Strategy & Planning prompts

Attack this strategy. Your job is to find where it breaks, not to improve it.

THE STRATEGY: [WHAT WE PLAN TO DO]
THE REASONING: [WHY WE THINK IT WILL WORK]
WHAT WE ARE BETTING ON: [KEY ASSUMPTIONS]
OUR SITUATION: [SIZE, RESOURCES, MARKET POSITION, CONSTRAINTS]
TIMEFRAME: [HOW LONG BEFORE WE EXPECT RESULTS]

Produce:

1. THE LOAD-BEARING ASSUMPTION - of everything I have said, the one that, if false, collapses the whole plan. Name it, and give the cheapest way to test it.

2. THE STRONGEST COUNTER-ARGUMENT - written as an intelligent critic would make it. Full strength, no strawman.

3. WHO ELSE HAS TRIED THIS - the general pattern, how it usually goes, and what distinguishes the cases that worked. Be honest about the base rate.

4. WHAT HAS TO BE TRUE - list the conditions required for this to work, and mark each: already true / probably true / unverified / unlikely.

5. THE COMPETITIVE RESPONSE - if this works, what do competitors do, and does our advantage survive it?

6. WHAT WE ARE NOT DOING - the opportunity cost of committing these resources here.

7. THE HONEST VERDICT - one paragraph. If the plan is weak, say so directly. If it is sound, say what makes it sound rather than agreeing.

Do not offer encouragement. Do not end on an upbeat note.

Run a SWOT analysis that leads somewhere.

BUSINESS/UNIT: [WHAT IT IS AND DOES]
MARKET: [WHO YOU SELL TO AND WHO ELSE DOES]
CURRENT SITUATION: [HONEST DESCRIPTION - SIZE, TRAJECTORY, RESOURCES]
THE DECISION THIS SUPPORTS: [WHAT YOU ARE TRYING TO DECIDE]

Rules for each quadrant:
- STRENGTHS: only things that are (a) true, (b) relevant to customers, and (c) hard for a competitor to copy within a year. Anything that fails all three is not a strength. Say which test each one passes.
- WEAKNESSES: only things that cost you customers or money. Include at least one uncomfortable one.
- OPPORTUNITIES: only external changes you could actually act on with current resources. 'Growing market' is not an opportunity, it is a condition.
- THREATS: ranked by likelihood x impact, with the earliest signal you would see for each.

No entry may be a single adjective. Each must be a sentence with evidence or an example.

Then - and this is the actual output - produce the cross-analysis:
- S+O: which strength lets you capture which opportunity. The best move on the board.
- W+T: which weakness makes which threat dangerous. The thing to fix first.
- S+T: which strength defends against which threat.
- W+O: which weakness will stop you taking which opportunity.

End with the single highest-leverage action from the cross-analysis, and what you would stop doing to fund it.

Analyse this competitor.

COMPETITOR: [NAME AND WHAT THEY DO]
WHAT I KNOW ABOUT THEM: [PASTE - THEIR SITE COPY, PRICING, REVIEWS, JOB ADS, ANYTHING]
OUR POSITION: [WHAT WE DO AND HOW WE DIFFER]
WHERE WE COMPETE: [SEGMENT, GEOGRAPHY, CHANNEL]

Produce:

1. THEIR STRATEGY AS THEY WOULD STATE IT - one paragraph, written from inside their business, taking them seriously.

2. WHO THEY ARE ACTUALLY FOR - the customer they serve best, inferred from pricing, positioning and features. Often narrower than their marketing claims.

3. EVIDENCE TABLE - Claim about them | Evidence | Source | Confidence (observed / inferred / assumed)
   Mark clearly what you know versus what you are guessing.

4. WHAT THEIR JOB ADS AND PRICING REVEAL - hiring and price changes are the two most honest public signals of strategy. What do they suggest?

5. WHERE THEY ARE STRONG - and specifically, where they would beat us head to head.

6. WHERE THEY ARE STRUCTURALLY WEAK - not 'their UI is dated' but constraints they cannot easily escape: their cost base, their existing customers' expectations, their channel, their funding model.

7. THE CUSTOMER THEY CANNOT SERVE WELL - and whether that is a market worth having.

8. WHAT I SHOULD NOT COPY - things they do that work for them because of their situation and would not work for mine.

Do not assert anything you cannot trace to my input. Mark inference as inference.

Help me decide between these options.

THE DECISION: [WHAT I AM CHOOSING BETWEEN]
OPTIONS: [LIST THEM]
WHAT I AM TRYING TO ACHIEVE: [THE UNDERLYING GOAL]
CONSTRAINTS: [BUDGET, TIME, PEOPLE, ANYTHING FIXED]
MY CURRENT LEAN: [WHICH ONE, AND WHY]
REVERSIBILITY: [how hard is this to undo]

Produce:

1. THE REAL QUESTION - restate the decision. Often the stated choice is a proxy for a different question. If it is, say so.

2. CRITERIA - derive 5-7 criteria from my goal and constraints, not generic ones. Weight each 1-5 by importance and justify each weight in a few words.

3. SCORING MATRIX - each option against each criterion, 1-5, with a one-line reason per cell. Weighted total at the bottom.

4. WHY THE WINNER MIGHT BE WRONG - the scoring's blind spots. What does this framework not capture?

5. MY LEAN, EXAMINED - I said I lean toward one. Is that supported by the analysis? If not, say so plainly and identify what I might be over-weighting.

6. REVERSIBILITY CHECK - if this is easily reversed, say that the right move may be to pick the fastest option and learn, not the best-scoring one.

7. WHAT WOULD CHANGE THE ANSWER - the one piece of information that would most alter the ranking, and how to get it.

Do not simply endorse my lean. If the analysis contradicts it, lead with that.

Write a positioning statement and test it.

WHAT WE DO: [DESCRIPTION]
WHO WE SERVE BEST: [SPECIFIC CUSTOMER]
WHAT THEY USE TODAY INSTEAD: [COMPETITOR, MANUAL PROCESS, OR NOTHING]
WHY THEY SWITCH: [WHAT ACTUALLY TRIGGERS A CHANGE]
WHAT WE DO BETTER: [YOUR CLAIM]
PROOF: [EVIDENCE FOR THAT CLAIM]

Produce:

1. POSITIONING STATEMENT in this form:
   For [specific customer] who [specific trigger situation], [product] is the [category] that [the one differentiated benefit]. Unlike [the real alternative], we [the specific difference], because [the structural reason it is true].

2. THE OPPOSITE TEST - for each element, state the opposite. If no sensible competitor would claim the opposite, that element says nothing. 'High quality' fails; 'the slowest, most thorough option' passes. Mark each element PASS or FAIL and rewrite the failures.

3. THE CATEGORY QUESTION - are we better off competing in an existing category customers already search for, or defining a new one? Give the trade-off plainly: existing category means demand exists but comparison is easy; new category means no demand but no comparison.

4. WHO THIS EXCLUDES - a position that excludes nobody is not a position. Name the customers this deliberately turns away.

5. PROOF AUDIT - can we actually substantiate the differentiated claim? If the proof is thin, say so - an unsupported position is a liability.

6. THREE ALTERNATIVE POSITIONS we could take instead, each with what it would require us to change.

Turn this strategy into quarterly objectives.

STRATEGY / ANNUAL GOAL: [STATEMENT]
WHY IT MATTERS: [THE REASONING]
TIMEFRAME: [WHICH QUARTER]
TEAMS INVOLVED: [LIST AND ROUGH SIZE]
CONSTRAINTS: [WHAT CANNOT CHANGE]
WHAT IS ALREADY COMMITTED: [EXISTING WORK THAT MUST CONTINUE]

Produce:

1. THE QUARTER'S ONE THING - if only one objective could be achieved, which, and why that one.

2. OBJECTIVES - maximum three. Each: a qualitative statement of what will be different by quarter end.

3. KEY RESULTS per objective - 2-3 each. Each must be:
   - A measurable outcome, not an activity. 'Ship feature X' is activity; 'X% of accounts using feature X weekly' is outcome.
   - Sourced from a metric that already exists, or accompanied by the work to start measuring it
   - Given a baseline (current value) and a target. Where I have not given a baseline, mark [BASELINE NEEDED].

4. TEAM CASCADE - for each team, what they own toward which key result, and what they should stop doing to make room.

5. CAPACITY CHECK - against my stated team sizes and existing commitments, is this plausible? If not, say so and name what must drop.

6. WHAT THIS QUARTER IS NOT ABOUT - explicitly, so teams can say no.

Rules:
- Never more than three objectives. If I gave you more, tell me which to cut and why.
- No key result may be a binary ship/not-ship.
- If a key result has no baseline and no way to measure it, it is not a key result.

Help me decide whether to continue or stop this.

WHAT IT IS: [THE PROJECT/PRODUCT/INITIATIVE]
ORIGINAL GOAL AND SUCCESS CRITERIA: [WHAT WE SAID AT THE START]
HOW LONG IT HAS RUN: [TIME]
WHAT HAS BEEN SPENT: [MONEY, PEOPLE, TIME]
RESULTS SO FAR: [HONEST NUMBERS AND OUTCOMES]
WHAT WOULD BE NEEDED TO CONTINUE: [FURTHER INVESTMENT]
WHO IS ATTACHED TO IT: [INTERNAL POLITICS, HONESTLY]

Produce:

1. THE FRESH-START TEST - if this did not exist and someone proposed it today, with everything we now know, would we start it? Answer directly. This is the central question and everything spent so far is irrelevant to it.

2. AGAINST THE ORIGINAL CRITERIA - a table: Criterion | Target | Actual | Met? Be literal.

3. THE CASE FOR CONTINUING - at full strength. Include the legitimate reasons: learning curve, delayed effects, a known fixable problem.

4. THE CASE FOR STOPPING - at full strength. Include the opportunity cost of the resources.

5. SUNK COST CHECK - identify every argument in section 3 that is really 'we have already spent a lot'. Name them and set them aside.

6. THE MIDDLE OPTIONS - between continuing as-is and killing it: reduce scope, hand to one person, pause and revisit at a stated date, open-source it, sell it, change the goal. Each with what it costs and preserves.

7. THE DECIDING QUESTION - the single piece of evidence that should determine this, and whether we have it.

8. IF WE STOP - how to do it well: what to salvage, what to tell people, how to treat those attached to it.

Answer section 1 before anything else, and do not hedge it.

Help me write a one-page business plan.

BUSINESS: [WHAT YOU SELL OR WILL SELL]
CUSTOMERS: [WHO BUYS AND WHY]
WHERE AND HOW YOU SELL: [shop, online, WhatsApp, marketplace, B2B]
PRICES AND COSTS (as known): [NUMBERS]
COMPETITORS: [WHO ELSE CUSTOMERS COULD BUY FROM]
MONEY AVAILABLE: [BUDGET]
GOAL FOR THE NEXT 12 MONTHS: [GOAL]

Produce one page with:
1. The problem and who has it
2. The offer and why customers would choose it over the alternatives
3. How customers find and buy it
4. The money: price, cost per unit or job, gross margin (show arithmetic), monthly fixed costs, and how many sales to break even
5. The 3 biggest risks and how to reduce each
6. A 90-day action plan with weekly milestones
7. The 3 numbers to track every week

Rules: use my numbers only; mark missing ones [NEED NUMBER]. Keep it to one page - cut, do not cram.

Build an issue tree for this problem.

CLIENT AND CONTEXT: [DESCRIBE]
THE QUESTION: [e.g. "Why have profits fallen 20% this year?" or "Should we enter market X?"]
WHAT WE ALREADY KNOW: [FACTS]
DATA AVAILABLE: [DATA]
TIME AND BUDGET FOR THE WORK: [CONSTRAINTS]

Produce:
1. THE KEY QUESTION rewritten to be specific and answerable (who, what, by when)
2. THE ISSUE TREE - 3-4 levels, with branches that are mutually exclusive and together cover the whole problem (MECE). Show it as an indented list.
3. HYPOTHESES - for the most likely branches, a testable hypothesis each
4. ANALYSIS PLAN - for each hypothesis: the data or analysis that would prove or disprove it, and the source
5. PRIORITY - which 3 branches to investigate first and why (likely impact x ease of testing)
6. GAPS - any branch where overlap or missing areas mean the tree is not MECE yet

Do not jump to answers. The point is the structure.