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.