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:
- Situational Analysis — Use AI to draft your SWOT and PESTEL as a starting point for team discussion.
- Objective — Use AI to sharpen your draft and stress-test your thinking.
- Goals — Use AI to benchmark your targets against industry norms.
- Strategies — Use AI to generate a broad range of options, then filter with your team.
- 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.
