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Section IV · For the Task

Prompts for doing strategy

Prompts for SWOT analyses, competitive landscapes, and strategic memos.

§ Overview

Strategy work is mostly structured thinking under uncertainty, and AI is a strong sparring partner for pressure-testing your reasoning before you commit. The Conduct a SWOT Analysis prompt forces specificity and evidence rather than the usual list of platitudes, ending in an actual recommendation, and the Build a Decision Matrix prompt turns a fuzzy choice into weighted criteria with a built-in check for the biases steering your scoring.

The collection covers the documents strategy produces. The Create a Competitor Analysis Report prompt structures a per-rival breakdown with positioning recommendations, the Write Quarterly OKRs prompt keeps goals outcome-focused with confidence scores, and the Write a Decision Memo for Leadership and Create a Startup Pitch Deck Outline prompts turn your thinking into something you can circulate. The Craft a Clear Value Proposition prompt anchors it all to what you actually offer. The pitfall AI helps you avoid is the strategy doc that sounds impressive and decides nothing, full of generic strengths and hedged options. Push it for evidence, tradeoffs, and a clear recommendation, and use it to challenge your assumptions rather than rubber-stamp them.

§ Field Notes

What makes a good prompt for doing strategy

A good strategy prompt gives the model real context, your market, your actual constraints, the specific decision on the table, and asks for evidence behind every claim rather than generic categories. A SWOT that lists "strong brand" as a strength is useless; one that ties it to a specific advantage and what it lets you do is strategy.

The most valuable instruction is to make it argue. Ask the model for the strongest case against your preferred option, the assumptions your plan depends on, and what would have to be true for it to fail. Used this way it's a devil's advocate, not a yes-machine. End every analysis with an explicit recommendation and the tradeoffs you're accepting, because strategy that doesn't choose isn't strategy.

§ Pro Tips

Get sharper results

  • 01Give the model your specific market and constraints and demand evidence for every point, so the SWOT or analysis is grounded rather than a list of generic truisms.
  • 02Ask it to argue the opposite case and name the assumptions your plan rests on, using it as a devil's advocate instead of a source of validation.
  • 03Insist on an explicit recommendation with the tradeoffs you're accepting, since an analysis that lays out options without choosing pushes the hard part back to you.
  • 04For competitor work, point it at real positioning and named rivals rather than abstractions, so the output is something you can act on this quarter.
§ FAQ

Common questions

Can AI actually do strategy or just format my existing thoughts?

Both, depending on how you use it. It won't replace your judgment about your market, but it's excellent at structuring messy thinking, surfacing angles you missed, and arguing against your plan. The strategy is yours; the model makes it sharper and harder to fool yourself with.

How do I stop strategy outputs from being generic?

Feed it specifics and refuse vague answers. Give it your real numbers, named competitors, and actual constraints, then push back on any point that could apply to any company. A good follow-up is simply 'be more specific and tell me the evidence,' which strips out the platitudes.

Is it risky to share competitive or financial details with AI for analysis?

It can be, so check your tool's data policy first and prefer an enterprise or no-training mode for sensitive material. When in doubt, anonymize the numbers and use ranges or relative figures, which still let the model reason about the strategy without exposing exact data.

§ The Prompts · 13
№ 014business

Conduct a SWOT Analysis for a Business

Get a specific, evidence-based SWOT analysis with a clear strategic recommendation.

For
chatgpt·claude
№ 040marketing

Craft a Clear Value Proposition Statement

Craft a positioning statement, feature-benefit table, and tagline for any product.

For
chatgpt·claude
№ 049business

Write Quarterly OKRs for a Team

Generate outcome-focused quarterly OKRs with confidence scores and risk notes.

For
chatgpt·claude
№ 050business

Create a Competitor Analysis Report

Generate a structured competitor analysis with per-competitor strengths, weaknesses, and positioning recs.

For
chatgpt·claude·gemini
№ 052business

Create a Startup Pitch Deck Outline

Generate a complete 12-slide VC pitch deck outline with per-slide content guidance.

For
chatgpt·claude
№ 055business

Write a Decision Memo for Leadership

Write a crisp one-page decision memo with options, recommendation, and next steps.

For
claude·chatgpt
№ 063productivity

Build a Decision Matrix for a Complex Choice

Build a weighted decision matrix with criteria, scoring, and a bias sanity check.

For
chatgpt·claude
№ 195business

One-Page Decision Memo to Drive a Clear Recommendation

Turns a messy decision into a crisp one-page memo with a clear recommendation and a single ask.

For
chatgpt·claude
№ 196business

SWOT Analysis That Ends in a Prioritized Action Plan

Goes beyond a four-quadrant grid to a TOWS matrix and three prioritized 90-day actions.

For
chatgpt·claude
№ 197business

Draft OKRs That Cascade From Company Goal to Team

Drafts outcome-based OKRs that ladder up to the company goal and weeds out tasks masquerading as key results.

For
chatgpt·claude
№ 199business

Market Analysis With TAM Logic, Segments, and Whitespace

Builds a transparent bottom-up market sizing with buyer segments, alternatives, and underserved whitespace.

For
chatgpt·claude
№ 201business

Vendor and Tool Comparison With a Weighted Scorecard

Screens tools against must-haves then ranks survivors on a weighted scorecard with a clear pick.

For
chatgpt·claude
№ 202business

Business Case for a Project With ROI and Payback

Frames a project as an investment with quantified benefits, a transparent ROI and payback calculation.

For
chatgpt·claude