPTION — industry, size, geography] - Price point: [AVERAGE DEAL SIZE OR PRICE PER UNIT] - Current revenue: [IF APPLICABLE] - Geography: [TARGET MARKETS] TASK: Build a bottom-up market sizing model with: 1. TAM (Total Addressable Market) — the total universe of potential revenue if everyone who could buy, did buy. Show your math. 1. SAM (Serviceable Addressable Market) — the subset we can realistically reach with our current product and go-to-market. Show your filters. 1. SOM (Serviceable Obtainable Market) — what we can realistically capture in the next 2-3 years given our resources. Show your assumptions. 1. Key assumptions — list every assumption in the model, with a confidence level (high/medium/low) 1. Sensitivity analysis — what happens to SOM if the two most uncertain assumptions are wrong by 50%? CONSTRAINTS: - Bottom-up methodology only — do not start with “the global X market is $Y billion” - Show all calculations transparently — the reader should be able to challenge any number - Be conservative on SOM — overestimation destroys credibility - Flag where you’re using estimates vs data - If the inputs are too vague for a credible model, ask for more information instead of guessing

2.3 — Porter's Five Forces (Applied)

CompetitiveFramework

You are a strategy professor who applies Porter's Five Forces to real business situations — not as an academic exercise but as a decision-making tool. CONTEXT: - Company: [NAME AND WHAT YOU DO] - Industry: [SPECIFIC INDUSTRY SEGMENT] - Key competitors: [LIST 3-5] - Your primary customers: [WHO BUYS AND WHY] - Your key suppliers or dependencies: [TECHNOLOGY PLATFORMS, TALENT POOLS, RAW MATERIALS] TASK: Apply Porter’s Five Forces analysis to this specific business: 1. Competitive Rivalry — how intense is direct competition, and what’s driving it? 1. Threat of New Entrants — how easy is it for someone new to compete with us? 1. Threat of Substitutes — what alternatives exist beyond direct competitors? 1. Bargaining Power of Buyers — how much leverage do our customers have? 1. Bargaining Power of Suppliers — how much leverage do our dependencies have? For each force: - Rate the force as High / Medium / Low with a one-sentence justification - Identify the single most important factor driving that force - Recommend one strategic action to strengthen our position Conclude with: an overall industry attractiveness assessment and the single biggest strategic implication. CONSTRAINTS: - Every point must reference this specific company and industry — no textbook generalities - The “substitutes” force must include non-obvious alternatives (e.g., “they do nothing” or “they build it in-house”) - Strategic actions must be actionable within 12 months - If a force is rated “Low,” explain what could change that — no force stays low forever

2.4 — Pricing Strategy Analyser

PricingStrategy

You are a pricing strategist who helps companies charge what they're worth — and capture the value they create. CONTEXT: - Product/service: [WHAT YOU SELL] - Current pricing model: [HOW YOU CHARGE — per seat, flat fee, usage-based, project-based, etc.] - Current price point: [SPECIFIC NUMBERS] - Competitor pricing: [WHAT COMPETITORS CHARGE, IF KNOWN] - Customer segments: [WHO BUYS — different segments may have different willingness to pay] - Value delivered: [WHAT QUANTIFIABLE OUTCOME DOES YOUR PRODUCT DELIVER FOR CUSTOMERS?] - Pain point with current pricing: [WHAT’S NOT WORKING — e.g., “deals stall at pricing,” “small customers churn,” “leaving money on the table”] TASK: Provide a pricing strategy assessment that includes: 1. Current model diagnosis — what’s working, what’s broken, and why 1. Three alternative pricing models — each with a clear rationale, pros/cons, and which customer segment it serves best 1. For each model: recommended price points with the logic behind them 1. Migration strategy — how to transition from current pricing without alienating existing customers 1. Pricing psychology — 2-3 tactical pricing moves (anchoring, tiering, decoy effect) that fit this specific product CONSTRAINTS: - Recommendations must be grounded in value delivered, not just competitor matching - Address the specific pain point mentioned — don’t ignore it - Migration strategy must be realistic — no “grandfather everyone” without addressing revenue impact - Include one “bold move” option that most companies wouldn’t consider but should - If the current pricing is actually fine, say so — don’t fix what isn’t broken

2.5 — Industry Trend Briefing

MarketTrends

You are a market research analyst who writes trend briefings that help leadership teams make investment decisions. CONTEXT: - Industry: [YOUR INDUSTRY] - Company context: [BRIEF DESCRIPTION OF YOUR BUSINESS AND WHERE YOU SIT IN THE MARKET] - Specific area of interest: [e.g., “AI in our industry,” “regulatory changes,” “customer behaviour shifts”] - Time horizon: [e.g., “next 12-24 months”] TASK: Produce a trend briefing that covers: 1. Five key trends shaping this industry over the stated time horizon 1. For each trend: what’s driving it, how far along it is (emerging / accelerating / mature), and who’s leading it 1. Impact assessment — for each trend, rate its impact on our specific business (High / Medium / Low) and explain how it affects us 1. Opportunities — which trends create openings for us, and what would we need to do to capitalise? 1. Threats — which trends could undermine our current model, and how should we hedge? 1. “Watch” list — 2-3 weak signals that aren’t trends yet but could become significant CONSTRAINTS: - Trends must be specific, not vague (“digital transformation” is not a trend; “mid-market B2B buyers demanding self-serve purchasing” is) - Each trend must cite or reference observable evidence — not just opinion - Impact assessment must connect to our specific business model, not the industry in general - Weak signals should be genuinely surprising — things most people in the industry aren’t talking about yet - Total briefing should be readable in under 10 minutes

Pro tip: For prompts 2.1-2.5, pair the AI output with real data. Paste in your latest earnings call transcripts, industry reports, or customer survey results. AI is excellent at synthesising patterns across large amounts of input — use it as an analyst, not an oracle.

3Business Model Design

Whether you're launching a new product line, exploring a pivot, or stress-testing your current model, these prompts help you think through the economics, mechanics, and viability of how your business creates and captures value.

3.1 — Business Model Canvas Generator

Business ModelCanvas

You are a business model strategist who uses the Business Model Canvas as a thinking tool, not a fill-in-the-blank template. CONTEXT: - Business idea or existing business: [DESCRIBE IN 2-3 SENTENCES] - Target customer: [WHO] - Revenue so far: [IF APPLICABLE] - Stage: [Idea / MVP / Growth / Established] TASK: Complete all 9 blocks of the Business Model Canvas: 1. Customer Segments — who are we creating value for? 1. Value Propositions — what problem do we solve, and why us? 1. Channels — how do we reach and deliver to customers? 1. Customer Relationships — how do we acquire, retain, and grow accounts? 1. Revenue Streams — how do we make money, and what are customers willing to pay for? 1. Key Resources — what do we need to deliver the value proposition? 1. Key Activities — what must we do exceptionally well? 1. Key Partnerships — who do we need to work with? 1. Cost Structure — what are the biggest cost drivers? For each block: - Provide 3-5 specific items (not generic placeholders) - Identify the single most critical element in each block - Flag one risk or assumption in each block that should be validated Conclude with: the 3 riskiest assumptions in the entire model and how to test them cheaply. CONSTRAINTS: - Every item must be specific to this business — nothing that could apply to any company - Value Proposition must articulate the “job to be done,” not just features - Revenue Streams must include pricing logic, not just “subscription” or “per unit” - The riskiest assumptions section is the most important output — be honest about what’s unproven

3.2 — Unit Economics Deep Dive

FinancialUnit Economics

You are a financial analyst who evaluates business viability through unit economics — because revenue without margin is just expensive vanity. CONTEXT: - Business model: [DESCRIBE HOW YOU MAKE MONEY] - Average revenue per customer: [MONTHLY OR ANNUAL] - Customer acquisition cost: [TOTAL COST TO ACQUIRE ONE CUSTOMER — marketing + sales] - Gross margin: [% OR ESTIMATE] - Average customer lifetime: [MONTHS OR YEARS] - Churn rate: [MONTHLY OR ANNUAL, IF APPLICABLE] - Current growth rate: [MoM OR YoY] TASK: Build a unit economics analysis that covers: 1. LTV (Lifetime Value) calculation — show the formula and the math 1. CAC (Customer Acquisition Cost) breakdown — where the money goes 1. LTV:CAC ratio — with interpretation (what’s healthy, where are we) 1. Payback period — how many months until a customer is profitable 1. Contribution margin analysis — what each customer actually contributes after variable costs 1. Sensitivity analysis — what happens to LTV:CAC if churn increases 20%, if CAC increases 30%, if ARPU increases 15% 1. Improvement levers — rank the top 3 levers to improve unit economics, with estimated impact CONSTRAINTS: - Show all formulas and assumptions — the reader should be able to rebuild the model - Be honest about whether the economics work — if they don’t, say so clearly - Sensitivity analysis must test the most vulnerable assumptions, not the safe ones - Improvement levers must be actionable (“reduce churn from 5% to 3% by improving onboarding”) not abstract (“improve retention”) - If data is missing, state what you’re assuming and flag it

3.3 — New Revenue Stream Brainstorm

RevenueInnovation

You are an innovation strategist who helps companies find new ways to monetise their existing assets, capabilities, and customer relationships. CONTEXT: - Current business: [WHAT YOU DO AND HOW YOU MAKE MONEY TODAY] - Core assets: [YOUR DATA, TECHNOLOGY, BRAND, CUSTOMER BASE, EXPERTISE, IP] - Current customers: [WHO THEY ARE AND WHAT ELSE THEY NEED] - Revenue today: [APPROXIMATE, AND % BREAKDOWN BY STREAM IF MULTIPLE] - Constraint: [WHAT YOU CAN’T DO — e.g., “we can’t build hardware” or “no enterprise sales team”] TASK: Generate 7 potential new revenue streams, organised into three categories: 1. Adjacent (low risk, 3-6 months) — extensions of what you already do 1. Expansion (medium risk, 6-12 months) — new offerings for existing customers or existing offerings for new segments 1. Transformational (higher risk, 12+ months) — fundamentally new business models For each revenue stream: - One-sentence description - Revenue model (how money flows) - Estimated revenue potential (rough order of magnitude) - Key resources required - Biggest risk or assumption - First step to validate (the cheapest, fastest test) CONSTRAINTS: - Every idea must build on an existing asset or capability — no “start a completely different business” - Revenue potential must be grounded in logic, not optimism - Respect the stated constraint — don’t propose things they can’t do - At least 2 ideas must be things the company hasn’t likely considered - Validation steps must cost less than $5,000 and take less than 30 days

Building a business case or investor deck?

The Strategy Prompt Pack includes financial modelling prompts, pitch deck frameworks, and board presentation templates — all engineered for real strategic work.

See All Prompt Packs →

4Growth & Market Expansion

Growth strategy isn't just "do more" — it's about choosing where to invest, which markets to enter, and which opportunities to ignore. These prompts help you evaluate expansion decisions with the same rigour you'd bring to any other investment.

4.1 — Market Entry Assessment

GrowthMarket Entry

You are a market entry strategist who helps companies decide whether and how to enter new markets — not just how to enter them. CONTEXT: - Current business: [WHAT YOU DO AND WHERE YOU OPERATE TODAY] - Target market: [THE NEW MARKET — geography, segment, or vertical] - Why we’re considering it: [WHAT’S PULLING US THERE — opportunity, customer demand, competitive pressure] - Resources available: [BUDGET, TEAM, TIMELINE] - Risk tolerance: [CONSERVATIVE / MODERATE / AGGRESSIVE] TASK: Produce a market entry assessment with: 1. Market attractiveness — size, growth, competition, barriers to entry, regulatory environment 1. Our right to win — what advantages do we have in this market? Be honest about gaps 1. Entry strategy options — recommend 3 approaches (e.g., organic build, partnership, acquisition, light-touch pilot) with pros/cons for each 1. Go/No-Go recommendation — based on the analysis, should we enter? Under what conditions? 1. If Go: a phased entry plan with milestones and decision gates 1. If No-Go: what would need to change for us to reconsider CONSTRAINTS: - The “right to win” section must be brutally honest — having capital is not a right to win - Entry strategy options must account for the stated resource constraints - Phased plan must include “kill criteria” — what would make us exit or pause - Regulatory and cultural factors must be addressed if entering a new geography - No “just test it and see” — even pilots need clear success metrics

4.2 — Partnership & Alliance Strategy

GrowthPartnerships

You are a business development strategist who designs partnerships that create value for both sides — not just logo swaps. CONTEXT: - Our company: [NAME, WHAT WE DO, SIZE] - Strategic goal the partnership should serve: [e.g., “access enterprise customers,” “add AI capability,” “enter European market”] - What we bring to a partner: [OUR UNIQUE ASSETS — distribution, technology, content, brand, data] - What we need from a partner: [CAPABILITY, ACCESS, OR RESOURCE GAPS] - Potential partner(s): [NAMES IF KNOWN, OR DESCRIBE THE IDEAL PARTNER PROFILE] TASK: Design a partnership strategy that covers: 1. Partner selection criteria — the 5 most important attributes in a partner, ranked 1. Value exchange map — what each side gives and gets, written as a balance sheet 1. Three partnership models — from lightest to deepest commitment (e.g., referral agreement → co-selling → joint venture) with pros/cons of each 1. Deal structure recommendation — which model fits best, and what the key terms should be 1. Risk assessment — what could go wrong, and how to protect against it 1. First 90-day plan — how to get the partnership operational quickly CONSTRAINTS: - The value exchange must be genuinely balanced — if one side gets significantly more, the partnership won’t last - Risk assessment must include relationship risks (misaligned incentives, cultural clash), not just contractual ones - First 90-day plan must include specific joint activities, not just “align teams” - Include an exit clause recommendation — good partnerships plan for ending gracefully - If the partnership idea doesn’t survive the value exchange analysis, say so

4.3 — Customer Expansion Playbook

GrowthUpsell / Cross-Sell

You are a revenue growth specialist who helps companies grow by expanding within their existing customer base — the most capital-efficient growth there is. CONTEXT: - Product/service suite: [LIST ALL YOUR OFFERINGS] - Average current spend per customer: [AMOUNT] - Maximum potential spend per customer: [AMOUNT IF THEY BOUGHT EVERYTHING] - Customer segmentation: [HOW YOU SEGMENT — by size, industry, usage, tier] - Current expansion revenue %: [WHAT % OF NEW REVENUE COMES FROM EXISTING CUSTOMERS] - Common expansion triggers: [WHAT EVENTS OR CONDITIONS LEAD CUSTOMERS TO BUY MORE] TASK: Build a customer expansion playbook: 1. Expansion opportunity matrix — map your products/services against customer segments to identify the highest-value cross-sell and upsell opportunities 1. For the top 5 opportunities: the trigger event, the talk track, the offer, and the expected uplift 1. Expansion signals — what behaviours or data points indicate a customer is ready for more 1. Process design — who owns expansion conversations, when do they happen, how are they tracked 1. Pricing & packaging — should you bundle for expansion? Create upgrade tiers? Offer expansion incentives? 1. Success metrics — how to measure expansion revenue health beyond just the number CONSTRAINTS: - Expansion must create value for the customer, not just extract revenue — every upsell must solve a problem - Talk tracks must be conversational, not scripted pitches - Signals must be observable in your existing data or tools — no “when the customer seems ready” - Process design must fit the team’s capacity — don’t propose a system that requires a team you don’t have - Include one “land-and-expand” motion for new customers that starts small by design

Pro tip: The most overlooked growth lever is expansion within existing accounts. Prompt 4.3 is the one most companies should start with — it's cheaper to grow within a customer you've already won than to acquire a new one.

5Decision Making & Prioritisation

Strategy is ultimately about decisions — and the best frameworks aren't the ones that give you the answer, but the ones that help you see the trade-offs clearly. These prompts bring structure to the messy, high-stakes choices that leaders face every quarter.

5.1 — Decision Matrix Builder

DecisionFramework

You are a decision scientist who helps leaders make high-stakes decisions with clarity, not gut instinct. CONTEXT: - The decision: [WHAT ARE YOU TRYING TO DECIDE?] - Options on the table: [LIST 2-5 OPTIONS] - Key stakeholders: [WHO IS AFFECTED AND WHO HAS INPUT] - Decision timeline: [WHEN DOES THIS NEED TO BE DECIDED] - What makes this hard: [WHY HASN’T THE DECISION BEEN MADE YET — competing priorities, incomplete data, political dynamics] TASK: Build a decision matrix that includes: 1. Evaluation criteria — 5-7 factors that matter most for this decision, with a weight for each (must total 100%) 1. Scoring — rate each option against each criterion (1-5 scale) with a brief justification 1. Weighted results — calculate the total weighted score for each option 1. Sensitivity check — which criterion, if re-weighted, would change the outcome? This reveals where the real disagreement lies 1. Recommendation — state the winning option, what makes it the best choice, and the trade-off you’re accepting 1. Pre-mortem — if this decision fails, what’s the most likely reason? CONSTRAINTS: - Criteria must reflect what actually matters to stakeholders, not what sounds objective - Scoring justifications must be honest — don’t inflate the option you already prefer - The sensitivity check is the most valuable part — it surfaces hidden disagreements - Pre-mortem must be specific, not “we didn’t execute well” - If two options score within 10% of each other, flag it — the matrix can’t choose between them and a different factor should decide

5.2 — Resource Allocation Prioritiser

PrioritisationResources

You are a COO who needs to allocate limited resources across competing priorities — and make the case to the leadership team. CONTEXT: - Available resources: [BUDGET, HEADCOUNT, OR TIME — be specific] - Competing initiatives: [LIST 4-8 PROJECTS OR PRIORITIES COMPETING FOR RESOURCES] - Strategic priorities: [THE 2-3 COMPANY-LEVEL GOALS THESE MUST ALIGN TO] - Current commitments: [ANYTHING ALREADY IN FLIGHT THAT CAN’T BE STOPPED] - Constraints: [e.g., “can’t hire for 3 months,” “Q3 budget is frozen,” “need 2 engineers on maintenance”] TASK: Produce a resource allocation recommendation: 1. Impact vs Effort matrix — plot each initiative on a 2x2 (High Impact/Low Effort = do first) 1. Strategic alignment score — rate each initiative against company priorities (1-5) 1. Sequencing recommendation — what to do first, second, third — and what to defer or kill 1. Resource allocation plan — who works on what, starting when, for how long 1. The “stop” list — initiatives to pause or cancel, with a clear rationale for each 1. Communication plan — how to tell the teams whose projects got deprioritised CONSTRAINTS: - Total resource allocation cannot exceed stated availability — no “and then we hire 3 more people” - The “stop” list is mandatory — if everything is a priority, nothing is - Sequencing must account for dependencies between initiatives - Communication plan must be empathetic but honest — teams deserve to know why - Include a quarterly review trigger to reassess allocation if conditions change

5.3 — "Should We Build, Buy, or Partner?" Assessment

DecisionBuild vs Buy

You are a strategy advisor who helps companies decide whether to build internally, acquire, or partner — the most common strategic crossroads in any growth company. CONTEXT: - The capability or product we need: [WHAT WE’RE TRYING TO ADD] - Why we need it: [BUSINESS CASE — growth, competitive pressure, customer demand] - Current internal capability: [HOW MUCH OF THIS CAN WE ALREADY DO?] - Timeline pressure: [HOW QUICKLY DO WE NEED THIS?] - Budget envelope: [WHAT CAN WE SPEND — one-time and ongoing] - Strategic importance: [IS THIS CORE TO OUR FUTURE OR ADJACENT/NICE-TO-HAVE?] TASK: Evaluate all three options: BUILD: - What it would take (time, team, cost) - Advantages (control, IP ownership, custom fit) - Risks (distraction, opportunity cost, execution risk) - Realistic timeline to value BUY (Acquire): - Ideal acquisition target profile - Estimated cost range and deal structure considerations - Integration complexity and cultural risk - Time to value vs build PARTNER: - Ideal partner profile and deal structure - What we gain vs what we give up - Dependency and exit risks - Speed to market Conclude with: a clear recommendation, the key assumption behind it, and what would change the recommendation. CONSTRAINTS: - “Build” estimates must include opportunity cost — what else could the team be doing? - “Buy” must address integration reality — most acquisitions destroy value through bad integration - “Partner” must address dependency risk — what happens if the partner changes strategy? - The recommendation must account for strategic importance — you build what’s core, you partner on what’s adjacent - If the answer is genuinely unclear, recommend the cheapest way to learn more before committing

5.4 — Risk Assessment & Mitigation Plan

RiskPlanning

You are a risk management consultant who helps leadership teams see around corners — not just react to problems after they hit. CONTEXT: - Initiative or decision: [WHAT ARE WE ABOUT TO DO?] - Investment at stake: [MONEY, TIME, REPUTATION — what do we lose if this fails?] - Key stakeholders: [WHO IS AFFECTED] - Known risks we’ve already identified: [LIST ANY] - Our biggest blind spot: [WHAT ARE WE MOST LIKELY WRONG ABOUT?] TASK: Build a comprehensive risk assessment: 1. Risk identification — list 8-12 risks across categories: strategic, operational, financial, reputational, and external 1. For each risk: likelihood (1-5), impact (1-5), and a composite risk score 1. Heat map summary — categorise risks as Critical (act now), Significant (plan for), and Watchlist (monitor) 1. Mitigation plan — for each Critical and Significant risk, provide: the mitigation action, the owner, the cost of mitigation, and the trigger that activates the response 1. Early warning indicators — what signals should we watch that would tell us a risk is materialising? 1. Residual risk statement — after mitigation, what risk are we still accepting? CONSTRAINTS: - Include at least 2 risks nobody wants to talk about — political, cultural, or reputational - Mitigation plans must be proportional to the risk — don’t spend $100K mitigating a $10K risk - Early warning indicators must be observable — not “if things start going badly” - The residual risk statement must be explicit — leadership should sign off on what risk they’re accepting - If the total risk profile is too high for the expected return, say so

5.5 — Strategic Memo (One-Pager for Leadership)

CommunicationExecutive

You are a strategic communications expert who writes the kind of memos that CEOs actually read — clear, concise, and decision-ready. CONTEXT: - Topic: [WHAT THE MEMO IS ABOUT] - Audience: [WHO IS READING — CEO, board, leadership team, investors] - Decision needed: [WHAT YOU WANT THEM TO DECIDE OR APPROVE] - Supporting data: [PASTE KEY FACTS, NUMBERS, OR ANALYSIS] - Political context: [ANY SENSITIVITIES — e.g., “the CEO is skeptical,” “the board wants lower risk,” “this contradicts our Q1 plan”] TASK: Write a one-page strategic memo with the following structure: 1. Headline recommendation — the decision you’re asking for, in one sentence 1. Context — why this matters now, in 3-4 sentences 1. Analysis — the key facts and reasoning that support the recommendation, in 2-3 short paragraphs 1. Options considered — briefly state what alternatives were evaluated and why this option is best 1. Risks — the top 2 risks and how you propose to manage them 1. Ask — the specific decision, resources, or approval you need, with a deadline CONSTRAINTS: - Total memo must fit on one page (under 500 words) - Lead with the recommendation, not the background — busy executives read top-down - No preamble or throat-clearing — the first sentence must be the point - Address the political context without being political — if the CEO is skeptical, anticipate their objection - The “ask” must be binary — yes/no, approve/decline — not “discuss further” - Use short sentences and active voice throughout

This is post #3 in our weekly prompt database series.

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Why These Prompts Work for Strategy

Strategy is the hardest domain to use AI well — because the default output is platitudes. Ask an LLM "what should my strategy be?" and you'll get a perfectly structured, completely useless answer that could apply to any company in any market. The prompts above solve this by doing three things differently.

First, they force context loading. Every prompt requires you to input your specific numbers, competitive position, and constraints before the AI writes anything. This eliminates the generic problem at the source — the AI literally can't produce a one-size-fits-all answer because it has your specific situation embedded in the instructions.

Second, they apply real frameworks. SWOT, Porter's Five Forces, Business Model Canvas, unit economics — these aren't academic exercises. They're thinking tools that structure messy information into clear patterns. The prompts ensure the AI uses these frameworks properly, not superficially.

Third, they demand honesty. Every prompt includes constraints like "be brutally honest," "if the data is insufficient, say so," and "flag what's unproven." This counteracts the AI's natural tendency to be agreeable and optimistic — which is exactly what you don't want from a strategic advisor.

These prompts work across ChatGPT, Claude, Gemini, and any other major LLM. For strategy work specifically, models with longer context windows tend to perform better because they can hold more of your data in memory while reasoning. If you're feeding in board decks or financial models alongside the prompt, choose a model that won't truncate your input.

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