AI Prompts for ChatGPT for Strategic Planning

Help me run a rigorous SWOT analysis for [COMPANY OR BUSINESS UNIT NAME]. Here is what I know about our current situation: [PASTE YOUR NOTES, INCLUDING REVENUE, TEAM SIZE, MARKET POSITION, RECENT WINS, RECENT STRUGGLES, AND COMPETITIVE CONTEXT]. For each quadrant, push me beyond the obvious. For Strengths and Weaknesses, focus on what is genuinely true versus what we tell ourselves. For Opportunities and Threats, focus on what is most material to our trajectory over the next two years, not a long list of everything that could matter.

I want to identify the most important constraint on our growth right now. Here is the context: [DESCRIBE YOUR BUSINESS, CURRENT REVENUE OR SCALE, WHAT YOU HAVE TRIED, AND WHERE YOU FEEL STUCK]. Apply a theory of constraints lens: where is the bottleneck that, if we removed it, would most unlock growth or progress across the rest of the business? Help me think through whether the constraint is in [SUPPLY / TALENT / PRODUCT / SALES / OPERATIONS / CAPITAL / STRATEGY] and what evidence would help confirm which one it is.

Help me evaluate how well our current strategy is working. Our strategy was broadly: [DESCRIBE YOUR CURRENT OR RECENT STRATEGY IN A FEW SENTENCES]. Here is what the data says: [PASTE KEY METRICS, TRENDS, OR OUTCOMES FROM THE PAST ONE TO TWO YEARS]. What does this evidence suggest about what is working and what is not? What should we consider stopping, doubling down on, or changing? Be direct. I want an honest reading of the evidence, not a framework that rearranges what I already know.

Help me map our competitive landscape for strategic planning purposes. We operate in [MARKET OR INDUSTRY]. Our main competitors appear to be [LIST COMPETITORS]. Our current differentiation is [HOW YOU DESCRIBE YOUR DIFFERENTIATED POSITION]. Based on this, help me identify: where competitors are investing that we are not, where we have genuine advantages versus where we think we do but may not, and what market dynamics over the next 12 to 24 months could change the landscape in ways we need to plan for.

We are considering a significant strategic shift at [COMPANY NAME]: [DESCRIBE THE PROPOSED CHANGE]. Before we finalise this direction, help me think through our organisational readiness for it. Consider: the skills and capabilities we have today versus what this strategy requires, the cultural or structural changes that would be necessary, the people who would need to lead it and whether they are positioned to do so, and the realistic time horizon to execute given where we are. What are the biggest organisational risks we should account for before committing?

Help me write a clear strategic direction statement for [COMPANY OR BUSINESS UNIT NAME] for [TIMEFRAME: E.G., THE NEXT 12 TO 18 MONTHS]. We are trying to move from [WHERE WE ARE NOW] to [WHERE WE WANT TO BE]. The key choices we are making include: [TWO OR THREE EXPLICIT CHOICES ABOUT WHERE TO FOCUS AND WHAT NOT TO DO]. The statement should be specific enough that someone could use it to make a decision about where to spend their time, but short enough to be memorable. No more than three to four sentences.

Help me write OKRs (Objectives and Key Results) for [COMPANY / TEAM / DEPARTMENT] for [TIMEFRAME]. Our strategic priorities this period are: [LIST TWO OR THREE PRIORITIES]. For each objective, write two to three measurable Key Results that would prove we achieved it. The objectives should be qualitative and aspirational. The Key Results should be quantitative and specific enough that there is no debate about whether we hit them. Avoid KRs that measure activity (e.g., "launch X feature") instead of outcomes (e.g., "X% of users do Y").

We have more strategic priorities than we can realistically execute well in [TIMEFRAME]. Here is our current list: [LIST ALL YOUR PRIORITIES]. Help me force-rank them. For each, help me think through: the likely impact if we execute it well, the resource requirement relative to the others, and what we would lose by deprioritising it. Then give me a recommended ranking with a short rationale for the top three and a clear explanation for why the rest should wait or be cut. Do not let me keep everything as a priority.

One of the most important parts of strategy is clarity on what we are not doing. Given our strategic direction of [BRIEF DESCRIPTION OF YOUR STRATEGY], help me articulate a clear list of what we are explicitly not pursuing, not building, or not prioritising in [TIMEFRAME]. This should include: market segments we are not targeting, product areas we are not investing in, and initiatives that seem logical but would dilute our focus. Frame each item as an active choice, not an omission, so the team understands the reasoning.

Help me think through how to allocate our resources in a way that reflects our actual strategic priorities. We have approximately [BUDGET / HEADCOUNT] to allocate across [TIME PERIOD]. Our strategic priorities are: [LIST PRIORITIES IN ORDER]. Currently, our resources are roughly allocated as: [DESCRIBE CURRENT ALLOCATION]. Does the current allocation match our stated priorities? Where are the biggest gaps? What would a resource allocation that genuinely reflects our strategy look like? Flag any hard choices we are avoiding.

Write an executive summary of our strategic plan for [TIMEFRAME]. The plan covers: our strategic situation: [SUMMARY OF CURRENT STATE AND KEY CHALLENGES]; our strategic direction: [WHERE WE ARE GOING AND WHAT WE ARE CHOOSING TO FOCUS ON]; our top three priorities: [LIST THEM]; and our key metrics for success: [LIST THE METRICS]. The summary should be no more than one page. It should be direct, avoid strategy jargon, and be written so a new board member or senior hire could read it and understand our direction in three minutes.

Create a 12-month strategic roadmap for [COMPANY OR TEAM NAME]. Our strategic priorities are: [LIST PRIORITIES]. For each priority, outline: the major milestones or stages across Q1, Q2, Q3, and Q4; who owns each initiative; and what the measurable outcome looks like by end of year. Format this as a structured table or timeline I can share with the team. Flag any dependencies between initiatives that could create bottlenecks if not planned for.

Help me write a one-page strategy document for [COMPANY OR TEAM NAME] that covers: where we are today (one paragraph), where we are going and why (one paragraph), what we will focus on and what we will not (one paragraph), and how we will measure success (three to five metrics). The document should be honest and specific. It should not contain phrases like "world-class", "best-in-class", "leverage our synergies", or any other language that obscures meaning. Someone reading it should finish knowing what we are actually doing.

Write a narrative strategy memo for internal use at [COMPANY OR TEAM NAME]. This is a working document, not a polished presentation. It should cover: the problem or opportunity we are responding to, the strategic bets we are making and why, the key assumptions those bets depend on, the risks if we are wrong, and the first three things we need to do to get started. Write it in plain prose, not bullet points. It should feel like smart thinking written down, not a strategy template filled in.

I want to stress-test our strategic plan before we commit to it. Here is the plan: [PASTE YOUR STRATEGIC PLAN OR SUMMARY]. Play the role of a sceptical board member or experienced operator. What are the three to five most important assumptions this plan depends on? What happens to the plan if each assumption is wrong? Are there any scenarios we have not considered that could materially change the picture? What parts of the plan feel like wishful thinking rather than grounded strategy? Be direct.

Write a communication to share our strategic plan with the full team at [COMPANY NAME]. The audience is [APPROXIMATE TEAM SIZE] people across [DEPARTMENTS OR FUNCTIONS]. The plan in brief: [SUMMARISE YOUR STRATEGY IN THREE TO FIVE SENTENCES]. The tone should be direct and honest, not corporate. Acknowledge the hard choices we made. Explain why they were made and what it means for each person. End with how we will track progress and when we will next share an update. Avoid the words "excited" and "thrilled" and "journey".

I need to present our strategic plan to [THE BOARD / INVESTORS / SENIOR LEADERSHIP]. Here is the plan: [PASTE OR SUMMARISE YOUR PLAN]. Help me structure a 15 to 20 minute presentation. What are the five to six things they most need to understand? What questions will they likely push on? How should I frame the trade-offs and risks we have accepted? What evidence should I prepare to defend the key assumptions? Give me an outline of the presentation and the two or three slides that will require the most preparation.

Help me design a review cadence for tracking progress against our strategic plan. We have [TEAM SIZE] and operate on [QUARTERLY / ANNUAL / OTHER] planning cycles. For each review type (weekly check-in, monthly review, quarterly deep-dive), define: what we should be looking at, who should be in the room, how long it should take, and what decision or action should come out of it. The goal is to catch drift early and make adjustments without turning every meeting into a strategic planning session.

Write a mid-year strategy update to share with the team at [COMPANY NAME]. We are at the [APPROXIMATE POINT IN THE YEAR OR PLANNING CYCLE]. Here is what has gone according to plan: [YOUR NOTES]. Here is what has changed or where we have fallen short: [YOUR HONEST ASSESSMENT]. As a result, here is what we are adjusting: [ANY CHANGES TO PRIORITIES, RESOURCE ALLOCATION, OR METRICS]. The tone should be transparent and grounding. Do not sugarcoat where we have fallen short, but also communicate confidence in the path forward.

The company's strategic priorities for [TIMEFRAME] are: [PASTE OR SUMMARISE COMPANY STRATEGY]. I am the [YOUR ROLE] and I lead the [TEAM NAME] team, which is responsible for [WHAT YOUR TEAM DOES]. Help me translate the company strategy into three to five specific priorities for my team. For each priority, explain how it connects to the company strategy, what it means in concrete terms for what my team should be doing differently or focusing on, and how we would measure whether we are delivering on it.