Rock Your Strategy

Tag: ChatGPT

  • The AI Strategy Audit: How to Use AI Tools to Keep Your OGSM on Track

    The AI Strategy Audit: How to Use AI Tools to Keep Your OGSM on Track

    You built a solid OGSM. You ran the launch meeting, shared the document, set a review cadence. And then life took over, and six weeks later you’re not sure which Goals are on track, which Measures haven’t been updated, and whether the strategy you committed to is still the right one.

    An AI strategy audit uses AI tools — Claude, ChatGPT, or similar — to systematically review your OGSM: flagging stale Measures, testing whether your Goals are still realistic, stress-testing your Strategies against current conditions, and generating specific questions for your next review meeting. A thorough AI audit takes 30 minutes and surfaces issues a standard review often misses.

    Here’s how to run one — and the exact prompts to use.

    Why AI Makes a Good Strategy Auditor

    AI tools don’t have the same blind spots you do. When you review your own OGSM, you see it through the lens of what you know, what you’re hoping for, and what feels uncomfortable to confront. An AI tool has none of those filters. Ask it the right questions, and it will push back on your assumptions with the consistency of a very patient, very well-read advisor who has no stake in the outcome.

    The key is knowing what to ask. Used poorly, AI just produces generic strategy advice. Used with the right prompts and your actual OGSM data, it becomes a genuinely useful thinking partner for the review process.

    What You Need Before You Start

    Before running an AI strategy audit, gather:

    • Your current OGSM document (or a typed summary of Objective, Goals, Strategies, and Measures with current RAG status)
    • Any recent performance data relevant to your Goals (revenue figures, traffic numbers, customer counts — whatever your Goals track)
    • The date your OGSM was last formally reviewed

    You don’t need to share the full document at once. The prompts below are designed to work section by section.

    The Five-Part AI Strategy Audit

    Part 1: Objective Clarity Test

    Paste your Objective into the AI tool and use this prompt:

    “Here is our strategic Objective: [paste Objective]. Please assess this against three criteria: (1) Is it specific enough to guide real decisions, or is it too vague? (2) Does it suggest a clear timeframe? (3) Would someone outside our organisation understand what we’re trying to achieve? Please flag any weaknesses and suggest a sharper version if needed.”

    A well-written Objective should pass all three. If the AI struggles to understand what you’re aiming for, your team probably does too.

    Part 2: Goal Integrity Check

    Paste each Goal (with baseline and target) and use this prompt:

    “Here are our strategic Goals: [paste Goals with baselines and targets]. Please assess each one against the SMART criteria — Specific, Measurable, Achievable, Relevant, and Time-bound. Flag any Goals that are missing elements, and identify any that appear too safe (unlikely to stretch the team) or too ambitious (unrealistic without a step-change in approach).”

    Ask a follow-up: “Given these Goals, what would need to be true about our business for us to achieve all of them simultaneously? Are there any that might conflict with each other?”

    This second question often surfaces tensions the planning process missed — for example, a Goal to grow volume while simultaneously improving margin, without a Strategy that explicitly addresses the trade-off.

    Part 3: Strategy Stress Test

    Paste your Strategies and use this prompt:

    “Here are the Strategies we have committed to this year: [paste Strategies]. For each one, please: (1) Identify the key assumption it relies on. (2) Describe what would have to be true in the market for this Strategy to succeed. (3) Flag any Strategy where the assumption seems weak or where an alternative approach might be more effective.”

    You can also ask: “Are there any obvious strategic options we appear not to have considered, given our Objective and Goals?”

    This prompt works especially well when you share some context about your market or competitive situation. The more specific you are, the more useful the output.

    Part 4: Measures Audit

    Paste your Measures and use this prompt:

    “Here are the Measures we are tracking: [paste Measures with targets and current status]. Please assess each one and tell me: (1) Is this a leading indicator (predicts future Goal performance) or a lagging indicator (reports past results)? (2) Does this Measure have a plausible causal connection to the Goal it’s meant to support? (3) Are there any Measures that appear to be output metrics rather than outcome metrics?”

    Then ask: “If all of these Measures were consistently green, which of our Goals would you be most confident will be achieved — and which Goals do you think would still be at risk? Why?”

    This last question tests whether your Measures actually cover your Goals — a common gap in OGSM design.

    Part 5: Review Meeting Preparation

    Once you’ve completed the first four parts, use this prompt to prepare your next strategy review:

    “Based on everything we’ve discussed about our OGSM — our Objective, Goals, Strategies, and Measures — please generate: (1) The five most important questions our leadership team should discuss at our next strategy review. (2) The two or three areas where you think we are most at risk of being off track. (3) One provocation — a question designed to challenge a core assumption we might not be examining.”

    The provocation question is often the most valuable output. Strategy teams have a tendency to examine tactics while leaving core assumptions unquestioned. A good provocation makes the meeting more honest.

    How to Use the Output

    An AI strategy audit produces observations, not decisions. The output gives you better questions to take into the review meeting, not answers to replace the meeting.

    Treat it as pre-work. Share the AI audit output with your leadership team 24 hours before the review. Ask them to come prepared to discuss the two or three risks the audit flagged. This shifts the meeting from information-sharing to genuine strategic dialogue.

    Running the Audit Quarterly

    The AI strategy audit works best as a quarterly habit — done two or three days before each major strategy review. It takes about 30 minutes to run, and the discipline of preparing your OGSM data to share with the AI tool is itself valuable: it forces you to update the document before the review rather than improvising status in the meeting.

    You can also run a lighter version monthly — just Part 4 (the Measures audit) — to catch any Measures that are drifting without being addressed.

    What AI Can’t Do

    AI tools are useful strategy thinking partners. They are not strategy consultants, and they’re not a substitute for genuine organisational knowledge.

    AI doesn’t know your specific market dynamics, your team’s actual capacity, or the political realities that shape what’s truly possible in your organisation. The audit questions are most useful when you’re specific about context — “we operate in a market where…” or “our main constraint is…” — and when you treat the output as input to human judgment rather than a replacement for it.

    The best strategy is still made by people who understand the business. AI helps them think more rigorously about what they already know.

    Ready to Audit Your Strategy?

    If you want to run an AI strategy audit on your OGSM, the first thing you need is an OGSM that’s properly structured — with clear Goals, connected Strategies, and trackable Measures. The OGSM Template for PowerPoint and OGSM Template for Excel give you that structure from the start, so when you bring the AI into the review process, you’re working from a solid foundation rather than trying to retrofit one.

    And if you would rather not run the audit prompt by prompt, the OGSM Strategy Builder has both the stress test and the review built in as phases: it runs the mechanical checks, challenges the judgement calls, says plainly what it cannot verify, and prepares your review agenda with the at-risk items first. More on how it works.

  • How to Use AI to Build Your OGSM: A Practical Guide for 2026

    How to Use AI to Build Your OGSM: A Practical Guide for 2026

    Strategy has always demanded two things most people are short on: time and objectivity.

    You can use AI to build your OGSM at every stage — from drafting your SWOT and stress-testing your objective, to generating strategic options and identifying the right KPIs. Feed an AI tool like ChatGPT or Claude the right context, ask the right questions, and you’ll compress hours of strategic thinking into minutes — without sacrificing quality.

    That’s the short version. The rest of this guide shows you exactly how to do it at each step, with practical prompts you can copy and use right now.

    First: What AI Is (And Isn’t) Good for in Strategy

    Before diving into the how, it helps to be clear about the what.

    AI is genuinely good at generating options quickly, structuring and stress-testing ideas, summarising large amounts of information, drafting text, and challenging your thinking with alternative perspectives.

    AI is not good at knowing your business the way you do, replacing strategic judgment, validating data it hasn’t seen, or making decisions on your behalf.

    The best way to think about it: AI is a fast, well-read sparring partner. It has read everything, remembers everything, and is always available. But it hasn’t lived through your last five years of business. You bring the context. It brings the horsepower.

    With that framing in mind, here’s how to use it across each stage of your OGSM.

    Step 1: Use AI to Sharpen Your Situational Analysis

    Every good OGSM starts before the OGSM itself — with a clear-eyed assessment of where you stand today. That typically means a SWOT analysis, a PESTEL scan, or a review of your competitive position.

    This is where AI earns its keep immediately.

    Rather than starting with a blank page, give an AI tool like ChatGPT or Claude the key facts about your business — your industry, size, markets, main products or services, and the biggest challenge you’re facing — and ask it to draft a starting-point SWOT. You won’t use the output directly, but it will surface angles you hadn’t considered and give you something concrete to react to, which is always faster than building from scratch.

    Try this prompt:

    “I run a [type of business] with [X employees] operating in [markets/geographies]. Our main products/services are [X]. We are currently facing [challenge]. Draft a SWOT analysis for my business, and for each point, explain the strategic implication in one sentence.”

    Review the output critically. Cross out what doesn’t fit, add what it missed, and you’ll find you’ve completed a quality situational analysis in a fraction of the usual time.

    You can apply the same logic to a PESTEL analysis. Ask AI to scan the macro-environment of your industry for political, economic, social, technological, environmental, and legal factors. It won’t know your local context, but it will catch trends you may have overlooked — especially in fast-moving areas like regulation or technology.

    Step 2: Use AI to Draft and Test Your Objective

    Your OGSM Objective is the most important sentence in your entire strategic plan. It needs to be inspiring, clear, and grounded — and it often takes several rounds of iteration to get right.

    AI is useful here in two ways: drafting and stress-testing.

    For drafting, describe your ambition in plain language and ask AI to turn it into a crisp strategic objective.

    Try this prompt:

    “Based on this business context: [paste your context]. Here is my current draft objective for our strategy: [paste it]. Please rewrite this as a sharp, inspiring strategic objective in one sentence. Then give me two alternative versions — one more ambitious, one more conservative.”

    For stress-testing, ask AI to challenge what you’ve written.

    “Here is our strategic objective: [paste it]. What are the top three weaknesses or blind spots in this objective? What is it not saying that it probably should?”

    This kind of challenge is exactly what a good strategy coach would give you in a workshop — and it’s available instantly, at any time.

    Step 3: Use AI to Benchmark and Validate Your Goals

    Your OGSM Goals translate your qualitative objective into 3 to 5 measurable, quantitative targets. The question most people struggle with isn’t what to measure — it’s what numbers to aim for.

    AI can help you benchmark.

    “We are a [type of company] in [industry]. We want to grow revenue from [X] to [Y] in [timeframe]. Is this growth rate realistic compared to industry benchmarks? What typical growth rates do companies like ours achieve, and what are the key drivers?”

    AI will give you a directional answer based on its training data. It won’t have access to your specific market’s most recent figures, so treat the output as a calibration tool rather than gospel. But it will quickly tell you whether your goals are realistic, stretched, or timid — and that alone is worth the conversation.

    Step 4: Use AI to Generate Strategic Options

    This is arguably the most powerful use of AI in your OGSM process. When it comes to defining your Strategies — the “how” of your plan — most teams default to the same playbook they’ve used before.

    AI breaks that pattern. It has been exposed to thousands of strategic frameworks, case studies, and industry examples, and it can generate a wide range of strategic options quickly. Your job is to filter, refine, and stress-test.

    Try this prompt:

    “Given this strategic objective [paste it] and these goals [paste them], generate 8 to 10 potential strategies for achieving them. For each strategy, describe it in one sentence using the format: ‘[Verb] [what] by [how]’. Then rate each strategy on a scale of 1 to 5 for both impact and feasibility.”

    You won’t use all 8 to 10 options. But the exercise will almost certainly surface one or two angles your team hadn’t considered — and that’s exactly what makes it valuable.

    Step 5: Use AI to Define the Right Measures

    The Measures column of your OGSM — covering both Metrics (what you track) and Initiatives (what you do) — is where most strategic plans either come to life or fall apart. The biggest risk is choosing measures that are easy to track rather than measures that actually tell you whether your strategies are working.

    Here AI can act as a useful check.

    “Here is our strategy: [paste it]. What are the best leading and lagging indicators to measure whether this strategy is succeeding? Give me 3 to 5 specific KPIs, and for each one, explain why it matters and what a good result looks like.”

    Leading indicators tell you whether you’re on track before the results arrive. Lagging indicators confirm what happened after the fact. A good OGSM uses both — and AI can help you design that balance.

    The Three Mistakes to Avoid

    Using AI in strategy is still new territory for most businesses, and a few common mistakes are worth calling out.

    Mistake 1: Taking the first output at face value. AI generates plausible-sounding content quickly, but “plausible” is not the same as “right.” Always treat the first draft as a starting point, not a finished product. Push back, ask follow-up questions, and test the assumptions.

    Mistake 2: Skipping the team conversation. AI is a tool for you, not a replacement for your team’s input. A strategy created in isolation — even a well-crafted one — rarely gets executed well. Use AI to prepare better material for your team discussions, not to skip them.

    Mistake 3: Using generic prompts. The quality of your AI output is directly tied to the quality of your input. The more specific context you give — industry, company size, specific challenge, desired format — the more useful the response. Generic prompts produce generic answers.

    Putting It All Together

    Here is a simple workflow to use AI across a full OGSM build:

    1. Situational Analysis — Use AI to draft your SWOT and PESTEL as a starting point for team discussion.
    2. Objective — Use AI to sharpen your draft and stress-test your thinking.
    3. Goals — Use AI to benchmark your targets against industry norms.
    4. Strategies — Use AI to generate a broad range of options, then filter with your team.
    5. Measures — Use AI to identify the right KPIs and design your leading/lagging indicator mix.

    At every step, you’re using AI to do the heavy lifting on the first draft — so your time and your team’s energy goes into the judgment calls that only humans can make.

    Start With the Right Foundation

    If you want to put this into practice, the best place to start is with a clean, well-structured OGSM template. Our OGSM Template for PowerPoint and OGSM Template for Excel give you the framework to capture everything your AI-assisted analysis surfaces — and to turn it into a one-page strategic plan your whole team can work from.

    AI accelerates the thinking. The OGSM gives it structure. Together, they make for a faster, sharper, and more actionable strategy.

    And if you would rather run the whole thing as one process than assemble it prompt by prompt, the OGSM Strategy Builder is a Claude Skill that facilitates all eight phases — diagnosis through review — and hands you the finished one-pager in HTML, Excel, PowerPoint and PDF. Here is what that session looks like, phase by phase.

    Want to go deeper on OGSM? Read What Is OGSM? or explore our full library of OGSM examples for inspiration.