Rock Your Strategy

Category: AI

  • How to Build Your OGSM With AI: A Step-by-Step Guide (With the Questions to Expect)

    How to Build Your OGSM With AI: A Step-by-Step Guide (With the Questions to Expect)

    Most people who sit down to build a strategy with AI make the same mistake in the first thirty seconds: they ask it to write the strategy.

    You’ll get something back. Well-structured, confidently worded, and completely generic — a plan that would fit any firm in your industry, which means it fits none.

    The alternative is to use AI the way you’d use a good facilitator: let it run the process, ask the questions and hold the standard, while you do the deciding. An afternoon’s work, and you get something you’ll still defend in June.

    Here’s what that session looks like, phase by phase, with the real questions and the quality bar each phase holds. It’s what the OGSM Strategy Builder does — but the process is the process, and you can get value from this post without buying anything.

    What do you need before you start?

    Not much, but the numbers matter. Have these to hand:

    • Revenue — last full year and the one before, so growth is visible.
    • Margin — gross, and operating if you have it.
    • Growth rate — actual, not aspirational.
    • Customer concentration — what share of revenue your largest customer represents, and your top five.
    • The one operational number your business runs on. Utilisation for a services firm, lead time for a manufacturer, covers per night for a restaurant, renewal rate for anything on contract. You know yours.

    Then two more things: two to four hours of real work, which almost nobody does in one sitting, and a working answer to why now? Nobody writes a strategic plan because it’s January. Something changed, or is about to, and that’s the real subject of the session.

    If a number isn’t to hand, estimate it, say so, and move on. It gets flagged later as something to verify.

    My worked example throughout: Marlow Instrumentation Services, a fourteen-person Midlands firm calibrating lab instruments for pharmaceutical and food-testing customers. Revenue £2.4m, growing 3% a year, gross margin sliding from 41% to 36%, largest customer 22% of revenue.

    Phase 0: What does the diagnosis actually ask you?

    Ten to twenty minutes, and the phase everyone wants to skip.

    It opens with real questions — what you do, who buys from you, how you’ve changed. Then the one that matters: what made you want to do this now?

    Then scope (whole business or one function?) and horizon — a 3–5 year strategic plan or a 1-year operating plan. Pick one. It governs how ambitious the objective can be, whether timelines read 2028 or Q3, and whether reviews are quarterly or monthly.

    Then the Five-Answer Test:

    Ask five of your leaders, separately, so they can’t hear each other: what is our strategy?

    You’ll get five answers. Each reasonable, each confident, and not one quite the same. Solo? The equivalent is: could your best customer say what you’re trying to be?

    Then the Seven Cardinal Sins self-diagnosis, asked one at a time. Are you deciding from a picture of your market that’s a few years old (Ignorance)? Do five leaders give five answers (Discord)? Could someone on the floor say what the company is trying to do (Confusion)? Does the daily work quietly contradict the stated strategy (Incongruity)? Is there someone who has to carry this who doesn’t believe in it (Doubt)? Does the plan need capabilities you don’t have yet (Incompetence)? Is it agreed, pinned up, and not moving (Inertia)?

    Most businesses recognise three or four. That’s normal, and worth saying out loud, because people get defensive here. The ones you name become the watchlist for every phase that follows.

    Finally: list everything the business is currently working on. Everything taking real time or money. It’ll be longer than you expect — twenty items is common. Nothing gets resolved now. That list comes back in Phase 5, and it’s the argument.

    Phase 1: How does the reality check work?

    Key figures first — the numbers you prepared. Then a SWOT, built by conversation rather than form-filling.

    The questions have teeth. Name a strength and you’ll be asked who else in your market would claim the same thing? Give a number and you’ll be asked where it came from. Each quadrant caps at three to five items: if a strength doesn’t make your top five, it isn’t a key strength.

    Marlow’s SWOT surfaced the pairing that mattered — their biggest weakness (a price list that hadn’t kept up with wage inflation) sitting against their biggest threat (two national providers undercutting them per instrument). That pairing became a strategy three phases later.

    Where your situation warrants it you’ll be offered PESTEL, market trends, Porter’s Generic Strategies, Five Forces or the 5P marketing mix. Where it doesn’t, you won’t. A fourteen-person firm doesn’t need Five Forces to work out that price competition has arrived.

    Phase 2: How do you land on an objective you’d defend?

    Twenty to forty minutes. It’ll feel long. It should — everything downstream is derived from this one sentence.

    You’ll be pointed back to your why now? answer, then asked a present-tense question that people find easier than the future-tense one:

    When a customer chooses you over the alternative today, why do they?

    The honest answer is usually the raw material for the second half of your objective.

    Then three options — three genuinely different bets, not three rewordings — each with what it commits you to and what it rules out. You choose, or say the real one is none of them.

    Marlow’s first attempt was typical:

    ❌ “Grow the business by delivering excellent service to our clients.”

    Three problems. “Grow” is an outcome, not a direction. “Excellent service” is a claim every competitor makes. And swap in a competitor’s name — it still reads fine, which means nothing was chosen.

    After three drafts:

    ✅ “Become the default calibration partner for regulated pharmaceutical and food-testing labs in the Midlands by making audit-ready documentation, not price per instrument, the reason customers stay.”

    That names a segment, names a mechanism, and rules something out — price-led work, about a third of their current enquiry flow.

    Then five quick tests: substitute a competitor’s name (does it still work?); could five people repeat it the same way after hearing it twice?; what does it rule out?; what would someone do differently on Monday?; and is it ambitious enough to be worth it, grounded enough that nobody laughs? More on the craft in how to write a great objective.

    Phase 3: How do you turn that into goals?

    Twenty to thirty minutes. Three to five SMART goals, each written so it can be checked without a conversation: [metric] from [baseline] to [target] by [date].

    It starts with the twelve-month question — we meet again in a year, it’s gone well, what’s different? — then two relentless follow-ups: how much? and is that ambitious enough? The second is where the real number appears. People’s first answer is almost always their safe answer.

    ❌ “Improve customer retention.”
    ✅ “Contract renewal rate from 81% to 92% by 31 December.”

    Two rules shape the set. At least one financial goal — every strategy eventually shows up in the money. And goals covering both halves of your objective, the “what” and the “how”. Marlow’s renewal and revenue goals cover the what; regulated-lab revenue share and documentation turnaround cover the how. A plan with only “what” goals can be hit by accident, doing all the things you said you’d stop.

    Then the gate, which is the most useful question in the method:

    If we achieve exactly these goals — and nothing else — have we succeeded?

    If something is missing, write a goal for it. If a goal could be missed entirely and you’d still say the objective was met, it’s a metric you like, not a goal — it belongs in the Dashboard. See Goals vs Measures.

    Phase 4: What makes the strategies phase uncomfortable?

    Thirty to fifty minutes, and the phase that matters most. Everything before this could be done by a thoughtful person with a spreadsheet. This is where something gets given up.

    You’ll be pushed back to the SWOT pairings — your biggest weakness is X and your biggest threat is Y; what specifically are you going to do about that? You’ll generate six or eight candidates and then be forced to cut to three to five. The cut is the work.

    Each one has to pass the tactic test. A strategy sets a direction; it does not spell out the work. If it still leaves a real “but how, exactly?” for the next phase to answer, it is pitched at the right level. If it already specifies the work in full, it is an initiative and belongs in Phase 5.

    ❌ “Improve our marketing.” — Too vague. Costs nothing to agree to.
    ❌ “Redesign the website.” — Too specific. That’s an initiative.
    ✅ “Win regulated-lab accounts from the national providers by selling audit-readiness and documentation turnaround instead of price per instrument.” — Owner: Priya.

    Every strategy gets a named owner. Not “the team”. A person who has to answer for it at the review.

    Then the We WILL / We will NOT list, which takes ten minutes and turns intentions into a decision:

    We WILLWe will NOT
    Focus on regulated pharma and food-testing labsQuote on single-instrument, price-only tenders
    Compete on documentation and turnaroundCompete on price per instrument
    Build accreditation depth in two instrument classesCover every instrument a customer owns

    The right-hand column is the one that matters and the one that gets skipped. When you resist, you’ll get prompts like what would your competitor be pleased to hear you’d decided to keep doing?

    For Marlow, that column meant walking away from roughly £180k of low-margin work. Someone had built that revenue. That’s what a real trade-off feels like.

    Phase 5: How do the measures get built?

    Thirty to forty-five minutes. Per strategy, two structurally different things, kept explicitly apart.

    The Dashboard — 2–4 KPIs, each with a definition, baseline, target, frequency and data owner. At least one leading, one lagging. Six to twenty across the plan.

    The Action Plan — 2–3 initiatives that cause the strategy to work, each with a caretaker and dates.

    The speedometer doesn’t make the car go faster. Without the Dashboard you’re flying blind; without the Action Plan you have targets and no engine. Full method in the complete guide to OGSM Measures.

    Three questions build a dashboard. If this strategy is working, what would change? Then the “so what?” filter — if this number moves, what decision follows? If none, drop it. Then: what would you need to see in ninety days, before the annual numbers land? That last one finds your leading indicator.

    ❌ “Number of sales calls made.” — Activity. Tells you what your team did, not whether it worked.
    ✅ Lagging: revenue from regulated labs — £912k to £1.44m — monthly — Priya.
    ✅ Leading: quotes issued to regulated labs — 4/month to 12/month — monthly — Priya.
    ✅ Initiative: rebuild the certificate pack so it’s audit-ready without customer follow-up — Dan — January to end of Q2.

    Anything without a baseline gets refused. If the baseline genuinely doesn’t exist, establishing it becomes the first initiative under that strategy.

    Then the capacity conversation, the antidote to Inertia. Your Phase 0 workload list comes back and every item goes into one of three buckets: continues, paused, stopped.

    You’ve got nine new initiatives on top of eighteen existing ones. Which existing ones stop? Not “deprioritised” — stopped. If everything stays, we execute nothing.

    Focus is not about adding. It’s about removing.

    Phase 6: What does the stress test look for?

    Fifteen to twenty-five minutes, delivered in three parts: what holds, what I’d challenge, and what I can’t verify.

    Mechanical checks first — counts, missing baselines, strategies without owners, activity metrics wearing outcome metrics’ clothing, an empty “will not” list. Then judgement: the competitor test, the arithmetic test (do these strategies plausibly deliver these goals, or is it 28% growth against three efficiency initiatives?), the resourcing test, the capability check and the belief check.

    That third section is usually missing from AI strategy work, and it’s the honest bit. It has read everything and lived none of it. Your market size, a competitor’s intent, whether your team can absorb nine initiatives — those come back to you to check before the plan goes live.

    Where you disagree with a finding, it’s recorded as an accepted risk with your rationale and a watch-for. Not a defeat — a decision made with eyes open.

    Phase 7: How does it get delivered and cascaded?

    Fifteen to thirty minutes. The one-pager is built in the formats you want — HTML to share, Excel to track, PowerPoint to present, PDF to pin up.

    Then cascade guidance, if you have layers: a higher-level Measure becomes a lower-level Goal, cascaded to business and function level only, never to individuals. The named failure is cascading by copying rather than translating — a divisional plan that restates the corporate strategies in different words hasn’t cascaded, it’s photocopied.

    Then the communication plan — to whom, what, how, when, by whom — with three to five key messages you could repeat from memory. And the review calendar: monthly for a one-year plan, quarterly for a three-to-five-year one, with every meeting in the diary before the session ends. Agendas in how to run an OGSM review meeting.

    It closes by asking for three concrete things: the first review date, the first thing that stops, and the first visible win.

    Phase 8: What happens at the review?

    This phase repeats, and it is the one that decides whether the other eight were worth the afternoon.

    Before each review you bring the workbook back. It goes through the plan strategy by strategy — not metric by metric, because you think in strategies and a list of thirty numbers produces thirty guesses. Where are the numbers, and where are the initiatives?

    Then it does three things you would probably skip on your own.

    It compares against the plan rather than against last month. Not “did it go up?” but “is it on the path we said?” If the goal is a 30% improvement over twelve months and four months in you have moved 3%, it will tell you that you are a third of the way through the time and a tenth of the way through the distance. That sentence is more useful than any adjective.

    It checks the “we will not” list. Strategies are rarely reversed in a meeting. They get reversed one exception at a time. “You said you’d stop taking price-led work. Two of your last four wins were price-led. Either the strategy has changed or the behaviour needs to.”

    And it flags the item that has been amber for four months and never discussed — because amber feels survivable, and an initiative holding the same non-green status for three cycles is not a status, it’s a decision nobody is making.

    You get a prepared agenda with at-risk items first, and the short list of things that need a decision rather than a status update. Afterwards, you come back and say what was decided, and it goes into the workbook.

    One rule it will hold you to: don’t change a strategy because it’s uncomfortable. Give it two or three review cycles. Most strategies look wrong at month three, because the cost has arrived and the benefit hasn’t. Folding then is the commonest way a sound plan dies. Change when the ground has genuinely moved — a competitor arrives, a customer concentration risk becomes an event — not when you have simply gone off it.

    How does saving and resuming work?

    At the end of every phase your progress is written to a workbook file and handed to you. Save it. To come back — next evening, next month — start a session, hand the file back, and you’ll be told in two sentences where you left off. Nothing you’ve decided gets redone.

    Use it. A plan built across four evenings beats one rushed in an afternoon, and Phase 4 benefits from sleeping on it.

    Frequently asked questions

    How long does it actually take?

    Two to four hours of real work — nearer two if your numbers are to hand and you decide quickly, nearer four if you take the analysis seriously. Most people split it across two or three sittings, which is what the save-and-resume is for. Phases 2 and 4 take the longest and should. If you finish in twenty minutes, you filled in a template.

    Can I use this if I already have a strategy?

    Yes — often the better use. Run Phase 0 and Phase 6 against what you have, then re-enter wherever your plan first breaks down. Usually Phase 4, because most existing plans have goals and initiatives but no actual choices.

    Do I need my leadership team in the room?

    Not to build the draft. But be clear what you’re producing. If you own the business, this is a decision. If you’re a manager in a company of four hundred, it’s a strong draft to take into a real conversation.

    What if I don’t have baselines for everything?

    Write [baseline: to be established by DATE] rather than leaving it blank, and make establishing it the first initiative. A target without a baseline is unfalsifiable — in nine months nobody will agree whether it was hit.

    Will the AI just agree with everything I say?

    It shouldn’t, and a good process is designed against it. Expect to be told an answer could apply to any company in your industry, and to be asked what you’d stop. If the session felt comfortable throughout, something was avoided.

    Can it decide my strategy for me?

    No, and you shouldn’t want it to. It doesn’t know your market, your customers, or what happened last time you tried this. It drafts options; choosing is yours. A strategy you didn’t choose is one you won’t defend when it costs you something.

    What happens after the plan is built?

    Phase 8, every month or quarter, for as long as the plan is live. Twenty to thirty minutes with the workbook before the meeting you run with your team. See how to run an OGSM strategy review meeting for the agenda itself.

    Is this different from prompting Claude directly?

    Yes, in the way that matters: consistency of standard. A prompt gets one good answer. A process holds the same bar across eight phases, remembers Phase 0 when you contradict it in Phase 5, and refuses the shortcuts. If you’d rather work from prompts, how to use AI to build your OGSM has them.

    Where to go from here

    Nothing here requires a purchase. Open Claude, work the phases in this order, hold yourself to the quality bars, and you’ll produce something far better than a filled-in template — because the hard part is the questions, not the format.

    Read the common OGSM mistakes alongside it, and 30 OGSM examples across six industries if you want to see finished ones first.

    And if you’d rather not have to remember the questions or hold the standard yourself, the OGSM Strategy Builder does all eight phases with you and is available in the shop.

    Either way, do it before January. The plan you write in a quiet week is worth three you write under pressure.

    Rock on.

  • Why AI Should Facilitate Your Strategy, Not Write It

    Why AI Should Facilitate Your Strategy, Not Write It

    Ask any decent AI to write a strategic plan for your business and you’ll have one in about two minutes.

    It will have an objective, four or five goals with plausible-looking numbers, strategies in the right format, measures with owners, initiatives with quarters against them. It will look better than most of the strategy documents I’ve seen inside real companies.

    And it will be worthless.

    Not wrong, exactly. Worthless in the specific sense that nobody will change what they do on Monday because of it.

    That isn’t a limitation of the technology. It’s a fact about what strategy is. Once you accept it, the question stops being can AI write my strategy and becomes the useful one: what is AI actually good for here?

    What is AI genuinely good at in a strategy session?

    More than the sceptics allow. Four things, and they’re not small.

    It has no stake in the outcome. The big one. In every strategy session I’ve sat in, some part of the room is defending something — a product line someone built, a market someone owns, a headcount someone fought for. An AI has no career riding on Strategy 3, and has never had lunch with the person whose favourite project should be cut. Ask it what should stop and you get an answer, not a negotiation.

    It has infinite patience for the uncomfortable question. A human facilitator asks “and what would you have to stop doing?” twice, reads the room, and moves on to keep things pleasant. An AI asks a fourth time in the same even tone. That’s not stubbornness, it’s the absence of social cost — and the fourth asking is usually where the honest answer lives.

    It recognises patterns. A goal of 28% growth sitting above three cost-reduction initiatives doesn’t add up. A strategy every competitor would also write hasn’t chosen anything. An empty “we will not” column means the hard conversation was skipped. These are the common OGSM mistakes, and they are almost always thinking mistakes rather than template mistakes — which is exactly the kind of thing a machine spots quickly.

    It holds a consistent standard. Underrated, this one. Humans get tired. By hour four of a workshop the fifth strategy gets waved through with less scrutiny than the first. An AI applies the same bar to the last item as the first, at 9pm on a Thursday, on the fourth evening.

    That’s a genuinely useful colleague. A fast, well-read sparring partner who will ask the same hard question on a Sunday night as on a Tuesday morning, and who has no stake in which way you answer it.

    But it hasn’t lived through your last five years of business.

    What can AI not do?

    Four things, and each one is load-bearing.

    It doesn’t know your market. It knows what has been written about your market, which is a thinner thing. It doesn’t know the competitor everyone’s worried about has quietly lost their best engineer.

    It doesn’t know your customers. It knows archetypes. It doesn’t know your three biggest accounts all came from one person’s relationships, and that person is sixty-one.

    It doesn’t know your team’s real capacity. It can count initiatives against headcount. It cannot know Dan has been carrying two roles since March, or that ops said yes to the last three plans and delivered one.

    It doesn’t know what happened last time you tried this. Every business has a graveyard — the segment you entered in 2021 and quietly exited, the pricing change that lasted six weeks. That history is the most useful input to any strategy discussion, and it exists nowhere except in the heads of the people in the room.

    A strategy that ignores those four things is a well-formatted guess.

    Why is a two-minute plausible OGSM the worst possible outcome?

    Because plausibility is the trap.

    An obviously bad plan gets rejected. A clearly generic one gets sent back. But a plan that looks right — right format, right vocabulary, sensible-looking numbers — gets adopted. It goes on a slide. It gets presented at an all-hands. And then it sits there doing nothing, because underneath the format there was never a decision.

    Strategy is a choice. A specific direction, paid for by everything you decide not to do.

    An AI can generate the appearance of a choice instantly. It cannot make one, because making a choice requires having something to lose.

    This is why most strategies fail: not because leaders aren’t smart enough, but because they mistake aspiration for direction. AI-generated plans are aspiration at industrial scale — beautifully formatted, internally consistent, and nobody had to give anything up to produce them.

    Why does a strategy nobody chose become a strategy nobody defends?

    Here’s the test that matters. It’s June. A good customer asks for exactly the kind of work your strategy says you’ll stop doing. Real revenue, this quarter, sitting on the table.

    Who says no?

    Only someone who made the choice. Not someone who received it, agreed with it in the meeting, and can’t quite reconstruct the reasoning six months later. Agreement is not alignment.

    A plan you nodded at is a plan you’ll make an exception to. And strategies don’t fail dramatically — they drift, quietly, one reasonable exception at a time, until the gap between where you said you’d be and where you actually are is too wide to close without a serious conversation.

    The defence of a strategy happens in small moments, by people who remember why. If the reasoning lives in a document and not in a person, there’s nothing to remember.

    That’s the argument for facilitation over generation. Not that a facilitated plan is better written — often it’s worse written. It’s that a facilitated plan is owned, and ownership is the only thing that survives contact with a tempting exception.

    Why is the discomfort of the strategies phase the point?

    In the OGSM Strategy Builder, the strategies phase is the longest and designed to be the least pleasant. It generates more options than you’ll keep and then forces the cut. It insists on the “we will NOT” column. It asks what you’d have to stop, and keeps asking.

    People sometimes read that as friction badly designed. It’s friction deliberately designed.

    Good strategy always feels uncomfortable. Because it forces you to say no.

    If the whole session was comfortable, something was avoided — and it’s always the same thing: the trade-off that costs a specific person something specific. That’s the moment the plan becomes real, and exactly the moment a generative tool skips, because nothing in it requires generating.

    A strategy that cannot tell you what to say no to is not a strategy. It is a wish list dressed in a slide deck. An AI will happily produce the slide deck.

    Where must the human decide?

    Four places, and no tool should take them from you.

    The objective. An AI can draft three genuinely different bets and show what each rules out — the craft of it is in how to write a great objective. Which one is your business is not a question it can answer.

    The trade-offs. Which customer gets less attention. Which product line stops. Which market you’re not entering. These land on people, and the person who has to live with it has to be the one who says it.

    The numbers you’d be embarrassed to miss. An AI can tell you a goal is unfalsifiable. It cannot tell you whether 92% is ambitious or safe in your business.

    Who owns what. A measure without an owner is a wish, not a commitment — and only you know who will actually answer for it at the monthly review.

    Everything else — the structure, the questions, the quality checks, the format, catching activity metrics dressed as outcomes — hand it over. That work is real, it’s tedious, and machines are good at it.

    What about Doubt and Confusion — the ones no document fixes?

    Two of the Seven Cardinal Sins make the point better than I can.

    Confusion is not understanding — a strategy no one can repeat. If the people who have to deliver it can’t tell you what it is, you don’t have a strategy. You have a secret. An AI can write a clearer sentence. It cannot stand in front of your team and say it, twice a month, until it sticks. Communication isn’t a document problem; it’s a leader-showing-up problem.

    Doubt is not believing — the plan is sound, the people aren’t sold. The most expensive of the seven, and no amount of writing touches it. You cannot communicate your way out of doubt. Someone who disagrees has heard you and disagrees. Their team watches what they do, not what’s on the wall.

    A good AI process can name both, which is worth something — for most of the seven, naming is most of the cure. Not for these two. Here naming is where the job ends, and it should say so. That’s why the stress test always closes with what it cannot verify, including this: is there anyone who has to carry part of this who doesn’t believe in it?

    An AI strategy audit produces observations, not decisions.

    So what should you actually use AI for?

    Use it as a facilitator. Let it run the process, hold the standard, ask the question you’d rather not answer, catch the goal without a baseline and the strategy without an owner. Let it draft options — three real ones, not three wordings — and choose yourself.

    Don’t use it as an author. A plan you didn’t build is a plan you won’t defend, and an undefended strategy is a document with good posture and nothing behind it.

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

    If you want that process rather than the two-minute version, the OGSM Strategy Builder is in the shop — eight phases, and it will make you choose at every one of them.

    Rock on.

  • The OGSM Strategy Builder: Build Your Whole Strategy With Claude, One Phase at a Time

    The OGSM Strategy Builder: Build Your Whole Strategy With Claude, One Phase at a Time

    You downloaded the template. You opened it on a Sunday morning with a coffee, and you got as far as the box marked Objective.

    Then you sat there.

    Not because you don’t know your business — you know it better than anyone. But because a blank box doesn’t ask you anything. It doesn’t ask why you’re doing this now. It doesn’t ask what you’d have to stop doing to make room. It doesn’t notice when you write “deliver growth” and let it stand.

    A template gives you a format. What most people actually need is a facilitator.

    That’s what we’ve built. It’s called the OGSM Strategy Builder, it’s available in the shop, and this post explains exactly what it does — and what it deliberately does not do.

    What is the OGSM Strategy Builder?

    It’s a paid Claude Skill that turns Claude into an OGSM facilitator and walks you through building a complete, execution-ready strategic plan in eight phases.

    You install it once. Then you open Claude, say something like “help me build our strategy for next year”, and it takes over: asking questions, pushing back on vague answers, drafting options for you to choose between, and saving your progress as you go. At the end you get a finished OGSM one-pager in the format you want, plus a workbook recording every decision and every option you rejected.

    It is built on the same method taught across this blog — the OGSM as described in what OGSM stands for — and on the Seven Cardinal Sins of Strategy from The Strategy Lie, the free ebook on this site.

    It does not write your strategy. I’ll come back to that, because it’s the whole design.

    What problem does it actually solve?

    The gap between a template and a process.

    We sell a $4.99 Excel template and a PowerPoint version, and they do their job well. Thousands of people have used them. But a template assumes you already know how to run the thinking — how to tell a Strategy from a Goal, how to spot an activity metric wearing an outcome metric’s coat, when to stop adding and start cutting.

    Most people don’t. Not because they’re not smart enough, but because nobody ever showed them. And so the classic thing happens: the plan gets written, the boxes get filled, and three months later nobody can remember what was in it. The plan isn’t bad. The process behind it never happened.

    The other half of the problem is that a facilitator is expensive. A good strategy consultant to run a two-day session costs more than most small businesses will ever spend on strategy. So the choice has been: a blank template, or a five-figure invoice.

    This sits in between. It’s the process, not just the page.

    What is a Claude Skill, and do I need to be technical?

    No. A Skill is a folder of instructions you add to your Claude account — Claude.ai, Claude Code or Cowork. Once it’s installed, Claude reads it and follows it whenever the topic comes up. You install it once, the way you’d install an app, and after that you just talk to Claude normally.

    There’s no coding, no API key, no subscription to anything except Claude itself. If you can download a file and drag it into a browser window, you can install this.

    What happens across the eight phases?

    The order matters. OGSM works left to right, and each element is built on the one before it. Skip a phase and the phase after it inherits the gap.

    Phase 0 — Set-up and Diagnosis

    Scope, time horizon (a 3–5 year strategic plan and a 1-year operating plan are different animals), and who has to agree. Then two diagnostics: the Five-Answer Test — ask five of your leaders separately what the strategy is and count how many different answers you get — and the Seven Sins self-diagnosis. It finishes by asking you to list everything the business currently has in flight. That list comes back to bite in Phase 5, which is the point.

    Phase 1 — Reality

    Key figures first, then a SWOT built by conversation rather than form-filling — the approach in how to do a SWOT right. Where your situation warrants it, it offers deeper analysis: PESTEL, market trends, Porter’s Generic Strategies, Five Forces, the 5P marketing mix. Where it doesn’t, it doesn’t offer them. Nobody needs a Five Forces analysis to decide whether to hire a second van.

    Phase 2 — Objective

    One qualitative, what-by-how statement. It drafts three genuinely different options — different bets, not different wordings — shows you what each one commits you to and what each one rules out, and makes you pick. Then it sharpens the one you picked and runs it through the tests in how to write a great objective. Expect to spend real time here. This is the sentence everything else hangs from.

    Phase 3 — Goals

    Three to five SMART goals, each with a baseline, at least one financial, and coverage of both halves of your objective — the “what” and the “how”. Then the gate: if we achieve exactly these goals and nothing else, have we succeeded? It’s the most useful question in the method and it’s in how to write SMART goals for your OGSM.

    Phase 4 — Strategies

    Three to five what-by-how choices, each with a named owner. Then the We WILL / We will NOT list, which is the exercise that turns a set of intentions into a decision. This is the uncomfortable phase, and if it isn’t uncomfortable it hasn’t worked.

    Phase 5 — Measures

    Per strategy, two structurally different things kept explicitly apart: a Dashboard of 2–4 KPIs, each with baseline, target, frequency and a data owner, at least one leading and one lagging — and an Action Plan of 2–3 initiatives, each with a caretaker and dates. Then the capacity conversation: your Phase 0 workload list comes back and every item gets sorted into continues, paused or stopped. If everything stays, you execute nothing. The full method is in the complete guide to OGSM Measures.

    Phase 6 — Stress Test

    The finished draft is run against the quality rules and the seven failure modes, and reported back in three parts: what holds, what it would challenge, and what it cannot verify.

    Phase 7 — Deliver and Cascade

    The one-pager in your chosen formats, plus cascade guidance (a higher-level Measure becomes a lower-level Goal — see how to cascade OGSM), a communication plan, and the review calendar with actual dates in it. Not “quarterly, we’ll find dates”. Dates.

    Phase 8 — Review (and this one repeats)

    The plan is built. Now comes the part that decides whether any of it mattered.

    Before each monthly or quarterly review, you bring the workbook back. The skill walks the plan strategy by strategy, updates the numbers and statuses with whatever you know, works out whether each goal is actually on the path you set — not just whether it moved — and checks the question almost nobody asks out loud: has anything on your “we will not” list quietly started happening again?

    That last check is the one that earns its keep. Strategies rarely get reversed in a meeting. They get reversed one exception at a time, and nobody notices until the trade-off that made the plan real has been eroded entirely.

    You come out with a prepared agenda, at-risk items first, and the two or three things that genuinely need a decision rather than a status update. Afterwards you come back, say what was decided, and it goes into the workbook.

    What do you get at the end?

    Three things.

    The OGSM one-pager, in HTML, Excel, PowerPoint or PDF — you pick, and most people take at least two. HTML is the living version you share by link. Excel is the one your OGSM caretaker updates each month. PowerPoint is what you present. PDF is what you print and pin up.

    The Strategy Workbook, which captures the reasoning: the options you rejected and why, the trade-offs, the accepted risks. This is more valuable than it sounds. At your first review, when someone asks “why did we decide that?”, the answer is written down.

    A cascade and communication pack — who hears what, how, when, and from whom, plus the review calendar.

    The skill also ships two scripts. One generates the four output formats. The other validates any plan against the OGSM rules: counts, what-by-how form, missing owners, targets without baselines, activity metrics masquerading as outcomes, and an empty “will not” list. You can run that validator against a plan you wrote years ago, on your own, without doing any of the rest.

    What happens if you have to stop halfway?

    You stop.

    The skill writes your progress to a workbook file at the end of every phase and hands it to you. Stop after Phase 2 on a Tuesday, come back three weeks later, hand the file back, and it tells you in two sentences where you left off and carries on. Nothing gets redone.

    This is deliberate. A strategy built over four evenings is worth more than one rushed in an afternoon, and pretending otherwise is how you end up with a plan that was really just a long meeting.

    What does the stress test actually check — and what can’t it check?

    The mechanical checks are easy and mostly automated: goal counts, missing baselines, strategies without owners, initiatives that are really operational routines, vanity metrics.

    The judgement checks are the interesting ones. Would five people read this page the same way? Could someone who joined three weeks ago say what the business is trying to do? Swap in your main competitor’s name — does the plan still read as sensible? If yes, you haven’t chosen anything. Is there anything in this plan that costs someone something specific? Do the strategies plausibly deliver the goals, or is the goal 28% growth against three efficiency initiatives?

    And then the part I insisted on: what it cannot verify.

    Every stress test ends with a section naming the assumptions it has taken on trust — your market size, a competitor’s intent, your team’s real capacity, whether the person who has to carry Strategy 3 actually believes in it. It has read everything and lived none of it. Those are the things you check before the plan goes live.

    An AI strategy review produces observations, not decisions. A tool that pretends otherwise is selling you confidence you haven’t earned.

    Who is this for — and who is it not for?

    It’s for you if: you run or lead a business and need a real plan; you’ve tried a template and stalled; you have a strategy nobody can repeat; you’re a functional leader who has to build a plan that connects upward; you want a sparring partner who won’t agree with you to keep the peace. It works for a five-person firm and for a division of four hundred — see OGSM for small business if you’re at the smaller end.

    It’s not for you if you want a plan written for you in two minutes. It will refuse. It will draft options and make you choose, and it will ask you what you’re going to stop doing, and it will keep asking until you answer. If that sounds like more work than you were hoping for — it is. That’s not a bug, and post three in this series explains why at length.

    It also won’t do the political work. If your real problem is that two directors disagree and everyone knows it, no document fixes that. It will name it. It can’t settle it.

    The honest summary

    This is a facilitator, not an oracle. It brings the method, the discipline, the questions and the standard. You bring the business, the judgement and the decisions.

    Your strategy doesn’t need to be complex to be good. It needs to be clear, owned, and reviewed. This is a structured way to get there in an afternoon or four evenings, instead of another year of meaning to.

    Ready to stop staring at the blank Objective box? The OGSM Strategy Builder is available now in the shop — install it once, and build your strategy the next time you can give it an afternoon.

    Founding price — $49 until 31 October 2026. After that it goes to $99, and stays there. Founding customers keep every future update at no extra cost, including the new phases and worked examples already planned for the next version.

    For scale: one facilitated strategy session starts at around $2,000, and five seats of the cheapest OGSM software is roughly €480 a year. This is $49, once.

    Rock on.

  • 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.